Where were you when Drew Barrymore flashed David Letterman on national television? What about when Tom Cruise jumped up and down on Oprah's couch and proclaimed his love for Katie Holmes? The list of iconic moments in talk show history goes on—and we've compiled them all for you in one place.
Arnold Schwarzenegger announces his run for governor
These days, Arnold Schwarzenegger is just as much a politician as he is a major movie star—but people were blown away when the Terminator actor announced his run for the governor of California on The Tonight Show with Jay Leno.
The then-56-year-old had been dropping hints here and there around the release of Terminator 3: Rise of the Machines. When he confirmed his plans in front of Jay Leno, the studio audience went wild. Schwarzenegger went on to win the election, only returning to the big screen after completing two terms as governor in 2011.
Kanye West cries while apologizing to Taylor Swift
Kanye West may be in the headlines often these days, but the rapper and fashion designer stunned audiences when he cried on The Tonight Show with Jay Leno. West had been publicly lambasted for his behavior at the MTV Video Music Awards, during which he interrupted Taylor Swift's acceptance speech to praise a Beyoncé music video.
West did seem genuinely remorseful for his actions, claiming that he wished to apologize to Swift in person for ruining her big moment. Leno then asked West what his deceased mother would think of his behavior. West burst into tears and admitted that she would have considered it unacceptable.
Christina Aguilera nails other artists' signature singing styles
Christina Aguilera is a coach on The Voice for a reason—the musical artist has quite a set of pipes on her. When Jimmy Fallon invited her to play the Wheel of Musical Impressions on The Tonight Show, Aguilera accepted, and subsequently blew the studio audience away.
Aguilera kicked off the segment with a shockingly accurate take on Cher singing a Folger's commercial. She then followed up with an impression of Britney Spears singing "This Little Piggy." Finally, Aguilera capped the performance with an impression of Shakira doing the Golden Girls theme song. She knocked it out of the park!
Hugh Grant confesses he "did a bad thing" after getting caught with Divine Brown
In 1995, Hugh Grant was two weeks from announcing his first big feature, Nine Months, when he found himself in the midst of some sticky legal trouble. Police caught Grant engaging in sexual activity in a public space with Estelle Marie Thompson, otherwise known as Divine Brown. Although Grant pleaded no contest, the news still made major headlines.
Leno opted not to skirt around the issue on his show, asking Grant directly what everyone wanted to know: "What the hell were you thinking?" In response, Grant confessed to doing "a bad thing." Thompson, on the other hand, only learned who Grant was after reporters besieged her house the day after her arrest. She has earned roughly $1.6 million from publicity.
David Letterman admits to having affairs with colleagues
On October 1, 2009, the levity of David Letterman's usual program disappeared when the talk show host told viewers that he was the victim of an attempted blackmailing scam. Behind the scenes, someone had threatened to reveal a series of covert affairs with female coworkers unless Letterman doled out $2 million.
Letterman confessed on-air that he had been having multiple affairs with several of the women with whom he worked. Instead of complying with his demands, Letterman worked with police to arrest producer Joe Halderman, the blackmailer, on charges of larceny. Due to Letterman's decision to get ahead of the scandal, his career remained largely unaffected.
Conan O'Brien sends Jennifer Garner back to grammar school
Some talk show hosts love to fluff up their guests, but not Conan O'Brien. During a 2010 interview, Conan said that Garner had "snuck into the room." Garner righteously corrected Conan, stating that "snuck" was not a word; he must have meant "sneaked into a room."
Garner mocked O'Brien, a Harvard graduate, for not using the appropriate tense—but O'Brien knew he was right. In fact, he pulled out a dictionary right on live television and looked up the word "snuck" just to prove to Garner that she was mistaken. O'Brien laughed maniacally at his triumph while Jennifer Garner appeared visibly irritated.
