These roasts had everybody squirming.

6 celebrity roasts that got seriously uncomfortable

These roasts had everybody squirming.

By Brianna Zigler

May 23, 2026 2:00 p.m. ET

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Tom Hardy on 'The Roast of Tom Brady' in 2024; Chelsea Handler at 'The Roast of Kevin Hart' in 2026.

*The Roast of Kevin Hart* has everyone talking.

Following its premiere on Netflix last week during the Netflix Is a Joke festival, the internet has been buzzing over the feud between roast participants Chelsea Handler, Shane Gillis, and Tony Hinchcliffe, with Handler slamming Gillis and Hinchcliffe for their “racist” jabs at Hart.

The celebrity roast is a time-honored tradition, with the recent Comedy Central and Netflix iterations taking the more amiable Dean Martin roasts of the ‘70s and ‘80s and pushing them into pricklier territory. Celebrities in the hot seat have included Bruce Willis, Hugh Hefner, Joan Rivers, and Charlie Sheen — but they’re not the only ones getting roasted. Everyone involved is fair game.

Of course, not every joke at a roast is going to land. And sometimes they don’t land to the point that it becomes a *whole problem*.

In the wake of the Handler/Hinchcliffe/Gillis dispute, we’re looking back at some celebrity roasts that got seriously uncomfortable.

Tom Brady at 'The Roast of Tom Brady' on May 5, 2024.

For all his success, NFL legend Tom Brady remains a divisive figure in both sports and culture. As such, a *lot* of people were happy to watch the Super Bowl winner get roasted. According to Netflix, *The Roast of Tom Brady* netted around 2 million views on the night it debuted.

Brady, however, was visibly uncomfortable during parts of the event, specifically when host Jeff Ross made a joke about Patriots owner Robert Kraft's 2019 arrest for soliciting prostitution in a Florida massage parlor. "Don't say that s---" again, he whispered in Ross' ear. (The vibe wasn't helped by the fact that fellow roast participant Kim Kardashian couldn't get a joke out without getting booed.)

In a 2025 appearance on Logan Paul's *Impaulsive* podcast, Brady said he had regrets about participating in the roast because its impact on his children. "It was tough on my kids for sure," Brady said, referencing the son he shares with ex Bridget Moynahan and the son and daughter he shares with ex-wife Gisele Bündchen. "There's some things as a parent you f--- up, and you don't realize until after. We're not perfect parents. You'll see as you grow up, there's no perfect manual for it."

Pamela Anderson

Pamela Anderson at the 'Comedy Central Roast of David Hasselhoff' on Aug. 1, 2010.

In the late '90s and early '00s, Pamela Anderson became a tabloid fixture who was frequently the butt of cruel jokes alongside many other female celebrities of the era. It took some real chutzpah for the *Baywatch* star to subject herself to a roast.

At the 2005 event, Anderson endured a barrage of easy bits aimed at her sexualized persona, though she was able to deliver some scathing retorts of her own. While Anderson appeared to take it all in stride during the event, she seemingly never forgot some of the comments made by roaster Sarah Silverman.

In 2025, Silverman revealed on SiriusXM’s *Andy Cohen Live* that she encountered Anderson at a gala, where the actress said, “You told horrible jokes about me on my roast," before sashaying away.

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Justin Bieber

Justin Bieber at his roast on March 14, 2015.

Justin Bieber’s roast in 2015 was notable for its brutal takedown of Bieber’s notoriously bratty antics, which had reached their zenith at the time of airing due to a series of scandals and legal problems — including an arrest. So, there was a certain air of eagerness from both roasters and audiences to see the pop star get skewered.

The burns were certainly epic, with one set delivered by Will Ferrell as his *Anchorman* persona Ron Burgundy. “Justin Bieber is a man," he said. "A man who sings songs for 9-year-olds and cuts his hair like a gay figure skater.”

What didn't land, however, were the numerous jokes made about *Fast and Furious* star Paul Walker, who had died tragically in a car accident the year prior. Ludacris, Walker's costar in the *Fast* franchise, seemed particularly uncomfortable with the jokes. But he wasn't the only one. Backstage, Bieber reportedly told *Variety* that he “didn’t particularly like the Paul Walker jokes,” which were later cut from the telecast.

