Howard Stern Reveals The Disastrous Celebrity Interview He Will Forever Regret

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Howard Stern has interviewed thousands of celebrities throughout his career. In a new candid interview with the Hollywood Reporter about his life, Stern opened up about the one celebrity he regrets interviewing because it was such a disaster.

After conducting interviews with Hollywood’s most famous faces, there is bound to be one that is full of regret. For shock jock Stern, who has been talking to celebrities for 30 years, there is one he will forever regret.

Robin Williams is the interview that continues to haunt Stern, especially since the comedian is no longer here making it impossible for a do-over.

THR cover: @HowardStern reveals cancer scare, Trump regrets and details of a dishy new book https://t.co/6nAhwcvnl7pic.twitter.com/2atbFKQkJP

— The Hollywood Reporter (@THR) May 8, 2019

The reason Stern regrets his interview with Williams is not because of the actor but rather the context of their talk. Instead of having a pleasant chat with a Hollywood legend, Stern was in full shock-jock mode asking nothing but inappropriate questions to appease his audience.

“I wasn’t rude with Robin Williams, but I asked some questions that perhaps went into areas that he had enough of,” the 65-year admitted to the famous magazine.

Stern is known for asking questions of a sexual nature, as well as crossing the line with his guests. Yes, anyone who agrees to go on the show is fully aware of what the interview will entail, but in the case of Williams, even Stern admitted it went too far.

“I think my whole demeanor and attitude was just shitty. I wasn’t trying to be mean to Robin Williams. I was just trying to be provocative and interesting for the audience and doing what it is that I thought had to be done. And I was an immature asshole. And so that always haunted me and then I kind of filed it away and forgot about it,” Stern continued to explain why he will always regret that particular interview.

To this day, an early 90s interview @HowardStern did with #RobinWilliams still ranks among his biggest regrets: "I could have had a great conversation, but I'm playing to the audience" https://t.co/7SJtk7A9XEpic.twitter.com/CCgSUfK8fb

— The Hollywood Reporter (@THR) May 8, 2019

Howard Stern will forever regret the way he conducted an interview with the late Robin Williams. He admitted the comedian deserved to be celebrated, not belittle by questions of his sexual escapades. Stern never got the chance to make it up to the actor, but the disastrous interview did help him evolve as a man and host.

These days he is less of a shock jock and is more focused on conducting meaningful interviews due in part to what happened with Williams, as well as the fact Stern never got to conduct the right kind of interview with the Mrs. Doubtfire star. It was a learning experience he will always regret, but at the same time, it also helped Stern grow and evolve, as man and host.