There’s no question David Letterman left a major mark on the late night landscape, particularly during his time on The Late Show over at CBS. Celebrities over the course of decades interacted with the famously curmudgeonly man, who often kept people on their toes with acerbic observations and pointed questions. Letterman would later say he “had it coming” when it came to any “criticism” lobbed his way, but did you know the late night host was so eccentric that major stars were told not to compliment him?

It’s not the only example of eccentric behavior by late night hosts, but Amy Poehler and Mindy Kaling both got candid about their experiences with Dave recently.

Mindy Kaling And Amy Poehler Revealed They Were Advised Not To Be Too Nice To Letterman

Kaling recently gave Amy Poehler a compliment of the highest order when she said she loved the positive vibes the other NBC comedian brings to her now-famous “Good Hang” podcast. You can feel the love in the room, but amusingly Kaling set up this compliment by pointing out she and Poehler used to get told “it’s like an insult” to say something nice about David Letterman.

The warning from her agents really stuck with her for years. In fact, it led her to go on shows over and over again where she spent time worrying about it not being “cool” to say something nice. She’s been working on it, and she wanted to tell Poehler she was a fan of the way "Good Hang" works in light of that.

Amy Poehler was also very familiar with the Letterman advice. Interestingly, when Kaling complimented her, Poehler in her typical way also did deflect the former Mindy Project star’s compliment, joking:

So, maybe not taking a compliment is an epidemic among hosts? Though, I will say Poehler was good-natured about the whole conversation, and it’s always fun when totally unrelated factoids about other people get brought up by celebrities. In this case, David Letterman is famously known for hating compliments, and this specific topic has come up again and again over the years.

Letterman Himself Has Admitted He Hates Compliments

Probably the most specific incident came in 2017, just two years after David Letterman had retired from The Late Show. That year, the former host was given an award: The Mark Twain Prize For American Humor. This meant there was an event and a bunch of celebrities attended. It also meant there were a lot of nice things said about Letterman, who even the Washington Post noted at the time, “hates compliments.” In fact, when asked about people fawning over him, he admitted the whole thing was cringy to him.

David Letterman’s entire comedic persona lives on that edge between funny and uncomfortable. He’s often at his most engaging and amusing when there’s just a sliver of awkwardness between himself and whomever he is talking with, whether that be a celebrity, a journalist, or just someone random he happens to be chatting with. He's always willing to ask the uncomfortable thing, and that sometimes made him the less popular late night host during his run.

No one is perfect, of course, and that means sometimes he doesn't tow that line correctly. Other times he does things like compare The Late Show ending to an adult bookstore coming in, and it works perfectly. No matter what, though, you never really know exactly what’s going to come out of Dave’s mouth. I’m sure that can be very difficult, particularly when you are early in your celebrity career, wearing uncomfortable celebrity fashion, and trying to make a positive impression on late night – without literally saying anything positive to said host.

David Letterman performed his final monologue on The Late Show on May 20th, 2015. Eleven years (and one day) later, Stephen Colbert was in the same position, walking onto the stage to have his final say on May 21st, 2026. You’d think that’s about all the two would have in common given The Late Show was being cancelled when Colbert said goodbye, but it turns out that’s not true.

In fact, one thing that really struck me as The Late Show was wrapping was something Stephen Colbert said about the show kicking him and the staff out immediately. He said essentially they were “fired” and he had to go into the office to clear out his stuff nearly immediately the following week.

His comments were so visceral they stuck with me, and I was surprised to come across similar statements from Letterman, who noted CBS did nearly the same thing to him when he left the show.

Unlike Colbert, it was Letterman’s choice to retire from late night. Still, when asked by the NY Times what his “favorite memory” from the CBS series was, he said they need to "talk to someone else” and he could only muster this negative final memory about the show.

It’s clear elsewhere in the interview that Letterman was unhappy with how things shook out with The Late Show. Despite a favorable opinion of Colbert's successor, he’s compared the show being taken over by Byron Allen to an “adult bookstore” coming into your childhood hangout space. He’s also seemingly not bullish about where late night will be going in the very near future, which is upsetting to hear.

He’s not the only one. CBS has taken a lot of flak from individuals like Jimmy Kimmel, who has said he feels late night is “being poisoned.” It’s been clear for years the TV landscape is changing, but for a long time, there were still dollars to go around, even when social media became a prominent place to consume late night clips. As every month goes on, that’s less and less true. CBS has said $40 million in losses is what actually led to the network's changing of the guard.

We’ll have to wait and see if anyone else is clearing out on an office in the next year or so. If Trump had his way, Seth Meyers and more would also get cancelled.

David Letterman may need no introduction, but it’s rare you’ll catch him in a room with a traditional outlet doing a traditional interview these days. The former late night host and current Netflix host did speak out around the time of Stephen Colbert’s big exit from CBS, and with good reason: Both men were tied to the Eye Network for years before breaking free to do new projects. So, I get why there would be curiosity around what Letterman thinks. Yet, I did not see his “adult bookstore” reference coming.

Here’s what happened. Not only did the New York Times snag an interview with the former host, they also caught him in time to talk about his feelings about Colbert’s show getting axed on the 2026 TV schedule. He didn’t hold back, which is where the adult bookstore analogy came in.

Now, that he put this analogy out into the universe, I can’t unsee it. I know exactly how he’s feeling. There was once something great and something familiar in this slot and now it’s been ceded to something that’s unexpected. In fact, Letterman also told the news outlet his first feelings were “disbelief.” Afterward, he felt like it had been a “botched holdup.” All of these visuals really paint a negative picture of how he felt CBS handled the situation as a whole.

As the former host of The Late Show with David Letterman, he knows more about the inner workings of late night, the network and what happened behind the scenes than most.

David Letterman Does Not Blame Byron Allen

Of course, David Letterman also was quick to point out he’s not mad at Byron Allen, the man at the head of the new series that took over The Late Show’s timeslot, Comics Unleashed. He and Allen have palled around before, and he’s not opposed to Byron coming in and making his mark.

[Editor Note: As Letterman himself noted, the "Winslow Twins" or the "Ellison Twins" are what Letterman likes to call the one son of Larry Ellison, David. That part is a bit.]

However, he definitely still feels Stephen Colbert got a raw deal. The Eye Network has claimed its choice to cancel The Late Show was all financial, but it’s not just Letterman who is skeptical. Fellow late night host Jimmy Kimmel also spoke out about how the choice may have been more related to politics than the money piece. Colbert himself famously said "my side of the street is clean" when it came to any political allegations.

Meanwhile, David Letterman himself had a somewhat tumultuous run on late night, eventually signing on with NBC as a potential successor for Johnny Carson on The Tonight Show. Then, executives at the time famously chose Leno instead. Letterman had a long and storied history on CBS, anyway, and retired of his own accord in 2015. (Other famous hosts like Conan O'Brien and Kimmel also spoke out about The Late Show at that time.)

It ended on his own terms, but Letterman still has a bit of a contrarian in him. If someone is calling out the network he formerly worked at, he'll lead the charge.

Just don't ask him to work that "tough" late night grind again.

Stephen Colbert has spent the last several months in a delicate dance, both looking back and looking forward. He signed on for an LOTR movie, he had sweet goodbye moments with Emma Stone and more big stars, and he’s done interviews trying to wrap up this portion of his career. Most recently, he called landing The Late Show as David Letterman was stepping down a “happy accident,” and shared the sweet story behind why he ultimately decided to sit behind the storied desk.

How Stephen Colbert And David Letterman “Perfectly Overlapped”

Colbert set the stage for his connection with David Letterman. The two men are only 17 years apart in age, and Letterman was just getting rolling when the other late night host was coming of age. They then were tied together years later when the fate of The Late Show was laid out.

It seems like it would have been an easy decision to make. Colbert already had plenty of experience in front of a TV camera at that point, having been on The Daily Show and then leading The Colbert Report for nearly 10 years. But network TV late night was a whole other budget behemoth (as Late Night fans would later learn), and signing on for the role was a big deal for the funnyman.

The actor told People he went to therapy for “four months” to make sure that signing on as Letterman’s replacement was what he really wanted to do. It's a big responsibility and not something one signs on to the dotted line for lightly. Part of the problem is that he really wanted to talk to his mother, whom he was very close to, but she had passed away by this time. So, instead, he called up his sister, Mary. Luckily for CBS, Mary “sealed the deal” for the late night host.

The year 2015 was an exciting time. The first episode of Colbert’s Late Show was up 203% over the same date the previous year. Colbert joining sparked a ratings race with Jimmy Kimmel and Jimmy Fallon that would continue over the years. What wouldn’t continue were the massive number of subscribers cable and network TV enjoyed for decades.

As those numbers fell off, so did ad revenue. By the end, The Late Show was losing $40 million a year, a number CBS recently confirmed. The show wrapped up last week after months of lead-up to the moment, but when it was done, it was done. Colbert even said the crew had to be out of CBS studios very quickly when it was all over.

I don't know that the Colbert who talked to his sister Mary knew the end would be quite like this, but I'm glad he still gets to hold onto that fond memory.

Hollywood’s a weird industry. Most of the time when a person takes a behind-the-scenes job, it isn’t necessarily for a particularly long time. Movie gigs may last for only weeks; TV shows may last for months before summer hiatuses and, all-too often, yearly cancelations. But it’s rare for a show like Jimmy Kimmel Live or The Late Show with Stephen Colbert to come along that all but guarantees job continuity for a much longer window. That is, until recently.

When news The Late Show was being canceled came down the pipeline, it sent shockwaves through the industry. But for the people who actually work on the show, it means they are also going to be out of the job and without banking the millions+ paydays a hosting gig offers. Putting out feelers could be key to where they land, which is why a joke fellow late night host Jimmy Kimmel made was funny, but also had rings of truth to it.

Late Show Staffers Are Maybe Looking To Switch To Jimmy Kimmel Live

Last week, Kimmel and Colbert made headlines when they decided to appear on each others’ shows on the same night. The so-called “crossover” event led to some great moments, including Kimmel revealing how his kids responded to his own ABC suspension. One other bit that stood out to me happened when Kimmel was talking about showing up to the set of his fellow late night host's show.

The audience roared with laughter about the remark, but what I liked about the joke is how it probably mirrored his real reality visiting the CBS show. Everyone on The Late Show with Stephen Colbert is going to need to start looking for a new gig within the next six months, and pitching yourself to Jimmy Kimmel when you already have the experience is not the worst idea I’d even heard.

Nor was it for Stephen Colbert, either, who took Kimmel’s joke and dryly responded, ‘as well they should.’

My good friend is an editor, and I know how stressful it can be hopping from gig to gig, so I appreciate Colbert's supportive comment back. The final episode of his show is expected to air in May of 2026 as the TV schedule is wrapping up ahead of the summer season. Even so, it’s certainly too soon for the former Daily Show host, who said of his team at CBS:

There’s nothing else to really say about that, though if you want CBS's perspective on the matter, George Cheeks has spoken out. Regardless, if you’re hiring talent, Stephen Colbert sounds like he’d likely be the first to sign the recommendation letters.

The cancellation of The Late Show with Stephen Colbert has stirred up a plethora of conversations. Many of those discussions revolve around the future of the late-night TV landscape, which is seemingly becoming increasingly unstable as viewers consume media in varied ways. On top of that, though, others continue to speculate as to whether CBS’ decision to axe the show was purely “financial” as stated. Amid that, one of the franchise’s ex-producers, who worked with OG host David Letterman, is now weighing in.

Rob Burnett, specifically, is among the latest people to share thoughts, and he has quite a bit of experience with late-night TV. In 1993, he started working as a writer-producer on Late Night with David Letterman, which aired on NBC. Burnett ultimately made the move to CBS with Letterman when The Late Show was picked up at that network. Deadline reached out to Burnett to ask about the Stephen Colbert news, during which he made a joke that referenced the corporate moves that have been occurring at the Eye Network as of late:

The seasoned writer is referring to the fact that Paramount Global – CBS’ parent company – has been in the midst of finalizing its merger with Skydance. At the same time, the corporation just settled the $16 million lawsuit involving U.S. President Donald Trump and 60 Minutes. As noted by the trade, that lawsuit was viewed as the final hurdle keeping Paramount from receiving FCC approval for its latest acquisition. Stephen Colbert himself, while on air, chastised his employers for settling the suit with Trump.