Ann Coulter at 'The Roast of Rob Lowe' in 2016.

Mark Davis/WireImage

The 2016 *Roast of Rob Lowe *is remembered less for jokes aimed at the *Parks & Recreation* actor himself (though there were certainly opportunities for them) and more for those directed at fellow roaster and controversial conservative commentator Ann Coulter.

Lowe’s roast essentially became *The Roast of Ann Coulter*, with roasters going all in on attacks against the author of *In Trump We Trust.* Pete Davidson, for example, said, “Ann Coulter is here. If you are here, Ann, who is scaring the crows away from our crops?”

Nikki Glaser cracked, “The only person you will ever make happy is the Mexican who digs your grave.” And British comedian Jimmy Carr called Coulter "repugnant" and "hateful" before encouraging her to “kill [herself].” Coulter became a lightning rod for the evening, ultimately overshadowing Lowe at his own roast.

In an interview with *The Hollywood Reporter**, *Coulter later expressed disappointment over roasters' jokes, though she claimed that they didn’t offend her so much as “bore” her.

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The 2002 *Roast of Chevy Chase* is among the most controversial roasts of all time. The comedian cited it as "the precise moment he hit bottom" in a 2004 interview with **.

The piece describes the roast thusly:

"What happened next was so awful that people who were there — from audience members to Comedy Central staffers — still have difficulty talking about it. Chevy Chase walked on stage and realized that almost none of his friends had shown up. He was led to a red overstuffed chair, where he blinked into the television cameras — first stunned, then angry, then devastated — as various basic-cable personalities and B-list comics marched to the podium and trashed him. Total strangers telling him that his movies were crap, his talk show was a comedy abortion, he had never been funny. Total strangers giggling about his addiction to drugs. There was no warmth in their comments. No real affection. Because after years of silence from Chase — and hundreds of thousands of words written about his behavior during the late ’70s and early ’80s — a consensus had emerged about the man. Everyone agreed without even having to think about it: Chevy Chase was a bastard.

He sat there in front of the world as it sank in for the first time. This was how he was remembered. This was his legacy. And when it was all over, he stood up, took a few bilious — and dreadfully unfunny — shots at his tormentors, and finally stared dead into the camera and uttered two words: 'That hurt.' He fled the theater and went directly to his hotel room."

Comedian Anthony Jeselnik, who worked on several Comedy Central roasts, later claimed that the network "threw away" the episode and vowed never to rerun it because it was such a "fiasco."

Another roaster, Marc Maron, told Howard Stern in 2023 that the Chase roast was “one of the worst nights" of his life, alleging that the elder comedian “didn’t want to be there.”

In a 2023 interview on Maron’s *WTF* podcast, Chase addressed the event. "I don't think people knew me on that roast," he said.

Shane Gillis, Chelsea Handler, and Tony Hinchcliffe at 'The Roast of Kevin Hart' on May 10, 2026.

The roast controversy du jour is currently the war of words between Chelsea Handler and comedians Tony Hinchcliffe and Shane Gillis.

Handler appeared on Deon Cole’s podcast to talk about Kevin Hart's roast on May 10, where she criticized Gillis’ joke in which he said that Hart is so short “they’re gonna have to lynch him from a bonsai tree.”

“I don’t find those jokes to be funny. Jokes about lynching black people — lynching is not a joke. It’s worse than rape," she said.

Handler also brought up the jokes aimed at fellow performer Sheryl Underwood. Hinchcliffe, for example, made jokes about the suicide of Underwood's late husband, Michael Sparkman.

"I found them making fun of Sheryl Underwood’s dead husband, who committed suicide, [to be disgusting],” Handler said. "You know, she’s fine with that. If she says she’s fine with that, she’s fine with that. I wasn’t fine with that."

Underwood did address the jokes in a chat with *Entertainment Tonight*. "I think people should be upset... the bonsai tree jokes, things like that," she said.

On May 20, Gillis fired back at Handler in a statement to *Variety*: “This is a big moment for Chelsea. I am glad she’s capitalizing. Good for her. We’re all rooting for her. Anyway, come see me July 17th at the football stadium in Philly.”

A representative for Hinchcliffe did not reply to EW's request for comment.

Original Article on Source

Source: “EW Comedy”