Crispin Glover almost kicks Letterman in the head
Crispin Glover is best known for playing George McFly in Back to the Future. After the film's success, Glover appeared on Letterman's show in 1987 to promote his next flick, River's Edge. Wearing a wig, glasses, and platform shoes, Glover refused to answer any of the questions Letterman asked him, with the talk show host growing visibly annoyed as time went on.
The show culminated in a dangerous stunt; Glover, claiming to be strong, kicked in the direction of Letterman's face, inches away from delivering quite a bruise. Glover was asked to leave during the commercial break.
David Letterman takes it too far with Paris Hilton
Paris Hilton made headlines in 2007 after going to jail as a consequence of driving with a suspended license. The star wanted to leave her time behind bars in the past and went on Letterman's show specifically to promote her clothing line and new fragrance. However, Letterman simply wasn't having it. He wasted no time in grilling Hilton about her stint in prison, despite her obvious discomfort.
Although she attempted to laugh it off, Letterman pursued the topic anyway, barraging her with questions and mocking her for the experience. Hilton finally snapped at the talk show host, telling him that she moved on with her life and no longer wanted to discuss the topic. The interview is easily among the most uncomfortable of Letterman's career.
David Letterman pranks Richard Simmons
When Richard Simmons appeared on Late Night in 2006, it seemed as though Letterman was deeply irritated by the eccentric fitness instructor, especially when Simmons wouldn't stop trying to promote a food steamer. The interview was quite uncomfortable until Letterman decided to pull a little prank on Simmons.
Simmons tried to demonstrate how the steamer operated, but when he hit the power button, smoke began to billow out of the machine. Seconds later, it burst into flames. Simmons screamed and leaped from his chair. Letterman, on the other hand, sat there and laughed, since the whole thing was a prank he had orchestrated.
Madonna drops the F-bomb 14 times
In 1994, Madonna's appearance on The Late Show with David Letterman made history as the most-censored late-night talk show in history. During the span of her interview, Madonna said the F-word 14 times. The segment was incredibly tense, with Madonna accusing Letterman of "sucking up" to his guests instead of challenging them.
By the end of the episode, Madonna had literally refused to leave the set, even though audience members were telling her to leave. Instead, she just sat there, puffing on a cigar. The episode was a disaster, but it drew the highest ratings Letterman had ever had.
Heidi Klum bears it all
In 2003, Heidi Klum was set to perform a striptease on The Tonight Show while wearing a diamond-studded, $8 million bra from Victoria's secret, as well as a pair of $3 million matching panties. Yes, you read that correctly—except that things didn't exactly go to plan.
During the interview segment, Klum suddenly realized that her bra had unclasped itself. She held her shirt with her hand, unsure what to do. Comedian Martin Short was also a guest on the show; together he and Leno used their suit jackets to create a makeshift shield for Klum to discreetly refasten the bra.
Sarah Silverman sings about how she "cheated" on Jimmy Kimmel
In 2008, Matt Damon served as the butt of a running joke in which Jimmy Kimmel would always "run out of time" before their interview segment. Vowing to get his revenge on Kimmel, Damon enlisted the help of Kimmel's then-girlfriend Sarah Silverman.
She and Damon appeared on an episode of Jimmy Kimmel Live! together to confess that she had been cheating on Kimmel with Damon via song. Although Kimmel pretended to laugh along, it was obvious that he was seething inside.
Danielle Bregoli wants you to "cash her outside, how 'bout dah?"
By now, we've all heard of the "cash me outside" girl, Danielle Bregoli, who managed to capitalize so heavily on one Dr. Phil episode that she's now worth millions. Bregoli, who now goes by Bhad Babie, went viral after appearing on the show.
Bregoli's mother didn't know how to handle her"car-stealing, knife-wielding" daughter anymore. In response to the audience's laughter, Bregoli yelled, "Cash me outside, how 'bout dah?" and the rest is history.
