Did you know late-night talk shows have been a staple in American culture since the mid ‘50s? That’s right—for almost seventy years we’ve been watching the most famous stars in Hollywood sit down for interviews, guest star in comedy sketches, and wow us with musical performances.
Over the years we’ve seen many amazing moments that were awkward, hilarious, and most of all memorable. Many of which we’re still talking about to this day. From famous feuds and celebrities acting oddly to the most epic Lip Sync Battles and Carpool Karaokes, these shows always keep us entertained. Did your favorite late-night talk show moment make our list?
Jimmy Kimmel vs. Matt Damon
Chances are your probably don’t remember how the long-standing feud between talk show host Jimmy Kimmel and actor Matt Damon began. Well, it all started after Kimmel joked about bumping Damon from the show one night, which turned into a recurring gag that eventually caught the actor’s attention.
This went on to be one of the very best celebrity “feuds” with Damon taking over Kimmel’s show holding him hostage and Kimmel trying to replace Damon in The Bourne Ultimatum. Even other celebrities got involved including Kimmel’s then girlfriend Sarah Silverman. The two men even went to couple’s canceling to try and work things out. We guess it didn’t go well…
Madonna Drops the F-Bomb
When Madonna goes on late night, anything goes and during her appearance on the Late Show with David Letterman she wasn’t holding back. In just one interview, the singer dropped the F-bomb a whopping 14 times! She even set the record for the most-censored late-night interview of all time. We feel sorry for the person who had to keep censoring her.
The whole thing was full of inuendoes and we’re not sure if the two love or hate each other. She even told Letterman that she’s only there because a Knicks game wasn’t on. Yikes.
Ariana Grande and James Corden Go to Starbucks
Can you imagine working at Starbucks and looking up from the register to see James Corden carrying Ariana Grande? Well, that’s exactly what happened during this Carpool Karaoke Clip.
In case the employees weren’t sure who they were serving, the singer introduces herself by saying, “Hello I’m Ariana Grande. I must be carried.” Other customers were in such shock seeing the stars that they pulled out their phones to document the whole thing.
And if you’ve ever wondered what the pop star drinks, it’s a grande soy latte, obviously. Were you expecting anything less from Grande?
Nicole Kidman Could’ve Dated Jimmy Fallon
It turns out that celebrities have awkward dating stories just like the rest of us and while on The Tonight Show Starring Jimmy Fallon, Nicole Kidman and Jimmy Fallon reminisced about how they first met. But their versions couldn’t have been any different.
Apparently, the actress has a crush on Fallen and the two were introduced via a mutual friend and she thought they were on a date. At the time, Fallon had no idea she was interested in him and he found out during this interview.
He was clearly a bit embarrassed as he lost his shot with an Oscar-winning actress.
Drew Barrymore Gives David Letterman a Show
After rising to fame as the cute girl from E.T. the Extra Terrestrial, Drew Barrymore showed her wild side on the Late Show with David Letterman. While things started off normal, they quickly took a turn after Letterman mentioned the actress’ recent appearance at a club. And you won’t believe what happened next…
Barrymore shocked everyone when she jumped onto the host’s desk and lifted her shirt up. Courtney Love even tried to replicate it in a future interview, but it wasn’t nearly as memorable as Barrymore’s.
Tom Hanks Whale Watching Prank
Guests dress to impress when they come on late-night shows and we bet when Tom Hanks wore one of his best suits, he had no idea he was going to have a waterpark experience. While talking about his whale watching adventures, he had probably his closest encounter to date with the mammal.
When he was admiring the whale backdrop behind him, one of the whales dove out of the water, making a huge splash and completely covering Hanks in water. Of course, Conan stayed completely dry.
Luckily the actor was a great sport about it—he even threw his mug of water onto his face for an added touch.
Harrison Ford vs. Chewbacca
Chewbacca is known for being a bit grouchy, especially during interviews, and after Jimmy Kimmel asked if the actor was okay taking audience questions, he agreed to it as long as they weren’t Star Wars-related.
Kimmel used this to his advantage and had audience members dressed up as characters from the film. One of which was Chewbacca who made his distinctive growls, which set Ford off. The actor then asks Kimmel, “How did he get in here.”
Chewbacca and Ford seem to have some unresolved drama centering around Ford’s wife. The actor asked Kimmel to take sides before he gets up and leaves the stage. Talk about an exit.
Conan O’Brien Gets Back at NBC for Taking “The Tonight Show”
When Jay Leno retried, The Tonight Show was given to Conan O’Brien, but after Leno decided that he was done with retirement, the network chose to give back the show to Leno.
