It was supposed to be a victory lap. When the lights went up at the Kia Forum for The Greatest Roast of All Time: Tom Brady, the vibe was electric, almost frantic. We’ve seen Tom win seven rings, but we’d never seen him take a punch he couldn't deflect with a quick release. Honestly, it was a weird night.
Kevin Hart walked out like he was ready to burn the whole building down. "Get comfortable being uncomfortable," he warned. He wasn't kidding. For three hours, the man who spent two decades being the most protected asset in New England was suddenly a wide-open target. No pads. No helmet. Just a lot of expensive dental work and a thick skin that eventually started to show some cracks.
The Gisele Elephant in the Room
Everyone knew they were going there. You can’t have the roast of tom brady and not talk about the divorce. It was the centerpiece of the night, even if it felt a little gross at times. Kevin Hart went for the jugular early, joking about Gisele's jiu-jitsu instructor, Joaquim Valente.
"Eight fucking karate classes a day and she's still a white belt?" Hart yelled. The crowd lost it. But looking at Tom’s face, you could see that "I'm a good sport" mask vibrating.
Nikki Glaser, who basically walked away as the MVP of the evening, didn't hold back either. She pointed out that Tom has eight rings now—the seven from the Super Bowls and the one Gisele gave back. Ouch. It was brilliant comedy, but it also felt like a reality check. We often forget these people have kids who have WiFi access.
When the "Unroastable" GOAT Snapped
There was one moment that didn't feel like a joke. Most of the night, Brady sat there and took it. He laughed at the Spygate jokes. He chuckled when Julian Edelman called him an asshole. He even leaned into the crypto jokes about losing $30 million.
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Then Jeff Ross stepped up.
Ross started telling a story about Tom’s early days with the Patriots. He mentioned the legend of Tom walking into Robert Kraft's office and saying he was the best decision the organization ever made. Then Ross added, "Would you like a massage?"
The air left the room.
Tom stood up, walked to the podium, and whispered—loud enough for the mic to catch—"Don’t say that shit again." It was the only time all night the "character" of the roast fell away. It wasn't a bit. Tom was genuinely protecting Kraft, who has been a father figure to him for twenty years. It reminded everyone that even in a room full of comedians, there are still some third rails you just don't touch if you want to keep your invite to the afterparty.
Why Nikki Glaser Actually Won the Night
If you haven't seen Glaser's set, you’re missing the clinic she put on. While others leaned on easy "Gronk is dumb" jokes (though Jeff Ross's "Forum is how Gronk counts to five" line was gold), Nikki was surgical.
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She hit him on the retirement. Then the un-retirement. Then the second retirement.
"It's hard to walk away from something that's not your pregnant girlfriend," she quipped, referencing Bridget Moynahan. That's a deep cut. It’s the kind of joke that makes you gasp before you laugh. Most people think roasts are just about being mean, but Nikki proved it’s about being accurate.
The Fallout Nobody Saw Coming
Months later, the dust has settled, but the impact hasn't. Tom has been surprisingly open about his regrets. He told Logan Paul on the Impaulsive podcast that the jokes felt like "a stake through the heart" when he talked to his kids the next day.
It’s an interesting pivot. We want our legends to be human, but when they show us they're hurt, we almost feel cheated. Brady admitted he "fucked up" as a parent by not realizing how the public ribbing of their mother would affect his children.
Gisele was reportedly "deeply disappointed." Bridget Moynahan posted some cryptic, yet pointed, quotes on Instagram. It turned a comedy special into a family therapy session played out in front of 22 million viewers.
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What Really Happened with the Patriots Dynasty?
The roast also served as a weird, public reunion for the New England power trio: Brady, Kraft, and Bill Belichick. Seeing Belichick and Kraft take a shot together was probably more shocking than any joke told that night.
Belichick actually had some of the best timing of the night. He joked that it was hard to butt heads with Tom because Tom was "so far up Alex Guerrero's ass." It was a rare glimpse of Bill with his guard down. For a few minutes, the tension that defined the end of the Patriots dynasty seemed to evaporate. Or maybe they just realized they all looked better together than they did apart.
Actionable Takeaways from the GOAT's Bad Night
If you're watching the roast of tom brady or thinking about how it changed the landscape of celebrity culture, here’s what you actually need to know:
- Comedy is shifting back to "danger." After years of everyone being worried about "cancel culture," this roast proved there is still a massive appetite for R-rated, offensive humor. Netflix grabbed nearly 2 billion viewing minutes in the first full week for a reason.
- Boundaries matter, even for the rich. Brady’s reaction to the Robert Kraft joke shows that even if you sign up for a roast, you need to set clear boundaries with your team beforehand. If you don't, things get awkward fast.
- The "Human" Element wins. The parts of the roast people remember months later aren't the scripted bits. It’s the unscripted moments: the boos for Kim Kardashian, the Kraft/Belichick shot, and Tom’s genuine protectiveness over his friends.
- Consider the collateral damage. If you're ever in a position to be roasted (lucky you), think about who isn't on that stage. The people at home—the kids, the exes—don't have a microphone to fire back.
Ultimately, the night was a reminder that Tom Brady is obsessed with winning, even at being made fun of. He wanted the biggest, meanest roast ever. He got it. But as he found out the next morning, sometimes the cost of "The Greatest Roast of All Time" is a price you didn't realize you were paying until the bill arrives.
If you're looking to dive deeper into the history of these events, check out the archives of the Comedy Central roasts. They set the blueprint that Netflix just supersized. You'll see that while the names change, the targets—ego, age, and failed relationships—stay exactly the same.