A little over a year ago, former NFL quarterback Tom Brady got torn to shreds by comedians on Netflix’s The Roast of Tom Brady.
While the event was a big success and garnered a lot of appreciation from viewers, Brady would later come to say he had regrets about participating.
It begs the question: why would the football superstar, known for keeping things close to the vest, do a public roast in the first place?
“Roastmaster General” Jeff Ross, who hosted the show alongside Kevin Hart, offered up an explanation during his Wednesday appearance on SiriusXM’s Howard Stern Show.
According to Ross, he noticed that Brady had been snooping around his Instagram feed on Super Bowl Sunday in 2021, which piqued his curiosity (via SI.com).
“I had seen him looking at my Instagram on Super Bowl Sunday a few years ago,” Ross told Stern. “I was like, ‘why the f*** is Tom Brady on my Instagram?’
“I had some jokes up. Maybe that’s how he unwinds before a big game. And he f***ing wins! So I hit him up the next day on Instagram going, ‘Dude, it’s time for a roast. You obviously love this s***.’
He writes me back, we start talking, and it turns out my agent and his agent work together, and we put a deal together to do a roast. Netflix was like, SURE!’ I’m like, let’s elevate this whole thing. Bring the roast back bigger.”
It was a long process to get Brady to eventually sign on the dotted line due, in part, to the fact that the plans were being hatched in the midst of a very volatile time in his life.
“I can say shock because it was like drip, drip, drip,” said Ross. “It took so long because he agreed. Then he retired. We were like, let’s go, now’s our chance. Then he unretired. Then we had to wait until he was done playing. Then he was going through a divorce. Let’s wait for that. Then Netflix was like, our festival is next May, let’s wait for that. And let’s do it live. So, he was already on the hook when I brought the live idea.”
Ross remained stumped as to why someone who had spent much of their professional career crafting a specific image of himself would want to let himself be roasted in front of the world.
“I said to Tom right beforehand, ‘Why are you doing this?’” Ross explained. “And he goes, ‘I love this kind of humor. People are too snowflakey right now. No fear. This is what we do.'”
If Brady wanted the “non-snowflakey” version of a roast, he got one. It included jokes about his recent divorce from Gisele Bündchen, Spygate, Deflategate, Bill Belichick, Robert Kraft’s 2019 soliciting prostitution charges, and former Patriots teammate Aaron Hernandez. When Ross referenced Kraft’s prostitution charges, Brady infamous got in his ear, telling them “don’t say that shit again.”
A bit snowflakey, if you ask us.
“I think Tom was checking me the way a lawyer objects on behalf of a client even when they know it’s kind of bull****,” Ross said to Stern. “I just shrugged it off and kept going.”
Brady would eventually come away from the experience saying he regretted how it impacted his kids.