While it’s often marketed as a lighthearted confluence of entertainment, celebrity, and comedy, late-night television has occasionally found itself at the center of national scandal. From explosive interviews to unscripted scandal, these late-night moments have cemented their place in television history.

1. David Letterman Reveals Affairs
2. Jack Parr Walks Off The Tonight Show
3. Drew Barrymore Flashes David Letterman 
4. Abel Ferrera’s Bizarre Conan O’Brien Interview 
5. Donald Trump’s 2016 Appearance on The Tonight Show

David Letterman Reveals Affairs

In September 2009, CBS News producer Joe Halderman attempted to blackmail late-night television host David Letterman by threatening to reveal details of Letterman’s extramarital affairs with female employees at his show. Halderman, an ex-boyfriend of Letterman’s longtime assistant Stephanie Birkitt, threatened to reveal Letterman’s affairs with Birkitt and others unless the late-night host agreed to paying him $2 million.

Instead of agreeing to the payment, Letterman revealed the affairs himself on his show, foiling Halderman’s plot. The Emmy Award-winning producer subsequently pleaded guilty to charges of attempted grand larceny and was sentenced to six months in jail. After serving just four months of his sentence, Halderman was released in September 2010. 

Jack Parr Walks Off The Tonight Show

Decades before it was hosted by the likes of Jay Leno, Conan O’Brien, and Jimmy Fallon, The Tonight Show was helmed by comedian Jack Paar. Serving as the show’s host from 1957 to 1962, Paar memorably walked off set during a February 1960 episode taping after learning a bathroom joke he’d made the evening before was censored by the program’s network. 

Afterwards, Paar refused to return to the show for weeks until NBC issued him an apology and granted him permission to tell the joke live on the air. 

After Paar left the show in 1962, hosting duties were handed over to comedian Johnny Carson. 

Drew Barrymore Flashes David Letterman 

On April 12, 1995, then-20-year-old actress Drew Barrymore made a now notorious appearance on The Late Show with David Letterman. Having appeared on the cover of Playboy magazine just a few months prior, Barrymore’s 1995 appearance coincided with a massive image overhaul for the E.T. child star. 

After hopping up onto the host’s desk to dance for him, Barrymore quickly flashed Letterman, leaving the late night host uncharacteristically speechless. 

More than 30 years later, Barrymore would have Letterman on her own talkshow Drew to discuss the incident. Reflecting on their “very special engagement,” Barrymore told Letterman she’d recently recreated the interview on The Late Show with Stephen Colbert as an homage to him. 

Abel Ferrera’s Bizarre Conan O’Brien Interview 

While hosting NBC’s Late Night with Conan O’Brien in 1996, O’Brien invited director Abel Ferrera onto the show for an interview. Known for his eccentric behavior, Ferrera smoked and slurred his words throughout the interview, providing nonsensical answers to Conan’s lighthearted questions. 

During a 2018 appearance on Dax Shepard’s podcast Armchair Expert, Conan named Ferrera as his worst guest of all time. O’Brien went on to tell Shepard that Ferrera had even tried to flee the set prior to his interview.

Donald Trump’s 2016 Appearance on The Tonight Show

Smack in the middle of one of the most contentious presidential races in American history, The Tonight Show’s Jimmy Fallon invited then-Republican nominee Donald Trump onto his show for a painfully tone deaf appearance.

After Fallon spent the first few minutes of the interview fawning over Trump, he playfully asked the now-president if he could mess up his hair. Following Trump’s appearance, Fallon was criticized for conducting what many saw as a playful, “humanizing” interview with Trump.

After initially trying to justify his actions, Fallon apologized for the imbroglio in 2018, garnering a few customary hate tweets from the president. 

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