1. Drew Barrymore Flashes Letterman
In this famous 1995 appearance on “The Late Show with David Letterman,” Drew Barrymore climbed up on his desk, performed what she believed to be a sexy dance, and flashed Letterman in celebration of his birthday. It was yet another awkward attempt to shake the innocent image of her E.T. stardom. Mission accomplished, Drew.
2. Joaquin Phoenix Bizarre on Letterman
With a Sasquatch beard, dark sunglasses, and an eerily unresponsive demeanor, Joaquin Phoenix drew hesitant laughter from the audience during his Letterman appearance on February 10, 2009. Phoenix was impervious — more like oblivious — to Letterman’s teasing, returning his one-word answers with a blank face.
3. Danny DeVito Drunk on The View
A visibly and admittedly inebriated Danny DeVito charmed the ladies of “The View” in his 2006 appearance, stumbling on set and slurring his speech. During the chaotic interview, DeVito joked about having sex with his wife in the White House and referred to President George W. Bush as “numb nuts.”
4. Michael Richards Tries to Apologize for his Racism on Letterman
During his 2006 appearance via satellite on the “Late Show with David Letterman,” Michael Richards of “Seinfeld” fame apologized for the uncontrollable racist tirade he unleashed at a comedy club days earlier. When Richards heard scattered laughter in response to his solemn apology, he grew even more uneasy. Talk about a bad week.
5. Letterman Lectures Paris Hilton on her Jail Time
Fresh from a brief stint in prison, Paris Hilton faced insistent grilling about the incident from David Letterman during a 2007 interview. Letterman’s prodding was so relentless and Hilton’s discomfort so palpable that we actually started to sympathize with the girl…until we realize it was Paris Hilton.
6. Bruno Gives Conan O’Brian a Lapdance
Sacha Baron Cohen appeared on “The Tonight Show” as Bruno, a character who performs outrageous homoerotic stunts for publicity. While dancing to Lady Gaga, Bruno began removing his clothes, climbed atop the desk, straddled Conan, and — as an impromptu maneuver in an otherwise planned stunt — placed Conan’s hands on his crotch. Awkward!
7. Crispin Glover Nearly Kicks Letterman in the Face
In an infamous 1987 interview with David Letterman, character actor Crispin Glover, best known for his eccentric and creepy roles, appears either in-character or high on LSD. Donning striped pants, high platform shoes, and what seems to be a messy wig, a stammering Glover acts nervous and uneasy until he musters the courage to stand up, flex his biceps, and nearly kick Letterman in the face as a comic display of virility.
8. Richard Simmons’s Exploding Steamer on Letterman
During a 2006 appearance on Letterman, flamboyant fitness guru Richard Simmons demonstrated his food steamer for the audience, only to have the machine unexpectedly explode and emit a flame dangerously close to his face. It was probably the only time Simmons was not the most flaming thing in the room… but probably not the first time something exploded in his face.
9. Things Get Heated Between O’Reilly and Letterman
Letterman knew that this 2009 interview with outspoken conservative Bill O’Reilly would be a far cry from light fare, saying before the interview, “I wish I was smart enough to make him look ridiculous.” The two battled it out on various topics, from the war in Iraq to Rush Limbaugh, and eventually Letterman wrapped up his feelings for his opponent with the terse summation, “I think of you as a goon.”
10. Rosie O’Donnell and Elisabeth Hasselbeck Quarrel on The View
Before this newsworthy dispute on “The View” in 2007, Rosie O’Donnell and Elisabeth Hasselbeck were already established at opposite ends of the political spectrum. During the incident, O’Donnell and Hasselbeck quarreled over O’Donnell’s controversial statement about U.S. troops in Iraq, and all hell broke loose from there. Joy Behar vainly attempted to cool down the heated hosts, but “The View” producers cleverly employed a split-screen (seen below) to prod the conflict.
11. James Brown High on Sonya
In this infamous 1987 interview on the talk show “Sonya,” viewers everywhere knew James Brown must have been on something when he sang “Living in A-merrr-i-ca!” in response to a question about his wellbeing. Brown’s incoherence led many to suspect that he was on drugs; after all, singing non sequiturs is not the best way to convince people of your sobriety.
12. Tom Cruise’s Couch-Jumping on Oprah
In perhaps one of the most famous talk show moments of the decade, Tom Cruise, in a frightening fit of enthusiasm, leaped onto a couch to proclaim his love for new girlfriend Katie Holmes. Cruise’s bizarre excitement deservedly spawned parodies, many of which could not trump the weirdness of the original.
13. Profane Madonna on Letterman
In what is considered the most censored American talk-show interview of all time, Madonna dropped thirteen F-bombs (including a reference to Letterman as a “sick f***”), playfully but rudely provoked Letterman, used a series of double entendres, and ultimately refused to leave the set. Needless to say, this 1994 interview resulted in some of the highest ratings in late night TV history.