Since The Late Show’s demise was confirmed, a number of celebrities have taken to social media to air their grievances. Jimmy Kimmel and Bowen Yang were among the stars to reach out, and many are of the belief that Stephen Colbert is being penalized for his comments as opposed to being cut for financial reasons. For his part, Rob Burnett cited Colbert’s popularity amongst talk show hosts as one of the reasons he’s not completely convinced that money was the driving force behind the cancellation:

Colbert’s stint on his current show, as it stands, is still slated to end in May 2026. It was in September 2015 that Colbert took over from David Letterman, who retired earlier that year. Since taking over The Late Show, Colbert has received 11 Emmy nominations for his hosting duties, and he also won a Peabody Award. Colbert addressed the cancellation news during an episode of his eponymous talk show and, since then, insiders have reported that the crew isn’t happy with the decision. The on-air address can be viewed below:

It seems that plenty of people have thoughts on The Late Show’s fate, and they aren’t holding back those opinions. We’ll see if any other fellow TV producers join Rob Burnett in discussing the situation as the 2025 TV schedule pushes on and Stephen Colbert and co. move closer to the end of their run.

History has seen many great late-night TV hosts, but David Letterman is really someone special. As the host of NBC’s Late Night from 1982 to 1993 and CBS’s Late Show until 2015, he brought an unprecedented energy and perspective to the world of comedy that has served as a clear inspiration to his peers ever since. As a tribute to the Letterman era, let’s look back on some of his greatest hits.

Dave Works The McDonald's Drive-Thru

One of the most iconic remote segments from David Letterman's days on Late Show saw him employed by McDonald's for a day, where he worked at the drive-thru window. Instead of simply taking orders, he indulges in giving the customers a hard time, asking one woman to drive around the building because they are too busy to answer for her at the moment and telling another guy asking for two #3's that he will give him a #6 instead.

Dave Visits General Electric

In 1986, when Letterman was still hosting Late Night on NBC, the network was purchased by General Electric, which gave him the idea to visit his new bosses' headquarters with a basket of fruit as a welcoming gesture. However, he would not make it past the front lobby, thanks to a security guard enforcing the building's strict laws against letting cameras inside.

Dave's Mom Reports The Olympics

Letterman enlisted his mother, Dorothy Mengering, to present a number of remote segments. The first instance of this was in 1994 when she was sent to Lillehammer, Norway, to cover that year's Winter Olympics for Late Show, during which she interviewed the likes of figure skater Nancy Kerrigan and then-First Lady Hillary Clinton.

The Top Ten Words That Sound Romantic When Said By Barry White

Barry White had the kind of voice that could make anything sound smooth and enticing, as demonstrated by one of David Letterman's most ridiculous Top 10 Lists. Accompanied by a trio of backup singers, the legendary R&B musician forever changes the way you might hear words like "jazzercise," "doo-hickey," and the Number One choice, "Oprah."

Joaquin Phoenix "Couldn't Be Here"

In 2009, Joaquin Phoenix appeared on Late Show to promote his film, Two Lovers, but he did not do much promoting and passively mumbled through most of the interview, which David Letterman capped with the perfect quip, "Well, Joaquin, I'm sorry you couldn't be here." The future Academy Award winner would later return to explain himself after it was revealed that his scraggly-haired aspiring hip-hop artist persona was all an act for his brother-in-law, Casey Affleck's, mockumentary, I'm Still Here.

Dave Hangs Out With Richard Simmons

Sometimes, just partnering Letterman with somebody whose personality greatly opposes his own was enough to conjure comedy gold. For instance, the time when the host shot a remote segment chronicling the day he spent with flamboyant fitness guru Richard Simmons, which consisted of visiting random people in their homes and searching for the latest Barbara Streisand album.

Crispin Glover Nearly Kicks Dave In The Face

One of David Letterman's most infamous interviews from his Late Night days, let alone his entire career, saw Crispin Glover from the Back to the Future cast seem to nervously struggle through the entire conversation, culminating in him performing a kick that came uncomfortably close to the host's face. The actor would later return only once more, but this time, he dodged any opportunities for a substantial explanation of his behavior and awkwardly giggled for much of it.

Biff Henderson's Fun With A Bullhorn

David Letterman's longtime stage manager, Biff Henderson, participated in many classic bits. One of his own personal favorites was a remote segment in which he travels the streets of New York yelling at random people with a bullhorn, and often providing them with valuable information, too.

Dave Wears A Velcro Suit

On Late Night, Letterman participated in many a ridiculous stunt that involved him wearing a funny suit constructed with some unusual material or substance. One of the more famous was a suit of velcro, with which he leaped onto a velcro wall and got stuck face first.

Jerry Lawler Slaps Andy Kaufman

In 1982, David Letterman had Andy Kaufman and wrestler Jerry "The King" Lawler on Late Night to discuss their feud, which grew heated before Lawler slapped him across the face, causing the already injured comedian to fall out of his chair. It was revealed years later that this infamous TV moment was not so authentic, as the pair were really good friends pulling a gag on the world.

The Long Debate Around The World's Largest Vase

On Late Night, David Letterman invited on the show a man who claimed to have the world's largest vase, which another person from Canada challenged, claiming his was taller. This inspired a lengthy debate involving polygraph tests and legal experts, before Dave decided to put it all to bed by placing a 35" radio transmitter on top of the vase they had in the studio, bringing its final length to 9'8".

Dave Assures "No One Is Blaming Conan"

David Letterman left NBC after losing the chance to host The Tonight Show to Jay Leno, who would, in 2010, leave the network's leading late-night program for Conan O'Brien to step in, only to take it back just months later. The Late Show host commented on the debacle, mentioning how Leno insisted that fans should not blame O'Brien, which prompted Letterman to point out that no one was pointing fingers at him in the first place.

Dave Is Startled By A Monkey

Like any other late night host, Letterman was known to bring animals on his show from time to time, but he did not enjoy his experience with a monkey on Late Night. The primate continuously lunged toward the host, causing him to exclaim, "She's gonna leap at me and pull a vein out of my neck and kill me!" To make matters even funnier, the monkey was wearing a dress.

The Final TV Appearance By Johnny Carson

David Letterman maintained a strong relationship with Johnny Carson even after both of them had left NBC. In fact, the former Tonight Show host made his last-ever appearance on television in 1994 to present Letterman with that night's Late Show Top 10, much to the audience's delighted surprise.

Dave Presents The Flashing Party Horses

Similar to saw horses with flashing lights placed around accidents or road construction sites to ensure safety, the "Flashing Party Horses" are smaller in stature and used to surround a party guest who has had a few too many and has collapsed on the floor. Future SNL one-season wonder Chris Elliott helps Letterman demonstrate the faux product by donning a tuxedo as the inebriated party guest.

Kamarr The Discount Magicians Puts Paul Shaffer In A Guillotine

One of the most amusing recurring guests that Dave Letterman would have on Late Night was Greece's own Kamarr the Discount Magician, whose illusions were always worth the price of admission. One of his most memorable appearances saw him place band leader and music director Paul Shaffer in a guillotine that he promised would pass right through his neck, leaving him unharmed, but would chop down on the cucumber beneath him.

John Candy Takes On Wasps In The Studio

One funny Late Night-era bit sees comedy legend John Candy interrupt his interview with David Letterman when a wasp appears on the back of his neck, prompting him to take care of the studio's infestation. He returns from his interspecies quarrel with a bag full of winged pests and a few gross clusters of stings on his face.

Dave's Shocking Diet Tip

In response to a fan letter asking for tips on how to lose weight, Dave presents a solution in the form of a visual demonstration. He takes a 12-volt car battery, attaches one clamp to his earlobe and the other to his soup spoon, and indulges in his meal, experiencing a shock that just "melts the fat" right off.

Camping With Barry White

After joking for several episodes about what it would be like to camp with Barry White, David Letterman invited the "Can't Get Enough of Your Love, Babe" singer onto the show for an official demonstration. He opens an episode of Late Night with a lesson on how to treat a snake bite, using White as his subject, and presents a few products essential for the occasion, including a walkie-talkie equipped with a woofer powerful enough to match the singer's deep baritone.

Dave Hounds Paris Hilton About Her Prison Stint

David Letterman himself has admitted that he could be a little too mean to his guests for the sake of getting a laugh, and one of the most notorious examples is when, in 2007, he repeatedly asked Paris Hilton about her 22 days in prison for violating parole. At one point, she pleads that she does not want to talk about it anymore, to which he responds, "This is where you and I are different because it's all I want to talk about." The following year, he brought the heiress back to apologize for offending her.

Dave Wears A Suit Made Of Alka-Seltzer Tablets

One of the strangest stunts that Letterman ever performed involving an unusual suit was the time he donned an outfit covered in Alka-Seltzer, which is a brand of effervescent tablets used to treat heartburn, indigestion, or even headaches. Also equipped with an oxygen tank, the stunt sees the host lowered into a vat of water, causing the tablets to dissolve and create a rousing fizz.

Larry Bud Melman's Hilarious Lack Of Interview Skills

Comedian Calvert DeForest recurred on Late Night as his comically average and inept character, Larry Bud Melman, whom Dave would send out into the world for various remote segments, such as one in which he interviewed tourists at New York's Port Authority. The mundane manner of his questions is funny enough, but what makes the bit especially hilarious is the way he continuously brings the microphone away from his mouth too early with each question.

Dave Visits A Store Called Just Bulbs

One of Dave Letterman's most amusing Late Night era remote segments sees him visit a New York store called Just Bulbs, where he asks an employee if they sell anything other than what the name suggests, constantly receiving an emphatic no. When he asks the remarkably patient employee if they sell lampshades, she suggests he "try a store called 'Just Shades,'" at which point the scene immediately cuts to the front of a store called Just Shades.

Dave Meets A Man Who Claims To Have Been Buried Alive Three Times

Letterman discovered and conducted an interview with a man who invented a device that would allow a person who is accidentally buried alive to notify loved ones that they are still breathing. The man was inspired to develop this product after he was mistaken for dead and placed underground more than once.

Brother Theodore's Perplexing Rant

Theodore Gottlieb, better known as Brother Theodore, appeared on Late Night with David Letterman several times, never inspiring a dull moment. The German-American comedian would indulge in an assertive and combative interview with the host before delivering one of his signature, riotous stream-of-consciousness monologues.

Chris Elliott As The Guy Under The Seats

Late Night writer and performer Chris Elliott participated in various recurring segments on the show, including one in which he plays a man living under the studio bleachers who interrupts the show. David Letterman would go meta by making comments about Elliott's approach to the segment that the comedian would immediately take great offense to and respond with petty, threatening remarks.

Paul Shaffer's Freudian Slip

Paul Shaffer is responsible for one of the most infamous moments in SNL history, being the first person to accidentally drop the F-bomb on the live program. However, it was no accident when David Letterman's musical director told the host that he meant to ask his mother to pass the salt, but instead gave an explicit, insulting admission that she ruined his life. It was only a joke, but it inspired Letterman to get Shaffer's actual mother on the phone. After she corrects his grammar, Letterman turns to Shaffer and says, "I see what you mean now."

Gerard Mulligan Fills In For Levon Helm

In 1983, Levon Helm was scheduled to appear on Late Night with David Letterman but did not show up for the interview. Instead, Letterman and segment producer Gerard Mulligan discussed what they would have asked the drummer and vocalist for The Band, inspiring much laughter from the audience over what could have been.

Chris Farley Cartwheels Into The Studio

Iconic '90s Saturday Night Live star Chris Farley never failed to make a grand entrance, just like when he showed up on Late Show with David Letterman and inspired a rousing round of applause by kicking off his appearance with a triple cartwheel.

