The Tom Brady roast was billed by Netflix as “The Greatest Roast of All-Time,” and somehow, it might have actually lived up to the hype. The jokes flew for nearly three hours and came from a variety of people including Ben Affleck, Peyton Manning, Bill Belichick, Rob Gronkowski, Julian Edelman along with experienced roasters like comedians Jeff Ross, Nikki Glaser and Tony Hinchcliffe.
Nothing was off limits and Brady learned that the hard way early on when Kevin Hart, who was the host of the event, kicked things off by making a few jokes about the quarterback’s divorce from Gisele Bundchen. Although Brady looked slightly uncomfortable with the one-liners about Gisele, only one joke seemed to get under his skin and that came from Ross, who is an experienced roaster.
When it was his turn, Ross made a joke about Patriots owner Robert Kraft. During the joke, Ross was recounting a conversation that Brady and Kraft had shortly after the seven-time Super Bowl winner was drafted with the 199th overall pick in 2000.
“‘I’m the best decision your organization has ever made,'” Ross said, pretending to be Brady.
After the crowd cheered, the comedian finished his joke.
“‘Would you like a massage?'”
Ross’ joke was making light of the fact that Kraft got hit with two charges of soliciting another to commit prostitution in 2019 following a multi-county police investigation that involved massage parlors in Florida. Although the Patriots owner was eventually cleared of all charges, the joke still didn’t seem to sit well with Brady, who left his chair to walk up to the podium where Ross was standing.
At that point, Brady gave Ross a stern warning.
“Don’t say that shit again,” Brady said.
Ross then responded by pointing to Kraft.
“OK, OK. He’s having fun, look at him,” Ross said of Kraft.
It’s certainly possible this was all part of the act, but it definitely felt like Brady was legitimately upset with the joke. On a night where there were plenty of uncomfortable jokes, this seemed to be the only one that truly got under Brady’s skin.
If you missed the roast, we ranked all the best moments and you can check those out here.
