During the Netflix Is A Joke Fest, which was hosted by Kevin Hart, roasters mercilessly made fun of NFL legend Tom Brady. Ross, who referred to himself as the “Roastmaster General,” was brutally honest in his Brady material.

Ross discussed Brady’s underdog start as the 199th overall pick in the 2000 NFL Draft five minutes into his set. “He waited for days on end, and then you were selected in the sixth round when Bill Belichick’s dog inadvertently trod on the keyboard,” teasingly said Ross.

Thinking Back on Brady Saying to Kraft “I’m The Best Decision Your Organization Has Ever Made”

Then, Ross related a tale from early in Tom Brady’s career about him telling Patriots owner Robert Kraft, “I’m the best decision your organization has ever made.” The crowd applauded with a roar of laughter.

But then Ross said, startling the assembled into an awkward silence, “Would you like a massage?”

The misguided joke alluded to Kraft’s 2019 allegations of soliciting prostitution at a massage parlor in Florida. Even though the charges were eventually dropped, people still talk about this incident.

With a clearly uncomfortable expression, Brady told Ross, “Don’t Say That Sh*t Again.”

Brady, who was seated in the middle of the stage, shifted in his chair nervously and gave Ross a stern look. Brady went up to Ross at the podium and firmly said, “Don’t say that sh*t again,” into the hot mic as Kraft giggled nervously from the crowd.

“All right, all right. Look at him, he’s having fun,” a startled Ross shot back. Robert Kraft, I adore what you do for the Jewish people. You’re amazing.

Even though Ross and Brady hugged each other after the joke, it was obvious that it went too far and made people cringe rather than laugh.

Roast humor frequently walks the fine line between offensive and funny.

Roast humor is renowned for its brutally unvarnished nature. The shock value humor of the genre often pushes boundaries with content that other people might find offensive or indecent.

But the lighthearted atmosphere and humorous background make controversial jokes more acceptable in society. In the roasting arena, laughter usually wins out over fury.

However, some felt that Ross went too far in using Kraft’s actual legal issues as material for a joke. When does a roast joke cross the line from inappropriate overreach to vulgar fun? That boundary is still arbitrary.

Those who watched the roast on Netflix were free to evaluate the content without any restrictions. Comedy knows no bounds, but discerning between tone-deaf and edgy comics requires an awareness of contemporary cultural norms. I sincerely hope you like reading this “Did Jeff Ross Cross the Line with His Tom Brady Joke? Fans React!” article.

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