Tom Brady's Netflix roast got vicious

The Greatest Roast Of All Time: Tom Brady featured appearances from Kim Kardashian, Peyton Manning, Bill Bilichick and more

By Mary Kate Carr | May 6, 2024 | 2:54pm

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This weekend was all about famous people flaming the shit out of each other, on camera or elsewhere. Netflix’s The Greatest Roast Of All Time: Tom Brady, at least, was full of sanctioned and consensual dissing. Nevertheless, the event—advertised as the first-ever live and unedited roast—had its share of eyebrow-raising moments, including one joke that had Brady out of his seat and warning the roaster “don’t say that shit again.” Hey, you might consider that a sign of a good roast.

Kevin Hart served as the host for the evening, with roasters including Jeff Ross, Bert Kreischer, Tom Segura, Nikki Glaser, Andrew Schulz, Tony Hinchcliffe, Sam Jay, Ben Affleck, Kim Kardashian, Will Ferrell as Ron Burgundy, Peyton Manning, Patriots coach Bill Belichick, former wide receivers Randy Moss and Julian Edelman, quarterback Drew Bledsoe, and tight end Rob Gronkowski. The jokes were along the lines you’d expect, given Brady’s public life. There were jabs about his un-retirement and subsequent divorce from supermodel Gisele Bündchen; leaving his ex, Bridget Moynahan, while she was pregnant; Deflategate; finishing his career in Tampa instead of Boston; and losing a whole lot of money in cryptocurrency investments.

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Typically, some of the jokes got quite edgy, including a few references to the suicide of former Patriots tight end Aaron Hernandez (who died in prison after being convicted of murder). Kardashian—after being loudly booed when she took the podium—jokingly compared Brady’s looks to her ex-stepparent, Caitlyn Jenner. “I think my stepdad is a great example for you. She’s one of the best athletes in the world who proved you can do anything in this next chapter of your life,” Kardashian quipped. “You can become a commentator or a far-right-wing Republican or even a strong confident woman.”

Kardashian, in turn, was subjected to some of the night’s most vicious barbs, including a joke from Brady that “Kim was terrified to be here tonight. Not because of this but because her kids are at home with their dad,” in reference to the erratic Kanye West. Comic Tony Hinchcliffe, meanwhile, went for old-school early 2000s misogyny, joking that the reality star “had a lot of Black men celebrating her end zone.” He said, “Kim, word of advice, close your legs. You have more public beef than Kendrick [Lamar] and Drake.”

But the one joke that seemed to cross the line was Jeff Ross’ anecdote that Brady approached Patriots owner Robert Kraft after he was hired and told him, “‘I’m the best decision your organization has ever made,’” adding, “‘Would you like a massage?’” Kraft, who was in attendance at the roast, was infamously charged as part of a human trafficking investigation surrounding a Florida massage parlor in 2019. The joke spurred Brady to get up from his seat and warn Ross not to “say that shit again.”

Brady had claimed, before the event, that he was completely prepared to be roasted: “It’s like a football game. You run with a game plan, and then you get to see kind of how the strategy goes, and then you adjust on the fly,” he said (via CBS News). “This is what a locker room has been like for me for all these years. So it’s not like I’m used to people not making fun of me.” He dished some out himself to close out the evening, taking aim at Kardashian, Manning, Belichick, and Taylor Swift and the Kansas City Chiefs: “You say your stadium is the loudest. It helps when all your fans are 14-year-old girls. And in honor of Tay-Tay, let’s take a look at the Chiefs ‘eras’: terrible for 50 years, good for five. Shake it off.”