The most vicious celebrity roasts of all time

Tom Brady's roast got off to a rocky start due to Jeff Ross' risky joke

Stars Insider

06/05/24 | StarsInsider


The concept of the comedy roast has been around for decades. It's a bizarre way of tearing someone to shreds in front of a crowd while still somehow paying tribute to them. A consensual person is chosen as the subject and is then "roasted" by a panel of friends, family, and professional comedians. Comedy Central revolutionized the format when they created their show 'Comedy Central Roast' in 2003, which has featured many high-profile celebrities over the years as well as a panel of the sharpest comedians in the business. Each event has a dedicated Roast Master who hosts the show and takes potshots at the other roasters, as well as the "guest of honor."

While many roasts feature robust subjects who can handle a few jokes from their good friends, there have been many occasions when the jokes were so vicious that they caused real offense. 

Such was the case at the recent Netflix roast of Tom Brady titled 'The Greatest Roast of All Time.' The live-streamed event took place on the evening of May 5, and the night began with an introductory roast from Kevin Hart. Then Roast Master Jeff Ross made his spectacular entrance wearing a jersey printed with the name 'Roast J Simpson'—a harbinger of the tasteless jokes to come. Ross detailed Brady's life story through a series of harsh but hilarious barbs, but one joke went too far for the former football star's comfort. Ross described Brady as a scrawny underdog showing up for his first day as a New England Patriot. He joked that Brady walked into team owner Robert Kraft‘s office and said, "I’m the best decision your organization has ever made. Would you like a massage?"

The joke referenced Kraft's involvement in a 2019 investigation into sex trafficking at several Florida massage parlors. Kraft was charged with solicitation after he was reportedly captured on secretly installed cameras at the parlors, but the evidence was determined inadmissible in court. The camera showed Brady's reaction to the joke and he certainly wasn't laughing. Ross blew a kiss to Robert Kraft who was sitting in the audience, and tried to continue, saying, "I love Robert Kraft, I….,” but was interrupted when Brady stood up and whispered in his ear, "Never say that s*** again." Ross acquiesced and expertly moved on with the roast. Other celebrities who took to the mic included Ben Affleck, Kim Kardashian, and Will Ferrell. 

Click through the following gallery to see which other celebrities offered themselves up to be roasted (and got absolutely annihilated).

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