Understandably so, Conan didn’t take it lightly and he got the ultimate revenge—spending a ton of the networks’ money.
Among his lavish purchases were buying the most expensive car in the world, a Bugatti Veyron and dressing it up like a mouse. And the car’s theme song was the original master recording of the Rolling Stones’ “Satisfaction”, which is “crazy expensive to play on the air”. According to the host, the total price tag for the comedy bit was a grand total of $1.5 million!
Joaquin Phoenix Bombs While in Character for “I’m Still Here”
David Letterman was spot on when he said Joaquin Phoenix looked different. Apparently, the appearance was a stunt performed by Phoenix and Casey Affleck for the film I’m Still Here.
Letterman wasn’t holding back any punches, insulting the actor for chewing gum during the interview and asking him how his time with the Unabomber was.
The host even ended the interview with a line that sums up the whole thing, “Joaquin I’m sorry you couldn’t be here tonight.” Since then, the actor has apologized for his bizarre behavior and things between the two have settled.
Adele’s Carpool Karaoke
James Corden has had quite the celebrity guest stars on his Carpool Karaoke including Mariah Carey, Elton John, Lady Gaga, Sia, and Justin Bieber. But if we had to pick a favorite it would be Adele.
Corden started off the segment with the lyrics from her song Hello, “Hello, it’s me
I was wondering if after all these years you’d like to meet”.
It wasn’t just Adele’s amazing voice that made the Carpool Karaoke one to remember, though. Her bubbly personality shined through as well.
While we loved the rendition of Adele’s “Someone Like You” and “All I Ask”, the best moment was the freestyle rap at the end, which Adele nailed. Can you say, “Mike drop?”
Marlon Brando Kisses Larry King
Marlon Brando is one of Hollywood’s most iconic actors and while he’s one of the best the industry has ever seen, he was also known for not doing many interviews.
Yet during one memorable interview with Larry King, that took place live at the two-time Oscar winner’s home, Brando surprised us all.
The interview was to promote his book Songs My Mother Taught Me and the two men ended it by singing “Got a Date with an Angel” before having a nice peck on the lips. They then said “Goodbye” and shook hands. It sure was awkward…
“Cheers” Cast Gets Tipsy After the Show’s Finale
When Cheers came to an end after 11 seasons in 1993, people had a lot of feelings. Following the last episode, Jay Leno interviewed the cast which included Ted Danson, Kelsey Grammer, Woody Harrison, Rhea Pearlman, George Wendt, and John Ratzenberger, live from the Cheers bar in Boston. And like any live show, Leno couldn’t have been prepared for what had happened.
While there were planned sketches, the cast has started drinking before they arrived at the bar and when Leno went to interview them, they were completely wasted. At the time, it was quite rare to see celebrities drunk on a late-night show. So, it was pretty shocking.
Jerry Lawler Slaps Andy Kaufman
After wrestler Jerry Lawler and actor/wrestler Andy Kaufman appeared as guests on the show, we were even more uncertain if the two’s rivalry was an act or if they actually disliked each other.
Kaufman showed up wearing a neck brace, which was a result of Lawler injuring his neck during a match. He insisted on an apology from the fellow wrestler but instead Lawler mocked him. He even slapped Kaufman, causing him to fall from his chair. And that wasn’t the end of it—Kaufman went on a verbal tirade and threw coffee at Lawler, across Letterman’s desk.
We’re still not sure if this was staged, but it sure was memorable.
Jimmy Kimmel Impersonates Jay Leno
The late-night talk show world was thrown for a whirlwind after NBC announced that Conan O’Brien would be taking over The Tonight Show for Jay Leno. Conan’s hosting was cut short after Leno decided he would be coming back from retirement and once again host the show.
But Conan wasn’t the only one that lashed out after hearing the news; Jimmy Kimmel also wasn’t happy about it. To show his disapproval he hilariously dressed up as Leno, impersonating him for an entire episode. He went all out wearing a wig, a giant plastic chin, and having a slight lisp.
We’re still not sure why Kimmel was so upset about NBC’s decision.
Lip Sync Battle with Emma Stone
We’ve seen a lot of amazing Lip Sync Battles like Will Ferrell’s, Joseph Gordan-Levitt’s, and Paul Rudd’s, but the one that we can’t stop thinking about is Emma Stone’s.
Stone absolutely went for it with her lip sync to “Hook” by Blues Traveler and DJ Khalid’s “All I Do is Win” against Fallon’s Iggy Azalea’s “Fancy” and Styxs “Mr. Roboto”. Her “All I Do is Win” was so epic and she even took on the Ludacris’ rap verse.
