8 Unbelievable Talk Show Moments — Drew Barrymore Did What to David Letterman?

Drew Barrymore has gone from child star to rebellious teen to A-list actor to talk show host whose biggest crime is maybe sitting a little too close to her guests. But 30 years ago on April 12, Barrymore’s talk-show antics were the talk of the town for a more NSFW reason.

In the timeline below, read about Barrymore’s infamous Late Show appearance and other outrageous late-night talk show moments, including guest behavior that turned offensive.

1987: Crispin Glover makes Letterman leave his own set.

What should have been a routine movie promotion on David Letterman’s Late Night took a turn for the bizarre in 1987 when River’s Edge actor Crispin Glover emerged wearing platform shoes and a wig and starting ranting about the press and his reputation. Then Glover did a high kick that nearly hit Letterman, and the talk show host walked off stage.

In a 2007 talk with Interviewing Hollywood, Glover marveled at the continuing chatter about that particular interview but didn’t elaborate on his oddball behavior. “I like there to be an air of mystery,” he said. “If I just said exactly what it is, it’s not interesting. It doesn’t let people think about things.”

1994: Jim Everett flips a table on Talk2.

NFL quarterback Jim Everett flipped a table and pushed Talk2 host Jim Rome to the floor of the ESPN2 talk show’s studio in 1994 after Rome repeatedly called Jim “Chris” in reference to Chris Evert. (Apparently, Rome considered it a diss, and Everett found it offensive, for Rome to liken Everett to tennis champion Chris Evert, a woman.)

Rome discussed that altercation in a 2021 interview on The Dan Le Batard Show, saying it wasn’t staged and expressing remorse for goading the football athlete. “I did it,” he said. “It was my fault. I own it.”

1995: Drew Barrymore flashes David Letterman.

Barrymore celebrated Letterman’s 48th birthday on April 12, 1995, by jumping on his Late Show desk, swishing her hips from side to side, and raising her top to flash him.

“I had no plan of doing that,” Barrymore said in 2021 as she welcomed Letterman to her talk show. “It was one of those moments in my life where I felt like a magnet was pulling me, and it was all very playful and well-intended, and I just had no idea where it was going. I couldn’t almost believe it was happening. I think a little bit I was on the ride, too, wondering what was going to happen next.”

2004: Courtney Love flashes Letterman.

Courtney Love pulled a Barrymore nearly a decade later, clambering onto Letterman’s desk and flashing the talk show host in 2004. The Hole singer was arrested later that day on assault and reckless endangerment charges after allegedly hitting a nightclub patron, as The New York Times reported at the time.

Love explained herself in 2010 as she made a sober return to the Late Show. “I took off my top because Drew Barrymore had done it when she was 19, and I was so out of my mind, I thought that I was 19, and I was actually 39,” she said. “It was just a different time.” (Note: Barrymore was actually 20 at the time.)

2007: Andy Dick gets handsy with Ivanka Trump.

During a 2007 episode of Jimmy Kimmel Live!, comedian Andy Dick repeatedly touched the leg of fellow guest Ivanka Trump, even as she tried to brush his hand away. Host Jimmy Kimmel tried to get Dick to stop, and when Dick wouldn’t, Kimmel and his security guards dragged him off set.

Dick cited the incident in a 2017 Instagram caption, writing, “The time I ‘groped’ Trump’s daughter, Ivanka, on Jimmy Kimmel Live. Her legs were sparkling, and I was trying to see if the glitter would wipe off. I also mistakenly thought she would date me. I was jokingly carried off by security. Is anybody going to carry Trump off? No joke. Confusing times.”

2009: Artie Lange goes on profane tirade on Joe Buck Live.

In the premiere episode of the short-lived HBO talk show Joe Buck Live in 2009, comedian Artie Lange peppered the conversation with homophobic jokes directed at NFL star Tony Romo and fat jokes directed at pop singer Jessica Simpson.

Lange addressed the incident in his 2013 memoir, Crash and Burn, per Uproxx. He wrote, “I know a lot of my fans, plus people who don’t like Joe Buck, still think this performance was f***ing genius, and I suppose some of it was, but let’s be honest, it’s a guy having a meltdown in an inappropriate way in the wrong place. That appearance represents what drugs had become in my professional life.”

2009: David Letterman reveals blackmail attempt over affairs.

Letterman got personal in a 2009 episode of The Late Show, telling audience members someone was trying to extort him over his workplace affairs with staff members, which the host then copped to.

“The [allegation] was that I have had sex with women who work for me on this show,” Letterman said on air. “Now, my response to that is, yes, I have. I have had sex with women who work on this show. And would it be embarrassing if it were made public? Perhaps it would. Perhaps it would, especially for the women.”

2010: Gordon Ramsay makes lewd comments toward Sofía Vergara.

When Sofía Vergara sat down for a 2010 interview on The Tonight Show With Jay Leno, fellow guest Gordon Ramsay made discomfiting jokes about her screaming in the bedroom and fitting things into her mouth. Vergara looked uncomfortable, but the celebrity chef prattled on, even slapping Vergara on the thigh and mocking the name of Vergara’s son, Manolo.

The interview resurfaced in 2019 when social media users criticized Ramsay for his conduct toward the Modern Family star, but he has yet to comment publicly about his behavior.