From David Letterman’s classic cringe-inducing interviews to the “Ellen” exchange heard ‘round the world, these are the celeb talk show appearances we can’t shake.

12 awkward celebrity talk show interviews that will make you squirm

From David Letterman's classic cringe-inducing interviews to the "Ellen" exchange heard 'round the world, these are the celeb talk show appearances we can't shake.

June 25, 2026 6:22 p.m. ET

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Crispin Glover on 'Late Night With David Letterman'; Cara Delevingne on 'Good Day Sacramento'; Madonna on 'Late Night With David Letterman'. Credit:

Talk shows have provided viewers with countless memorable moments over the years, many of them the result of awkward interactions between hosts and guests. But those memories aren't always pleasant for the celebrities involved.

Take a look at Clay Aiken, who recently recalled an infamously uncomfortable exchange with Kelly Ripa when he guest-hosted *Live With Regis and Kelly* in 2006. Seemingly unable to get a word in, the *American Idol* winner jokingly placed a hand over Ripa's mouth in an attempt to "shush" the host, leading to what Aiken describes as a "huge blowup."

Of course, Aiken is far from the only celeb who's endured an awkward interaction on a talk show. Below, we're taking a look back at 12 incredibly uncomfortable celebrity talk show moments, from David Letterman's classic cringe-inducing interviews to the *Ellen* exchange heard 'round the world.

Russell Brand on Piers Morgan Uncensored

Russell Brand on 'Piers Morgan Uncensored' in 2026.

Piers Morgan Uncensored/YouTube

Controversial comedian and novice right-wing podcaster Russell Brand unwittingly demonstrated a perfect example of the overly long gag — when a bit goes on for so long that it stops being funny, but then keeps going and eventually becomes funny again.

During his April appearance on *Piers Morgan Uncensored*, the host asked Brand about the Bible he was holding at a February court hearing in the U.K., where he pleaded not guilty to two charges of sexual assault, including one of rape.

Brand, who has denied the allegations and been very public about becoming a born-again Christian, brought the same Bible with him to the interview. "What was your thinking of taking it into court? And you were seen looking at some passages — what were the relevant passages?" Morgan asked.

Brand proceeded to flip through the Bible, mumbling incoherently about being "chill" and sighing as he looked for the passage for a full 90 seconds. "I can't actually find the verse that I had that day," he finally conceded, "but this is good enough. This is from Isaiah 12."

Cara Delevingne on Good Day Sacramento

Cara Delevingne on 'Good Day Sacramento' in 2015.

During a remote interview with *Good Day Sacramento* to promote *Paper Towns* in 2015, Cara Delevingne's dry sense of humor didn't translate to the hosts. When they asked if she had read the John Green novel that inspired the film, the actress joked that she hadn't even read the script. Not long into the interview, one of the hosts noted that Delevingne seemed more "excited" at a recent promotional event, leading his cohosts to rudely remark on her lack of energy and suggest that she take a nap.

Delevingne later made light of the exchange on Instagram, posting a photo of herself with Green's novel accompanied by the caption, "I JUST FOUND THIS BOOK! ITS AWESOME!" She also wrote, in a since-deleted tweet, "Some people just don’t understand sarcasm or the British sense of humour."

Andy Dick and Ivanka Trump on Jimmy Kimmel Live!

Comedian Andy Dick was such an inappropriate guest that he had to be physically removed from the set of *Jimmy Kimmel Live!* in 2007 after he repeatedly touched fellow guest Ivanka Trump despite being told to stop. In the clip, which has resurfaced several times in the years since, Kimmel repeatedly asks Dick to stop touching Trump, who appears visibly uncomfortable with his behavior. "Andy, please don't touch Ivanka," Kimmel says. "Donald Trump will kill both of us."

Dick, whose struggles with substance addiction and history of sexual misconduct allegations — which he has denied — have been widely reported, was ultimately carried off Kimmel's set by two security guards.

Crispin Glover on Late Night With David Letterman

Crispin Glover on 'Late Night With David Letterman' in 1987.