Biff Henderson Gets Hypnotized

For one fun Late Show segment, David Letterman invited a hypnotist to put members of his staff under his spell, including Biff Henderson, who was supposedly still under hypnosis and fell into a deep sleep on the show. In a YouTube video recalling his favorite moments, the long-serving stage manager did not confirm whether or not he was truly hypnotized, but he did reveal that he saw the hypnosis as an opportunity to relax at work.

Drew Barrymore Flashes Dave

One of the most surprising moments from David Letterman's entire career saw guest Drew Barrymore stand on the host's desk and lift her shirt up right in front of him.

Madonna's Expletive-Filled Interview

Pop star Madonna's 1994 appearance on Late Show gave the censors a lot to worry about. In fact, due to her use of 14 F-bombs, the episode became the most censored in talk show history, according to EW.

Whether it was Late Night or The Late Show, David Letterman had one of the best talk show bits in the history of the medium with his recurring Top 10 lists. Over the years, the legendary TV host touched on topics ranging from “words that almost rhyme with peas” to Tom Cruise internet stories to things celebrities always wanted to say to him before ending his run in 2015.

And while we would love to share the hundreds of lists Dave shared over the years, we thought for the sake of everyone’s time we would keep this relatively short and sweet with 32 ridiculous things David Letter did a Top 10 about. That said, it’s a diverse and outrageously funny list…

Top 10 Words That Almost Rhyme With Peas

David Letterman started making lists way back in September 1985 when he provided Late Night views with “10 Words That Almost Rhyme with Peas.” Little did anyone know at the time, but Dave’s rundown of words like heats, rice, ice, nurse, and meats would be the start of a long tradition that would be a staple of his shows for the next 20 years.

Top 10 Ways The New Show Will Be Better

The Top 10 bit moved to CBS with David Letterman when he became the host of The Late Show in August 1993. Just months after his NBC departure and infamous feud with Jay Leno, Letterman poked fun at everything in this hilarious moment. While “A whole new wardrobe for Vanna!” earned the top spot, the new “Rappin’ Dave” character, and the G.E. jokes line were just as great.

The Beach Boys Sing David Letterman’s Numbers From His First Year On The Late Show

Though this one feels like a clip show from the first year of The Late Show, David Letterman found a way to make it stand out by including the Beach Boys singing the numbers between each joke. Hilarious, memorable, and random as random can be, this great look at Dave’s first year away from NBC was full of all kinds of wonderful moments.

Top 10 Craziest Things People Say About Tom Cruise On The Internet

There are so many wild stories about Tom Cruise on the internet. Some are true, some not so much. Back in December 2008, the Mission: Impossible and Top Gun star got in on the fun when he helped David Letterman with “The Top 10 things people say about Tom Cruise on the internet.” Cruise didn’t hold back and included jokes about everything from his views on mental illness to the couch incident to his ego. Nothing was off limits.

Top 10 California Names

In 1996, The Late Show with David Letterman went on the road and made a stop in San Francisco. During his unforgettable episode, Dave came up with a list of the Top 10 California names, and it didn’t disappoint. Some of these names are straight-up bonkers and hard to believe. But each person did include their driver’s license photo.

Top 10 Messages On Alex Rodriguez’s Answering Machine

After Alex Rodriguez’s steroid scandal, the New York Yankee found himself being the butt of countless jokes for weeks, if not months, on end. David Letterman got in on the fun with “Messages Left on Alex Rodriguez’s Answering Machine,” which included lines about Madonna, Michael Phelps, Mark McGwire, and other celebrities who had stood trial in the court of public opinion.

Top 10 Hockey Player Pick-Up Lines

The Late Show with David Letterman had a series of Top 10 lists involving pick-up lines, and the funniest has to go to the group of hockey players looking for dates. With lines like “My Zamboni or yours,” jokes about pucks, and plays on famous hockey players’ names, there was enough to earn a seat in the penalty box.

Words That Sound Creepy When Said By John Malkovich

There’s something so off-putting about John Malkovich’s line delivery in movies like Con Air and In the Line of Fire, which is what made this Top 10 so much fun. Appearing on The Late Show with David Letterman, the classically-trained actor brought the ick to CBS.

Casey Kasem’s Top 10 Numbers

Years before his passing in 2014, Casey Kasem appeared on The Late Show with David Letterman to share his favorite numbers. This hilarious, ridiculous, and downright preposterous bit was the kind of stuff that made the CBS show so much fun. And if you thought one was Kasem’s favorite number, you would be wrong. Very, very wrong.

Top 10 Things Celebrities Have Always Wanted To Say To Dave

The Late Show with David Letterman had one killer final run of guests back in 2015, and it all culminated with a star-studded “Top 10” during the series finale. “Top 10 things celebrities have always wanted to say to Dave” featured Chris Rock, Bill Murray, Steve Martin, Julia Louis-Dreyfus, and so many others getting one last dig at their old friend.

Top 10 Things You Don’t Want To Hear From A Lifeguard

Back in the early days of The Late Show with David Letterman, Dave had some wild Top 10 segments, like the one involving a lifeguard sharing comments no one would want to hear from him. This included everything from “Shark!” to “If the water’s a little warmer around here, it’s my fault.”

Top 10 Things Never Sung By A Gospel Choir

A full gospel choir does make everything sound better, or at least that’s what David Letterman was trying to prove on The Late Show. When this talented ensemble of singers took to the stage, they made things like “Oh my God, they killed Kenny,” “Dave’s Insane,” and “Lather, rinse, repeat, lather, rinse, repeat” sound like songs from the heavens.

Top 10 Things That Make Bob Barker Angry

The late Bob Barker, who passed away in 2023 at the age of 99, made an iconic appearance on The Late Show with David Letterman a The Price is Right themed Top 10 list. Items included “Losers who guess that the price of a toaster is $50,000,” “Recent allegations that game shows are fixed,” and “Recent allegations that I’m fixed.”

Top 10 Things You Don’t Want To Hear From A Gas Station Attendant

Another great Top 10 moment came in the early days of The Late Show with David Letterman when the host gave viewers “Things you don’t want to hear from a gas station attendant.” These included some wild remarks like “Regular, premium, or ranch flavor,” and “This is my car! You stole my car!”

Alex Trebek’s Top 10 Rejected Jeopardy Categories

The world lost a good one in 2020 when Alex Trebek passed away at the age of 80. Years before his passing, the Jeopardy host shared some hilarious rejected categories from the iconic quiz show. Sections like “Guys I, Alex Trebek, have beat the crap out of,” and “Gap-toothed freaks,” and “Exciting shows on at the same time as Jeopardy” were just too good.

Reasons Larry David Did Not Win An Emmy

Larry David never won an Emmy for his work on Curb Your Enthusiasm, and he had a fun time joking about it on The Late Show with David Letterman back in 2006. David, very much on-brand, had responses like “I don’t know and, frankly, I don’t care,” and “Hey, at least I didn’t lose to Barry Manilow.”

Top 10 Rejected Sean Connery Movie Lines

Sean Connery died in 2020, leaving behind an untouchable legacy. And one of the funniest moments of his career took place on The Late Show with David Letterman when he shared rejected movie lines like “The name’s McDonald. Ronald McDonald,” and “Dr. No, Dr. Kevorkian. Dr. Kevorkian, Dr. No.”

Top 10 Words That Sound Romantic When Spoken By Barry White

Barry White could make anything sound cool, and that’s probably why David Letterman invited the late singer to provide a Top 10 list back in the day. Could anyone make “Jazzercise” or “Oprah” sound so romantic?

James Earl Jones’ Top 10 Things That Sound Cool

No one had a voice like James Earl Jones, the late actor behind characters like Darth Vader, Mufasa, and Terence Mann. Back in the day, David Letterman had him on to read 10 things that sounded cool with his voice, including “Pinhead,” “Heebie-jeebies,” and “Oprah.”

Top 10 Good Things About Having The Same Name As A President

No surprise here, but there are a lot of people out there who share names with former United States presidents. Well, several appeared on The Late Show with David Letterman to share why it’s not such a bad thing. And with comments like “It’s fun to buy rounds for everyone and send the tab to the White House,” and “I’m named after the guy who actually, I’d never heard of him until today” it’s easy to see these guys had a sense of humor.

Top 10 Things Every New York City Tourist Needs To Know

In 2004, David Letterman invited a group of tourists to share some much-needed advice regarding trips to New York City. Going one by one, the visitors shared lessons like “A cab from JFK to Midtown should run you about $600,” and “If your car is towed, it’s cheaper to buy a brand-new one than to pay the fines” to a great number of laughs.

Top 10 Things You Don’t Want To Hear From The Guy At Starbucks

Sometimes, a Starbucks barista getting your name wrong can seem like the worst thing that could happen in a coffee shop, but a Top 10 list on The Late Show proved that wrong with comments like “Let me make sure that’s not too hot,” and “Some whipped cream for you… and some whipped cream for me.”

Reasons I, Homer Simpson, Am Proud To Be An American

Homer Simpson was on The Late Show with David Letterman more than pretty much any animated character in history. Back in the day, the family patriarch popped in to say why he was proud to be an American with reasons like “Warning signs on cups tell you hot things are hot,” and “Even a dumb guy can have his own show.”

James Earl Jones’ Top 10 Effects Of Y2K

Remember all the insanity surrounding the Y2K bug back in 1999? Well, The Late Show with David Letterman got in on the fun with the help of James Earl Jones, who shared scenarios like “Stuff’s gonna ‘splode,” and “Kraft Macaroni & Cheese will become even cheesier.”

Don Rickles’ Top 10 Insults For Dave Letterman

The legendary Don Rickles died in 2017, leaving behind a legacy that included everything from the Toy Story franchise to movies like Casino. Back in the day, Rickles joined The Late Show with David Letterman to share signature insults like ‘Letterman, let’s face it – you put the ‘suck’ in success,” and “Don’t look now, but something died on your head.”

Things Jim Carrey Will Always Say Yes To

Jim Carrey and Larry King in a tub? That sounds like some kind of nightmare, right? Well, it was a real situation on The Late Show with David Letterman when the Hollywood funnyman was asked to share his Top 10 things he’d always say yes to, including “Tub Time with Larry King,” and “Lucrative endorsement deals: remember, you’re not fully clean unless you’re zestfully clean.”

Reasons It Took Dale Earnhardt 20 Years To Win The Daytona 500

The late, great Dale Earnhardt finally won the Daytona 500 back in 1998, and one of his rewards was appearing on The Late Show with David Letterman. Wearing a leather jacket and his signature mustache, the NASCAR legend gave reasons for taking so long like “This year, whenever I passed somebody, I gave them the finger,” and “Who cares if it took 20 years - at least my name's not Dick Trickle.”

Top 10 Things Mick Jagger Learned After 50 Years In Rock N’ Roll

Legendary rocker Mick Jagger came on The Late Show with David Letterman to share some of the best things he had learned after 50 years in rock n’ roll. Words of wisdom like “Song royalties are great, but even they can’t match the guaranteed cash flow from a reverse mortgage,” and “You can’t always get what you want – like a good joke on the Top 10 list” made it an unforgettable night.

Rodney Dangerfield’s Top 10 Things He Likes To Do

Rodney Dangerfield was one of many legendary comedians to show up on The Late Show with David Letterman over the years. His appearance included a walkthrough of his favorite things to do, which included “Sing the ‘Star Spangled Banner’ at street fights,” and “Tell people who work with fertilizer – ‘Have a nice day!’”

Eminem’s Top 10 Pieces Of Advice For Kids

Eminem probably isn’t the first person you’d want giving advice to your kids, but that’s what made his appearance on The Late Show such a treat. How could you not like words of wisdom like “If I sign something for you, and I see it on eBay, when you go home, I’m gonna be under your bed,” and “Don’t waste your time watching this show”?

Top 10 Signs You’re A Lame Superhero

David Letterman poked fun at some of the lesser superheroes on The Late Show during its run, including the night he provided tell-tale signs like “Your signature catchphrase is ‘Please don’t hurt me,’” and “Can only fight crime until 10 p.m., then mom wants you home.”

