Top 10 Times Celebs Broke Late Night Hosts
#10: Bradley Cooper
“The Tonight Show Starring Jimmy Fallon” (2014-)
Way back in 2014, Jimmy Fallon brought on the star then best-known for “The Hangover” and “Silver Linings Playbook” to talk about his Broadway return. But things fell apart quickly. Fallon’s habit of breaking into fits of laughter soon got the best of him. A mention of the real Elephant Man’s bones had the two unable to get through the rest of the segment without laughing. They had to retake this several times. This went on so long that the show’s YouTube channel actually released an extended version of what we saw on the actual episode. It took almost 10 minutes for them to get their act together.
#9: Drew Barrymore
“Late Show with David Letterman” (1993-2015)
That’s one way to wish someone a happy birthday. In her wilder and more unpredictable days, the actress turned daytime talk show host had an infamous 1995 appearance on “Late Show.” Drew Barrymore threw caution to the wind, got up on David Letterman’s desk, doing a suggestive dance for him. That included a mid-song flashing. Letterman’s thousand-yard stare let the audience know it was okay to laugh with them. Though it was widely publicized at the time, and certainly took Letterman by surprise, the two look back on it as a starting point for a genuine friendship.
#8: Nicole Byer
“Conan” (2010-21)
This standup’s not-safe-for-work appearance on “Conan” had the host changing subjects very quickly. It started with Nicole Byer’s one very simple criteria for what she wants in a romantic partner. Then it went downhill from there. O’Brien practically had to shut down and reboot himself. Still, every time he tries to talk about something else, her vulgarity shines through. It gives him plenty of opportunities for comedy points once he gets over his shock. His playful embarrassment and desperation to keep things on track and her cheerful, foul-mouthed honesty make a great pairing.
#7: Meryl Streep
“Late Show with David Letterman” (1993-2015)
It’s not every day a guest shares breaking news on a late-night show. Meryl Streep explained her nervousness in Letterman’s chair by saying it was odd to be on his show so soon after their affair. Seeing that it’s three-time Oscar winner Meryl Streep, she delivers that bit of information with such seriousness that it’s hard not to believe her. Luckily, it makes the audience chuckle so much that he has time to load up a well-timed response of his own, but she definitely got him. Streep is a natural on talk shows. Even over Zoom, her unforgettable COVID-era appearance with Stephen Colbert gave us a great moment.
#6: Elaine Stritch
“Late Show with David Letterman” (1993-2015)
The cantankerous Broadway legend performed an entire three-act play on a 1996 episode of “Late Show with David Letterman.” Elaine Stritch would interrupt the show to play out a scene as a rich woman in love with her virile young pool boy. Of course, she’s cast an incredulous Letterman in the part of the pool boy. While clearly planned, the skit saw the host reacting with such believable shock and stammering fear that it seemed like a genuine interruption. Stritch’s electrifying and intimidating persona is definitely enough to throw even a seasoned pro off their game.
#5: Cher
“Late Night with David Letterman” (1982-93)
Through the years, the tension between David Letterman and Cher gave her numerous appearances on his late-night shows an extra layer of drama. Sometimes it seemed romantic. Other times, that wasn’t the case. During her first guest spot with him in 1986, she explained why she had reservations about being on his show, despite being asked numerous times. She saw how he treated guests he didn’t seem to like, and didn’t want to subject herself to an embarrassing interview. He knew from that point on that he had to be on his toes with her. Over the years, their dynamic eased into an irreverent and often flirty friendship.
#4: Helen Mirren
“The Late Show with Stephen Colbert” (2015-26)
Oscar-winning British actress Helen Mirren was clearly a Colbert fan. When the host went to greet her for her entrance, she planted the smoothest, old movie kiss on him we’ve ever seen. She took her seat, as usually happens on these shows. Colbert stood in place, frozen by what had just happened. Only once he wiped the sweat from his brow could he work up the nerve to speak. Mirren didn’t help the situation, explaining that she had been dreaming of that kiss for years. It certainly filled the rest of the segment with some steamy tension, even for late night.
#3: Nicole Kidman
“The Tonight Show Starring Jimmy Fallon” (2014-)
Finding out you missed your chance with an A-list star as gorgeous and magnetic as Nicole Kidman is devastating enough. Jimmy Fallon found that out in front of an audience of millions. Watching him as she breaks the news that their one-time hangout was what she assumed to be a date is like seeing a child realize in real time that there’s no Santa Claus. He even falls to the floor, mortified, before pretending to walk off. Who could blame him, really? Fallon’s not usually speechless, but this was a lot to process in the moment.
#2: Jane Fonda
“The Tonight Show Starring Johnny Carson” (1962-92)
Even the king of late night had guests who left him speechless. During a 1989 “Tonight Show” appearance, Academy Award-winning actor and activist Jane Fonda referenced a longtime urban legend about one of Johnny Carson’s previous guests. For years, an incredibly cheeky story about Carson’s response to Zsa Zsa Gabor bringing a cat on stage with her was retold like a campfire story. Fonda finally helped put the rumor to rest. However, it’s hard to tell if Carson’s signature deadpan response was for real at that moment. He looks like a man teetering on the edge of violating censorship regulations as the audience falls apart with laughter.
#1: RuPaul
“The Tonight Show Starring Jimmy Fallon” (2014-)
How do you make a late-night host’s entire life and career flash before his eyes? RuPaul found a way. When Jimmy Fallon had the absolute cheek, nerve, gall, audacity, and gumption to call RuPaul a “drag queen,” RuPaul’s feigned offense had him thinking he was about to be canceled. But Ru’s objection wasn’t “drag queen.” She insisted instead that she was the “queen of drag.” Fallon laughed once the adrenaline wore off and offered a stammering apology. Ever the diplomat, Ru just threatened to key his car after the show. Recalling the incident after it went viral, the host joked that his career was over.
Which late-night host handles uncomfortable moments the best? Tell us in the comments.