After watching her performances, we fell in love with the actress even more.
Jimmy Kimmel Calls Out James Corden
When Kimmel appeared on James Corden’s show and participated in a game of “Spill Your Guts or Fill Your Guts”, he ended up embarrassing Corden. The point of the game is for the hosts and guests to either answer a question or eat something gross.
The last question really stunned Corden. He was challenged to name two of the cameramen in the room. While it should’ve been easy, Corden actually couldn’t answer the question.
We get that the show probably has a huge crew, but not being able to name two of them? Pretty embarrassing, right?
Rihanna Pranks Jimmy Kimmel
Jimmy Kimmel is known for loving practical jokes, especially April Fool’s jokes and one pop star by the name of Rihanna was a huge fan of his jokes. With the help of Jimmy’s wife, Rihanna played her own joke on Kimmel that was totally epic.
Rihanna gave him a literal wakeup call he would never forget full of dollar bills and strobe lights while her song “B—h Better Have My Money” played. He was completely confused and this was the first of many surprise appearances to the hosts’ bedroom. Can you imagine getting woken up by Rihanna?
Jason Sehorn Proposes to Angie Harmon
It’s clear that actress Angie Harmon had no idea that her boyfriend, Jason Sehorn, then cornerback for the New York Giants, was going to propose to her. When Jay Leno asked her about who she was dating she tried to avoid the questions. But after the host mentioned him by name and the football player walked on stage, she had to have known something was up.
Sehorn then got down on one knee and popped the question. Of course, she said yes, and her father happened to be there to celebrate. Who doesn’t love a happy ending?
Kevin Hart vs. Animal Guest
You may not know that Kevin Hart isn’t an animal guy, which made the animal segment with Robert Irwin on The Tonight Show with Jimmy Fallon even more entertaining.
As soon as the first animal was brought out, Hart couldn’t get out of his seat fast enough and throughout the whole segment he stands at a safe distance while Fallon interacts with the animals.
But he isn’t afraid to egg-on the host when he holds a tarantula. Fallon somehow convinces Hart to take part in the falcon trick, even though he’s terrified. The whole bit had us laughing uncontrollably.
History of Rap with Justin Timberlake
One of the best friendships in the entertainment industry would have to be Jimmy Fallon and Justin Timberlake’s. The pair have had some hilarious sketches, but the best would have to be the two of them teaching the History of Rap.
The duo looked like they were having the time of their life, choreographing each song with singing and dance moves and The Roots played each hit live. They sang Souja Boy’s “Tell’em – Crank That” Kanye West’s “Gold Digger”, and Missy Elliot’s “Work It”.
The two had so much fun that they went on to do the sketch five more times!
Craig Ferguson Becomes a U.S. Citizen
Glasgow-born Craig Ferguson showed just what it’s like to become a citizen of the United States and all jokes aside, the funny man passed with flying colors. He got 100%! He didn’t get a single question wrong. And to be honest, we’re not sure we would’ve passed.
The comedians’ quick wit and ability to think on his feet was clutch in this case. We definitely got some good laughs listening to the way he answered the questions. He seems proud to be an American.
Ew! with Channing Tatum
Many guests have joined Fallon for this hilarious sketch and one of the most memorable would have to be Channing Tatum. He completely nails the part of Susie, staying in character throughout the whole bit. We even got a taste of his Magic Mike days when he dances to a song, busting out some of his jaw-dropping moves that left us thirsty for more.
But while Fallon’s Sara is into the film, Tatum’s Susie isn’t a fan. We couldn’t stop thinking about Fallon and Tatum’s chemistry.
Steven Colbert’s Tolkien Parody
We bet you didn’t know that Stephen Colbert had a cameo in The Hobbit: The Desolation of Smaug. In one of his sketches, the host visited New Zealand and met with director Peter Jackson in hopes of getting a spinoff franchise for his character Laketown Spy.
The director seems less than impressed with the pitch, but the best part is a trailer clip in which Jackson joins him as his sidekick but keeps referencing other franchises like Harry Potter.
Lord of the Rings actors Ian McKellen, Viggo Mortensen, and Elijah Wood even had cameos. Even if you’re not a LOTR fan, you can appreciate this bit.
Will Ferrell and Chad Smith Drum-Off
There are some celebrities that look so much alike that it’s hard to tell them apart like Amy Adams and Isla Fisher and Katy Perry and Zooey Deschanel, but the resemblance of Will Ferrell and Red Hot Chili Peppers’ drummer Chad Smith is uncanny.