Top 10 Things Never Before Said By A Star Wars Character

One night, David Letterman brought out all kinds of Star Wars characters to make statements they never said before. This included some bangers like “I once used the force to open a jar of Vlassic kosher pickles,” and “The only people more powerful than I are Emperor Palpatine and Oprah.”

David Letterman is one of the most recognizable names in late night television, even as the ten-year anniversary of his retirement from CBS' Late Show with David Letterman approaches in the 2025 TV schedule. Retiring from the CBS gig (which then went to Stephen Colbert) didn't mean retiring overall, and he has hosted My Next Guest Needs No Introduction with celebrities like Kim Kardashian (which resulted in big numbers for the show) on Netflix since 2018. Now, with his new project going live, he reflected on criticism of his interview skills from back in the day.

Letterman of course hosted two major network nightly shows over the course of the career that made him into the longest-serving late night host in television, with NBC's Late Night with David Letterman from 1982-1993 and then CBS' Late Show with David Letterman from 1993-2015. Speaking with GQ toward the end of the 2024 TV schedule about his new Letterman TV FAST Channel on Samsung TV Plus, he said this in response to a question about being criticized early in his career for not being the best interviewer:

Letterman went on to say that criticism of his interview skills affected his "presence on television" and he realized that "maybe I need to have a broader lens of this pursuit." Whatever criticism he received, there's no denying the success of his career between NBC and CBS, although it was during his NBC days that he experienced the worst day of his TV career.

Some celebrities who appeared on his various shows have also spoken about less than stellar experiences, with SNL alum Maya Rudolph feeling humiliated when he said her name wrong and Anna Kendrick stating that "everyone is afraid of Letterman." For his part, though, Jay Leno clarified years ago that he was a "huge fan" of Letterman despite their purported feud when Letterman was on CBS and Leno was on NBC.

Considering the length of his network TV career which has since led to his Netflix show, the late night legend weighed in to GQ on whether he feels like he improved over time:

My Next Guest Needs No Introduction, with five seasons available streaming now with a Netflix subscription, certainly enables him to continue just talking to people... with those people being some of the biggest names in pop and world culture, including Barack Obama, Robert Downey Jr., and Miley Cyrus, to name just a few. It remains to be seen if there will be a Season 6, but Letterman went on the record with his opinion that "Retirement is nonsense."

As for his latest project, the Samsung TV Plus streaming service (available for free on Samsung devices) launched Letterman TV, which streams content from the comedian 24/7. The content includes Late Show with David Letterman, curated moments, and commentary from Letterman himself as he looks back on some of his particularly iconic interviews. Check out how he and Paul Schaffer explained the FAST Channel in the video below:

Letterman TV is available now for fans with Samsung devices. According to Walter Kim, the executive producer for Letterman's Worldwide Pants, Inc. production company, there are "more than 4000 hours from which to choose" with continuous changes. If you're not a Samsung fan, you can always check out My Next Guest Needs No Introduction on Netflix. The most recent season includes interviews with Miley Cyrus and Charles Barkley.

One of the things that makes talk shows so popular is the friendly intimacy they create. As viewers, we all want to feel like we're welcoming the show into our own homes. Obviously, the best talk show hosts drive the conversation, but every great host needs a great foil and that's where the sidekicks come in. Here's our list of the best sidekicks on talk shows, and how each was used to make the show better. 

Ed McMahon (The Tonight Show With Johnny Carson)

The granddaddy of all talk show sidekicks has to be Ed McMahon. For 30 years, McMahon was Johnny Carson's right-hand man on The Tonight Show. He served as the announcer, coining the famous "Heeeeeeeeere's Johnny!" intro to the show, and he also sat on the couch next to Carson's desk for the entire show, mingling with the guests and laughing at Carson's jokes. 

Paul Schaffer (The Late Show With David Letterman)

Paul Schaffer wasn't the first bandleader to be incorporated into the banter of a talk show, but he was the first to be the bandleader AND sidekick. Schaffer was first the leader and keyboard player for the "World's Most Dangerous Band" on Late Night With David Letterman on NBC, then served the same role in the CBS Orchestra when Letterman switched networks and started The Late Show With David Letterman. He was also the guy Letterman bounced jokes off nightly and was a true sidekick in all senses of the word. 

Andy Richter (Late Night With Conan O'Brien)

When Conan O'Brien took over for David Letterman on Late Night, he brought with him comedian Andy Richter. Or, more accurately, head writer Robert Smigel brought in Richter. He was an important member of the cast for the show's first seven years before departing. He would later rejoin O'Brien on his short-lived stint as host of The Tonight Show and again on Conan for TBS, from 2010 to 2021 when that show ended. 

Geoff Peterson (The Late Late Show With Craig Ferguson)

By far the most unique sidekick on this list has to be Geoff Peterson. Geoff, you see, isn't a person, he's a robot. A robot that was actually designed by the late Mythbusters host, Grant Imahara. He was the sidekick on The Late Late Show with Craig Ferguson and he was voiced by Josh Robert Thompson.

Guillermo Rodriguez (Jimmy Kimmel Live!)

Guillermo Rodriguez has to be the least likely person to become a talk show sidekick on this list. Rodriguez started as a security guard at the theater where Jimmy Kimmel Live! is filmed and by complete chance ended up as one of the most beloved people on the show as his appearances became more and more frequent and he got more and more comfortable playing bits in skits and commenting on the show's happenings. 

Questlove/The Roots (The Tonight Show With Jimmy Fallon)

Jimmy Fallon doesn't really have a traditional sidekick on The Tonight Show, instead, he has a whole band. Sure, Questlove is the most prominent member of the house band, The Roots, in respect to the show, but the whole band plays its part as the host's sidekicks. 

Fred Armisen (Late Night With Seth Meyers)

Seth Meyers has the ultimate sidekick in Fred Armisen on Late Night With Seth Meyers. Not only is Armisen a comedian and SNL vet along with Meyers, but he's also a great musician and as such, is both a comedic foil for Meyers AND his bandleader. 

Chuy Bravo (Chelsea Lately)

Chuy Bravo had an interesting road to fame. Unconfirmed legend has it that he fell in love with acting when the Steve Martin movie Three Amigos was filmed in his village in Mexico when he was young. While that may or may not be true, it still took Bravo years to get into the industry, but when he did, he made the most of it as the sidekick on Chelsea Lately for the show's entire run. Bravo died in 2019. 

Stephen "tWitch" Boss (The Ellen DeGeneres Show)

Stephen "tWitch" Boss tragically died by suicide in 2022 just a few months after the show that helped make him famous, The Ellen DeGeneres Show, went off the air. He was a beloved part of the series, serving as both DJ and sidekick, as well as the occasional guest host when Ellen DeGeneres was on vacation. 

John Melendez (The Tonight Show With Jay Leno)

One wouldn't think that a guy with the nickname "Stuttering John" would make for a good announcer, but John Melendez proved that wrong as the announcer and sidekick on The Tonight Show With Jay Leno. In addition to traditional announcer duties, Melendez was often a part of skits and other bits on the show alongside host Jay Leno. 

Regis Philbin (The Joey Bishop Show)

It's almost impossible to imagine Regis Philbin as anything other than a host. The television legend set records in his career doing just that, but he started as Joey Bishop's sidekick on The Joey Bishop Show. Throughout the show's brief run (less than three years), Philbin played the role of the young apprentice to the Rat Pack veteran, often as the butt of Bishop's jokes about his young age (though Philbin was in his mid-30s when the show aired). 

Reggie Watts (The Late Late Show With James Corden)

Reggie Watts has the distinction of being the sidekick on not one, but two shows. First, he served as DJ/band leader on Scott Aukerman's mock talk show Comedy Bang! Bang! and left that show to do the same thing on The Late Late Show With James Cordon in 2015, where he remained until the show ended in 2023. 

Max Weinberg (Late Night With Conan O'Brien)

In 1989 Bruce Springsteen broke up his longtime group, The E Street Band, and drummer Max Weinberg was left in the wilderness. After bobbing around for a while looking for a steady gig, he landed a spot as the bandleader for Late Night With Conan O'Brien. At first, he was just that, in charge of the music, as Andy Richter was the real sidekick. When Richter left the show in 2000, Weinberg started filling that role, in addition to playing drums and leading the band.  

Hannibal Buress (The Eric Andre Show)

As sidekick on The Eric Andre Show, Hannibal Buress was unique. He was expressly disdained by the audience (on purpose) and rather than support host Eric Andre, he was often critical of Andre's performance. Like the whole show, it turned the standard talk show fare on its head and it was brilliant. 

Branford Marsalis (The Tonight Show With Jay Leno)

When Branford Marsalis landed the bandleader job on the new Tonight Show With Jay Leno he was already a world-renowned jazz star. The saxophonist served both as bandleader and sidekick, as Leno didn't have a traditional sidekick. It was that second role that Marsalis came to dislike, and it eventually led him to leave the show after just three years. 

Gene Rayburn (Tonight With Steve Allen)

Tonight with host Steve Allen, which aired in the mid-1950s, was the forerunner to NBC's Tonight Show and it set the template for pretty much all talk shows that followed. That template included announcer Gene Rayburn as a sidekick, participating in comedy skits and banter with the host. 

Steve Wilkos (The Jerry Springer Show)

Steve Wilkos is a different kind of sidekick. As head of security in the heyday of The Jerry Springer Show, Wilkos' main job was to break up the endless fights that happened between guests. He was so prominent that his role evolved into one of foil for host Jerry Springer and he eventually parlayed that into his very own talk show. 

Hugh Downs (Tonight With Jack Parr)

Hugh Downs was ubiquitous on television from the 1940s until his retirement in 1999. His first major exposure came as the announcer and sidekick to host Jack Parr on Tonight With Jack Parr, the second iteration of what would become The Tonight Show. Like other announcers in the show's history, Downs served as a comedic foil to the host. 

Steve Higgins (The Tonight Show Starring Jimmy Fallon)

The most recent in the long line of announcers/sidekicks on The Tonight Show is Steve Higgins, who has been in the role since Jimmy Fallon took over as host in 2014. Like the others, he's involved in comedy sketches and banter with the host. He previously served the same role when Jimmy Fallon hosted Late Night. 

Jon Batiste (The Late Show With Stephen Colbert)

Following in the path first taken by Branford Marsalis with The Tonight Show, jazz great Jon Batiste was the bandleader and de-facto sidekick for the first seven years on The Late Show With Stephen Colbert, before leaving for other career opportunities in 2022. 

"Weird Al" Yankovic (Comedy Bang! Bang!)

"Weird Al" Yankovic needs no introduction. For more than 40 years he's been a legend in the music industry, known for his hilarious parodies of hit songs. Less well-known to the general public was his brief stint as the bandleader and sidekick in the final season of Comedy Bang! Bang! where he brought his trademark surrealism to an already completely surreal show. 

Edd Hall (The Tonight Show With Jay Leno)

Like Ed McMahon before him, Edd Hall served as the announcer for The Tonight Show when Jay Leno took over for the retired Johnny Carson. While he didn't sit on the couch like McMahon, he was an important part of the show, often participating in comedic sketches and bantering with Leno during the monologue. 

Skitch Henderson (Tonight With Steve Allen)

The first bandleader in Tonight Show history was Skitch Henderson, who led the band for both the Steve Allen-headed show and later in the first few years of the Carson-led show. He wasn't as involved as a sidekick as his successors, and in what few clips that survive, didn't seem comfortable in that role. He left in 1966 to pursue a more serious career as a conductor. 

Doc Severinsen (The Tonight Show With Johnny Carson)

The Tonight Show has had a lot of bandleaders over the years, but maybe the most beloved is Doc Severinsen. Severinsen was in the band on the show from the very first iteration with Steve Allen in 1953, until Johnny Carson retired in 1992, for the last 25 years of which, he was the leader. He also assumed sidekick duties when Ed McMahon was out, or both McMahon and Carson were off and there was a guest host. 

Tom Scott (The Chevy Chase Show)

Tom Scott is an incredibly accomplished musician, having played on albums by George Harrison, Pink Floyd, The Grateful Dead, and many more. He also has the unique distinction of being a bandleader/sidekick on two infamous talk shows by celebrities that didn't last. First, The Pat Sajak Show, and second, The Chevy Chase Show. 