John Oliver pays off $15 million in strangers' medical debts
During a segment Last Week Tonight in 2016, John Oliver discussed how predatory entities will buy debt from banks for cents on the dollar, earning a profit by harassing debtors to cough up the money. He then announced his plan to fight back.
Oliver created his own "debt-buying company" and purchased $15 million in medical debt for a mere $60,000 by comparison. He noted how frightening it was to wield that much power over the lives of roughly 9,000 individuals. Fortunately, he announced that every cent of that debt would be forgiven. The stunt helped to draw attention to the issue.
Nicole Kidman had a crush on Jimmy Fallon, but he didn't take the hint
Talk about a missed opportunity. When Jimmy Fallon and Nicole Kidman recounted the story of when they first met through a mutual friend many years ago, the recently divorced Kidman revealed that she had a crush on Fallon and hoped something would blossom between them.
Fallon had no idea about any of this until Kidman dropped the bomb on national television. Overwhelmed by the discovery, he went to lay on the guest couch while Kidman took his seat at the desk.
Obama reads mean tweets about himself
One of Jimmy Kimmel's funniest bits is "Mean Tweets", a segment in which celebrities read mean tweets about themselves on video. One particular segment was groundbreaking for a number of reasons, the primary being that it involved none other than President Barack Obama.
It quickly became obvious that Obama had an excellent sense of humor, delivering each scathing tweet in his signature presidential voice. He even managed to get in a few shots at the commenters as well.
The unexpected reunion of Jesse and the Rippers
Full House may have gotten its own revival on Netflix, but the show's fictional band, Jesse and the Rippers, seemed to be gone forever—until they reunited for a live performance on Late Night with Jimmy Fallon.
Reprising his role as Uncle Jesse, John Stamos donned a mullet wig and sang their classic tune "Forever" along with a mix of other tunes. At the end of the performance, Lori Loughlin came out on stage and the two kissed in front of the audience.
Joaquin Phoenix has a total meltdown
During a 2008 interview with Joaquin Phoenix in which the actor was meant to promote Two Lovers, Letterman was beyond confused when Phoenix claimed that the movie would be his last, as he was moving on to become... a rapper? He was unable to answer most of the questions Letterman threw at him and seemed generally unwell throughout the segment.
Later, it was revealed that Phoenix was simply remaining in character for the mockumentary I'm Still Here, directed by Casey Affleck. However, he failed to disclose this information to Letterman.
Jimmy Kimmel pretends to be Jay Leno for the entirety of his show
One of the most intense late-night controversies occurred in early 2010 when Jay Leno took over The Tonight Show from Conan O'Brien after briefly leaving the program. Fans were furious, accusing Leno of forcing O'Brien off the air—including Jimmy Kimmel, who took the opportunity to dress up like Jay Leno and do an entire episode of his show posing as the talk show host.
While in character as Leno, he claimed that he would be taking over all the talk shows, not just O'Brien's. If it wasn't already apparent, Kimmel always disliked Leno, having openly proclaimed, "F*** him!" However, their feud drew to a close in 2017 when Leno was kind to Kimmel in the aftermath of his son's surgery.
Inebriated Andy Dick has problems with personal boundaries
In February 2007, people were discussing Ivanka Trump for reasons totally unrelated to politics. Trump appeared as a guest on Jimmy Kimmel Live! with comedian Andy Dick, who was quite obviously "out of it" on national television.
Dick wouldn't stop touching and groping Trump despite her clear discomfort. Kimmel tried to make Dick stop, but he refused, and eventually, security guards were called to forcefully remove him from the show.
Richard Branson dumps his drink on Stephen Colbert
When billionaire Richard Branson appeared on The Colbert Report in 2007 to promote Virgin American Airlines, the last thing anyone was expected was an on-air altercation. The segment ended before Branson had the chance to promote the airline by name. After throwing a tantrum, Branson threw water from his mug at the late-night talk show host.
Colbert, surprised, had a staffer retrieve a bottle of water for him to dump on Branson. It remains unclear whether this was staged or intentional, but most assumptions lean toward the former.