Fallon had both on his show, and they showed up dressed in the same exact clothes. We could barely tell the two apart. The actor and drummer took the stage for an epic drum-off to see who was the better drummer. Obviously Smith was the better drummer, but we were still impressed with Ferrell’s skills.
Jennifer Garner Gets Outsmarted
During an interview with America’s sweetheart Jennifer Garner, Conan talked about the time she snuck into a room. The actress quickly corrected him and said “sneaked” and followed by saying, “Snuck isn’t a word, Conan, and you went to Harvard and you should know that”.
But in fact, “snuck” is a word and Conan being the gentleman that he is just went on with the interview. A bit later on, Conan used the opportunity to school her by pulling out a dictionary from under his desk and finding the word “snuck”. He made sure to rub it in a bit. The whole thing was pretty uncomfortable to watch.
Farrah Fawcett Spaces Out
Sometimes we’re left totally confused after watching late-night interviews and this one with Charlie’s Angels’ Farrah Fawcett falls into that category.
The late actress told a bunch of stories that made no sense and even David Letterman had trouble catching up with her. We’re not sure if she was under the influence or if she was playing the part of the dumb blonde. After all she was on the show to promote a Playboy magazine shoot.
Either way, everyone was talking about the interview, so regardless of her intentions, we’d say it was a successful appearance.
Johnny Carson’s Last TV Appearance
It’s always a huge ordeal when a late-night show host retires and one has to fill their spot but when Johnny Carson left The Tonight Show this was probably the biggest late-night good-bye.
While Jay Leno got the part to officially replace Carson, David Letterman had Carson on his show for his last TV appearance. Letterman even let the iconic host sit in his host chair. Carson sat down for a moment and the audience couldn’t stop cheering. After a break in the applause, Carson shook his head and walked off stage like a true legend.
Letterman finished the segment by sitting back in his chair and saying, “It’s still a little warm. I wish a little of that would rub off on me. Wow.”
Crispin Glover Kicks David Letterman
Actor Crispin Glover’s interview with David Letterman sure was bizarre. Glover showed up in a wig, glasses, and platform shoes and he was acting off, reading random clips about himself from the newspaper and rambling on incoherently.
Letterman went along with the act until the actor stood up and kicked just inches from Letterman’s face. That’s when the host decided he had enough before saying he was going to “check on the top ten” and walking off stage. The interview was a train wreck and we couldn’t take our eyes off the screen.
Bradley Cooper and Jimmy Fallon Can’t Stop Laughing
We always love it when talk show hosts have trouble keeping their composure and that’s exactly what happened in what should’ve been a pretty normal interview that lacked any performance, sketch, or game, with Bradley Cooper.
The actor went on The Tonight Show Starring Jimmy Fallon to talk about his latest performance in the Broadway show The Elephant Man, but the host and Cooper wore football visors with wigs attached and they couldn’t stop laughing about how ridiculous they looked.
At one point Fallon even ends up on the floor and Cooper has to help him up. Even after they take the visors off, the interview couldn’t get back on track.
Seth Meyers’ Birthing Story
Sometimes talk show hosts’ lives are comic gold and Seth Meyers’ story about how his wife had to give birth in a lobby had us dying from laughter.
Meyers’ wife is the one we have to thank for the story—she had to give birth to their son on their building’s lobby floor. The host spoke about his minute-long conversation with 911 that went along the lines of, “We’re about to have a baby, we’re having a baby, we had a baby”. Can you imagine?
It seems like Seth Meyers may not be the only funny man in the family—his son Axel was hilarious right out of the womb.
Kanye West Apologizes for MTV Video Music Awards
Who doesn’t remember when Kanye West grabbed the mic from Taylor Swift at the 2009 Video Music Awards when she was giving her acceptance speech for Best Female Video? It was awkward. What you may not know is the rapper went on The Tonight Show with Jay Leno to issue an apology to the singer.
Kanye and Rihanna were there to perform, but before they did Kanye gave an impromptu interview in which he apologized and described his behavior as “rude”. Leno wasn’t holding back any punches and he brought up how his late mom would’ve felt about the situation. Well, the question hit hard for Kanye, who was close to his mom, and he started tearing up.
Crosswalk the Musical “Frozen”
We’ve seen some great Crosswalk the Musical segments on The Late Late Show with James Corden including Aladdin, Beauty and the Beast and Grease. One of our favorites to date was Frozen.
