14 of the Most Awkward Moments in Talk Show History

With talk shows having been on air for so long, it makes sense that there have been a few awkward interviews over the years. Celebrities typically come on to promote a project they're in, whether that be via TV or film, but every once in a while something happens that doesn't work with the format we're accustomed with, leaving us to wonder if the surprise moment was planned beforehand—or genuinely as cringy and awkward as it felt from the couch.

Dakota Johnson on 'Ellen'

This interview starts beautifully passive aggressive, as the two celebs bicker over whether DeGeneres was invited to Johnson's recent birthday party. The vibe is off the whole time, with other bits of awkwardness including Ellen's thousand-yard stare when Johnson dared to say Tig Notaro was her favorite comedian, and asking more questions about her The Peanut Butter Falcon Shia LaBoeuf than about Johnson's own experience filming the movie.

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Elizabeth Warren on 'The Late Show with Stephen Colbert'

Stephen Colbert really came into his own as an interviewer after dropping his satirical persona from The Colbert Report, and has led some of the best discussions with politicians at the late night time slot. In this video, he asks Senator Elizabeth Warren point-blank whether the Senate should be abolished, calling it "the most anti-Democratic institution." It was certainly an awkward and pointed moment as Warren guffawed at his question before realizing it was 100% serious, but at least a good conversation came from it.

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Jerry Lawler & Andy Kaufman on 'Letterman'

One of the best staged talk show bits ever, Andy Kaufman's tussle with Jerry Lawler on Late Night with David Letterman, has lived in infamy after it aired in 1982. It wasn't clear whether this was planned at first, revealed years later that Kaufman coordinated it as part of his interest in professional wrestling (which he sometimes used in his act).

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Jimmy Kimmel on 'The Late Late Show with James Corden'

Kimmel might have been the guest on this segment of "Spill Your Guts or Fill Your Guts," but ex-Late Late Show host James Corden ended up in the hot seat this time around. The last question of the segment rolls around with Kimmel challenging Corden to pick: sip on a fish smoothie or name two of the show's camera operators. Corden, the host of the show, looks helplessly around for a moment before sipping on the smoothie.

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Star Jones on 'The View'

The View is no stranger to thorny and awkward conversations, but one absolutely stunning moment happened in 2006 when Star Jones announced the end of her nine-year stint in an off-script moment that blindsided her co-hosts.

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Paris Hilton on 'The Tonight Show with Jimmy Fallon'

This interview, recorded at the peak of the awful NFT trend that has thankfully withered away to a shell of its 2022 self, is the epitome of robotic celebrity product promotion. It even triggered a lawsuit against Bored Ape creators Yuga Labs and the fintech firm Moonpay for misleading wording that said both celebrities bought NFTs when they were allegedly given the tokens for free to promote them on TV.

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Ray Liotta & Jennifer Lopez on 'Watch What Happens Live'

The late, great Goodfellas star Ray Liotta was refreshingly and brutally honest in the infamous "Plead the Fifth" segment from the Bravo talk show WWHL. Without hesitating, he named Sigourney Weaver as his worst onscreen kiss, and also didn't pause to mention that he felt Clint Eastwood was overrated in his '80s and '90s heyday. He also couldn't name more than one Jennifer Lopez song, which was a little awkward given he was handcuffed to her for the segment.

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Donald Trump on 'The Tonight Show with Jimmy Fallon'

It's the hair tussle that will live in infamy. In general, Trump's Tonight Show appearance where Fallon completely soft-balled him with no questions about the many controversies that had arisen from his 2016 campaign wasn't well-received... for obvious reasons.

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Jon Stewart on 'Crossfire'

Not a lot of TV interviews lead to the the show getting canceled, but that's sort of what happened when Stewart came on to promote his book. He pleaded with its hosts Paul Begala and Tucker Carlson to stop with the "partisan hackery" of the show's right vs. left debate format, and it was canceled just a couple of months later in January of 2005.

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Nicole Kidman on 'The Tonight Show with Jimmy Fallon'

It must feel odd to find out on your own show that Nicole Kidman had a crush on you... and you blew it. Kidman remembered that she went to Fallon's apartment after being introduced by a mutual friend, but he wasn't particularly talkative at the time and decided to play a video game instead. What a massive fumble, Fallon!

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Harmony Korine on 'The Late Show with David Letterman'

Hot off his debut feature film Kids, a young Harmony Korine gave this strange interview with David Letterman. Korine went on rambling tangents in response to Letterman's simple questions, leaving the host in silence several times while maintaining that endearing energy he always carries.

After three appearances, Korine was later banned from the show when Letterman caught him rifling through Meryl Streep's purse, a stunning but true story that Letterman himself confirmed.

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Abel Ferrara on 'Late Night with Conan O'Brien'

Conan O'Brien was a young writer from SNL and The Simpsons suddenly tapped to host the Late Night program after David Letterman left. O'Brien was naturally talented in a lot of ways, but was basically learning on the job, and there are some rough interviews in those early days.

This chat with Bad Lieutenant director Abel Ferrara was a bit unfocused, but Conan still did his best to steer the ship and got some funny quips in.

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Robert Pattinson on 'The Tyra Banks Show'

When R Patz and Taylor Lautner were on Banks' since-canceled talk show, she got him to bite her neck in the middle of an interview. The only thing funnier than the moment itself was when Banks asked him in a British accent, and Pattinson's genuine look of bewilderment in response.

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Bobcat Goldthwait on ''The Tonight Show with Jay Leno

Even if the surreal stand-up Goldthwait hadn't ended up setting his chair on fire by spraying lighter fluid on it and lighting it up, this 1993 Jay Leno interview wasn't exactly going smoothly leading up to it. This is probably the quickest a guest was able to launch an interview off the rails, and it's probably a miracle that more wasn't burned on that set than just the chair.

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