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News

Talk Show Hosts Expose Their Most Difficult Guests Ever

Published on: March 1, 2026 at 3:45 PM ET

These guests were not very fun to talk to.

Arpita Samaddar
Written By Arpita Samaddar
News Writer
Talk show, Robert De Niro, Conan O'Brien
Talk show hosts like Conan O'Brien talk about their worst guests like Robert De Niro (Image Credit: Wikimedia Commons: @Jay Dixit, @Harald Krichel)

Talk shows are a great platform for celebrities to give insight into their real selves or promote upcoming projects. But to appear likable, guests must also create a bond with the host for a smoother interview.

However, some guests can be difficult to work with, and talk show hosts do not shy away from revealing their names.

Conan O’Brien is widely regarded as one of the most respected hosts in his field. He is known for cracking jokes with his guests and making them feel at ease. But even he had trouble with director Abel Ferrara in 1996.

Conan O’Brien’s chat with Abel Ferrara is probably the worst talk show interview in the history of late night TV: https://t.co/ASSQT1j1KN pic.twitter.com/QZFFIu0t7y

— Decider (@decider) December 4, 2018

On the “Armchair Expert” podcast, O’Brien revealed how Ferrara “fled” during the show. “He ran away, got on the elevator, and was out on the street running away, and Frank gave chase.”

Ferrara then started yelling at O’Brien after he returned. Though this made for an entertaining story for O’Brien, Wendy Williams had it far worse.

Her guest allegedly sexually harassed her, which she revealed on her talk show, “The Wendy Williams Show.” She refused to name him but stated, “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.”

Later, users on X identified the culprit as comedian Gilbert Gottfried.

While Williams wanted to keep her worst guest a secret, Andy Cohen was more direct in naming Amber Rose. In an interview with E! News, Cohen said, “She didn’t want to answer any of my shady questions.”

Their interaction appeared more balanced, as Rose herself acknowledged the dynamic and asked Cohen, “Am I a horrible guest?” To which Cohen agreed, saying, “…you are in the running for one of the worst guests we’ve ever had.”

Craig Ferguson was also asked about his worst guest, and he named her but also defended her. On “Watch What Happens Live,” Ferguson revealed that Macy Gray was not a very engaging guest on his show.

Craig Ferguson named Macy Gray the worst guest he ever interviewed, and others have also had difficulty with her as a guest. https://t.co/Dq0sQiBQSm

— The Things (@Thethingscom) May 26, 2024

But he also clarified, “I think she was in a bad mood that night. I don’t think she’s a bad person … and I was very new and I couldn’t handle it.”

Graham Norton had a very peculiar experience precisely because his guest was already known for being a man of few words. Norton revealed how the Oscar-winning actor, Robert De Niro, is his worst guest on Cheltenham Literary Festival.

Mikey Madison will be on The Graham Norton Show sofa with Robert DeNiro, Alan Carr and Holly Willoughby today at 5:40 PM (EST). pic.twitter.com/FdZJsipKhv

— Mikey Madison Updates (@mikeymupdate) February 7, 2025

As reported by the Daily Mail, Norton stressed, “He’s not a storyteller, or very verbal…He’s a benign presence. Last time he started telling a story — he went on and on.”

TAGGED:Conan O'BrienRobert De Niro
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