The Worst "Late Night" Guest Conan O'Brien Ever Had
Sarah Rodriguez
Updated on February 23, 2026
After nearly 30 years appearing on our TVs after hours, Conan O'Brien announced on Nov. 17 that he would be leaving late-night television in June 2021. Following a 16-year stint as the host of Late Night With Conan O'Brien, O'Brien had a decade-long run on TBS with Conan, and now he's moving over to HBO Max to start a new chapter. Throughout the host's TV tenure, he's interviewed thousands of celebrity guests, but one stands out as the worst of the worst for Conan O'Brien: Abel Ferrara. To see why Ferrara was the most terrible guest, read on, and for the celebrity another famous interviewer banned, check out The One Guest Anderson Cooper Banned From His Show.
Before his infamous 1996 interview with Ferrara, O'Brien says chaos ensued. "He fled during the show before his segment," O'Brien said during a Nov. 2018 interview on Dax Shepard's Armchair Expert podcast. "He ran away, got on the elevator, and was out on the street running away."
What followed was a chase between one of the show's producers, Frank Smiley, and Ferrara. Ultimately, Smiley won and was able to get the filmmaker back in the studio, but the trouble didn't end there. "He came on camera against his will, came out, and started yelling at me," said O'Brien. During the interview, Ferrara was slumped over in his chair, mumbling non-answers as O'Brien tried to salvage their disastrous chat.
O'Brien described the experience as "If you ate 15 cloves of garlic, you wouldn't say that was a great experience, but you'd remember it."
And the interview wasn't only memorable for the late-night host, either; actor William Dafoe brought up the infamous incident when he was on Conan in Nov. 2019.
"I always remember your interview with my good friend Abel Ferrara. That's a classic," said Dafoe. "You did your best." O'Brien then shared the story with the audience, and Dafore mimicked Ferrara's posture during the interview. "That was a fantastic, crazy, strange moment," O'Brien said, before moving on.
During his interview on Shepard's podcast, O'Brien put some of the blame for Ferrara's behavior on classic brooding actors like James Dean and Marlon Brando.
"It's the tail wagging the dog," explained O'Brien. "'If I'm difficult, I must be a genius.' No! Be a genius first, and then if the side effect is you're difficult, we'll accept it. Don't be difficult in the hopes that maybe you're a genius."
Ferrara is hardly the only unsavory celebrity guest in TV history, of course. Here are some other celebrities that hosts have dubbed their least favorite, and to see who Ms. Winfrey liked the least, check out Oprah Says This Was the Worst Guest She Ever Had.
Read the original article on Best Life.
1 Hugh Grant
Jon Stewart once said actor Hugh Grant was the worst guest he ever had on The Daily Show. During a sold-out fundraiser, Stewart said Grant spent his time in the studio complaining. However, Grant promptly acknowledged the error of his ways once he learned Stewart was upset by his behavior.
And to see which movie Grant said caused him to leave Hollywood for a bit, check out Hugh Grant Says This Movie Almost Killed His Career.
2 Frank Sinatra Jr.
Frank Sinatra Jr., the son of legendary singer Frank Sinatra, didn't make a great impression during his time on Today. While Hoda Kotb was playing "Plead the Fifth" on Watch What Happens Live with Andy Cohen in Oct. 2020, Kotb's former Today co-host, Kathie Lee Gifford, asked her, "Who do you think was my least favorite guest of all time? And I bet it was yours, too."
"It's Frank Sinatra Jr. It was the worst guest we've ever had, bar none," Kotb responded immediately. "He had a book he was promoting, and he didn't want to talk about it, so he didn't say anything. So weird."
The pair was not being dramatic; the interview is as awkward as the hosts claim. And for more celebrity content delivered straight to your inbox, sign up for our daily newsletter.
3 Russell Brand
Chelsea Handler, comedian and former host of Chelsea Lately, told Grazia, "The only person who was a pain in the a** was Russell Brand. He stopped all of our production schedules because he needed three espressos before he could even come on for his interview." To see which star was named the worst host of the most iconic late-night show, check out This Is the Worst "SNL" Host of All Time, Cast Says.
4 Macy Gray
While on Watch What Happens Live in 2014, during a game of "Plead the Fifth," Cohen asked Craig Ferguson to reveal the worst guest he ever had on The Late Late Show with Craig Ferguson. After giving it some thought, Ferguson pointed to singer Macy Gray, who appeared on his talk show in 2005. "I think she was in a bad mood that night," he said. "I don't think she's a bad person … and I was very new and I couldn't handle it. But now I think it would be OK." And for more on who Alex Trebek couldn't stand, check out The One Type of "Jeopardy!" Contestant Alex Trebek Hated the Most.
Filed UnderCelebrities • Entertainment • NewsRead This NextThis Was the Worst "DWTS" Contestant
Although they agree he was the worst dancer the show has seen, he made it to the fourth episode.November 23, 2020Who Fans Want as the Next Host of "Jeopardy!"
They even started a petition to get this celebrity considered for the job.November 16, 2020Matthew McConaughey Responds to Kate Hudson
The actor defended himself after his co-star complained about his onscreen kissing.November 20, 2020Who Alex Trebek Wanted as Next "Jeopardy" Host
Before he passed, the beloved host said he would want this celeb to be his replacement.November 9, 2020Conan O'Brien Is Leaving Late-Night For This
"I'm thrilled that I get to continue doing whatever it is I do," he said in a statement about his next move.November 17, 2020This TV Provider May Have a Blackout This Week
Subscribers with this television provider may lose access to more than 160 channels come Dec. 2.November 30, 202010 Things You Didn't Know about Justin Trudeau
Athlete, nerd, hopeless romantic, thespian. Yes, there’s a lot more to Canada’s Prime Minister than just politics.March 21, 2017Jon Hamm: The Best Life Interview
Jon Hamm, star of TV's Mad Men, reveals the secrets of manliness in a postmodern world.November 15, 2016Driving Tips Smart Men Know
Ten easy ways to be the safest driver on the road. April 3, 2017Men Who Set the Time: Cash Warren
The successful producer, entrepreneur and husband of Jessica Alba reveals how you, too, can live your best life.October 31, 2016