Louis Cato (The Late Show With Stephen Colbert)

When Jon Batiste left The Late Show With Stephen Colbert in the summer of 2022, they wasted no time installing fellow Stay Human musician Louis Cato as the new band leader. Cato has a more traditional approach to being a bandleader and is less of a comedic sidekick as a musical one, often performing full songs with the band and with guest musicians. 

Arthur Treacher (The Merv Griffin Show)

When Merv Griffin developed The Merv Griffin Show, he chose Arthur Treacher as his sidekick, who played the part very much like Ed McMahon played it on The Tonight Show. Treacher was a show business veteran, but found his highest degree of fame sitting next to Griffin and bantering on the show. 

Kevin Eubanks (The Tonight Show With Jay Leno)

Jay never never had a traditional sidekick during his long run as host of The Tonight Show, instead, he used his bandleaders, like Kevin Eubanks, as his bantering partner. Eubanks took over from Branford Marsalis in 1995 and remained there until leaving the show in 2010, a few years before Leno retired himself.

Craig Shoemaker (The Magic Hour)

For eight magical weeks in the summer of 1998, NBA superstar Magic Johnson hosted The Magic Hour in first-run syndication. For about the first three of those weeks, his sidekick was comedian Craig Shoemaker. Shoemaker was fired after publicly calling the show "The Titanic." Turns out, he was right, and the show was canceled a few weeks later. 

Glenn Humplik (The Tom Green Show)

One of the weirdest talk shows of all time was The Tom Green Show on MTV. Host Tom Green, who was never afraid to earn an R-rating, picked his sidekick because it was his childhood friend Glenn Humplik, whose main job, it seems, was to just take abuse from Green. Sure, it was funny, but wow, it was pretty denigrating, also. 

Jimmy Vivino (Late Night With Conan O'Brien)

While Max Weinberg was the bandleader for Late Night With Conan O'Brien, he was often away later in the show's run, touring with Bruce Springsteen. On such occasions, Jimmy Vivino took over. Eventually, Weinberg left the show and Vivino took over the role Weinberg had played as the bantering partner for O'Brien. 

Norman Baker (The Wendy Williams Show)

The Wendy Williams Show was unlike anything else, mostly because of Williams' unique personality. She was mostly a one-woman show, but occasionally bantered with the show's producer Norman Baker. 

Every great host needs a great partner, so as long as there are talk shows, there will be sidekicks to joke with. 

Maya Rudolph is a brilliant actress and comedian known for a slew of iconic performances in films like Bridesmaids and shows like Netflix’s Big Mouth. Rudolph was a cast member on Saturday Night Live from 2000 to 2007, and followed her impressive tenure with a variety of interesting projects. She has returned to SNL periodically to play Vice President Kamala Harris starting in 2020, and recently revealed her rise to becoming one of the most successful comedic performers working today wasn’t always smooth sailing, specifically mentioning an upsetting appearance on David Letterman’s late night show.

The Loot star opened up to The Wall Street Journal about some of the more difficult situations she ran into during her meteoric rise to prominence. In particular, she detailed an instance when she visited the Late Show with David Letterman, and was made to feel embarrassed during her first-ever talk show appearance. She blames her lack of experience for how she handled the incident, saying:

This is a very awkward situation, and was probably difficult to open up about. As a first time talk show guest, the experience must have been overwhelming. In addition, Rudolph clearly admired Letterman quite a bit, so such an experience meeting him for the first time may have thrown her off. Having a public persona to showcase on a talk show is a lot to ask for a novice. The SNL alum probably would have handled the situation much differently now, as she has plenty of experience.

Since her awkward Letterman appearance, the Wine Country star has shined on talk shows, and seemingly has reflected back on the experience artistically. In her show, Loot, her character appears on the popular (real) spicy-wing talk show Hot Ones, where celebrities answer serious questions while eating impossibly spicy chicken wings. Her character, Molly, has a complete meltdown. The scene is hilarious, and may act as an homage to past talk show appearances gone wrong. 

Rudolph doesn’t have to “try to be funny” as she puts it. At least from the outside, she comes off as naturally hilarious, especially on Loot, which is currently streaming for Apple TV+ subscribers. She plays the ex-wife of a billionaire who is trying to create her own legacy post-divorce. In addition, Rudolph will be starring alongside Amy Adams in Disenchanted, a sequel to 2007’s Enchanted. The film will be available with a Disney+ subscription on November 18.

You can currently catch Maya Rudolph on Loot, or hosting a baking reality show, Baking It, which is streaming for Peacock subscribers. Amy Poehler is joining her for the upcoming season, so it should be a lot of fun, especially ahead of the holiday season. For more information on other shows coming to streaming, make sure to consult our 2022 fall TV premiere dates.  

It has been four years since David Letterman decided to retire from his late night position over at CBS, and it has been three years since the man ended his reign as the host of the Late Show with David Letterman. At the end of that reign, Letterman had hosted 6,028 episodes of the long-running show, a record that even beat that of his mentor Johnny Carson. In fact, he was on the late night airwaves for longer than any other late night host. Now, however, Letterman has revealed that he feels like he should have retired way earlier than he eventually did. During a recent Emmys event, Letterman said:

If David Letterman had retired in 2005 and not 2015, he wouldn't have hit that record number of episodes, although it's seemingly something he doesn't particularly care about. From what Letterman was saying in his conversation with Jerry Seinfeld (via Vanity Fair), he feels he would have been far better off if he had cut out of the game a bit earlier and focused on doing something else with his "energy and focus."

David Letterman had a lot of memorable moments on the Late Show with David Letterman over on CBS as well as his earlier late night series Late Night with David Letterman on NBC. Many of those happened earlier in his career, however, and the Late Show was never the winningest in late night viewers, although Letterman's legacy is still long-lasting and his final episode did quite well in the ratings.

These days, David Letterman has stepped back from the spotlight quite a bit, but he's still doing more than a little bit of talking. His Netflix show, My Guest Needs No Introduction with David Letterman, has already had an auspicious start, kicking off with an interview with former President Barack Obama back in January. So far, Letterman has also spoken with a variety of big names, including George Clooney I am Malala's Malala Yousafzai, Jay-Z and Tina Fey. He's set to speak with longtime radio host Howard Stern later this month.

Oh yeah, and he's grown out a mean beard, a beard he previously said everyone hates. Plus, he's done other small events, events like the Emmys chat or co-hosting The Essentials with Alec Baldwin for TCM. There are certainly worst things you can do with retirement than have a little fun, and that's what David Letterman seems to be doing these days... even if he feels he could have retired sooner. Perhaps he would have had more energy to do more elsewhere, but there's nothing wrong with leaving behind a late night legacy of Top 10 lists and stupid pet tricks.

After a brief glimpse into the post-retirement life of David Letterman, I'm convinced of two things. First, that dude really knows how to grow a beard that will put Santa Claus to shame. Second, Letterman knows comedy. In an interview that ranged everywhere from retirement to politics, Letterman revealed who he thought were the funniest comedians out there, and it just so happens one is a politician. According to Letterman, the funniest comedians out there are Al Franken, Norm Macdonald, and Jim Downey.

The selection of names, judging from the interview, appear to be at least somewhat politically based. Al Franken, of course, represents the Democratic party as a Senator in Minnesota, and Letterman mentioned in his interview to Vulture that the two had spoken about Texas senator Ted Cruz prior to the election. As for Jim Downey, one of his biggest claims to fame as an SNL writer was coming up with the "strategery" bit made iconic by Will Ferrell during the presidency of George W. Bush. Downey would also write for David Letterman for two years in the 80s as well, so they have a personal connection. The only real exception to this is Norm Macdonald, who is self-described "apolitical," so how does he fit into all this?

While politics may not play into David Letterman's love of Norm MacDonald, mutual respect does. It's no secret that Letterman has had a love for the comedian, and often had him on the show because he could legitimately make him laugh, which I'm sure Norm appreciated. In fact, Norm has credited Letterman to his love of stand-up. In his final appearance on Letterman, MacDonald recalled a joke he first heard Letterman tell when he was 13 and how it inspired his current career path. Check out the clip and a choked up Norm around 6:40 in the video below:

These three also share another connection, which could be random, but a connection nonetheless. All three of the men mentioned have, at one point, worked on Saturday Night Live. Al Franken was on the show for 15 years spaced between two stints in the 70s to the late 80s and mid 90s. Norm Macdonald was on the show for five years and shared one of his years alongside Al Franken's second run on the sketch series. Jim Downey wrote for the series when both Franken and Macdonald were a part of it and beyond. It would appear that David Letterman may love humor that gears itself to SNL, or at least loves the comedians and writers on it. I wonder what he thinks of the current series?

It's clear David Letterman a unique guy. I think you could ask 1,000 people their top three favorite comedians and no one would replicate this list. That's what made Letterman a household name for 33 years of television, and possibly how his beard is so damn terrific. David Letterman is out of the TV business, but that doesn't mean you have to stop watching! Jump on over to our midseason premiere guide and find something to fill the void his presence left behind.

When most people leave a job, they don’t get to do it with even a small percentage of the class and style that David Letterman exuded when he hosted his last Late Show before retiring from the biz. From this night of touching flashbacks and hilarious moments, something that might surprise you is the fact that two of the funniest jokes were actually written by a 21-year-old intern on the show.

Staff writer Bill Scheft recently documented his time working on the final episode through a ridiculously interesting Tumblr post, in which he went through the entire day, detailing each aspect. When talking about the stellar Top Ten list – Top Ten Things I’ve Always Wanted to Say to David Letterman – he had this to say.

It’s worth noting that Scheft updated the story to say that her full name is Caroline Schaper. And while Louis-Dreyfus’ gag was indeed hilarious, it was aimed more at Jerry Seinfeld than at Letterman, so Schaper’s line for Tina Fey was all the more effective because of that.

Scheft goes on about Schaper’s contributions.

That is indeed one hell of a career highlight for someone branching into the business. I can’t imagine ever writing anything that Bill Murray would read aloud on TV, unless I get creatively obsessive with some fan mail. Check out the full Top Ten below.

Scheft also talks about that epic montage that closed out the show, and how its compiler Barbara Gaines leaped on the stage and hugged Foo Fighters’ Dave Grohl after their first rehearsal performance. The whole thing just makes me miss Letterman even more.

David Letterman’s retirement from late night has been a big deal thanks to the longevity of the man’s career and the impact he had on the late night landscape over the years. With that in mind, it’s no real shock that The Late Show with David Letterman nabbed plenty of eyeballs last night. However, I’m not sure anyone expected the finale to average 13.76 million total viewers--a huge number, in case you aren't familiar with what Letterman's show normally averages in the ratings.

Honestly, 13.76 million viewers is a huge number for any TV series, but especially for late night television. In fact, The Wrap says that the last time CBS’ The Late Show saw ratings that were quite this high was way back on February 25, 1994, when the late night series aired an episode right after CBS’ scheduling of the Winter Olympics. Letterman's finale also did well in the 18-49 demographic, nabbing a 3.1 rating.

There’s no doubt Letterman’s last episode was special. It was peppered with old and recent footage of the late night host and featured a whole slew of the show’s favorites coming back for one last bit or gag. The Top 10 was phenomenal; of course, the moment we’ll all be talking about during the weeks to come is the final montage from the episode, which featured longtime Late Show favorite The Foo Fighters performing the band’s classic hit “Everlong” while footage from the show rolled. It was a memorable finale to a memorable career, and no doubt after Live+ ratings roll in, we’ll learn that even more eyeballs tuned in.

Although the ratings should have been a nice moment for Letterman, it’s interesting that the final episode brought in 13.76 million, which is just a little less than the 14.6 million total viewers who tuned in for Jay Leno’s final episode of The Tonight Show just over a year ago. Interestingly, however, Leno’s last bow benefitted from airing right after the Winter Olympics on NBC, which likely helped to raise the profile of his last show considerably. Still, there’s something poetic about Letterman’s final episode landing just a teensy bit behind Leno’s in terms of overall viewership, considering that Letterman was a critical favorite but often fell behind Leno in the ratings. It’s fitting that his end followed suit.