The segment had Kristen Bell, Idina Menzel, Josh Gad, and Jonathan Groff singing songs in a busy intersection in Los Angeles when the lights turned red. Corden decided to play Elsa and made Menzel play Sven the reindeer. Don’t worry, Menzel won back her role as Elsa in a sing-off. There were even costumes!
Bill Murray Dresses Up as Liberace
Bill Murray was the first guest on the Late Show with David Letterman and to mark the 20th anniversary, Letterman had the frequent guest back on the show. Murray was no stranger to making a grand entrance—he’s popped out of a cake, showed up in 1700s attire, and to celebrate the New York Giants victory he came in full football attire.
This time, Murray showed up as Liberace, making one of the best stage entries in history. The actor went all out arriving in a white Rolls-Royce, wearing furs and a cape, and holding a small dog.
Tattoo Roulette with One Direction
James Corden had One Direction on his show many times with the best moments being their Carpool Karaoke and Tattoo Roulette. The latter has to be our favorite. The game is pretty straightforward—there are five boxes and five players. Four of the boxes are safe boxes and the other has a tattoo.
The tension was high as Niall Horan was the only member without ink at the time. So, who ended up getting tatted? Harry Styles ended up getting the tattoo of “Late Late”. But you could barely see it among his others.
Stephen Colbert Gets Touchy With Kristen Stewart
Sometimes technology can get in the way and result in uncomfortable interviews. That’s exactly what happened when Kristen Stewart was interviewed by Stephen Colbert. Everything seemed to be going fine until there was an issue with the mic that was hitting a necklace she was wearing and causing audio issues.
Instead of just telling her about the issue, Colbert went ahead and moved her necklace adjusting the mic and getting a bit too close to her chest. She clearly was uncomfortable and she ended up just taking the necklace off. But the damage was already done…
Abel Ferrara Acts Under the Influence
Guests don’t always show up sober on late-night shows and that was most likely the case with Bad Lieutenant director Abel Ferrara. He was accused of showing up drunk, refusing to go on stage, and trying to leave the studio.
Throughout the whole thing, the director slurs his words—Conan even suggested that viewers should have subtitles to understand the interview. Later on, Conan said Ferrara was the worst guest he ever had on his show.
David Letterman Insults Paris Hilton
Paris Hilton was released from jail; she went on the Late Show with David Letterman yet the host wasn’t very sensitive about it. Moments after Paris walked on stage, he mentioned her jail stay, calling it the time in the “slammer”. Paris obviously didn’t want to talk about it and he just kept on going with the jokes.
While she tried to play off how annoyed she was, at one point she even said, “you’re making me sad that I came because you’re hurting my feelings.” Pretty much sums it up.
Jimmy Interviews “Khaleesi”
Whenever one of Jimmy Fallon’s fellow SNL alumns make an appearance on his show, it’s always a great gag. One of the best was when Kristen Wiig came on as Khaleesi from Game of Thrones. Wig often comes in as a character, and more often than not, she knows nothing about them.
The comedian clearly had never watched GOT because her answers to Fallon’s questions were completely off. Wiig even said she does spells for fun. While there was nothing accurate about it, the interview was a joy watch as they both couldn’t stop laughing.
Harrison Ford Pierces Jimmy Fallon’s Ear
Jimmy Fallon will do almost anything to make a great show and when Harrison Ford showed up, he let the Star Wars actor pierce his ear on TV. Ford even took a shot before prepping Fallon’s ear for the piercing. We were squirming during the sketch as we watched Fallon sweating and shaking while Ford fooled around.
Fallon ends up getting his ear pierced and he rocks a feathered dangled earring. By the end of the segment the two are sporting matching earrings.
Jennifer Lawrence’s Crush on Seth
Apparently, while at SNL for a week Jennifer Lawrence had a crush on Seth Meyers and was hopeful he would ask her out. When it didn’t happen, she came up with a plan to ask him out. But her dreams were crushed when she found out from the wardrobe lady he was engaged. Awkward.
Even recounting the story, Lawrence is uncomfortable, but Meyers handles it like a pro and the two end up laughing about the whole thing and we were laughing along with them!
Tom Holland Describes Dancing for Madonna
Even celebrities have uncomfortable experiences and Tom Holland shared his while on The Graham Norton Show. Holland recalled attending an Oscars after party and being introduced to Madonna by an old friend who told the pop icon about his dance skills. He then tried to show her some of his moves but she wasn’t impressed. Can you imagine how lame Spider-Man must’ve felt?
The best part was when he recalled his little brother’s reaction to the story, saying, “Who’s Madonna?” The other guests couldn’t stop laughing.
