Winners & Losers From the Tom Brady Netflix Comedy Roast

It was hard to know what to expect from the Netflix Roast of Tom Brady which aired live on the streaming network Sunday night.

Full disclosure, I wasn’t optimistic. In fact I entered the night with a fair amount of trepidation.

A lot of people Patriots fans hold in extremely high regard were leaving themselves open and exposed in a way they never had before. It’s unimaginably difficult to play in front of tens of thousands of screaming fans. But a live roast is a level of pressure and scrutiny I’m not sure anyone up on that dais Sunday night had ever faced before.

Mix in some existing hostility involving some of the main players in attendance and there was potential for this to go very badly.

This however was not the squirmy cringe fest I feared it might be. In fact, Sunday night turned into the Patriots reunion no one asked for, and none of us knew we needed.

The event was hosted by actor/comedian Kevin Hart and ‘Roast Master’ Jeff Ross. It also featured outsiders like former QB Peyton Manning, actor Ben Affleck, and a host of standup comedians.

But this was about Brady and all the people his greatness has pulled into this immediate orbit over the years.

Patriots former head coach Bill Belichick and team owner Robert Kraft were in attendance and both spoke, as did former teammates Randy Moss, Rob Gronkowski, Drew Bledsoe, and Julian Edelman. Several other former Patriots also shared the stage.

What followed was a hilarious, raunchy, no holds barred gauntlet run through memory lane. But like in sports, there are winners and losers, so without further ado…

Winner: Kevin Hart

“You gotta get uncomfortable, before you get comfortable.” That’s what host Kevin Hart told the audience after joking that Brady’s ex-wife Giselle attended the roast as Antonio Brown’s plus one. That was the first but definitely not the last time we saw Brady squirm and collectively realized ‘oh, he’s NOT ready for this.”

As roast master, Hart set the tone for what the entire evening.

And it got worse. Much, much worse.

Moments later talking about how Brady ‘f–ked’ his coach by leaving for Tampa Hart turned it back to Giselle.

“You know who else f–ked their coach? Giselle, when she ‘f–ked that karate instructor.”

And that was it. That was the moment Brady realized he had made a huge mistake. This was not going to be some tame affair and absolutely nothing was going to remain off limits.

Winner: Drew Bledsoe

There was NO reason for Drew Bledsoe to be here. He has accomplished much in his life on the football field and off but he is largely known as a footnote in Tom Brady’s Hall of Fame career. The guy whose job Brady took on the way to becoming the GOAT.

But Drew slayed as the first non-comedian to roast Brady. He was comfortable, self deprecating and delivered his zingers with incredible timing. The former rocket armed QB took aim not just at his successor but Bill Belichick, the man who pulled the plug on Bledsoe’s Patriots career after he got injured week 2 of the 2001 season.

“At least when I got fired somebody else wanted me,” Bledsoe quipped about his former head coach’s inability to find a new head coaching gig after being let go by the Patriots.

Loser: Ben Affleck

It kills me to say a bad thing about Ben Affleck so I’d rather pretend his ‘roast’ never took place but it did and, sheeesh.

Never at any point did Affleck attempt actual comedy. I’m not sure anyone even told him what a roast is. Instead the Boston born actor ranted angrily, and incessantly about all of Brady’s online ‘haters.’ And then he took aim directly at Bill Belichick as the NetFlix production team was trying to get him to wrap up his interminably long and meandering monologue.

“Bill!” Affleck shouted looking directly at the coach. “Like, the look on your face that everybody works for you. I’ve got season tickets! You work for me, motherf*cker!

Affleck then called out Belichick for his evasive press conferences before pressing him on why he doesn’t show Tom Brady more love.

“What does [Tom Brady] have to do to make Bill Belichick happy? How do we see some teeth, like you got to cure a cancer? They’re watching the Superbowl, Tom throws a touchdown pass win again, and Bill’s looking at him like, no, like f*cking Tom sh*t in his cereal or something.”

Winner: Bill Belichick

Considering how poorly things have gone for Belichick since Tom Brady left the Patriots in 2019, (losing record in 3 of 4 seasons, fired, didn’t get another job, divorce) just showing up to this event puts him squarely in the win column.

But Bill wasn’t there just to show he can take a punch, he was there to throw some haymakers of his own. And on this day he settled all family business.

“It’s an honor to be at the ‘Roast of Tom Brady’ on Netflix tonight. Not to be confused with the 10-part Bill Belichick roast during the Apple TV documentary,” Belichick said, referencing Apple TV’s “The Dynasty” which featured heavy involvement from the Kraft family.

Belichick mainly took kid glove jabs at Brady but went hard at his former trainer and business partner, with whom Belichick did not see eye to eye.

“People say that Tom and I butted heads a lot, and in a way, that was true, but not really,” Belichick said. “It was hard to butt heads with Tom because he was so far up Alex Guerrero’s ass.”

He absolutely crushed Rob Gronkowski when he told his former Patriots tight end and current Fox Football analyst to ignore the Patriots long standing mantra and the “stop” doing his job.

