10 Late-Night Interviews Living On in Infamy, Including That Madonna Appearance (VIDEO)

Madonna made headlines 30 years ago when she dropped the F-bomb 14 times (including her description of host David Letterman as a “sick f—k”), made sexual innuendos, and refused to get off the stage during her Late Show appearance on March 31, 1994.

Arguably, however, Letterman fired the first shot while introducing Madonna, saying that the pop star had “slept with some of the biggest names in the entertainment industry.”

In 2015, Madonna told Howard Stern she was in “a weird mood” that day in 1994. “I was dating Tupac Shakur at the time, and the thing is, he got me all riled up about life in general,” she said.

As you’ll see below, though, Madonna’s Late Show appearance is one of many late-night interviews that took a controversial, scandalous, or chaotic turn — and two even went down on the same night.

Jerry Lawler & Andy Kaufman on Late Night With David Letterman

Letterman had barely started his Late Night tenure when he hosted wrestler Jerry Lawler and Taxi actor Andy Kaufman on the show in 1982. Lawler and Kaufman’s purported feud boiled over during that appearance, and Lawler slapped Kaufman so hard that Kaufman fell out of his seat. Many years later, fans learned the entire feud was a performance, per Bleacher Report.

Madonna on The Late Show With David Letterman

“David Letterman knew I was going to do it,” Madonna later said of her obscenity-laden 1994 Late Show interview, per People. “I talked to the producers of the show. Everybody was like, ‘This will be really funny if you say f—k a lot, they’ll just keep bleeping you.’ Well, I came out and started doing it, and David freaked out. The way he introduced me was derogatory, so my whole thing was, ‘OK, if that’s how you want to play it, you cannot beat me at this game.’”

Bobcat Goldthwait on The Tonight Show With Jay Leno

In 1994, just weeks after causing havoc on the set of The Arsenio Hall Show in an apparent protest of Paramount’s treatment of Arsenio Hall, this stand-up comedian one-upped himself by lighting his chair on fire on the Tonight Show set. Host Jay Leno and guest Lauren Hutton doused the flames, and Leno later said he scolded Goldthwait off camera. Goldthwait eventually pled no contest to a charge of recklessly causing a fire and was ordered to pay $3,880 in fines and to record public-service announcements for a local burn center, per the Los Angeles Times.

Drew Barrymore on The Late Show

A then-20-year-old Drew Barrymore gave Letterman a shock in 1995 when — after describing her patronage of a “nude art performance art space” — she climbed on his desk and flashed him. After becoming a talk show host herself, Barrymore reflected on that moment with Letterman in a 2021 episode of The Drew Barrymore Show. She said she surprised herself in that moment, and she thanked Letterman for “let[ting] something innocent and spontaneous be innocent and spontaneous.”

Jennifer Aniston on The Late Show

David Letterman sucks on a strand of Jennifer Aniston's hair, April, 1998. pic.twitter.com/c4MVuPX92o

— CCTV IDIOTS (@cctvidiots) October 29, 2023

Jennifer Aniston was trying to promote her film The Object of My Affection on The Late Show in 1998 when Letterman put a tress of her hair in his mouth for reasons only he can explain, making the Friends star visibly uncomfortable. That clip resurfaced online in 2023, with viewers calling the host’s antics “disturbing” and “not OK,” as Glamour reported at the time.

Ryan Phillippe on The Tonight Show

When Ryan Phillippe reflected on his days playing gay teenager Billy Douglas on One Life to Live during a 2008 Tonight Show appearance, Leno asked him to demonstrate his “gayest look” on camera. The actor refused, saying, “That is so something I don’t want to do.” GLAAD called out Leno’s “thoughtless attempt at humor,” and Leno later apologized, saying he “certainly didn’t mean any malice” but “agree[d] it was a dumb thing to say,” per People.

Joaquin Phoenix on The Late Show

Joaquin Phoenix confused fans with his disheveled appearance, mumbling speech, and talk of pivoting from acting to hip-hop on The Late Show in 2009. As it turns out, it was all a bit for the 2010 mockumentary I’m Still Here, directed by Casey Affleck. “It’s a terrific performance, it’s the performance of his career,” Affleck, then Phoenix’s brother-in-law, later told The New York Times.

Lindsay Lohan on The Late Show

Lindsay Lohan called out Letterman for needling her with questions about her multiple rehab stays during her 2013 Late Show sit-down, pointing out that those questions weren’t in the pre-interview. Letterman didn’t relent, however, and Lohan beseeched him to move on. (“We’re here for a movie,” she said. “Let’s stay on the positive.”) That interview came under fire again in 2021, when social media users called Letterman’s line of questioning “vile” and “manipulating,” per Entertainment Weekly.

Donald Trump on The Tonight Show Starring Jimmy Fallon

Jimmy Fallon playfully tousled Donald Trump’s much-discussed hair in a 2016 episode of his version of The Tonight Show, after which viewers criticized Fallon for being too soft on the then-Republican presidential nominee during the interview. “I did not do it to ‘normalize’ him or to say I believe in his political beliefs or any of that stuff,” Fallon later said on The Hollywood Reporter’s Awards Chatter podcast. “I made a mistake. I’m sorry if I made anyone mad. And, looking back, I would do it differently.”

Jimmy Kimmel on The Late Late Show With James Corden

That same night, James Corden hosted fellow late-night host Jimmy Kimmel for a game of “Spill Your Guts or Fill Your Guts” on The Late Late Show (the very same segment activists cited as they said the game perpetuated anti-Asian racism). Toward the end of the segment, Kimmel challenged Corden to name two of his camera operators, and Corden could not. Years later, this clip resurfaced amid reports of Corden’s less-than-affable off-camera behavior.