On Sunday, during Netflix’s live special of “The Roast of Tom Brady,” comedian Jeff Ross delivered a joke that left the legendary quarterback visibly uncomfortable. The moment occurred when Ross referenced Patriots owner Robert Kraft and asked Brady, “Would you like a massage?” The audience erupted into laughter, but Brady quickly turned to Ross and whispered into his hot microphone, “Don’t say that shit again.”
The Controversial Joke
Ross, known for his sharp wit and fearless roasting style, had been introduced as the roastmaster for the event. Dressed in a bloody No. 32 football jersey with the words “Roast J Simpson” on the back, he wasted no time diving into Brady’s career. Ross playfully mocked Brady’s early days as the 199th pick in the NFL draft, quipping, “He sat there for days, waiting and waiting, and then you were finally picked in the sixth round when Bill Belichick’s dog stepped on the keyboard by accident.”
But it was the subsequent joke that caused the stir. Ross recounted a moment when a scrawny rookie Brady told owner Robert Kraft, “I’m the best decision your organization has ever made,” upon joining the Patriots. The audience applauded, anticipating a punchline. Ross delivered it: “Would you like a massage?”
The reference was clear. It alluded to Kraft’s previous controversy involving accusations of soliciting prostitution in a Florida massage parlor. Although Kraft was never charged in the case, the incident had made headlines and left a lasting impression.
Brady’s Reaction
Seated front and center on stage, Tom Brady shifted uncomfortably in his seat after the massage joke. He turned toward Ross and, with a stern expression, warned him, “Don’t say that shit again.” Ross, taken aback, nervously replied, “Okay, okay. He’s having fun, look at him. I love what you do for the Jews, Robert Kraft. You’re incredible.”
The camera captured Kraft laughing in the audience, seemingly unfazed by the jab. After completing his set, Ross and Brady hugged on stage, exchanging words with smiles on their faces. Host Kevin Hart playfully teased Ross, urging him to “stop being a bitch” and sit down. Hart then quipped, “Make sure to check out Jeff’s one-man show. It’s playing at the Hollywood Cemetery. His career is literally dying. If we stop doing these roasts, you will not see Jeff Ross ever again.”
The Context
As part of Netflix Is a Joke Fest, “Greatest Roasts of All Time: Tom Brady” featured the former quarterback, who played 20 seasons for the New England Patriots and three for the Tampa Bay Buccaneers. The roast brought together some of the biggest names in comedy to take playful jabs at Brady’s illustrious career.
In the end, the incident served as a reminder that even in the world of comedy roasts, certain topics can hit a nerve. Jeff Ross learned firsthand that crossing the line with Tom Brady could lead to an awkward moment on stage.
