The Most Awkward Moments Of Tom Brady S Roast The Cut

Bonisiwe Shabane

-Dec 16, 2025, 5:42 PM

the most awkward moments of tom brady s roast the cut

Find this story in your account’s ‘Saved for Later’ section. The Roast of Tom Brady aired live on Netflix on Sunday night as the retired football star gamely sat through three hours of jokes at his expense. That’s far too long to watch anything that isn’t Titanic, so let’s cut right to the stuff you really want to know about: What were the most awkward moments of the night? Let’s get into it. Kevin Hart was the emcee and started the show with a string of jokes about the dissolution of Brady’s marriage to Gisele Bündchen. This set the tenor for the rest of the night, which at times seemed as though it was mostly about Brady’s wife leaving him.

“The world knows you left Bill Belichick high and dry, man. You left him and then you went to Tampa and you won a championship,” Hart said. “That’s what you gotta do to maintain your happiness. Sometimes you gotta fuck your coach. You know who else fucked their coach? Gisele.

She fucked that karate man.” Bündchen’s new man is actually a jiujitsu instructor, but that’s neither here nor there. Brady suffered through what felt like hours of Gisele jokes and did it all with a toothy smile plastered across his face. The lack of light in his eyes told a different story, however. Jeff Ross gets told off, Kim Kardashian gets booed, and more. Christian Holub is a writer covering comics and other geeky pop culture.

He's still mad about 'Firefly' getting canceled. There's always a risk when you bring in a non-comedian for a roast. Comedians have to develop a thick skin in order to survive hecklers and haters, but star athletes are more accustomed to being cheered on and worshipped. So when a legendary NFL quarterback sat down for Netflix's The Roast of Tom Brady, there were definitely some awkward moments amidst all the jokes. A shot glass is not a ball: In the final decade of his time leading the New England Patriots, Brady had no better partner than Rob Gronkowski. So naturally, the retired tight end was in attendance at Brady's roast.

But when the two took shots together, it seemed like Gronkowski may have forgotten he wasn't on a football field anymore, and spiked the shot glass after he finished. Unlike a ball, those things are made out of glass, and could potentially hurt someone. "Don't say that s--- again": Even outside the NFL, Brady is still protective of his old boss. When roast master Jeff Ross took the stage, he had not just Brady but also Patriots owner Robert Kraft in his sights. Reenacting the first conversation the two had, when 199th draft pick Brady confidently told Kraft "I'm the best decision your organization has ever made,” Ross added, "Would you like a massage?" The dig at... The expert roaster was rattled by that experience, made even worse by host Kevin Hart's subsequent dismissal: "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.” The Roast of Tom Brady streamed live on Netflix on May 5, 2024 and left absolutely nothing on the field. The three-hour event was hosted by Kevin Hart and put the future Hall of Fame Quarterback Tom Brady on the hot seat where virtually no subject was completely off limits. Despite one moment in which Brady stood up to warn Jeff Ross not to touch on a certain subject regarding New England Patriots owner Robert Kraft, Brady and the panel of his former teammates...

The panel of roasters included comedian and roastmaster Jeff Ross, seasoned roast battle veteran Nikki Glaser, celebrated comedic podcasters Andrew Shultz and Tony Hinchcliffe, and stand-up comics Bert Kreisher, Tom Segura, and Sam Jay. Many of Brady's legendary former Patriots teammates were also in attendance and delivered incredible sets, such as Drew Bledsoe, Julian Edelman, and Randy Moss. Rob Gronkowski took just as many hits as Brady, leading to a hilarious set of his own. Even Ben Affleck showed up, and Will Ferrell appeared as Ron Burgundy from Anchorman to roast the NFL's G.O.A.T. on Netflix. The Roast of Tom Brady on Netflix featured a wide range of wild moments and hilarious punchlines, but Ben Affleck's material sunk in the spotlight.

Kevin Hart set the tone early at The Roast of Tom Brady, making it clear from the start that no one would be going easy on him. Several roasters took advantage of Tom's recent and very public split from his ex-wife Gisele Bündchen. The two got divorced in October 2022 after Brady chose to come out of retirement following his Super Bowl LV win with the Tampa Bay Buccaneers in 2021, which earned him his seventh Super... Hart jokes that the decision ultimately backfired on Brady, who ruined a picture-perfect retirement story by coming back to the NFL, having a losing season, and ending up with a divorce. The only person who may have taken more hits at The Roast of Tom Brady was his star tight end, Rob Gronkowski. The night was full of jabs at Gronkowski's intelligence, few of which were better executed than Jeff Ross's creative dig at Gronkowski's ability to count.

