Matt Damon Will Never Understand Why Tom Brady Made a ‘Horrible’ Decision That He Instantly Regretted Afterwards

The Tom Brady roast was one for the ages! A couple of months ago, Netflix hosted The Greatest Roast of All Time: The Roast of Tom Brady, which featured a bunch of associates and comedians who are well-wishers of the former NFL superstar. These roasts are notorious for the highly offensive jokes their dais tends to deliver, but they never fail to entertain the fans. 

The Roast of Tom Brady featured iconic comedians like Kevin Hart, Nikki Glaser, Sam Jay, Andrew Schulz, and the roast master himself, Jeff Ross. The dais also featured a bunch of former NFL players like Rob Gronkowski, Peyton Manning, Drew Bledsoe, Julian Edelman, and a few more. 

Kim Kardashian and Ben Affleck made guest appearances on the show, while former New English Patriots coach Bill Belichick and owner Robert Kraft were also present. Even though the roast was a massive success, one of Brady’s good friends didn’t understand why the retired NFL star agreed to it. 

Matt Damon never understood Tom Brady’s intent behind the roast

For those who follow every bit of Tom Brady’s life via the tabloids, you’re probably aware that he’s good friends with Ben Affleck and Matt Damon. However, the latter once appeared on The Rich Eisen Show and addressed his thoughts on the roast. 

Keep in mind, The Roast of Tom Brady was one of the most-watched events of its kind, being the sixth-most-watch event during the week it went live. Damon said, 

The roasting culture as fun as it is to watch. I never understand why people do it. You know what I mean? Like, I don’t want to hear, a bunch of my friends get up and like, rip me apart in public. But it was a lot of fun.

While Matt Damon thought they did a great job with the roast, especially the comedians that were featured that night, he believes roasts could sometimes get cringy. 

Kevin [Hart] was unbelievable as always, and all the comedians I thought were great. But it’s you know, it’s kind of a blue room. It touches on stuff that you’re like, ‘woof,’ you know, it kind of it can get a little cringy. But, I had a lot of fun with it.

There were a ton of questionable moments that conspired during the 3-hour long event. However, it was the exchange between Tom Brady and Jeff Ross that went viral after the latter made a joke on a touchy subject involving Robert Kraft. 

Though it was an incredible night overall, Brady eventually revealed that it affected his family a lot. 

Tom Brady claimed the roast affected his children terribly 

It was all fun and games until Tom Brady realized how badly the roast impacted his children. And this is something the sports legend wasn’t okay with following the roast.

Several jokes were made about his relationships from the past. However, one stuck out the most, a joke that Nikki Glaser made. She said, 

Five-time Super Bowl MVP, most career wins, most career touchdowns. You have seven rings. Well, eight, now that Gisele gave hers back.

This was a blatant jibe at Brady’s divorce from Gisele Bundchen, which took place back in 2022.

Your morning reminder that Nikki Glaser dominated the #TomBradyRoast. pic.twitter.com/Cqm4t2ULYy

— Netflix (@netflix) May 6, 2024

The former Tampa Bay Buccaneers player shares two children with the Brazilian fashion icon, Benjamin (14) and Vivian (11). Brady had a child with another ex-partner, Bridget Moynahan. 

After the roast ended, the NFL legend appeared on The Pivot Podcast, where he revealed how he felt about the event. He said, 

I loved when the jokes were about me. I thought they were so fun… I didn’t like the way it affected my kids… When you do something that you think is one way and then all of a sudden you realize ‘I wouldn’t do that again’ because of the way it affected, actually, the people I care about most in the world

However, he said that it has motivated him to be a better father moving forward. But at the same time, he was happy about the outcome of the monumental roast. 

The Roast of Tom Brady can be streamed on Netflix.