“Roasts have never been nominated before for anything, ever,” says Jeff Ross, “Roastmaster General” of Netflix’s The Greatest Roast of All Time: Tom Brady, still giddy and in shock over the special’s Emmy nomination. “Yet it’s this great American tradition that’s been going on for over 100 years. To see it up there with the Oscars, the Tonys, the Grammys and the Super Bowl halftime show makes me very proud.”
The anything-goes event — which featured the likes of Kevin Hart and Rob Gronkowski taking shots at arguably the greatest quarterback of all time — was three years in the making. The idea began on a Super Bowl Sunday, when Ross noticed Brady looking at clips of old roasts on Ross’ Instagram Stories.
Related Stories
“I wrote him, joking around, that we should roast him,” Ross recalls. Brady replied “LFG” — “Let’s fucking go” — and after some backroom dealing at WME (where both are represented), the wheels were in motion. When the stars finally aligned, Netflix offered Ross “a format to do whatever we want, uncensored.” He assembled a murderers’ row of insult comics — not all of them household names. “Watching my friends like Nikki Glaser, Tony Hinchcliffe and Sam Jay pop off gives me a lot of pride,” he says.
If the blockbuster event — it notched 1.67 billion viewing minutes in its first week, by far the biggest audience for a Netflix special — will be remembered for any viral moment, it was when Brady approached Ross onstage after Ross made a crack about New England Patriots owner Robert Kraft’s massage-parlor scandal and cautioned, “Don’t say that shit again.”
Ross insists he was given no guidelines by Brady ahead of time and that the admonition was not that serious. “I think he was just checking me the way an attorney would object on behalf of his client, even though he knows it’ll probably get overruled.”
Kraft, who was in the audience, “came off like a great sport,” Ross adds. “I talked to him afterward, and he loved it. The jokes might sting a little — but it always ends with a hug. We only roast the ones we love.”
Ross’ proudest moment? Emerging in a “Roast O.J. Simpson” No. 32 jersey — the NFL running back turned accused killer died a month earlier — saying, “What’s up, Patriots? I just came from hell. Aaron Hernandez says hello.” As that tasteless gag might suggest, there is no line when it comes to roast jokes — and Ross has no regrets about cracks that didn’t make the telecast. “I put the best meal on the table,” he says. “If there are jokes I want to do, I’m going to go for it.”
This story first appeared in the August 7 issue of The Hollywood Reporter magazine. Click here to subscribe.
