Talk Show Hosts Reveal Their Worst Guests Ever

While everyone loves a really compelling interview, talk shows — much like everything in pop culture — thrive on drama. Throughout talk show history, some of the most memorable moments were also the most confrontational, including David Letterman's awkward talk with Joaquin Phoenix or Arsenio Hall standing his ground against protestors.

But for talk show hosts, it's not always the most obvious guest encounters that stand out as the worst. This may be because those appearances, however negative and notorious, make for compelling television. In fact, many of the worst guests happen to be some of the most forgettable for audiences. The talk show hosts on this list have collectively interviewed thousands of guests. While they've spoken to the who's who of the world, including some of the most fascinating people who have ever lived, they still remember the very worst of their careers. It is those guests on the talk show wall of shame that we hone in on today. 

Read on to find out who these bad interview culprits are, as some of our favorite talk show hosts reveal their worst guests ever.

Speaking to Dax Shepard on his Armchair Expert podcast, Conan O'Brien got to discussing his worst encounters on Late Night with Conan O'Brien. He recalled his sit down with director Abel Ferrara in 1996, an appearance that apparently almost never happened. 

"He fled during the show, before his segment," O'Brien said. "He ran away, got on the elevator, and was out on the street running away, and Frank [segment producer] gave chase." Eventually, they coerced the "eccentric" filmmaker on camera "against his will." Now, O'Brien seems to remember it worse than it really was, saying, "He came out, and I think started yelling at me."

It's possible the yelling was off camera or cut, because it didn't exactly happen that way in the aired interview. That said, what did air wasn't pretty. Appearing to be intoxicated, Ferrara shuffled in his seat and mumbled his way through questions. O'Brien could only laugh in spots, struggling to understand his guest, joking at one point, "We're going to get those Stallone subtitles in here."

When Shepard asked if Ferrara was intoxicated, thinking back to his own intoxicated adventure on his guest's show, O'Brien responded, "Yes. I mean, I'm sure. Or if not, he should have been." He added, "It was entertaining ... You wouldn't say that was a great experience, but you'd remember it. It was what we call 'compellevision.'"

After taping a segment on the Charlie Rose sexual assault scandal, former shock jock Wendy Williams got to discussing her own encounter with inappropriate touching on The Wendy Williams Show. "My worst guest, I'm not gonna name. But I can tell you this. It had to do with some groping," she said. "And you all saw it but didn't say a word. And I felt it and I didn't say a word. My staff saw it, and that guest will never be here anymore. He's not relevant anymore, anyway," Williams added to an applauding audience. 

"I believe it was the third season of our show. It might have even been the second season," Williams continued, adding, "He comes out, little man ... You know I hug my guests. He hugs me, but lays in my breast inappropriately, and I didn't know what to do, 'cause I'm brand new on TV." 

Though many in the audience were likely scratching their heads as to who the mystery guest was, Twitter users were quick to identify the alleged culprit as comedian Gilbert Gottfried, with some even posting a screenshot of interaction.

When Andy Cohen was asked to name his worst guest ever during an interview with E! News, he didn't hold back. "Amber Rose," the Watch What Happens Live host said. "She didn't want to answer any of my shady questions." Apparently, Rose was aware that her unwillingness to contribute gossip might make her look bad. "She turned to me, she goes, 'Am I a horrible guest?'" Cohen recalled. "I go, you are in the running for one of the worst guests we've ever had." 

One year later, Cohen doubled down on Rose being the worst guest during a Q&A session at a For Your Consideration Emmys event, saying, "She did not come to play" (via The Daily Dish). However, a close second appears to be Debra Winger, as an audience member suggested — to which Cohen had to agree. "Oh my god, it was bad," he said. "I almost can't talk about it." In her appearance on Cohen's show, there appeared to be tension between the two. 

"You know what's weird about Debra Winger?" Cohen went on. "We really did connect, and during the commercial break, she kept saying, 'You know, you're like my Jewish little brother. I feel connected to you.' But then when the camera came on, she wasn't having me."