In July 1987, Crispin Glover — then best known for playing George McFly in *Back to the Future* (1985) — stopped by* Late Night* to promote his new drama, *River's Edge*. Wearing a wig and platform shoes, Glover seemed a bit *off*. He went on a tangent about the press and offered to arm-wrestle Letterman before throwing a kick that came dangerously close to hitting the host in the face, prompting Letterman to exit the set.

While Glover remains evasive about the interview (as well as his slightly-less bizarre return appearance a few weeks later), based on the wig and costume, it seems likely that he was appearing as his character from the film *Rubin & Ed*, which was released in 1991.

Dakota Johnson on The Ellen DeGeneres Show

Dakota Johnson on 'The Ellen Degeneres Show' in 2019.

Dakota Johnson set a new bar for celebrity talk show interviews with her 2019 appearance on *The Ellen DeGeneres Show*. The host started by asking about Johnson's then-recent 30th birthday party in Malibu. "I wasn't invited," DeGeneres noted, to which Johnson replied with one of the most instantly iconic sentences in talk-show history:

"Actually, no, that’s not the truth, Ellen."

Johnson recalled her previous appearance in 2018, when DeGeneres also ribbed the actress for not sending a birthday party invite. "Last time I was on the show, last year, you gave me a bunch of s--t about not inviting you, but I didn’t even know you wanted to be invited," Johnson said. After a little more back and forth, DeGeneres kept insisting that Johnson didn't invite her to the 2019 party.

"Ask everybody. Ask Jonathan, your producer, who says you were," Johnson said pointedly, at which point DeGeneres' producer seemed to confirm that the host was too busy to attend the party.

Samuel L. Jackson on KTLA

Samuel Jackson on KTLA 5 in 2014.

Samuel L. Jackson's remote interview with KTLA to promote the 2014 *RoboCop* reboot was arguably even more awkward than Delevingne's. As soon as the legendary actor joined the feed, entertainment reporter Sam Rubin congratulated him on his recent Super Bowl commercial—mistaking Jackson for Laurence Fishburne. "You're as crazy as the people on Twitter!" the actor replied. "I'm not Laurence Fishburne!"

Rubin tried to apologize and move on, but Jackson hilariously wouldn't let it go, telling the reporter, "We don't all look alike," and, "That must be a very short line for your job." He also delivered a classic "Oh, hell no!" before explaining the differences between himself, Fishburne, and Morgan Freeman.

Grace Jones on The Russell Harty Show

Grace Jones is not the kind of person you turn your back on, but that's exactly what British talk-show host Russell Harty did on his eponymous chat show in 1981. Harty kept turning away from Jones to speak with his other guests, which the model and singer perceived as a slight.

As Jones explained in her 2015 memoir, she was suffering from a combination of bad cocaine, exposure to pigeon feces, and a sinus infection. Also, she claimed the live show was different from what they rehearsed. "Being stuck there while he ignored me made me feel very uncomfortable," Jones recalled. "I felt I was provoked. I was feeling exhausted, had no idea where I was, and was coated in pigeon s--t; now it seemed I was hallucinating that I was on a live chat show and the host was ignoring me. Pissed off, I poked him in the back."

The poke escalated to Jones playfully slapping at Harty, whose team later invited her back to the show. "The ratings soared," wrote Jones. "I had done him a favour. They wanted a rematch. It was all so tacky."

Michael B. Jordan and Kate Mara on Atlanta’s Rock 100.5

Michael B. Jordan and Kate Mara in 2015. Gustavo Caballero/Getty Images

A morning radio show isn't *technically* a talk show, but this intensely awkward interview deserves mention. Back in 2015, Michael B. Jordan, Kate Mara, and Jamie Bell were interviewed by local Atlanta DJs while promoting their *Fantastic Four* reboot. Jordan had already weathered backlash about his casting as Johnny Storm, the brother of Mara's Sue and a character depicted as white in the comics. He even wrote an essay about it for **.

All of which is to say that the radio host should have known better than to lead with a question about the characters' racial differences, especially one posed so clumsily. "From what I understand, you're brother and sister," said the host, Steven J. Rickman. "Am I missing something? … But you're white and you're Black. How does that happen?"

