The Most Awkward Moments From Tom Brady’s Roast
The roast was three hours long, and at least one of those hours was just Gisele jokes.
The Roast of Tom Brady aired live on Netflix on Sunday night as the retired football star gamely sat through three hours of jokes at his expense. That’s far too long to watch anything that isn’t Titanic, so let’s cut right to the stuff you really want to know about: What were the most awkward moments of the night? Let’s get into it.
Kevin Hart kicked off a night of Gisele jokes
Kevin Hart was the emcee and started the show with a string of jokes about the dissolution of Brady’s marriage to Gisele Bündchen. This set the tenor for the rest of the night, which at times seemed as though it was mostly about Brady’s wife leaving him.
“The world knows you left Bill Belichick high and dry, man. You left him and then you went to Tampa and you won a championship,” Hart said. “That’s what you gotta do to maintain your happiness. Sometimes you gotta fuck your coach. You know who else fucked their coach? Gisele. She fucked that karate man.”
Bündchen’s new man is actually a jiujitsu instructor, but that’s neither here nor there. Brady suffered through what felt like hours of Gisele jokes and did it all with a toothy smile plastered across his face. The lack of light in his eyes told a different story, however.
At this roast and I can report that with every new Gisele joke Brady appears to be disassociating
— Mina Kimes (@minakimes) May 6, 2024
Jeff Ross brought real tension to the evening
Jeff Ross came out dressed as “Roast J. Simpson,” wearing a football uniform detailed with flames (he arrived “from hell”) and a pair of leather gloves. “If the glove don’t fit, you must talk shit,” he said. The comedian, most famous for his roasting skills, followed through on that promise and produced the most tense moment of the night.
Ross wound up by recounting a moment when Brady, drafted 199th in the NFL, walked into Patriots owner Robert Kraft’s office and said, “I’m the best decision your organization has ever made.” The audience gave a big round of applause before Ross delivered the punch line: “Would you like a massage?”
Tom Brady wasn't a fan of this Robert Kraft joke...
— Ari Meirov (@MySportsUpdate) May 6, 2024
Felt like a near Will Smith moment.pic.twitter.com/UX89tlw7f1
The arena erupted with laughter at Ross’s reference to Kraft’s 2019 arrest for soliciting prostitution at a Florida massage parlor. Brady kept his smile glued to his face but went up to Ross at the podium and audibly told the comedian, “Don’t say that shit again.” Was he joking? Well, as we learned later in the evening, Brady can be pretty funny, but it’s unclear if he’s that funny.
Nikki Glaser went hard
Of all the roasters, Nikki Glaser might have gotten the biggest reaction of the night. The stand-up comic and roast regular received a standing ovation for her razor-sharp set, which, of course, included several jokes about Bündchen.
“Tom Brady: five-time Super Bowl MVP, most career wins, most career touchdowns,” Glaser said. “You have seven rings — well, eight, now that Gisele gave hers back.”
“The only thing dumber than saying ‘yes’ to this roast was when you said, ‘Hey, babe, you should try jiujitsu,’” Glaser joked. “How much must that suck to know that your ex-wife’s new boyfriend can beat your ass while eating hers?”
Kim Kardashian was not welcome
Kim Kardashian came onstage and was greeted with boos from the audience. Like a true professional, she brushed it off and dived right into her prepared jokes.
They're booing Kim Kardashian pic.twitter.com/bJyHRUAaNY
— CJ Fogler account may or may not be notable (@cjzero) May 6, 2024
Someone continued to heckle her from the audience as she began to address the rumor that she and Brady had briefly dated.
“I do know it would never work out,” Kardashian said. “An ex-athlete, high cheekbones, silky hair — you remind me too much of my stepdad now.” A meme was then put onscreen that had four photos of Brady through the years and then two photos of Caitlyn Jenner. “The Evolution of Tom Brady” was written over them in case you really couldn’t put it together yourself.
This got a big laugh from the room and from Brady himself. He actually seemed to be the person who found Kardashian the funniest. Maybe they really did date.
Brady tried his best
Over two and a half hours into the roast, it was time for Brady to make some jokes. This is the inherent flaw of a celebrity roast. The show’s closer is usually the least funny person on the stage. Brady did well enough, but he is not beating the robot allegations anytime soon. He joked about Taylor Swift and the Chiefs. (“Kansas City, you say your stadium is the loudest? It helps when your fans are 14-year-old girls.”) He took a shot at Kanye West. (“I know Kim was terrified to be here tonight — not because of this but because her kids are at home with their dad.”) He even made a joke about Bündchen, though it was fairly meek in comparison to everyone else’s:
“There’s been a lot of jokes tonight, but the truth is I miss the love of my life: football,” he said. Not the best, not the worst — a fitting cap for the entire evening.