Michael Richards apologizes for racist rant
Once a beloved sitcom star on Seinfeld, Michael Richards' career went down the drain after going on a bizarre, rageful, racist tangent during a 2006 comedy show. The whole scandal was caught on camera.
Jerry Seinfeld arranged for Richards to appear on The Late Show with David Letterman and offer a public apology, but the audience kept laughing at him, even though Seinfeld begged them to stop. In the end, Richards never recovered, and the segment remains a cringeworthy moment in late-night television.
Drew Barrymore flashes David Letterman for his birthday
In 1995, Drew Barrymore was struggling to cope with fame, acting out in a number of ways—one of which happened right on the set of The Late Show. Letterman invited Barrymore on the program for an episode that would take place on his birthday.
Barrymore had a special "gift" she had planned for Letterman, which involved flashing him on-air. Letterman was shocked, and it made for some fantastic television. 26 years later, Letterman returned the favor (well, sort of) by surprising Barrymore on her own series, The Drew Barrymore Show. The gesture brought her to tears.
Conan trolls NBC after they fire him
The infamous fiasco between Jay Leno and Conan O'Brien has lived on in talk show history. Essentially, Leno left The Tonight Show to start his own program. O'Brien took over The Tonight Show, but Leno's show tanked so badly that NBC put Leno back into his old slot. Conan was taken off the show and paid millions just to leave.
On his way out the door, O'Brien figured he should waste some of NBC's money by running skits that weren't so much funny as they were very, very expensive. At one point, O'Brien unveiled a Bugatti, the most expensive car in the world, dressed up as a mouse. A song by the Rolling Stones played in the background, whose licensing fees are notoriously astronomical.
Jennifer Lawrence admits she almost asked out Seth Meyers
It took quite a few years, but in 2015, Jennifer Lawrence admitted to Late Night host Seth Meyers that she once had a crush on him. The Hunger Games star hoped Meyers would act first and ask her out, but she eventually took matters into her own hands, deciding that she would be the one to bite the bullet... before learning from someone in the wardrobe department that he was already engaged.
Oprah's interview with Meghan Markle and Prince Harry
Heads were reeling after Meghan Markle and Prince Harry's devastating tell-all interview with Oprah this year. Markle expressed to the talk show host that a royal family member expressed concern about how dark her baby's skin color would be, as well as the "constant" suicidal thoughts that plagued her. Needless to say, their relationship with Prince Harry's family is a complicated one.
Craig Ferguson becomes a U.S. citizen on The Late Show
Scottish comedian Craig Ferguson managed to ace the U.S. citizenship test on national television. Ferguson passed the test back in 2008, documenting the process on his CBS late-night talk show. As it turns out, he knew more about America than most of the people who were actually born there.
Chewbacca crashes Harrison Ford's interview
Prior to Harrison Ford's return to the Star Wars franchise, he was known to resist talking about the films. Still, Jimmy Kimmel insisted on grilling the star about his time on the franchise, even opening up the floor to the audience for questions—which happened to include Chewbacca. The silly segment led audiences to learn that Ford had fallen out with the Wookie after Chewbacca slept with his wife.
Jon Stewart puts Jim Cramer on blast
Mad Money host Jim Cramer learned that Jon Stewart takes no prisoners the hard way. Stewart had been criticizing the CNBC financial analyst for days leading up to his interview, and Cramer was totally unprepared for what Stewart was about to unleash upon him. In the end, the controversial episode forced Cramer to admit that he could have been better at his job. CNBC ratings dropped soon afterward.
David Letterman bans Harvey Pekar from the show
Although you may not recognize the name Harvey Pekar, he was once big news, having authored a successful comic book series called American Splendor, which was later adapted for film. Pekar went on Letterman's show several times, during which it was fairly obvious that the two men didn't get along. In 1988, things became heated between the two, and Letterman informed Pekar that he would never be invited back on the show, calling his comic a "Mickey Mouse magazine."
