“I live in Roast world,” Ross, an executive producer on the special, says. “But I think the rest of the world is getting back in touch with their sense of humor and leaving politics out of it — which was a mission of mine, to make it as inclusive and fun so people could let loose. I think that helped. It was a break for the fans.”
The Brady special was the biggest project Ross, who has been doing roasts since 1995 at the Friars Club and eventually brought them to television as specials on Comedy Central, has ever helped to assemble.
He had been discussing the idea with the champion quarterback, who is also an executive producer on the project, for three years, and the special grew to the size and scope of an NFL spectacular: A sprawling three-hour live comedy event on Netflix, held at the massive Kia Forum in Los Angeles.
By amassing a murderers’ row of comedians (like host Kevin Hart and breakout Nikki Glaser ), A-list athletes (including Brady’s former teammate Rob Gronkowski and rival QB Peyton Manning) and other big stars (Ben Affleck, Will Ferrell and Kim Kardashian ), executive producer Casey Patterson says it was the perfect marriage of concept and “roastee.”
“Hearing that Tom was a fan of this style of comedy was, at first, a little surprising, and then you scratch the surface,” she says. “You’re like, ‘Of course. It’s locker room talk.’ It’s so endemic in sports that it made perfect sense. But what was surprising was he could quote every roast, and you say, ‘Oh, this guy has a real love of comedy.’ Given that he’s a stadium player and knowing how broad his shoulders are, he really understands this style of comedy. They’re going to hit you hard, but it’s coming from the people who know you.”
“You’re teasing them. You’re building them up to take them down,” he says. “You’re hitting them about something they’re proud of, not something they’re embarrassed by. The fact that he has all these Super Bowl wins and beautiful love affairs in his life and has all this lore around him — to me, that’s what’s funny. It reminds me of roasting any other big shot. Tom, to his credit, sensed that. He wasn’t sure what was going to come at him, and he was open to it. For me, the perfect roast joke is something that everyone gets, even if they’re not a football fan. Even if they’re not a sports fan, they could still understand what this is about.”
The combination of huge stars, big jokes and the tightrope of live TV created a pop culture phenomenon.
Per Nielsen ratings, 1.7 billion minutes were watched, and postgame analysis flooded entertainment news sites for days after: Who killed it, who bombed and Brady’s real thoughts about the jokes fueled headlines and clicks.
Even if things seemed tense at the time, Ross says it was all love between Brady and the roasters. One of the most talked-about moments was when Ross made a joke about Patriots owner Robert Kraft getting a massage, which evoked the billionaire’s charges of solicitation of prostitution in a Florida massage parlor in 2019. Although those charges were eventually dropped, Kraft was in the audience and the joke appeared to trigger Brady, who walked up to Ross and whispered, “ Don’t say that shit again ” into a hot mic.
Kim Kardashian and Jeff Ross speak onstage during “The Greatest Roast Of All Time: Tom Brady.”
“It didn’t even clock for me at the moment,” Ross says. “Tom’s my friend, my partner. I wasn’t feeling like he was coming at me. I feel like he was being fun , and I was in the zone. I didn’t even remember that happened until later on when people asked me about it. I think he was just pissed at me that I stole his O.J. bit entrance, so I apologized for that. But Tom was a great sport and so was Robert Kraft. Robert Kraft is used to being up in his private box. Here, he was down on the field getting muddy with everybody else. I’ve gotta give him a lot of credit for that.”
While the internet crowned Glaser as delivering the night’s funniest set, Ross also gives credit to the non-comedians who held their own — including Kardashian, who was audibly booed .
“I was impressed by Kim,” he says. “She worked really hard on her roast and stayed until the end. She wanted to stay there and take the hits, and I got to give her credit for that.”
He also applauded former Patriots wide receiver Julian Edelman, who took a different approach to the roast, meeting with the writers to tailor his jokes. When he appeared nervous, Ross invited him to the Comedy Store.
“I said, ‘You can do a rough rehearsal, and I’ll play Tom. You’ll get your jitters out,’” Ross recalls. “He rehearsed, he practiced and that’s what makes these guys champions.”
The outstanding live variety special Emmy nomination is a testament to the hard work of the massive production crew, Patterson says.
“It was risky,” she says. “I feel the same way about behind the camera. You have to be lionhearted warriors to put yourself out there in that way and do something like this live. You can all get killed, right? I’m so gratified for the team and how they handled the process.”
Although Ross is interested in bringing home some Emmy hardware — “It’ll be fun to see Tom figure out how to wear an Emmy on his finger,” he quips — he’s just happy to see roasts still make an impact after all these years.
A conspicuous sign in his house reading “Enjoy the Process” helps keep him focused, whether he’s telling jokes in a comedy club or an arena.
“For me, it’s more of a state of mind that lays over the actual day-to-day work,” Ross says. “There’s good days, there’s bad days, there’s great days and there’s terrible days. If you’re waiting for your Emmy nomination your whole career, you’re gonna be miserable. If you can get joy from trying out the jokes, trying on costumes, hiring your friends, working with your friends … If you can find joy in the ups and downs of it, to me, that’s the goal. That’s the way towards a long career.”
As for the future of televised roasts? Ross is keeping his dream punching bags to himself, but he’s thrilled that a streaming service took a chance on his comedic passion.
“I gotta give Netflix credit,” he says. “I think doing it live was a bold move, and that’s why it became this cultural moment.”
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