Cher vs. David Letterman
Apparently, Cher didn’t want to come on Letterman—It took her over four and a half years to come on the show—and when she finally did things started off confrontational. The two got right to it speaking about why she didn’t want to have the interview. So, what stopped her?
After beating around the bush, she told the host it was because she thought he was an a–hole. We’re still not sure if she was being serious or not, but to us it seemed like she wasn’t joking. To be honest, Letterman took it as well as he could’ve.
Seth Meyers Brings Jon Snow to a Dinner Party
Do you remember when everyone couldn’t stop talking about Game of Thrones? Kit Harington’s Jon Snow actually appeared on Late Night with Seth Meyers and in a hilarious sketch, Meyers brought the character to a dinner party.
It’s great to see the GOT character out of context, trying to pick up on dinner party etiquette but Jon Snow isn’t exactly the best guest. The best part? There’s a game of charades where Meyers says, “you know nothing Jon Snow.”
Marc Summers vs. Burt Reynolds
Most of the time guests get along, but there’s always a few situations when they don’t. When this happens, it’s usually bad. Such was the case with Marc Summers and Burt Reynolds when they came on The Tonight Show with Jay Leno. The two share one normal conversation before the insults start coming.
It all began when Summers made jokes about Reynold past marriages, which resulted in Reynolds spilling water in Summers’ lap. Things only went downhill from there and by the end of the interview, they threw pies at each other. We’re still wondering why they had pies lying around backstage though.
Point Pleasant Police Department with Bill Hader
Another SNL alum Bill Hader showed up to The Tonight Show Starring Jimmy Fallon for the unforgettable sketch, “Point Pleasant Police Department”. An ‘80s cop show with Fallon and Hader playing cops, it had the two stuffing their faces with food while emphasizing the letter “P”. Food just keeps spilling out of their mouth and into the other’s face.
While it may’ve been a bit immature, it was fun to see the two not afraid to get a bit dirty for some laughs.
Jimmy Kimmel and Katherine Langford Speaking English
Sometimes interviews don’t go as planned and jokes don’t always land. We’re not sure which happened when Jimmy Kimmel interviewed 13 Reasons Why Australian actress Katherine Langford and asked her where she learned to speak English. Perhaps he noticed he had blundered as he then said, “our regular English that we speak here”.
Langford handles the questions gracefully, but the awkwardness could’ve been avoided if Kimmel asked about accents or he would’ve said he misspoke. Instead, he just continued to go with it.
Cooking With Gordan Ramsay
When it comes to celebrity chefs, Gordon Ramsay is the one to beat. We weren’t expecting much when James Corden challenged Ramsay and his daughter Matilda to an English breakfast cook-off. Corden even admitted that he had only cooked the meal after a night of drinking.
Not surprisingly, Ramsay and Matilda don’t work well together. Ramsay acts frantic and he burns the bacon before setting the pan on fire. Can you imagine if one of the contestants on Master Chef did that? To be honest, Corden’s breakfast doesn’t look half bad.
Justin Bieber’s Tattoo
While Justin Bieber is now covered in tattoos, during the beginning of his career he didn’t have any. To mark the release of his 2012 album Believe, the singer got a new tattoo. Letterman, who’s obviously a bit old-school, wasn’t impressed with the new body art. He even begged Bieber to make it his last one.
If that wasn’t enough, the late-night host grabbed Bieber by the arm and tried to rub the ink off. It was like watching a parent disapprove of their child. Some things are better kept to yourself.
Miriam Margolyes Doesn’t Know the Other Guests
Every time the Harry Potter actress makes a guest appearance, we’re left dying in laugher. First, Miriam Margolyes didn’t know who rapper will.i.am was and he happened to be sitting next to her.
Then, she was sitting next to actor Dominic Cooper. What she did have to say about the Mama Mia! actor wasn’t exactly wonderful—not knowing he’s in it, she called the movie “dreadful”.
Jimmy Kimmel Shows Behind-the-Scenes Clips of “Joker”
Joaquin Phoenix is no stranger to awkward late-night talk show appearances and when promoting The Joker on Jimmy Kimmel Live!, things got uncomfortable.
Jimmy Kimmel surprised the actor with a blooper sent over by director Todd Phillips which showed Phoenix cursing out the film’s cinematographer Lawrence Sher while trying to film a scene. Sher even joked that the actor was acting like a diva, comparing him to Cher.
The clip ended with him storming off set. Phoenix was clearly surprised and he was visibly sweating and at a loss for words after the clip was shown.