It was already weird to live in a world where Leno and Letterman weren’t competing for eyeballs, but now, after more than 6,000 shows on the air, it’s going to be even odder without Letterman around at all. Luckily, CBS is already moving forward with plans for a new late night host. If you somehow missed the memo, Stephen Colbert is set to take the timeslot when The Late Show returns to the schedule next fall. Colbert’s new show is expected to premiere on Tuesday, September 8, 2015. In the meantime, here’s what CBS has going on this summer.

Last night gave us one of the most monumental 90 minutes (or so) of television ever, as the late night legend David Letterman took the stage as the Late Show host for the very last time. And yes, all the emotions were had. But just because he didn’t have any official guests (beyond Foo Fighters’ performance over that amazing montage) doesn’t mean that the show lacked celebrities. Check out the final star-studded Top Ten list below.

Even though it wasn’t Letterman doing the delivery, this was still one of the best Top Ten’s in the show’s history, because he was having a blast. Judging by his laughter at times, it seemed like he wasn’t even aware of what the list entries were ahead of time. It’s depressing that we’ll never get to see Letterman’s surprised laughter anymore. But this is a yet another great clip, among many thousands of others, to remember him by. (I know he’s not dead.)

For the “Top Ten Things I’ve Always Wanted to Say to Dave,” celebs and Late Show frequenters like Alec Baldwin, Steve Martin and Tina Fey came out, with Chris Rock predictably poking fun at the Late Show producers for hiring another white guy as Letterman’s replacement. One of the highlights included a burly-bearded Jim Carrey coming out in a T-shirt and reverting back to his old rubber-face routine.

From an attire standpoint, he looks so strange standing next to Jerry Seinfeld, whom Letterman picked at for being all decked out in a tuxedo. And it was Seinfeld’s former co-star and Veep lead Julia Louis-Dreyfus who delivered the best shot of the night.

Everybody loves a good rip on the Seinfeld finale, right? Seinfeld and everyone else on stage seemed to. And even though Bill Murray’s item, the last Top Ten entry ever, wasn’t overly hilarious, it was still great to see the iconic comedy star return to the show for a second night in a row, after bursting from a cake in the previous episode. I assume he slept under Letterman’s desk that night.

The final Late Show, which Conan O’Brien was actively telling his own audience to change the channel to watch, was not only awesome, but it was also a solid ratings hit. According to Zap2It, it brought in the highest local ratings since the 2005 episode where Oprah Winfrey and Letterman squashed their beef, and it outrated every primetime broadcast for the night. That’s outstanding.

Thanks, Dave. We’ll always be here if you want to come back at some point, with far more than ten reasons guiding us.

When most celebrities say goodbye to the soon-to-retire David Letterman, they do it with words – even if those words are written on undergarments. But when Bill Murray does it, no words are needed. Just massive cakes. Check out the video below.

Oh, to hold the distinction of being someone that Bill Murray popped out of a cake for. Sure, there are tons of other arguably more prestigious events in Letterman’s life that I’m jealous of, but this one takes the cake was really special. Because it wasn’t just a cheap pre-made birthday cake from a grocery store that Murray had to awkwardly crouch down in because it was technically too small to fit his entire body. This was a specially crafted baking success that was capable of housing one of the greatest comic minds of the modern era. I presume he wasn’t in there when the cake was baking, but then I’ve never had anyone pop out of a cake for me, so I can’t be sure.

From the very first second that he’s seen, this is pure Bill Murray goodness, as he kicks things off by not really popping, but falling out of the cake and sliding onto the floor. And while most guests would have been too reverent to get messy with the late night legend, Murray was there for Letterman’s first Late Night outing, so he basically gets to do whatever he wants. And what he wanted was to muss up Letterman’s hair with cake-filled hands.

Still sopping with sugary sweetness, Murray later expressed his wishes that Letterman would stick around, getting the studio audience to join him in a chant. But then he took things a step further and kicked open the studio doors to the outside world, gathering a crowd of hyped-up, selfie-taking people in the middle of the street for another chant.

The show ended with a dessert-free Bob Dylan’s first Late Show performance since Season 1 of the show, and he and Murray served as Letterman’s final official guests, as the icon’s last show tonight will be full of surprises. I can’t imagine anything quite topping Murray’s confectionary arrival, but anything could happen.

Speaking of anything, Murray also showed off his flopping skills when he recently popped by MSNBC’s Last Word and fell off of a chair, as seen below.

Thankfully, there will still be more Bill Murray in the world even after Letterman has left The Late Show. But we’re always going to miss seeing them together.

Well, we’re just two episodes away from bidding farewell to David Letterman forever – at least as the Late Show host, as he’s not dying or being exiled or anything – and to contrast all of the celebrity tributes that have peppered the past handful of episodes, Letterman decided to let the Late Show crew in on the fun by giving them their own Top Ten list: Top Ten Things I’ll Miss About Working at The Late Show. Check it out!

It just wouldn’t be a Top Ten list if things were completely sincere and honored the show in a straightforward way. And so they brought out the jokes, with such esteemed vets as executive producer Barbara Gaines, writer Steve Young, costume designer Sue Hum and many more. The most recognizable one, of course, is CBS Orchestra leader and Late Show musical director Paul Schaffer, who was with Letterman for his entire late night career. I expect Schaffer to have some kind of a spoof reality show following Letterman’s retirement, where he tries to find other jobs.

As for the list, I love the Twitter joke-stealing item, the doubled-up high heel gag, and of course the inseam joke. All in all, these could have hit harder, but really, how do you get better than the alibi-needing Alan Kalter and the headphone-wearing Biff Henderson?

Letterman may only have one Top Ten list left in him, as the entire final episode is up in the air, with no guests or any other announcements coming out for it. So it presumably won’t be a normal episode, with a monologue and amusing segments, but will hopefully still be a great time. His last guests for the penultimate episode will be Bill Murray, who was his very first guest back in 1993, and musical guest Bob Dylan, who also appeared on the show back in its first season.

It’s hard to imagine that either of those two guys will bring the kind of emotion that comedian and Late Show regular Norm Macdonald brought to the stage on Friday night, when he delivered an amusing set followed by a tear-filled shout out to Letterman’s career. Check it out below.

If only Letterman would clue audiences in on who his top ten guests were. Although I guess these past couple of weeks were evidence enough. I don’t want to say goodbye!

The past couple of weeks have been pretty amazing for fans of The Late Show with David Letterman, as his impending retirement has offered all of his final guests the chance to pay tribute to the late night stalwart in ways that are both touching – such as Ray Romano’s photo session – and hilarious – such as Adam Sandler’s goodbye song. And now we know for sure what celebrities will be appearing on Letterman’s final episodes, and it includes the man who served as Letterman’s very first guest: Bill Murray.

But before that…

Tonight, Oprah Winfrey will make her third in-person guest appearance on Late Show, following spots in 2005 and 2013. (She also took part in a phone call for an episode in 2014.) Winfrey was also on Letterman’s previous NBC show Late Night. The second guest for this episode will be Saturday Night Live vet Norm MacDonald, who will make his twelfth appearance on Late Show, having last been seen in March. I can’t wait to see how these two choose to honor the host.

On Monday, May 18, Tom Hanks will stop by Late Show with David Letterman for a whopping 27th guest appearance, to go with his four spots on Late Night. These guys should have teamed up for a talk show years ago. The musical guest that night will be Pearl Jam frontman Eddie Vedder, who has performed on the show five times previously. Fingers crossed he plays a version of “Better Man” that takes shots at Jay Leno.

For the penultimate episode on Tuesday, Bill Murray will indeed return to Late Show for the 22nd time, bringing the show full circle, as he was the first guest when Letterman made his CBS debut back in 1993. He was also on Late Night nearly a dozen times, making him one of Letterman’s most frequent guests. And making a rare appearance on the late-night scene will be the legendary Bob Dylan for his second Late Show performance. He was also a part of Letterman’s first Late Show season.

Oddly, no guests have been announced for Letterman’s final episode on Wednesday, May 20. Should we expect to see the revered host taking an hour to personally reflect on his 33-year late night career, the same way Johnny Carson did when he left The Tonight Show? Or should we expect a smorgasbord of people stopping by to surprise Letterman during his farewell?

Don’t expect to see a new episode of Jimmy Kimmel Live! that night, as the host has already stated he would be airing a repeat to honor Letterman’s last show. Fellow late night host Conan O’Brien said on Charlie Rose that he doesn’t expect anyone to watch Conan that night, so he might just show up naked. Will you guys be watching the final Late Show with David Letterman?

Leave it to Tina Fey to give David Letterman the best send-off gift ever. The comedian stripped down to her spanx to honor her wearing her last dress for the retiring talk show host. Take a look.

In the video of her recent trip to the Late Show with David Letterman, comedian Tina Fey gave David Letterman the best parting gift, since her appearance on the show will likely be her last. Fey actually stripped down to her skivvies, which were appropriately labeled “Last Dress Ever,” right in front of Letterman and the entire viewing audience. After that stunt, the comedian just might get offers with more revealing roles. Tina Fey looks great, even in spanx.

It all started when the Late Show host brought up the fact that Fey looked lovely in her blue dress. Though Fey appreciated the audience applause, she quickly pivoted the conversation to bring up the point that it was likely the last time that she would wear a dress. She even mentioned that it was highly unlikely that Letterman’s competition would ever get her to dress up like that. It was her final chance to put on a nice dress, and it was all out of respect for the retiring Late Show host. Even Letterman didn’t see what was to come next. I don’t think anyone did.

With a little help from Letterman, of course, Tina Fey took off her dress and revealed her message-worthy undergarments. Fey confessed that getting dressed up like that was a lot of work and now, I think we all believe her; by the look of relief on her face, and the fact that she shouted “never again,” it’s pretty clear how serious she was. And of course no strip down is complete without some slick moves, and Fey didn’t disappoint. In between uncomfortably pulling at her spanx, she was sure to show off the words written across the front and back of her black leotard by bending over and squatting for the camera.

The audience may have enjoyed it, but I think Letterman was particularly honored that Fey would go to such lengths for his benefit. Who wouldn’t? After all, it won’t be long before Letterman retires from his post as host of the Late Show and Stephen Colbert officially steps in. The Late Show with Stephen Colbert is scheduled to premiere on September 8, 2015.

As David Letterman’s retirement is drawing near, his fellow late night hosts are figuring out ways to honor the key CBS player. NBC’s Jimmy Fallon has already borrowed Letterman’s “Top 10” list for a nice tribute, and now ABC’s Jimmy Kimmel has decided exactly what he would like to do during Letterman’s May 20 finale. Namely, he won’t be doing much of anything, at all.

While May 20 actually falls on a Wednesday, which is right in the middle of Jimmy Kimmel’s work week, the Jimmy Kimmel Live! host says he will be taking the day off. Instead, that evening ABC will air a repeat of an old episode in order to pay tribute to David Letterman and to hopefully get a few more eyeballs geared toward his stage (Plus, honestly, it's probably a nice change up to get a random Wednesday off). Kimmel recently explained to The New York Times that the move is out of deference to his predecessor.

Kimmel’s never been shy about how much Letterman has influenced his own career, and it’s not a huge surprise that the late night host would sacrifice ratings for a respectful gesture. Kimmel is, in fact, the only direct Letterman rival who will be taking the evening off on May 20. Fallon, but also Conan O’Brien, both plan to air a new episode that night, but I can’t imagine the whole evening will go by without either of them at least mentioning that it’s David Letterman’s final evening onstage.

Letterman’s been a part of the late night landscape for years, having hosted Late Night with David Letterman over at NBC for sometime before picking up the gig as The Late Show host on CBS, a position he has held for the last 22 years. When he retires later this month, CBS will have a few months to get replacement host Stephen Colbert ready for the big time; the former Comedy Central Colbert Report host will sit down at his brand new desk on Tuesday, September 8. We'll have to wait and see how he stacks up against the two Jimmys.