To the untrained eye, Bob Hope and Johnny Carson were good friends. In fact, Hope appeared on The Tonight Show more often than most, and even had his own theme music when he came on, with the band playing "Thanks for the Memory."

Yet, according to Richard Zoglin, the author of the biography, Hope: Entertainer of the Century, there was apparently some tension there. "After some banter with Johnny, sprinkled with obviously prepared gag lines, [Hope] would introduce a reel of taped highlights from his upcoming NBC special. Then he would scoot away, always with somewhere urgent to go," Zoglin wrote. "One of those who grew tired of the routine was Johnny Carson."

It was competition that was said to be at the heart of the strife. Though he recognized Hope's position in the industry, the talk show host supposedly didn't necessarily appreciate the humor that got him there. "Carson never warmed to the older comedian, either personally or professionally," Zoglin wrote. "The Tonight Show host would often mimic and pay homage to the classic comedians he adored — Jack Benny, Groucho Marx, George Burns. He almost never referenced Hope."

While appearing on Watch What Happens Live, Craig Ferguson was asked to reveal the worst guest he ever had on The Late Late Show with Craig Ferguson. After some consideration, Ferguson confessed it was singer Macy Gray. "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."

However, Ferguson later had someone else in mind when discussing a similar topic in an interview with Seth Meyers after his appearance on Late Night with Seth Meyers. "I have one guy who was such a d**k even on the air," he revealed. "I thought, 'Oh man, you must be like a cataclysmic f**king a**hole when you're just in your regular life.'" Though Ferguson promised to tell Meyers who this mystery guest was after the interview, the audience was left in the dark. Any guesses?

While sitting down with Craig Ferguson on The Late Late Show with Craig Ferguson, Jay Leno was asked, "Did you ever get tired? Did you ever glass over when they were talking sometimes?" Referring to the many guests he'd spoken with as the longtime host of The Tonight Show with Jay Leno, Leno began, "The classic example of this: I had one of these reality stars on." 

Bringing up Trista Sutter, the original star of The Bachelorette, he started to reenact their conversation: "I'm talking to her like this, and I'm looking at the side of her head ... I couldn't be less interested. I've never seen this stupid reality show. I didn't know what it was." 

After the show, Leno was approached by a woman for a photo in the studio's parking lot, but it was only after he asked for her name — "Trista" — that he realized who it was. Yikes! "It was a nightmare," he added. After this episode of The Late Late Show aired, Sutter took to Twitter to speak about the namedrop. "After 10 yrs, ironic that I'm the topic of convo on @CraigyFerg last show," she wrote, adding alongside a wink-face emoticon, "Thx 4 the shoutout @jayleno! Next time, plz mention my book."

In 2012, Stephen Colbert interviewed his friend and former coworker, Jon Stewart, in a fundraiser event for the Montclair Film Festival. As the two TV hosts shared funny stories with audience, Stewart declared that Hugh Grant was his least favorite guest on The Daily Show, adding, "And we've had dictators on the show" (via Third Beat Magazine).

"He's giving everyone s**t the whole time, and he's a big pain in the a**," Stewart said of Grant's visit to the Comedy Central show, adding that the actor went on to complain about the clip used to promote his film, Did You Hear About the Morgans? "What is that clip?" an angry Grant said. "It's a terrible clip." To which Stewart quipped, "Well, then make a better f**king movie." 

After these quotes made the rounds online, Grant addressed his behavior on Twitter, owning up to it as best as you could expect: "Turns out my inner crab got the better of me with TV producer in 09. Unforgivable. J Stewart correct to give me kicking."

Dick Cavett spoke with many guests over the years on the various incarnations of The Dick Cavett Show – many good, a few bad, and even one that died during a taping. The very worst, however, according to Cavett's interview with The New Yorker, was the trio of John Cassavetes, Peter Falk, and Ben Gazzara.

They were there to promote their 1970 film, Husbands ... but it didn't take long for the appearance to go off the rails. Cavett's guests could barely decide who should sit where and then they refused to even speak to their host. "It was out of the blue. It was astonishing. I could not believe it, while it was happening," Cavett said. "I think I watched it a year or so ago, and it seemed even worse than I remembered it."

