onan O’Brien reminisced about his unforgettable encounter with director Abel Ferrara, a guest on Late Night with Conan O’Brien back in 1996. Ferrara’s attempt to flee just before the show went live set the tone for a disastrous interview filled with mumbling and confusion.

Andy Cohen didn’t mince words when recalling his interview with Amber Rose, who refused to engage with the questions on Watch What Happens Live. Cohen didn’t hesitate to dub her as one of his worst guests, and Rose herself seemed aware of her less-than-stellar performance.

Craig Ferguson candidly admitted to struggling with singer Macy Gray’s mood during an episode of The Late Late Show.

Gray’s apparent bad mood left Ferguson feeling out of his depth as a new host.

Even Jay Leno, known for his affable demeanor, couldn’t hide his disdain for reality star Trista Sutter’s lackluster appearance on The Tonight Show. Leno’s candid revelation of his disinterest during the interview left Sutter in an awkward spot.

Stephen Colbert’s friend and former coworker Jon Stewart didn’t hold back when labeling Hugh Grant as his least favorite guest on The Daily Show. Stewart’s frustration with Grant’s attitude and behavior during the interview was palpable, making it a memorable moment for all the wrong reasons.

The tension between Dick Cavett and his trio of uncooperative guests, John Cassavetes, Peter Falk, and Ben Gazzara, made for cringe-worthy television during The Dick Cavett Show. Their refusal to engage with Cavett left the host and audience bewildered.

Even Larry King, the king of interviews, had his share of disappointing encounters, with Phyllis Gates’ lackluster responses leaving him struggling to fill airtime.

Despite the glitz and glamour of the talk show world, these worst guests serve as a reminder that not every interview goes according to plan. From diva behavior to outright rudeness, these moments live on in talk show infamy.

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