But surprisingly, Belichick’s harshest dig came at the expense of Danny Amendola. The former Patriots receiver has been critical of Belichick since leaving New England and took some shots at his former coach in the “Dynasty” docu-series.

“Danny joined us in 2014 and had 200 yards,” Belichick quipped. “In 2016 he had 250. Or what Randy [Moss] would call a decent first half.”

Boom. Roasted.

Loser: Dana White

Does there have to be a reason?

Loser: Robert Kraft

Kraft didn’t deliver a roast as much as a toast with a couple one liners mixed in. After which he was drawn to the stage by Hart who coaxed Kraft and Belichick to take a shot together. It was….awkward and clear Belichick didn’t want any part of it. While on stage Kraft tried diffuse the obvious tension.

“I want to say this is the greatest coach in the history of the game that did what no one else has done. And having Tom Brady and him was the greatest honor the good Lord gave me,” Kraft said.

Look, we all believe Kraft believes that. But, it rings pretty hollow in light of the “Dynasty” series and some recent reporting about how Kraft trashed Belichick to prospective employers. Best to stop the charade and allow all parties to move on and see if time heals some of these gaping wounds.

Winner & Loser: Rob Gronkowski

What can you say about Gronk, he’s a big target.

His buffoonish charm left him rife for jokes about his perceived lack of intelligence and he may have gotten it just as bad as Brady all night long.

Tony Hinchcliffe thanked Gronk for taking time away from “writing letters to Santa” to attend and said he “knew [Gronk was] here after we ran out of chocolate milk in the back.”

Comedian Nikki Glaser also took a jab at him while roasting Tom Brady, saying, “Tom lost $30 million in crypto. Tom, how did you fall for that? Even Gronk was like, ‘Me know that not real money.’”

But Gronk wins because, rather than try and run from his well earned meathead persona, he leaned into it. Hard.

He was shockingly at his best when he went off script. Which was good because he seemed to be struggling with the teleprompter and was hilariously urged by Hart at one point to “sound it out.”

But Gronk was real, and raw. And though I’m not sure what he did up there qualifies as comedy, it was a show well worth the price of admission.

The performance ended with a toast and shared shot with Brady and Belichick whom Gronk genuinely lamented he’d never had a drink with before. The toast was punctuated by a signature spike of Gronk’s empty shot glass.

Pure Gronk. Nothing else would do.

Loser: Randy Moss

Randy, comedy is hard. Maybe ask someone to write your jokes for you next time like everyone else did.

Winner: Actual Comedians

If you have beef with some of the jokes and some of the targets, I don’t blame you. Nothing was off limits and there were some cringy and uncomfortable moments and more than a fair share of jokes that crossed a lot of lines.

But, this is what roasts are. They are meant to be raunchy and push boundaries, and if you sign up to be part of it, it’s open season. From Nikki Glazer to Tony Hinchcliffe to Andrew Schulz and Sam Jay, the actual comedians killed it.

Loser: Tom Brady

Why Tom?

Did you really need this?

I’m not sure if this was a money grab after blowing $30 million in a crypto scam. Or to maintain a high profile for future business ventures. Whatever the reason, it didn’t make sense to me beforehand and it doesn’t now.

Brady never struck me as a guy who has much of a sense of humor, certainly not about himself. He is a serious guy who has used every slight he’s ever received in his life as jet fuel on his path to becoming the greatest of all time.

But on this night he broke and broke early. It was evident from the jump that the Giselle divorce jokes were hard to stomach. He also really didn’t like being called a deadbeat dad for leaving Bridget Moynihan while she was pregnant with their first child.

And Brady almost had his Will Smith moment during Roast Master Jeff Ross’s set after Ross took a shot at Robert Kraft for soliciting an illegal massage. While Ross blew a kiss to Kraft in attendance, he was then approached by Brady at the podium, who whispered into Ross’ hot microphone, “Don’t say that shit again.”

When it was Brady’s turn to take the microphone to defend himself there was nothing good natured about any of his routine. In fact it was oddly arrogant and cruel.

And while it’s not clear whether Brady needed this, it’s certain his family didn’t. They caught a lot of strays and I can’t fathom Brady’s 3 kids – all aged 16 and under – watching this or being able to avoid hearing about it today and all days going forward. Like Brady’s football legacy, this roast is now part of his permanent record.

Winer: Patriots Fans

This coulda gone sideways and at times it almost did. But this entire special felt like it was produced just for you and your closest pals. Like getting together with your high school buddies. Sharing the same stories you’ve been tossing around for 25 years and laughing just as hard at each re-telling. A safe space where no one is truly safe.

And yes there was a certain level of catharsis seeing a few participants air some grievances, some good natured, others more recent and real. But also to know that there is genuine love and respect among the majority of those brave enough to take the stage. All of whom blessed Patriots fans with 20 plus years of unforgettable memories and for at least one night reminded us what it was like to be great.