From Drew Bledsoe to Bill Belichick: Ranking the Funniest Guests of Netflix’s Tom Brady Roast

Former quarterback Drew Bledsoe is introduced at the 2023 Patriots Hall of Fame.

The Roast of Tom Brady was a truly unique night in the world of entertainment. Both legendary NFL figures and some of today’s most popular comedians delivered hilarious jokes at Brady’s expense and others in attendance.

From an evening filled with laughs across the board, we discuss the top 10 funniest performances from Sunday’s epic night of comedy.

Funniest Performances of Netflix’s Tom Brady Roast

10) Sam Jay

To the general public, Sam Jay wasn’t near the top of most well-known acts that were on the stage, but it’s safe to say she made some new fans after her performance.

From self-depreciating humor to lusting over Brady, and everything in between, the Boston-born comedian made her presence known with some classic one-liners.

9) Jeff Ross

Jeff Ross is a veteran of the roast game. He knows how to work a crowd, how to perform in these environments, and delivered in this setting like he always does.

Perhaps the most talked about moment of the night was when Ross delivered a line about Patriots owner Robert Kraft, which prompted Brady to stand up and whisper in his ear — telling him in harsher words — to not go there again.

8) Andrew Schultz

Andrew Schultz, by now, is well-known in the comedy/podcast world and performed as a pro would. Everyone in the room got the wrath as he pushed boundaries and was able to tie it all together with his classic delivery and charm.

7) Rob Gronkowski

Rob Gronkowski was the true wild card of the evening, with not many knowing how he was going to perform. By all accounts, the future Hall of Fame tight end met every mark for the night and surprised those who may have doubted his ability to command a stage.

Gronk tip-toed the line of absurdities in a way only he could while keeping the crowd and his peers engaged through it all. He even ended up “Gronk Spiking” a shot glass that enlisted a large reaction from the crowd.

6) Drew Bledsoe

Drew Bledsoe may have had the toughest assignment of the night — he had to go first. With all that pressure and expectations for a good start to the night on his shoulders, he delivered in a major way.

Bledsoe was the butt of many jokes while sitting on the stage, but when it was his turn to talk, he was able to dish it out as well. How he was able to move the crowd, tell the jokes with the right emphasis, and keep his peers laughing, was the first sign that we were all in store for a good night.

5) Tom Brady

After a long night that included almost three full hours of listening to his friends and peers clown him, Brady finally got a chance to get on stage and get his revenge.

It was his night, and he was the subject, but Brady wasn’t going to go out without swinging a few shots himself. He spoke with confidence one would expect from the greatest QB to ever play the game. Brady was able to deliver funny one-liners to attending celebrities with relevant trending topics in pop culture.

At the end of it, Brady took his moment by smashing his phone on stage and gave the crowd and any haters out there, the two-finger salute. Legendary.

4) Bill Belichick

The biggest surprise of the night was just how funny Bill Belichick was. The quiet, often standoffish former Patriots head coach is known for his short, worth-nothing answers, but he took the chance to show the world his humorous side.

Belichick was the subject of many jokes, but when he got on the stage, he made sure to also dish it. The coach was able to be funny and let loose while not going as far as many others had.

Most importantly, he did it his way. Belichick was a big winner of the evening.

3) Julian Edelman

Julian Edelman may have been the best non-comedian of the night. The player who most wanted Brady’s approval for years was unafraid to unload on his former quarterback.

From ribbing Belichick for not having a job, to Brady and his lifestyle, Edelman was unafraid to make fun of his former coach and long-time quarterback. Edelman stepped up and held his own.

2) Tony Hinchcliffe

Tony Hinchcliffe is a pro’s pro. He put on a master class of what it looks like to work a room at a roast. Everybody on stage — almost one by one in order — got his wrath, and he executed it perfectly.

Although he came on later in the night, with the vibes already high, Hinchcliffe was able to almost inject more life into a stage and a crowd that was already lively. He was slinging jokes that will be talked about for years, and the comedic superstar showed once again why he is where he is in his career.

1) Nikki Glaser

Hats off to the queen of the night. Nikki Glaser got on stage and rocked the house. From marital jabs to fawning for Brady, Glaser was unafraid to hit all subjects and did so with perfect delivery.

Many will view her performance as one of the all-time best roast performances, and she belongs in that conversation unequivocally. Glaser pulled no punches, delivered her message like a pro, and got the crowd to erupt in applause, setting up the night’s absolute best performance.