6 Most Awkward Live Interviews in Celebrity History


When you think about how often it happens, it’s kind of weird when live celebrity interviews go sideways. After all, big celebrities are experts at both talking about themselves and promoting whatever their latest work is. As long as they have a professional interviewer, you’d expect the celebs to have no trouble speaking their mind.

However, there have been countless times when the interviewer is less than professional. In that case, the celebs reacted with everything from anger to tears. Don’t believe us? Keep reading to discover the most awkward live interviews in celebrity history!

Howard Stern’s insanely inappropriate Anna Nicole Smith interview

Howard Stern made a name for himself as the king of the shock jocks, and more than a few of his interviews with celebs would turn weird and blue (like when he got Donald Trump to admit how hot he thought Ivanka looked). But when Stern interviewed the now-deceased celebrity Anna Nicole Smith, he wasn’t just blue…he was relentlessly mean in a way that fans are still talking about.

“The way you dress I don’t think you’re aware that you’re a heavy-set woman” Stern said. This provoked an understandable reaction from Smith: “I know I’m a big woman, so what?” That would have been bad enough, but the host kept trying to get Smith to step on a scale to prove him wrong, eventually making an inappropriate offer that was quite easy to refuse: “I’ll show you my penis.”

That time Samuel L. Jackson was mistaken for Laurence Fishburne

Back in 2014, the Marvel Cinematic Universe was gathering steam and Nick Fury actor Samuel L. Jackson sat down for an interview with KTLA. Things were going well enough until interviewer Sam Rubin asked the actor “Did you get a lot of reaction to that Super Bowl commercial?”

There was just one problem: the most prominent Black actor appearing in a Super Bowl commercial that year wasn’t Jackson…it was Laurence Fishburne. And Jackson began going off on Rubin with the intensity of his most beloved characters. After asking what commercial he was talking about, Jackson started going off: “You see, you’re as crazy as the people on Twitter. I’m not Laurence Fishburne!” Continuing, he said, “We don’t all look alike! We may be all black and famous, but we all don’t look alike.”

Later, Rubin would claim he had seen a Captain America commercial with Jackson in it and that was what he was thinking of. Still, he took the blame for the on-air gaffe with the beloved celeb.

When David Letterman made Lindsay Lohan cry

These days, David Letterman is seen as something of an elder statesman of entertainment. And many fans think of him as a kinder, gentler late-night host than his rival Jay Leno. But to see the darker side of Letterman hidden behind his giant beard, all you have to do is watch his old interview with Lindsay Lohan.

Instead of letting Lohan promote the upcoming Scary Movie 5, Letterman went hard on the actor regarding her past issues with alcohol and substance abuse. “Aren’t you supposed to be in rehab now?” he asked, and after getting a confirmation, followed it up by asking “How many times have you been in rehab?”

A stunned Lohan kept reminding Letterman that she didn’t approve of this discussion in her pre-interview talk, and if you look closely, you can see her wipe away the tears that Letterman’s intense questioning brought out!

Tom Cruise blows up about his ex-wife

Normally, Tom Cruise is one of the most cool and collected actors in Hollywood. But he has some very hot-button issues, and his previous marriage to Nicole Kidman is one of them. And that is something that Peter Overton discovered during a 60 Minutes interview with the star.

Overton kicked things off by asking “Was Nicole the love of your life?” This caused a baffled Cruise to counter with, “How do you answer that question?” Things might have ended there, but Overton went on to ask about Cruise and Kidman’s co-parenting relationship. “Listen here’s the thing Peter,” Cruise told him. “You’re stepping over the line now. You’re stepping over the line and you know you are.”

It got even more awkward when Overton claimed the public might want to know these things. “You want to know. Take responsibility for what you want to know, don’t say what other people [want to know],” Cruise said, and he bluntly told the interviewer to “put [his] manners back in.” 

Taylor Swift gets feisty about her ex-boyfriends

Ellen DeGeneres is no stranger to controversy. Back before her own staff-led cancellation, she used her show as a platform that often made celebrities deeply uncomfortable. This was certainly the case when she interviewed music icon Taylor Swift and asked how her “boyfriend Zac Effron” was doing. Swift quickly replied they “actually never dated,” and it just went downhill from there.

After first insisting Swift really did date Effron, the host subjected Swift to a slideshow of pictures where Swift was in the company of male celebs. She asked the increasingly uncomfortable Swift to ring the bell in front of her when she saw someone she dated. Swift never rang that bell and eventually asked Ellen a deeply rhetorical question: “Do you know how bad this makes me feel?” 

The world watched David Letterman suck Jennifer Aniston’s hair

David Letterman has more than a few tricks to make his guests uncomfortable. And when he interviewed Friends megastar Jennifer Aniston, it led to a horrific moment that nobody who has seen it will ever forget.

After the star shared an anecdote about running into fans in a steam room, Letterman creepily asked if she was naked, and then things took a truly bizarre turn. “Forgive me if this is rude, I just want to try one thing,” he said before leaning forward, taking some of Aniston’s hair into his mouth, and sucking on it.

Aniston was understandably traumatized, and Letterman joked (or perhaps honestly thought) that the weird moment would be edited out. It wasn’t, though, securing Letterman a place in the creeper hall of fame!

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