Andy Kaufman fights Jerry Lawler on Late Night
It's unclear whether or not Andy Kaufman's infamous fight with Jerry "The King" Lawler was real or not, but it seems quite likely, given their relationship. The two were invited onto Letterman's show to work things out, but Lawler ended up striking Kaufman across the face. Later, Kaufman delivered a profanity-laden rant against both Lawler and Letterman.
Wendy Williams faints while dressed as the Statue of Liberty
During her Halloween show in 2017, Wendy Williams collapsed on the ground. Despite the incident, Williams finished the show and later stated that she had been diagnosed with Graves Disease. "It was a beautiful fall," she said. "Unfortunately, we went to commercial, so nobody saw it."
Tom Cruise jumps up and down on Oprah's couch
During his infamous 2005 interview with Oprah, Tom Cruise was so excited about his relationship with Katie Holmes that he climbed onto the couch and began excitedly leaping up and down, shouting, "I'm in love with Katie Holmes!"
Nicole Kidman trashes Giada De Laurentiis' cooking on Ellen
When famed Food Network chef Giada de Laurentiis appeared on a segment of The Ellen DeGeneres Show alongside Nicole Kidman, it ended up becoming the most awkward six minutes in TV history. De Laurentiis talked down to Kidman so many times that Kidman eventually bit back, calling De Laurentiis' focaccia "a little tough," despite the fact that she knew she was "not supposed to criticize."
Whoopi Goldberg farts on The View
Whoopi Goldberg appeared to pass some serious wind on a 2014 episode of The View. However, Goldberg announced that the incident was allegedly a joke to cover up a sound effect. "There was a sound effect that we had never heard before," she said. "I'm thinking, 'Damn, that's weird, what can I do?' Oh, I know! I'm gonna pretend I let a little something go. As a joke." Sure, Whoopi. Whatever you say.
Joaquin Phoenix has some beef with The Joker cinematographer
Apparently, Joaquin Phoenix earned the nickname "Cher" due to his diva-ish tendencies. The actor was blindsided with the footage during an appearance on Jimmy Kimmel Live! "The constant whispering..." Phoenix can be seen saying. "Just shut the f*** up, dude. I'm trying to find something real." Phoenix was incredibly embarrassed opposite Kimmel. "That was supposed to be private," he commented.
Ellen forgets Katy Perry was once married to Russell Brand
Ellen DeGeneres was introducing Will You Perry Me?, a celebrity dating game which she planned to play with Katy Perry when the singer had to remind DeGeneres that she used to be Mrs. Brand. "December, you gave me some wedding gifts on the show?" Perry said.
Mel Gibson isn't very willing to address his past
In 2010, Mel Gibson sat down with WGN-TV Chicago's Dean Richards for a standard interview for his upcoming film Edge of Darkness. However, when Richards asked Gibson about his seven-year hiatus from acting following his anti-semitic rants and drunk driving incidents, Gibson lost it. "That's almost four years ago, dude," he said. "I've moved on, I guess you haven't." Then, after signing off, Gibson muttered a curse under his breath.
Kanye West's bizarre rant on Ellen
When Kanye West came on Ellen in 2016, the comedian didn't know he would hijack the show, going on a strange nearly seven-minute monologue about... well, everything.
"Picasso is dead. Steve Jobs is dead. Walt Disney is dead. Name somebody living who you can name in the same breath as them," West said. "Don't tell me about being likable. We've got 100 years here. We're one race. The human race. One civilization. We're a blip in the existence of the universe, and we're constantly trying to pull each other down. Not doing things to help each other. That's my point. I'm shaking, talking about it. I know it's daytime TV, but I feel I can make a difference while I'm here. I feel I can make things better through my skill-set. I'm an artist."