Indeed, it really was that bad, with three grown men doing pratfalls, wrestling, and showing off their feet. While the audience appeared to enjoy it at first, the extended gag got old — and quick. According to Cavett, the film's producer, who was backstage, laid into them for the performance. "In the wings, afterwards, their producer grabbed the three of them, like three kids who are acting up," Cavett said. "He got them in a group and said, 'I really have to congratulate you. You probably unsold more tickets to this movie than most movies get.'"

In 2019, Lorraine Kelly celebrated 35 years of being on television, most of which she's spent as the titular host of Lorraine. The Brit sat down with Dan Wootton from Hello! to answer some questions about her career to that point, the high and the lows. On the topic of worst interviews or interviewees, Kelly pointed to an interview with Kevin Spacey. "He was horrible," she said of the disgraced House of Cards alum. "Just very arrogant. I didn't like him at all." 

While Spacey was a bit of a safer target considering his now-controversial place in pop culture, she also took aim at some higher profile actors, namely Harrison Ford and Bruce Willis. "I don't think [Ford] particularly liked the movie that he was promoting, and he just wasn't really happy," Kelly said. In regard to Willis, the longtime TV host said that he was "just weird." She then explained, "You would ask him a question and he would give you an answer that had absolutely nothing to do with you just said."

Fans of The Graham Norton Show will no doubt remember the 2015 episode with Robert De Niro, in which fellow guest Tom Hiddleston famously performed an impression of the legendary actor in front of him. But it's what we didn't see that made De Niro Graham Norton's least favorite guest. 

At the Cheltenham Literary Festival, Norton revealed that De Niro's yarn-weaving abilities left a lot to be desired. "He's not a storyteller, or very verbal," Norton said (via the Daily Mail). "He's a benign presence. Last time he started telling a story — he went on and on. We were all leaning in, willing it to be amazing ... then he finally went, 'why am I telling this?' Nobody had an answer. We cut it."

He also made mention of the episode featuring the cast of Ocean's 8. "I felt like the guy driving the bus on a hen party," Norton went on. "For 45 minutes people were talking over each other and laughing ... They were having a great time but the audience was nonplussed."

Larry King interviewed some of the most legendary people on the planet on Larry King Live and surely has plenty of talks he would rather forget. For example, asking Jerry Seinfeld whether he gave up on Seinfeld or was let go is probably high up on that list. But getting slammed and mocked by the comedian was not, according to King, his worst interview.

Per his interview on Sway in the Morning, that honor goes to Phyllis Gates. While reflecting on the Gates interview, King revealed how hard they'd promoted what promised to be a juicy talk with the then-mystery wife of the late actor, Rock Hudson. But the interview fell quite short of expectations. After Gates explained how she met and married Hudson, she went on to provide very little gossip. King asked if they'd kept in touch after their divorce. "No," she replied. How did she feel to learn Hudson had been diagnosed with HIV/Aids? "Terrible," Gates said. Was she surprised to learn he was gay? Another one-word answer: "Yeah."

"I look up at the clock," King later said on Sway in the Morning, having used up all his interview ammo. "I'm four minutes in. I got another 56 minutes to do with this woman, who has nothing to say." He added, "I almost said, 'Did you know him?'"

Over seven seasons of Chelsea Lately, Chelsea Handler interviewed plenty of guests, but only one — Russell Brand — was truly a "pain in the a**," according to her interview with Grazia magazine (via Her). While it's unclear when the talk show host formed this opinion, considering she had him on the show three times (including appearances in 2009, 2012, and 2013), Handler declared that he was apparently a bit of a diva. 

"I would never want him back," Handler said. "He stopped all of our production schedules because he needed three espressos before he could even come on for his interview." Looking back on these interviews, the seemingly playful back-and-forth banter between the two now appears a bit more barbed. After joking about Brand's sex addiction in their first meeting, for example, Handler told her guest, "The way you're looking at me makes me want to cover up my vagina." To which, Brand quickly retorted, "Madam, if I had rubber gloves, I'd do it for you." Yikes.