CBS has put together a pretty incredible list of stars who have or are expected to pop up on The Late Show with David Letterman before he takes his final bow. Just a few days ago, CBS also aired a special hosted by Ray Ramono that looked at Letterman’s prolific career. Letterman's been so prominent in the news lately, it leaves little doubt that an era is ending. We're just happy to be here for his last hurrah.

In less than a month, television will lose one of its most longstanding personalities when David Letterman steps down from his duties as The Late Show host, retiring with as much grace as one could hope for after this long of a career. Fittingly, CBS will be sending him off in the proper style with a 90-minute primetime retrospective called David Letterman: A Life in Television.

Set to air on Monday, May 4, David Letterman: A Life on Television will cover Letterman’s entire small screen career, starting when he was a weatherman for an Indianapolis news program. Viewers can probably expect to see his guest spots on The Tonight Show, which led to him hosting Late Night with David Letterman after a brief stint on a morning show. Video clips from his 30+ year career will be shown, including those with big celebrities and musical acts, as well as some focusing on his most well-known segments like the Top Ten List and his Stupid Pet/Human Tricks. As well, some of his more somber and poignant clips will be showcased, particularly his first show back after the 9/11 attacks in 2001.

The special will see comedian and TV star Ray Romano taking on hosting duties, which makes a lot of sense, as Romano’s hit series Everybody Loves Raymond came to be after his successful stand-up appearance on Late Show in 1995. Letterman’s company Worldwide Pants even produced the show.

Letterman will have hosted 6,028 late night broadcasts by the time he retires next month, and was the recipient of 16 Emmy Awards, a Peabody Award and a Kennedy Center Honor, among many other accolades. His final show will be on Wednesday, May 20, and he’s got a slew of impressive guests lined up for the following weeks, including Julia Roberts, George Clooney, Will Ferrell, Robert Downey Jr., Steve Martin, Oprah Winfrey, Paul Rudd and many more. Romano will be one of them, as will Bill Murray, who was one of Letterman’s first guests for his debut on NBC’s Late Night in 1982.

Reports recently surfaced that Letterman put out an offer to former late night competitor Jay Leno to appear on one of his final episodes, seemingly burying the hatchet that inspired the acclaimed exposé book The Late Shift in 1994. Leno has yet to respond. Letterman also reportedly offered a spot to Brian Williams, who canceled an appearance in February following the controversy over his past as a war reporter. No word on that one yet, either.

Again, David Letterman: A Life on Television will air on CBS on Monday, May 4, at 9:30 p.m. ET. I wonder if Stephen Colbert will be making an appearance, since he’s the guy taking over Late Show later this year.

Over time, late night hosts develop relationships with certain guests who then pop up numerous times over the years. David Letterman has been in the game longer than most, and it makes sense that his laundry list of people he would want to interview on The Late Show before he retires would be longer than others. In fact, Letterman has special guests planned for his final 28 broadcasts on the air, a set of episodes which will commence tonight on CBS. His list includes comedians, actors, musicians and even zookeeper Jack Hanna. Oh, and Oprah, just because that's a have-to situation. You can check out the list of big names, below.

The full list isn't available yet, which makes a lot of sense, considering we are still six weeks out from Letterman’s actual retirement. However, the list of people who are already confirmed to appear sometime over the next six weeks is pretty incredible. The big countdown will commence with a slew of big names who will pop up this week. Tonight, Sarah Jessica Parker is the big guest on The Late Show with David Letterman. Tomorrow, Billy Crystal will pop up, doubtless to promote his new FX series The Comedians. Wednesday, Michael J. Fox will appear. Thursday, Kevin James is the a-list guest on the show, and on Friday, Alec Baldwin will pop up for a chat with Letterman.

It’s also not surprising to see some of the other names on the list. Bill Murray has always been a favorite guest of Letterman’s. Tom Waits had a memorable interview with Letterman following the release of Swordfishtrombones back in the 1980s. While a few people on this list have big upcoming projects to promote (like Kevin James, who has Paul Blart 2 coming up), during his final weeks on the air, Letterman seems to be surrounding himself with the people he’s most enjoyed interviewing.

After 33 years, Letterman will be retiring from late night. The Late Show with David Letterman will finish out its run on Wednesday, May 20, 2015. In Letterman’s place, former The Colbert Report host Stephen Colbert is expected to take over the timeslot later in 2015. In the meantime, don't forget to tune in to check out Letterman's last hurrah on the late night stage.

If you introduce Will Smith to the tune of his own music, there's a chance he'll grab a microphone and put on what appears to be an impromptu performance. Case in point, the rapper/actor visited Late Show with David Letterman and before he sat down to be interviewed, he rapped for the audience...

Will Smith appeared on Late Show with David Letterman this week in anticipation of the release of his latest movie Focus. As you can see, Paul Schaffer and the CBS Orchestra played Smith onto the stage with an instrumental performance of his hit 1998 song "Gettin' Jiggy wit It." Not content to merely acknowledge the song, Smith happily grabbed a microphone and performed part of it for the crowd before taking the couch for his interview.

Not only does he obviously still remember the words to the Big Willie Style song, but it's evident Will Smith is still very comfortable taking the stage and performing. This wouldn't be the first time in recent years that Smith has performed one of his classic songs on a talk show. A few years back, he performed the theme song to The Fresh Prince of Bel-Air on The Graham Norton Show. Check it out...

It's been about a decade since he released an album. That was Lost and Found, back in 2005. The Fresh Prince of Bel-Air star has been much more active on the big screen than he has with music in recent years, with starring roles in I Am Legend, Men In Black 3 and After Earth among his recent credits.

It's been fairly hit or miss for the actor on the big screen, with After Earth coming in as a big miss both critically and at the box office. Winter's Tale was also a miss. So those of us who want to see him in a hit are hopeful that Focus will deliver. The film, which hits theaters February 27, has Smith playing a con artist who's teaching a novice (Margot Robbie) the tricks of the trade.

Beyond that, we have Suicide Squad lined up for 2016, in which Will Smith will play Deadshot. So there's that bit of potential awesomeness to look forward to.

On a more personal note, as a fan of Smith going back to his Fresh Prince days, I love the random bit of rapping on Late Show for the flashback it gives us to the days when Smith was everywhere, both as a rapper and an actor. His enthusiasm and sense of humor are two of the things that make him stand out as a celebrity as well as an entertainer. And that's a big reason I will probably forever be optimistic that his next movie -- whatever it happens to be at the time -- will be a hit. Here's hoping that's the case with his upcoming projects... and that we see him grab the mic more often when he does TV appearances.

Brian Williams opted to cancel an appearance on CBS' The Late Show shortly after stepping down from NBC Nightly News for an undetermined period of time. Both incidents stem from allegations that a story the news anchor has been telling for years is false. Public opinion surrounding the controversy has been loud, and canceling his appearance on David Letterman’s late night show is reportedly part of Brian Williams’ “recovery strategy.”

Williams was initially scheduled to appear on The Late Show with David Letterman on Thursday, February 12. Politico reports that Williams decided not to commit to The Late Show appearance after he took some time off of NBC Nightly News. While the anchor is expected to return to the anchor desk, his future is currently up in the air, and the man doesn’t even know when he will return to primetime at this point. If I were him, I wouldn’t want to answer questions thrown at me by the sharp-as-a-tack David Letterman, either.

If you haven’t been keeping up with the Brian Williams scandal, here’s what has been going on. Basically, in 2003 Williams was sent to Iraq where he briefly acted as a war correspondent. When he returned, he told several variations of a story about being hit with ground fire while in a helicopter in Iraq. Williams actually recounted the story when he appeared on Letterman in 2013.

In the video, Williams blatantly talks about being in a helicopter and getting hit by ground fire, including RPGs and AK-47s.

However, recent evidence has suggested that Williams may not have been hit by ground fire, and was certainly not part of the helicopter crew that was hit with a rocket-propelled grenade. Further reports indicated Williams may have only heard about the attack via radio. After those reports surfaced, Williams apologized, noting he was in a “following aircraft” when the incident actually occurred. He then decided to take some time off of NBC Nightly News.

While Williams has appeared on David Letterman’s The Late Show many times in the past, the timing is extremely poor this time around. Letterman would no doubt ask about the controversy that is currently still in motion, and it would probably be better to stay out of the public eye rather than contribute to the fire at this point, especially while NBC mulls over whether or not to keep the journalist in his current role. We’ll update you as more news breaks.

David Letterman gave audiences a ton of advance notice regarding his retirement when he let us know last spring that the end was drawing near. As a direct result, his retirement has subsequently felt like an event that would happen sometime down the road rather than an event that is imminent. But imminent it is. On Wednesday, CBS announced that The Late Show with David Letterman will officially be ending on Wednesday, May 20, 2015.

The move isn’t exactly shocking. When Letterman stated he would retire in 2015, most people assumed he would finish out the TV season, which usually wraps up in May. Still, putting a date stamp on the end of Letterman’s storied career as a late night host is a pretty emotional event. The man has been a part of the television landscape for more than 32 years and has hosted The Late Show on CBS for the past 22 of those years. He’s racked up plenty of Emmy nominations and wins during his career and will be remembered for numerous iconic late night moments, including his post 9/11 monologue, his recent Robin Williams tribute and his epic interview with Paris Hilton.

When he retires, he will have hosted more than 6,000 late night TV episodes—that’s a longer run than Johnny Carson even had.

Whether you are a fan of David Letterman or not, the man has made a lasting impression on the late night landscape and his loss will be momentous. Luckily, CBS already has plans in moment to build a new late night landscape. Comedy Central’s Stephen Colbert has already been signed on as Letterman’s replacement. Colbert’s political talk show, The Colbert Report, will be ending in 2014, giving him time to figure out the tone and pace of his own version of The Late Show. (The Late Show with Stephen Colbert has yet to announce a premiere date, but it's likely to hit the schedule next fall.)

Letterman’s retirement isn’t the only big late night shakeup at CBS. The Late Late Show with Craig Ferguson is also ending this month, and comedian, writer and actor James Corden is set to take over that timeslot in March. In the interim, CBS has signed on a bevy of big names to guest host the series until Corden is ready to take over.

Fans of CBS’ late night lineup still have a few days to spend with Craig Ferguson and a few months to spend with David Letterman before he takes his last bow, but it’s clear an era is ending at the network. Expect the late night landscape to be very different over at CBS next fall.

Meryl Streep is widely regarded as the best actress of her generation. In fact anyone who wants to argue with her credentials will have to debate with three Academy Awards that have her name etched on the bottom. But we have Emily Blunt to thank for the fact that Meryl Streep is still around to show off her talents, because she saved her Into The Woods co-star’s life.

Emily Blunt relived Meryl Streep’s brush with death, which occurred while the pair shot Into The Woods, during her appearance on The Late Show With David Letterman. I’ll leave it to the effortlessly witty and charming gal to tell her heroic tale.

Cue rapturous applause from The Late Show’s audience, who were overjoyed to hear that Emily Blunt, despite the fact that she was pregnant with her first child, Hazel, at the time, had leapt into action. It’s clear why Tom Cruise sought her action attributes for Edge Of Tomorrow now. Emily Blunt did confirm that she might have slightly embellished her version of events. She admitted that Meryl Streep might have only received a mild concussion rather than permanent death if her head had collided with the floor. But it would be harsh to deny the actress her moment of glory. Especially since in their two films together, The Devil Wears Prada and Into The Woods, Meryl Streep’s characters have treated Emily Blunt terribly.

Emily Blunt even admitted that The Deer Hunter actress now owes her big. In fact she has even worked out what she can do to repay her. She wants Meryl Streep to play the lowly dressmaker to Emily Blunt’s Queen Of Versailles. Unfortunately when Emily Blunt proposed this potential movie to Meryl Streep she simply responded, "Dream on." You would have thought that Meryl Streep might have been a bit more responsive when you consider what Emily Blunt did for her.