Dakota Johnson Tells Her Gap Tooth Story
While appearing on The Tonight Show Starring Jimmy Fallon to promote her movie The Peanut Butter Falcon, Fifty Shades of Grey‘s Dakota Johnson set the record straight about the disappearance of her tooth gap, which was making headlines.
“The fact that this is a newsworthy event in our world right now is pretty Chaka Khan to me,” Johnson said. What made the interview awkward was Fallon tapped on Johnson’s teeth to see if they were fake.
Caitlyn Jenner Confronts Jimmy Kimmel for Mocking Her Transition
The world was pretty shocked when Bruce Jenner came out as trans and announced her new name as Caitlyn Jenner. While appearing on Jimmy Kimmel Live! she opened up about her transition and spoke about how it was difficult because it was all over the media. But things got weird when she turned to the host and called him out for his jokes, saying, “In fact…guys like you making some jokes.”
She was referring to a parody promo package with edited clips of Jenner’s Diana Sawyer interview and Bachelorette Kaitlyn Bristowe. Kimmel was clearly nervous, but he did apologize.
Famous Woman Read “Beautiful Women Complaints About Men”
We can’t help but think this clip wouldn’t fly today, but back in ’96 somehow it was okay to air it. David Letterman had famous women like Tyra Banks and Rosie Perez read a Top 10 list titled “Beautiful Women Complaints About Men”, and nothing was left unsaid.
Items on the list included things ranging from “When they run out of snacks and starting eating your birth control pills” to “Sometimes big feet just mean big feet.” And those are the more PG ones.
David Letterman Makes Joke About Martha Stewart’s Jail Sentence
To say the world was surprised when America’s sweetheart Martha Stewart served time in federal prison in 2004 would be an understatement. And like Paris Hilton’s interview, David Letterman didn’t hold back making rude jokes about her five-month jail sentence.
During a cooking segment, while making a cheese football and listing the ingredients, he asked her, “Do you ever hear from any of the cons?” The joke was completely out of place.
The Handsome Men’s Club
One of the first viral videos on a late-night talk show was “The Handsome Men’s Club”, which came from a 2010 episode of Jimmy Kimmel Live!. The segment joked about how some men in Hollywood are considered handsome and some are not.
Some of the most popular actors and musicians including George Clooney, Matthew McConaughey, Patrick Dempsey, Sting, and Lenny Kravitz were in the pretend annual meeting. And of course, Matt Damon’s ongoing feud with the host was featured.
I Told My Kids I Ate Their Halloween Candy
I Told My Kids I Ate Their Halloween Candy is one of the saddest, yet entertaining segments, and year after year, we can look forward to it. The segment started in 2011 and it’s still going strong. While some people believe the prank where the parents tell their kids that they ate their candy and record their kids’ reaction is too mean, at least the parents tell the kids after it isn’t true.
The kids’ responses are the best—some throw tantrums and others reassure their parents that it’s okay.
Tilda Swinton Reads Mean Tweets
Mean Tweets has become one of the most recognizable segments on late-night TV and it features celebrities reading mean tweets that are written about them on camera. For some, it’s the first time they’ve seen the tweets, which makes for priceless reactions.
There have been tons of additions, each with millions of views, but our favorite is the Oscar Edition, which features Tilda Swinton. The best part is she manages to stay in character throughout the mean tweets which include one where she’s compared to a dog.
Driving Lessons with Ice Cube and Kevin Hart
Driving is stressful as it is, but imagine learning to drive with Conan, Ice Cube, and Kevin Hart. Talk about pressure. Conan took one of his staff members named Diana for a driving lesson with the other celebs in the car.
While the talks between the stars are hilarious, we couldn’t stop laughing at the terrible advice given to Diana, which included telling her to yell out the window, “you’re my b-tch!”
Ariana Grande’s Musical Impressions
Lip Sync Battle isn’t the only musical segment Jimmy Fallon has on his show, there’s also the Wheel of Musical Impressions, which has a digital wheel spun revealing an artist and song each has to sing. This segment is just as entertaining.
While lots of stars have appeared on the segment, we couldn’t get over Ariana Grande’s impersonation of the other singers.
Grande sang “Mary Had a Little Lamb” as Britney Spears, “The Wheels on the Bus” as Christina Aguilera, and “Can’t Feel My Face” as Celine Dion. It was epic!
John Oliver Buys a Train
After John Oliver made fun of a model train on the set of Scranton, Pennsylvania’s ABC affiliate that runs behind the weather forecasters all year round during an And Now segment, some viewers were really offended.
To rectify it, he bought them “an irresponsibly large” train set using HBO’s resources to get them a new one. “It’s not the train set that Scranton needs, but it is the train set it derives,” Oliver passionately explained.
