Comedy ‘Roasts‘ are enjoyable given the boldness and irreverence of the comedy style. It is a refreshing and entertaining take on the usual stand-up. While the intention is to make the audience laugh, roasts could cause someone to take offence too. There’s a thin line between both, one which a comedian needs to tread very carefully basis the audience’s reactions.

Things got a little awkward during Netflix‘s The Greatest Roast of All Time: Tom Brady. The seven-time Super Bowl champion agreed to be roasted in the LIVE and unedited roast as part of Netflix Is a Joke Fest. It is the first-ever roast that was telecasted LIVE on May 5. But when the “Roastmaster General,” Jeff Ross came on stage to roast Brady, one particular joke seemingly ticked off the former football player.

Tom Brady Netflix The Greatest Roast of All Time Jeff Ross comedy controversy

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The Roast Set

Hosted by Kevin Hart, the roastmaster for the day was Jeff Ross. He entered the arena wearing a seemingly bloody No. 32 football jersey with the words “Roast J Simpson” on the back. “If the gloves don’t fit, you must talk shit,” Ross quipped.

Five minutes into his set, Ross delved into Brady’s career after being the 199th pick in the NFL draft. “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,” Ross joked.

The Joke That Didn’t Land For Brady

Jeff Ross was talking about how the New England Patriots selected Tom Brady in the sixth round of the NFL draft and became the 199th overall pick. “So Tom became a Patriot and moved up to New England, and on the first day of training camp, that scrawny rookie famously walked into the owner Robert Kraft‘s office and said, ‘I’m the best decision your organization has ever made. Would you like a massage?‘” Ross joked.

As the audience reacted to the burn, the camera cut to Tom Brady, who was seemingly uncomfortable with the joke. Jeff Ross turned to Robert Kraft, owner of the New England Patriots, who was in the audience, to greet him, blowing him kisses. “I love Robert Kraft, I….,” Ross began saying before Brady approached him at the podium to whisper in his ear and say, “Never say that sh** again.

Tom Brady Netflix The Greatest Roast of All Time Jeff Ross controversy

OK, OK,” Ross responded, sounding nervous. “He’s having fun, look at him. I love what you do for the Jews, Robert Kraft. You’re incredible.” The camera then captured Kraft laughing in the audience. After completing his set, Ross and Brady hugged on stage, exchanging words and smiling at each other.

The Reference

In 2019, Robert Kraft and others were charged with solicitation as part of an anti-sex trafficking investigation into several Florida massage parlours. Prosecutors ultimately dropped a misdemeanour charge against the Patriots owner after courts blocked the use of video from secret cameras installed by police inside the parlours.

What Followed

As host Kevin Hart returned to the microphone, he teased Ross, “Wow, wow. Stop being a bitch, Jeff, and sit down. Stop kissing his ass. ‘Are you OK? It was just jokes?’” Hart then transitioned to the next roaster, saying, “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.

About The Show

Other roasters included comedians Bert Kreischer, Tom Segura, Nikki Glaser, Andrew Schulz, Tony Hinchcliffe, and Sam Jay, as well as former wide receivers Randy Moss and Julian Edelman, quarterbacks Drew Bledsoe, and tight end Rob Gronkowski.

Have you watched it yet? The Greatest Roast of All Time: Tom Brady went LIVE on the OTT platform yesterday, May 5. “Netflix Is a Joke Fest” is taking place in Los Angeles from May 2 through May 12, with over 400 live stand-up shows across 35-plus venues and a dizzying number of professionally funny folks. To know more about this year’s lineup and how to buy tickets, visit