Charlie Sheen's infamous quote about "bi-winning"
In 2011, Charlie Sheen gave an interview with Good Morning America that proferred one of the best quotes of the century. "I am on a drug, and it's called Charlie Sheen," he said. "It's not available because if you try it you will die. Your face will melt off and your children will weep over your exploded body."
Perhaps even more famously, Sheen also delivered this line: "I'm not bipolar, I'm bi-winning."
Jessica Simpson's drunken appearance on Ellen
In 2017, Jessica Simpson stunned audiences by appearing on The Ellen DeGeneres Show while visibly intoxicated. Her stories made no sense, her words were slurred, and her behavior seemed erratic. In 2020, Simpson went on Today and explained that it was a "weak moment" for her. "I had started a spiral and I couldn't catch up with myself, and that was with alcohol," she conceded.
Nicholas Cage shares his experience with mushrooms
In 2010, Nicholas Cage explained to David Letterman that he went on a mushroom trip with his cat, Lewis. Unfortunately, Lewis seemed to enjoy snacking on the psilocybin mushrooms, and Cage decided that if Lewis was going to trip, Cage better join him. "I remember lying in my bed for hours, and Lewis was on the desk across from the bed for hours, staring at each other... not moving. But he would stare at me," Cage said. "And I had no doubt that he was my brother." Okay...
Oprah brings out the wagon of fat
To this day, Oprah claims she regrets this stunt she pulled for her "Diet Dreams" episode. She kicked off the episode by dragging out a Radio Flyer that held 67 pounds of fat—the amount of weight she'd shed to become a size 10. She did end up gaining back the weight, but this was surely one of the most iconic moments in talk show history.
Marlon Brando kisses Larry King on the lips
Sadly, TV legend Larry King passed away this year at the age of 87. One of his most memorable moments was the infamous kiss he shared with Marlon Brando, which happened at the end of the interview with the two men singing "Got a Date with an Angel".
Tyra Banks tells everyone that they can "kiss her fat a**!"
When Tyra Banks delivered this infamous monologue, it became one of the most famous moments in daytime talk show history. Banks addressed a photo that had surfaced of her on the beach which sparked headlines like "Thigh-ra Banks" and "America's Next Top Waddle". Tyra then delivered this emotional, powerful statement:
"I love my mama. She has helped me to be a strong woman so I can overcome these kinds of attacks, but if I had lower self-esteem, I would probably be starving myself right now. But, that's exactly what is happening to other women all over this country. So, I have something to say to all of you that have something nasty to say about me or other women who are built like me...women whose names you know, women whose names you don't, women who've been picked on, women whose husbands put them down, women at work or girls in school, I have one thing to say to you: kiss my fat ass."
Daniel Radcliffe raps Blackalicious's "Alphabet Aerobics"
Is he an actor, a wizard, or a rapper? Well, the answer is all three. In 2014, Harry Potter himself delivered an impressive version of Blackalicious's complicated tongue-twister, "Alphabet Aerobics." Radcliffe's performance is certainly one for the books—he didn't miss a single syllable!
Katharine Hepburn redecorates the set of The Dick Cavett Show
In 1973, the notoriously bossy movie star arrived at Cavett's studio still unsure whether or not she would agree to be interviewed. Once there, Hepburn rearranged the furniture, complained about the carpet, and even asked for the set to be repainted another color—all without realizing the cameras were already rolling.
Bette Midler says goodbye to Johnny Carson
The day before his retirement, the king of late-night television was serenaded by Bette Midler, who warbled "One for My Baby (and One More for the Road)" until Carson was nearly in tears. Midler could barely hold it together herself, fleeing the set immediately after her song ended.
Jason Sehorn proposes to Angie Harmon
When Jay Leno started plying model and actress Angie Harmon with questions about her boyfriend, New York Giants cornerback Jason Sehorn, Harmon was none the wiser. Much to everyone's surprise—most of all Harmon's—Jason came walking out on stage and dropped to one knee. The two tied the knot and stayed together for 13 years.