Ross gave a hilarious overall set, but his greatest highlight of the night was “Tom, your teammates are all here at the beautiful, sold-out Los Angeles Forum. By the way, “Forum” is also how Rob Gronkowski counts to five.” Ross added, "Four, um. Five, um." to nail to joke home. New England Patriots fans remember little-known sixth-round draft pick Tom Brady, right? As things turned out, he grew up and did some good. He led the Pats to six Super Bowl championships and is, in many minds, the greatest quarterback in the history of the NFL.

Does that make him the best player ever? You can debate that at your pleasure. Brady is also a pretty good sport about things as well. So much so that Netflix decided to hold a roast of Tom Brady on Sunday and the program was hosted by Kevin Hart. Heck, Hart could not even know who Tom Brady is and the event would be funny. But for Patriots fans, there was an extra bit of magic in knowing Sir Tom was being roasted and we have lived through all the details.

The Netflix trailer was funny enough. Silencing out Brady saying the eff word and then the explosion? If New England football fans were not already in then they likely were after the trailer. Plus, we were promised a "lineup of surprise guests" and Netflix delivered. The best moments were saved for those Pats fans love most, though. Hart warned us before the show that no jokes were off-limits and he was correct.

That's the good thing. The issue was there was one moment that might have gone too far. Comedian Jeff Ross made a reference to Patriots owner Robert Kraft receiving massages. Kraft had received a misdemeanor charge in Florida in 2019 for an issue at a massage parlor. To this, Brady got out of his chair, walked over to Ross, and said (audibly on the live stream), "Don't say that (expletive) again." For those who may have missed it, Netflix had a special roast session involving NFL legend Tom Brady, and the night and event were downright hilarious.

Some of the best and brightest roasters came to town, and several of Brady's former teammates and coaches were on hand for the big event. All in all, the stars shined. There were jokes, SEVERAL jokes. Robert Kraft was even in attendance, dropping a line about Tom Brady owning the Raiders and mentioning how Las Vegas parted ways with Jimmy G to appease Brady. The majority were downright hilarious, but there were a few that crossed the ethical line. But that's the only problem of the night, that and going at Drew Bledsoe's injury that could have nearly killed him.

Everything else? Pefection to a crisp. Let's take a look at five other spectacular moments from a night of drop-dead laughter. Was Roger Goodell at the event? How many boos did Kim get? Long story short, a LOT.

Kardashian stepped to the stage while recognizing, according to the Hollywood Reporter, rumors about the two being in a relationship. Here's a fun fact. They are NOT. However, Kardashian did joke about "releasing a tape" while dropping one joke about her family having to defend an athlete that drew gasps and laughs. For those unaware, Robert Kardashian, Kim's father, was on O.J. Simpson’s defense team during the latter’s murder trial back in the 90s.

Simpson has since passed away from cancer. Was it the best joke of the night? No. But it was still worthy of mentioning, considering the Simpson case is still talked about to this day. Kardashian didn't drop jaws like her fellow comedians of the night, but at this point, they'd have taken anyone to take a shot at Brady. After torturing opposing fans on Sundays for over two decades, former New England Patriots quarterback Tom Brady was finally on the receiving end of some torture on Sunday night.

Brady was the target of Netflix’s live special, ‘The Greatest Roast of All Time.’ The night started off with a hilarious moment, as former Patriots head coach Bill Belichick informed Drew Bledsoe that it wasn’t his night, since he was essentially being benched for Brady once again. That kicked off what would turn out to be an R-rated night, as there was arguably as much profanity thrown about as there were jokes. However, Brady might have immediately regretted his decision to volunteer as the target of Netflix’s live roast. Brady was roasted by several comedians, former teammates, and other famous celebrities. Will Ferrell turned back the clocks and appeared as Ron Burgundy from ‘Anchorman’ to remind Brady that he lost twice to former New York Giants quarterback Eli Manning.

The Most Awkward Moments Of Tom Brady S Roast The Cut

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