Clueless Gamer, “Grand Theft Auto V”
Conan O’Brien is good at making us laugh, but he’s certainly not a gamer. Some would say he’s even a clueless gamer. This makes for a great sketch where novices and experienced gamers can learn about the latest releases through Conan’s eyes.
While there have been many games featured on the segment, one of the best has the host playing Grand Theft Auto V. We can really see how bad Conan is at video games and he gets kicked out of a strip club twice and he fails to get revenge on it by blowing it up.
Lip Sync Battle with Tom Cruise
We mentioned that Emma Stone’s Lip Sync Battle was one of the best, but Tom Cruise’s is also worth mentioning. While appearing on the show to promote his new film Mission Impossible: Rogue Nation, he performed a Lip Sync Battle to the Weeknd’s “Can’t Feel My Face”.
As Cruise said, “[it] is so ridiculous.” And that it was. The show’s band, The Roots, also played the opening bars to Bob Seger’s “Old Time Rock and Roll” and the actor slid over to the microphone in true Risky Business style.
Sia’s Carpool Karaoke
Adele’s Carpool Karaoke wasn’t the only epic one—Sia’s was a close second. Before the singing even started, we couldn’t stop laughing at Sia trying to find Corden’s car, but being unable to see because of her iconic wig. She also went on to describe why she wears the wig.
Of course, Sia’s singing was top-notch, but we also loved the twos’ back and forth about aliens. The host even sported a wig like the singer. They sang Rihanna’s “Diamonds” and Sia’s “Chandelier”, “Elastic Heart”, “Alive”, and “Titanium”.
Tom Holland Drops Spoilers
Tom Holland is known for dropping spoilers and one of the most epic ones he dropped was on “Jimmy Kimmel Live!” while appearing on the show with the Avengers: Infinity War cast.
Holland just casually dropped that he was under Downey’s care on the first Spider-Man, before correcting himself and saying, “Not that I’ve done more than one.” He also revealed that he thought he was reading a fake script about Spider-Man going to space, but it turned out to be real. This fact still wasn’t public knowledge.
Craig Ferguson and Peter Capaldi Reminisce
It’s always nice when stars have a relationship with the host, and such was the case with Craig Ferguson and Peter Capaldi. When Capaldi stopped by the show, the host introduced the Doctor Who star by saying he’s taken acid with him.
The two then went on to reminisce about the good old days which included being in a band together 25 years ago. It was like watching best buds reunite after a long time.
Seth and Rihanna Go Day Drinking
Rihanna has shown us time and time again that she can hold her own when it comes to starring in late-night TV show sketches and such was the case when she went day drinking with Seth Meyers. The two spent the day drinking at The Jane Hotel with Meyers making Rihanna-themed cocktails.
The names were super creative and included “Under My Rumbrella”, “Diamonds in the Rye”, “We Found Veuve in a Hostess Place”, and “B-tch Better Have My Bunny”. During the entire sketch, Meyers was super clumsy and Rihanna didn’t mind laughing at him.
Shaq Lifts Kevin Hart
Whenever Shaq stands next to anyone other than basketball players, he looks ginormous, which shouldn’t be surprising since he’s over seven feet tall! While on The Tonight Show with Jay Leno, he made quite the entrance.
Shaq picked up Hart and started bench-pressing him like the actor was light as a feather. Even Leno joked, “put him on your keychain”. Fellow star Justin Timberlake couldn’t believe his eyes and the four men had a good laugh.
Larry King Asks Jerry Seinfeld if “Seinfeld Was Canceled”
Some interviews don’t go as planned and the guests don’t always get along with the host, which is what happened when Jerry Seinfeld appeared on Larry King Live. Things quickly became awkward when the conversation went to the Seinfeld finale.
King asked if the show was canceled or if Seinfeld “canceled them”. King quickly tried to take back the statement after the actor asked if King knew who he was. We’re still not sure if Seinfeld left the interview with bad feelings.
David Letterman Puts Jennifer Aniston’s Hair in His Mouth
David Letterman has had some cringy moments, but the worst was probably when Jennifer Aniston showed up in 1998, during the height of her Friends fame. The interview appeared to be going fine until Letterman asked for forgiveness and leaned in close to her, taking a strand of her hair in his mouth.
“Forgive me if this is rude, I just want to try one thing,” he said before putting her hair in his mouth. Not surprisingly, Aniston let out a big scream. At least she was handed a napkin to wipe it off and she handed it like the seasoned pro she is.
