ben affleck as vic from deep water and tom brady

What Went Wrong With Ben Affleck's Roast Of Tom Brady

The Roast of Tom Brady on Netflix threw just about every punch imaginable at the greatest NFL quarterback of all time. No one who participated in the historic live event was safe from a punchline, including the legendary head coach of the New England Patriots, Bill Belichick, and even the team’s 82-year-old owner, Robert Kraft. While the night was full of hilarious jokes from Brady’s former teammates and some of the best comedians working today, a few of the presentations weren’t as strong as others, particularly one from Boston-based actor and director Ben Affleck.

The Roast of Tom Brady is just one of Netflix’s live comedy specials that was released in May 2024. Katt Williams’ latest special “Woke Foke” streamed live on the platform on May 4, and John Mulaney’s “Everybody’s in L.A.” is a week-long live comedy event streaming each night from May 3 to May 10. The Roast of Tom Brady, otherwise known as “The Greatest Roast of All Time”, is certainly the most off-the-rails of Netflix’s new slate of live comedy specials, running over three hours straight with zero commercial breaks. While there were plenty of comedic highlights of The Roast of Tom Brady, Affleck’s efforts ultimately missed the mark.

As one of the last performers on the tail end of The Roast of Tom Brady, Affleck came and left the stage within a span of 5 minutes. He didn’t stick around with the rest of the guests on stage and left without making the most of a fatigued but highly enthusiastic audience. Moments before his arrival, Robert Kraft and a reluctant Bill Belicheck took a shot onstage with Brady, marking a historic moment of mutual celebration for the three titans of the Patriots’ dynasty. Given this, the crowd was still loose and ready for more from the night, but Affleck’s jokes were long-winded, poorly timed, and just didn’t land.

Affleck pointed out their celebrated Dunkin Super Bowl commercial in which he, Brady, and Matt Damon wore outrageous orange jumpsuits and crowned themselves the “DunKings”. He started to lose the crowd with a rambling bit about an internet commenter named “Tall Boy Henry”, going off about how Tom’s toxic online haters would be instantly hospitalized if they set foot on an NFL field. Affleck extended his unfunny albeit true rant about “Tall Boy Henry”, spending most of his time onstage roasting the internet troll rather than Brady himself. He did get a few decent jabs in at Tom, calling him “the slowest, least physically impressive non-kicker ever to put on an NFL uniform.

In a night full of shocking moments that instantly made The Roast of Tom Brady one of the best roasts of all time, Affleck’s material simply wasn’t up to par. His rushed delivery also didn’t help him, and at times his points sounded disjointed and just didn’t make a lot of sense, disrupting a cohesive, polished flow. Even Rob Gronkowski was able to win over the crowd through his natural charisma, and the elite comedic talents of Nikki Glaser and Sam Jay made Affleck look even worse by comparison. Essentially, Affleck brought a dull blade into a room full of sharp daggers.

All the presenters before him, apart from a hesitant Randy Moss and an out-of-place Ron Burgundy appearance, went straight for Brady’s neck, but Affleck deflated the room with his out-of-touch softballs. He deserves some acknowledgment for going straight at Belichick, calling him “a miserable pโ€“ck” at one point and bringing up Belichick’s notorious decision to sit star defensive back Malcom Butler during Super Bowl LII, which the Patriots would ultimately lose to the Philadelphia Eagles. Affleck also took a jab at himself and his underwhelming blockbuster Justice League, but left Brady mostly unscathed, defeating the point of the roast.

Affleck ended his time at The Roast of Tom Brady with a sexual gesture, setting up Kevin Hart perfectly for his “white boy humor” callback to Julian Edelman’s roast of Tom which was full of sexual themes. After Affleck exited the stage, Jeff Ross said, “This is the first time I wished Netflix had commercials,implying that he was less than impressed with the quality of Affleck’s material. Affleck was in the perfect position to elevate The Roast of Tom Brady before Brady took the podium himself to end the night, a task that former NFL rival Peyton Manning was better equipped to accomplish.