Jordan answered politely, but the interview got worse from there. "You're way, way hot," Rickman said, turning his attention to Mara. "Why'd you cut the hair? Your hair was beautiful." Mara answered that she cut her hair for the role, which somehow led Rickman to note that he's more of a "toe guy."

Madonna on Late Night With David Letterman

Madonna on 'Late Night With David Letterman' in 1994.

Madonna's 1994 appearance on *Late Night* was deemed "shocking" and "off-putting" by the press, but in hindsight it was kind of radical. Not because the Queen of Pop said "f--k" 14 times or made a suggestive comment about the microphone, but because she refused to play along with the preconceived bit — that she was upset with Letterman for joking about her sex life. Instead, Madonna lit up a cigar, challenged the host to smell her underwear, and rejected his pitch to kiss a man in the audience.

By the end of the episode, which earned record-breaking ratings for Letterman, Madonna refused to leave the set and had to be escorted offstage by the show's talent coordinator.

Howie Mandel on Live With Kelly & Mark

Howie Mandel on 'Live With Kelly and Mark' in 2026.

Here's a good rule of thumb: Don't comment on someone's age, especially if that person is a celebrity and they didn't bring it up first. Kelly Ripa and Mark Consuelos learned this lesson the hard way in March 2026, when Howie Mandel dropped by *Live With Kelly & Mark*. After Consuelos noted that Mandel just turned 70, Ripa said, "It doesn't make any sense," which seemed to push a button for the comedian.

"What do you mean it doesn't make any sense?" Mandel asked, to which Consuelos cheerily replied, "You look great!" But Mandel wasn't having it.

"I look great? That doesn't mean anything to me," Mandel said. "No, no, no, no. I don't like that, because that's a caveat."

"We're not saying you look great *for* 70. You look great," Ripa tried to explain. "Yes you are, without saying '70,'" Mandel replied, adding, "It's like saying you're smart for a stupid person."

Harvey Pekar on Late Night With David Letterman

Harvey Pekar on 'Late Night With David Letterman' in 1988.

In 1988, Letterman welcomed returning guest Harvey Pekar, the disgruntled cult comic book writer from Cleveland, and the creator of *American Splendor*. (Paul Giamatti would later play Pekar in the excellent 2003 film of the same name.) Letterman enjoyed ribbing Pekar, but during that particular appearance, the comic-book writer turned the tables by criticizing General Electric, the parent company of *Late Night* network NBC, and calling the host a "shill."

Letterman interrupted his guest and said he was banned from returning, but Pekar made two more appearances on *Late Night* before his death in 2010.

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Joaquin Phoenix on Late Night With David Letterman

Joaquin Phoenix on 'Late Night With David Letterman' in 2009.

When Joaquin Phoenix announced in 2008 that he was retiring from acting to become a rapper, no one knew whether to take him seriously. Then, in 2009, a heavily bearded Phoenix appeared on *Late Night* for an instantly infamous interview that didn't really help to clear the air. Phoenix mumbled through the interview, appeared unamused by Letterman and his questions, and stuck his chewed-up gum under the desk.

Bits of the interview were later included in 2010's *I'm Still Here*, the mockumentary charting Phoenix's transition from acting to hip-hop. The actor returned to *Late Night* that year — as himself — but it wasn't until 2025 that he really opened up about what happened.

During an appearance on *The Late Show With Stephen Colbert*, Phoenix said of the stunt: "It was horrible. It was *so* uncomfortable. I regret it, I'll never do it again. I'm so sorry."

Keanu Reeves on The Rosie O’Donnell Show

Reflecting on her popular talk show in 2025, Rosie O'Donnell said that Keanu Reeves was among her worst guests. "I love the guy, but he's not good on talk shows," the actress and comedian said of Reeves, who appeared on her show in 1997 to promote *The Devil's Advocate*.

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Though Reeves is much more natural in interviews these days, he's definitely awkward in the clip from *The Rosie O'Donnell Show*, in which the host tirelessly attempts to get him talking, only to receive short responses in return. "You don't do a lot of these shows, do you?" O'Donnell asks at one point, to which the actor admits, "No, I don't. I'm not comfortable with them."

Original Article on Source

Source: “EW Talk”