During her interview with David Letterman, Emily Blunt once again reminded the world why men and women of all ages have become so smitten with her. Not only did she describe Meryl Streep as being so "amazing it is annoying" but she also confessed that despite her near fatal fall, Blunt believes Streep isn’t "supposed to die". What. A. Woman.

Letterman’s retiring at the end of the TV season, but the last few months on The Late Show are proving to be a little more tumultuous than most people might expect. This weekend, CBS announced that it had let go Tony Mendez, the outspoken Late Show staff member who was responsible for Letterman’s cue cards and who occasionally appeared on The Late Show with David Letterman. Mendez was fired after getting into a physical argument with staff writer Bill Scheft.

Here’s how the whole thing went down. According to Mendez himself, he had a bad day in the office earlier this month, getting hot and bothered when Scheft kept interrupting him during his regular duties. He even traded barbs with Letterman, who told him to cool off. But he didn’t cool off. Instead, he became even more agitated about the incident and shoved Scheft into the wall the following day to give him a piece of his mind. Here’s what Mendez had to say to the NY Post.

Mendez may say he shouldn’t have pushed the guy, but there’s clearly little love lost between him and Scheft. It seems like the problems on the set have been ongoing for quite some time. Drama behind the scenes rarely crops up in the form of large one-off incidents. Usually there are a few personalities in any given workplace that don’t mesh, and it’s up to the workers themselves to deal with each other and keep things running smoothly, which obviously wasn’t happening this month.

Right after the incident, Mendez was made to leave the building and shortly thereafter Late Show executive producer Rob Burnett announced the longtime employee was fired. CBS’ response to Mendez’s outburst is very in keeping with network standards related to physical incidents of that nature. Mendez is 69 and may be from a different generation, but there’s just no room to shove your co-worker in the entertainment profession, unless you’ve signed a WWE or MMA contract.

Letterman’s show is not going to be on the air for much longer. The veteran late night host announced his retirement some time and ago, and he’s expected to give up the reins in 2015. CBS has wasted no time in finding a replacement either, with Stephen Colbert taking over for Letterman once he officially calls it quits. Now, the employees on The Late Show with David Letterman just need to get through the next few months unscathed so they can move on to their next big adventure.

Once upon a time, Dave Chappelle had an increasingly popular Comedy Central TV show and a bright future at the network. And then in 2005, partway through production of the third season of Chappelle's Show, the comedian up and left, heading off to South Africa and walking away from a very big deal with Comedy Central in the process. This week on Late Show with David Letterman, Chappelle opened up a bit about his abrupt departure from Chappelle's Show.

"Here it is," he said, when Letterman addressed the topic of his Comedy Central series. "Technically, I never quit. I'm seven years late for work." He's joking there, obviously, but he does get a bit more serious when he admits he made a "series of decisions" when he walked away from the deal and massive amount of money he was being offered by Comedy Central to continue to the show.

"Money is the fuel for choices," Chappelle said to Letterman. "Money gives me choices. So that's not nothing. It's something. I could choose where I want my kids to go to school. I can choose where I want to eat in a given day. But it's not the end all be all. There are other things in life that I cannot purchase with money that are very valuable."

With the above said, Chappelle says -- possibly jokingly -- that he might be a happier person if he'd gone for the money.

Looking back to 2005 when Dave Chappelle seemingly disappeared at the height of the comedian's popularity, fans may recall feeling confused and even disappointed over the whole situation. As a fan of the show, it was frustrating, not knowing what was going on at first or why he just up and left soon after signing a reported $50 million deal with Comedy Central. Of course, there was also concern about Chappelle's wellbeing, given the abruptness of his exit from the spotlight. Chappelle's recent interview with Letterman doesn't fill us in on much as to what caused him to abandon his career right when it was blowing up. But it does point to a very simple truth; money is a lot, but it isn't everything.

Of course, those of us who aren't being offered millions of dollars to do a job we're really good would question Chappelle's decision to walk away from such a deal and deflate all of the momentum his career was generating in the process. But who knows what he was really going through when he made those decisions? Maybe it was just too much for him. Maybe the reality of his life and work at that point in his career just wasn't what he wanted. He certainly wouldn't be the first performer to be negatively affected by fame and success. Some choose to walk away, others don't.

In Chappelle's case, walking away from it all might have been the best possible thing he could have done for himself and his family if he wasn't happy or felt out of control, or whatever his personal reasons actually were. We can really only speculate. And from the sound of it, Chappelle can only speculate too. He made a choice -- or a series of choices -- and all he can do now is know the outcome of the ones he made, not the ones he didn't.

"I don't know," he said, when Letterman talked to him about being a happier or better person for the choices he's made. "There's no way of knowing. But you know, sometimes i listen to a Jay-Z record and I start feeling bad about the choices I've made. This guy's having more fun on two songs than I've had in the past eleven years."

Yesterday, we learned that David Letterman plans to retire from Late Show with David Letterman in 2015 when his contract expires at the long-running late night talk show. The video above has Letterman and Paul Shaffer talking about how much time they've spent working together and doing this show.

Letterman builds up to the part about retiring, first telling a funny story involving bird identification, and then finally led into his discussion with CBS head Les Moonves about his future. Letterman says he approached Moonves before the show and said, "It's been great, you've been great, the network has been great, but I'm retiring." After thanking the viewers and everyone else, he went on to announce (joke) that now Paul and he can be married.

The timing for the retirement isn't entirely set, but it'll be happening in 2015. We'll miss you, David Letterman!

Via Deadline, there have been some notable reactions to Letterman's announcement, including one from the President, who Tweeted his fondness for Letterman along with a photo...

Seth Meyers called Letterman's retirement "heartbreaking news" and discusses watching Letterman when he was growing up.

"If it wasn't for David Letterman, this show wouldn't exist," Meyers said. "And if it wasn't for David Letterman, I wouldn't be here. And if I wasn't here, you would just be an audience full of people watching nobody."

Good point!

And here's Arsenio Hall joking that late night talk show hosts are dropping like flies...

"My plan is working perfectly! Hahahaha"

It doesn't look like Jimmy Fallon addressed the news on The Tonight Show, but it's possible the show was taped before that news was announced. Oddly though, Letterman's show was addressed during Fallon's monologue, but it had nothing to do with his retirement:

Breaking Bad star Bryan Cranston made a splash at Comic-Con earlier this month when he revealed at the panel that he walked the floor wearing a Walter White mask. The topic came up during Late Show with David Letterman when Cranston sat down to be interviewed on the late night talk show last night. The video above not only shows Cranston explaining to Letterman why he put the mask on, but also gives us some footage of Cranston walking the floor as Walter White. One observer actually notes how hilarious it would be if it were really Cranston in that mask. Anywhere else, the likelihood of that would probably have been slim to none, but lightning tends to strike at Comic-Con, where anything is possible.

Had Cranston walked the floor as himself, it's likely he would've been spotted sooner or later and eventually flooded by Breaking Bad fans and enthusiastic Heisenberg supporters. Due to the high volume of people in attendance at the annual San Diego-set convention, autograph signings and photo-opps need to be planned out in advance. A face as familiar as Cranston's might draw the kind of crowd that would warrant security interference. But it's easy to understand the appeal of getting to walk through the crowded convention center floor, enjoying the people, costumes and booths just as any other attendee might. Dressed in costume, Cranston stood a much better chance at anonymity, but going as Heisenberg in a mask that's creepily realistic was a stroke of genius, and it's paid off in laughs. Sure, he was approached by people who wanted a photo, as anyone else in costume might, but most people don't seem to be bothering him.

If you haven't seen it yet, watch the panel video below. Cranston walks out onto the stage wearing the mask. He and moderator Chris Hardwick discuss the mask within the first few minutes…

As intense and superb as Cranston's performance is as Walter White, I love the constant reminders of just how funny he is. I remember watching the first season of Breaking Bad when it aired and not even recognizing Cranston as the dad from Malcolm in the Middle. Lest we ever forget Cranston's funnier side, he pulls a hilarious mask gag at Comic-Con to remind us. And then there are moments like these from his sitcom days…

While it’s become almost standard for American politicians to visit late night talk shows, it’s quite a bit more unusual to see a British politician take a seat on the after-hours stage. In fact, it will be a first for Letterman this week when he welcomes as his guest British Prime Minister David Cameron. It marks the debut appearance for any sitting UK PM on an American late night talk show.

Cameron, according to Deadline, will pop by The Late Show With David Letterman on Wednesday night. The PM is in town as the keynote speaker for the U.N. General Assembly. The planned appearance has the British press wondering how Cameron will perform when faced with the American sense of humor; Letterman is known for asking some awkward questions. While American politicians can roll with the punches and take self-deprecating humor pretty well, the British are not quite so relaxed when it comes to a laugh at the expense of an important figure in government.

Of course, this move is a sign of the times. The Brits may not be quite so stiff anymore, and as British programming continues to soar in popularity Stateside with shows like Downton Abbey and numerous adaptations of British series over here, our funny bones might be slowly reaching a similar place. It might be the more serious questions that could catch Cameron off-guard, especially if Letterman brings up the current News Corp scandal, which will see several of Cameron’s relatives testifying in court this week. Either way, it’s a big move for David Cameron and sure to have people on both sides of the pond watching curiously to see how he does.

Late Show with David Letterman airs weeknights at 11:35 p.m. ET on CBS.

Post Keith Olbermann’s firing from Countdown and Current TV, a slew of insults from both Olbermann and Current TV’s end have spotlighted the fact a large and likely court battle is likely to ensue, with Olbermann hoping for compensation for unlawful termination. To speak out about the event, Olbermann headed over to The Late Show with David Letterman, where he got out a few thoughts about his former relationship with the AL Gore-led Current TV.

The interview starts out with a cutesy joke from Letterman, but quickly the conversation turns to Olbermann’s actual thoughts on the firing. Interestingly, the man who has hopped networks like a frog with multiple lily pad options is not scared to step up and admit a teeny tiny part of the onus may be on him.

Then he gets to the more pertinent point of this thought, calling himself a $10,000,000 chandelier and saying the “house” – in this case Current TV – just was not quite good enough to hold him. There’s the Olbermann we know and do not love.

I get that the Current TV situation wasn't exactly ideal; however, at some point, a person needs to learn to play nice and just make the best of a situation. If Olbermann could do that, maybe he would be able to stick around at jobs for longer and give his fans the content and personality they want. I for one, am not certain we will ever be able to see that from the newscaster.

Michael J. Fox appeared on The Late Show with David Letterman last night and showed off the shoes inspired by Back to the Future II, which are being auctioned for charity. Watch the video, which includes a look at the futuristic looking Nike MAG sneakers.

If you’re familiar with Back to the Future II, then you know that one of the first things Marty McFly learned about fashion upon arriving in Hill Valley in 2015 was that shoes come with power-laces. As high-tops were all the rage back in the '80's, the shoes looked like a futuristic version of what any kid from that era would love.

The Nike MAG shoes don’t appear to have power laces (we still have a couple years before we get to 2015, after all), however as evidenced in the video below, they do light up.

As Fox and Letterman discussed, the shoes will be available for auction on eBay. Here’s the information listed at MichaelJFox.org:

While it seems unlikely that I’ll manage to get myself a pair of these shoes, I may still begin wearing my clothes inside out around 2014, just to get ahead of the fashion-curve in preparation for the predicted trend.

Ashton Kutcher, Jon Cryer, and Angus T. Jones appeared on the Late Show with David Letterman to present the Top Ten Reasons to Watch The New Season of Two and a Half Men last night. Is it me, or did they seem less than excited to be participating in this? Watch the video and judge for yourself.

The reasons listed ranged from joking about how fast Jones is aging, to Ashton Kutcher threatening to do a sequel to Dude, Where’s my Car. Either they were trying to be funny by playing up a sort of casual attitude, or that’s really how they were feeling as they sat slumped back on the Men set couch, smiled politely and read off the list.It’s also possible that Letterman was right when he joked that they might have been under the impression that this was a rehearsal.

Am I being overly critical here, or do they just not seem into this at all?

The Late Show with David Letterman airs Weeknights at 11:35/10:35 p.m. on CBS.