14. Farrah Fawcett Spaced-out on Letterman
During this 1997 interview, Farrah Fawcett proved that the actresses on “Charlie’s Angels” really are as bright as they seemed. Throughout the interview, Fawcett appeared distracted and a bit stupefied, often searching for the right word for minutes on end. Months later, Fawcett admitted to Howard Stern that her silly behavior was intentional. Needless to say, she delivered a convincing performance.
15. Courtney Love Flashes Letterman
In yet another sad attempt to get attention by exposing her breasts, Courtney Love flashed David Letterman in 2004 as a tribute to Drew Barrymore’s famous stunt. Singing “Danny Boy” off-key (why?) and clumsily climbing onto Letterman’s desk, Love made this homage to Drew an expectedly awkward parody of the original.
16. Tom Cruise Tries to Argue Intelligently and Fails
Following his couch-jumping incident and general public insanity, Tom Cruise decided to give the people a little more fodder for ridicule with this 2005 Matt Lauer interview. After Cruise openly criticized Brooke Shields for using psychiatric medication as a treatment for postpartum depression, Lauer thought it necessary to question the Prince of Scientology about his need to get in everyone’s business. What ensued was a classic example of how not to defend your inane beliefs.
17. Jon Stewart Berates Hosts of Crossfire
Comedian Jon Stewart was uncharacteristically serious during this 2004 appearance on CNN’s debate show “Crossfire.” While both hosts tried to steer discussion toward current events, Stewart focused on the quality of the show itself, insisting that the hosts “stop hurting America” with their “partisan hackery.” “Crossfire” was cancelled months later. Way to kick partisan ass, Jon!
18. David Blaine Creepy on the UK’s “GMTV”
David Blaine is not the most outgoing guy in the world, but during this 2002 interview in the UK, he was downright creepy. Throughout most of the interview, Blaine stared blankly into the eyes of his interviewer, barley muttering one-word answers; he then revealed an eye drawn on his left hand, which he claimed “protects him from death.” Uhh, I don’t think I’ll be able to sleep tonight.
19. Andy Kaufman Gets Beat Up on Letterman
Prior to this 1982 incident, Andy Kaufman and professional wrestler Jerry “The King” Lawler had been feuding in the wrestling world. When Letterman invited the two on his show to air their differences, Lawler smacked Kaufman in the face, sending him off his chair and, well, to the moon. Kaufman responded with a profanity-laden tirade that caused NBC to nearly keep him off the air for good.
20. Bobcat Goldthwait sets Leno’s Set on Fire
Wild, scratchy-voiced comedian Bobcat Goldthwait once again undermined his mental fitness when he set fire to Jay Leno’s guest chair in 1994. This was no wacky accident. Bobcat squirted lighter fluid on the chair before he set it aflame. He was banned from the show for his destruction, but somehow this crazy sonuvabitch still finds work in Hollywood.
21. Hugh Grant Admits to Soliciting Prostitution on Larry King
Who can forget the bumbling Brit’s run-in with the law in 1995, teaching all of us that, yes, charming movie stars need hookers, too. Unlike most celebrities, Grant went public with his “transgression,” admitting to Larry King that he had done something “dishonorable, shabby and goatish.” Nice diction, Hugh. Where I come from, we just call that a ten dollar BJ.
22. Letterman Admits His Affair
In October of 2009, David Letterman revealed that he had affairs with female staff members and that he paid a phony $2 million to an extortionist who threatened to reveal such information. It was quite eerie to see the host in a rare moment of weakness, though he still managed to draw huge laughs from the audience, both intentionally and unintentionally. Only Letterman could make extortion and infidelity hilarious.
23. Kimmel mocks Leno to his face on The Jay Leno Show
In perhaps the most uncomfortable (see: hilarious) moment of NBC’s late night fiasco, late night host Jimmy Kimmel saw an opportunity to openly mock Leno on his own show, and had no problem seizing it. When Leno asked him “What’s the best prank you ever pulled” during his “10 at 10″ segment, Kimmel replied “I told a guy that—five years from now — I’m gonna give you my show. And then when the five years came, I gave it to him, and then I took it back almost instantly.” He was referring, of course, to Leno’s reclaiming of “The Tonight Show.” Kimmel continued to riff on the host while Leno had to grin and bear the humiliation.
24. Sean Connery tells Barbara Walters It’s Okay to Hit Women≥
During this unforgettable 1987 interview, when Barbara Walters asked Connery about his comments on hitting women, he calmly nodded his head and affirmed our suspicions by saying “I haven’t changed my opinion.” The suave actor asserted that a woman “merits” a smack to the face if she continues to provoke a man after an argument has been resolved. Look, I know what you’re thinking, but Sean Connery is not a monster: he advocates the open hand technique as opposed to a closed fist. What a charmer.
25. Howard Stern Brings Lesbians onto the Tonight Show
In 1995, shock jock Howard Stern appeared on “The Tonight Show” and, in regular Stern fashion, brought some uninvited guests. Two hot blond models joined Stern (do they just follow him around everywhere he goes?), causing general uproar and pissing off Jay Leno. The chaotic interview caused media headlines when the models kissed each other, a then provocative display.
