The 10 Most Shocking Moments And Regrets From 'The Roast Of Tom Brady'

The Greatest Roast of All Time: Tom Brady, which aired live on Netflix on Sunday, May 5, 2024, has cemented its place as one of the most talked-about comedy specials in recent history. It was a brutal, no-holds-barred spectacle where the NFL legend took hits on everything from his divorce from Gisele Bündchen to the infamous Deflategate scandal. However, the true shockwave from the event wasn't felt until weeks later when Brady himself admitted to deep regret over the special, specifically citing the negative impact the personal jokes had on his three children. The controversy surrounding the roast has kept the special in the news well into late 2024, shifting the focus from the hilarious, often offensive, jokes to the real-life consequences of celebrity comedy. This analysis dives into the most shocking moments, the key players, and the lasting fallout that has turned the "Greatest Roast of All Time" into a major cultural conversation about boundaries and family in the age of viral content.

Thomas Edward Patrick Brady Jr.: A Full Biography Profile

Thomas Edward Patrick Brady Jr. was born on August 3, 1977, in San Mateo, California. He is widely regarded as the greatest quarterback in NFL history.

• Full Name: Thomas Edward Patrick Brady Jr.
• Born: August 3, 1977 (Age 48 as of late 2025)
• Birthplace: San Mateo, California, U.S.
• College: University of Michigan (1995–1999)
• NFL Draft: 2000, Round 6, Pick 199 (New England Patriots)
• NFL Teams: New England Patriots (2000–2019), Tampa Bay Buccaneers (2020–2022)
• Major Accomplishments:
  • 7x Super Bowl Champion (6 with Patriots, 1 with Buccaneers)
  • 5x Super Bowl MVP
  • 3x NFL MVP
  • 2x NFL Offensive Player of the Year
  • 15x Pro Bowl Selection
  • NFL career leader in passing yards and passing touchdowns.
• Marital Status: Divorced from Gisele Bündchen (married 2009–2022)
• Children: John "Jack" Edward Thomas Moynahan (born 2007, with Bridget Moynahan), Benjamin Rein Brady (born 2009), and Vivian Lake Brady (born 2012).

Brady’s career spanned 23 seasons, concluding with his final retirement announcement in February 2023. His move from the New England Patriots to the Tampa Bay Buccaneers in 2020 and subsequent Super Bowl LV victory further cemented his legendary status.

The A-List Lineup: Comedians, Teammates, and Roasters

The "Greatest Roast of All Time" featured a deep and diverse bench of talent, blending some of the biggest names in comedy with key figures from Brady's legendary NFL career. The show was hosted by comedian Kevin Hart, who set a blistering, often chaotic, pace for the evening. The lineup was a critical factor in the roast’s success, ensuring that no aspect of Brady's public or private life was off-limits.

The Comedy Heavyweights

The professional comedians brought the heat with their fearless, often dark, material.

• Jeff Ross: Known as the "Roastmaster General," Ross was relentless, delivering some of the most personal and controversial material, including the joke that touched on Robert Kraft’s legal issues—a line Brady reportedly cut off on stage.
• Nikki Glaser: Glaser was widely praised for her sharp, surgical jokes, particularly those targeting Brady's divorce and his career longevity. Her material on Gisele Bündchen was among the most cited in post-show analysis.
• Bert Kreischer & Tom Segura: These stand-up stars, known for their podcasts and touring success, contributed to the relentless barrage, often focusing on the physical and financial aspects of Brady’s life.
• Andrew Schulz & Tony Hinchcliffe: Known for their edgier, crowd-work-style comedy, they ensured the roast maintained a high level of shock value.

The NFL Legends

The appearance of Brady's former teammates and coach provided a unique, insider perspective, making the jokes feel more authentic and cutting.

• Bill Belichick: The legendary Patriots coach, whose relationship with Brady was a source of constant speculation, made a rare comedy appearance. His dry delivery and focused jabs were a highlight, primarily centered on their dynasty and the Deflategate scandal.
• Rob Gronkowski: "Gronk" brought his signature high-energy, simple humor, focusing on their time together and his own party-boy reputation.
• Julian Edelman: Edelman, a key Patriots receiver, delivered some of the night's most surprisingly offensive and sharp material, proving athletes can be just as brutal as comedians.
• Randy Moss: The Hall of Fame wide receiver’s appearance added another layer of NFL history to the proceedings.

The surprise appearance by Will Ferrell, reprising his role as Ron Burgundy, added a surreal, classic comedy touch to the proceedings.

The Regret: Why Brady Called the Roast a 'Parenting F--- Up'

The biggest story to emerge from the event was not a joke, but Tom Brady’s candid post-show reaction. Months after the May 2024 special aired, Brady revealed his deep remorse, stating he would "absolutely not" do it again.

The Gisele Bündchen and Family Line

The primary source of Brady's regret centered on the relentless jokes aimed at his ex-wife, Gisele Bündchen, and their subsequent divorce. Comedians, particularly Nikki Glaser and Kevin Hart, repeatedly joked about Bündchen moving on to her new boyfriend, a jiu-jitsu instructor. Brady explained that while he "loved when the jokes were about me," the material about his family crossed a line, especially for his three children: Jack, Benjamin, and Vivian. In a podcast interview, Brady described the experience as a "parenting f--- up," acknowledging that he hadn't fully considered the emotional toll the jokes would take on his kids, who watched their parents' private life become a public punchline. This sentiment highlights a crucial modern dilemma for high-profile celebrities: the cost of viral fame versus protecting one's family.

The Robert Kraft Controversy

Another moment that caused palpable tension on stage involved a joke directed at former New England Patriots owner Robert Kraft. During his set, Jeff Ross began a joke referencing Kraft’s legal issues involving a massage parlor. Brady quickly stood up and approached Ross, whispering, "Don't say that sh*t again," before returning to his seat. While the joke was quickly brushed off by Ross, the moment was a stark reminder of the unwritten rules of roasting—some topics, particularly those involving powerful friends and sensitive legal matters, are off-limits, even in a no-holds-barred environment. This was one of the few instances where Brady visibly reacted to a joke, underscoring the severity of the line that was crossed.

Top 5 Most Memorable (and Controversial) Jokes

The roast was a two-hour marathon of insults, but a few jokes stood out for their brutality, cleverness, or sheer shock value.

1. Nikki Glaser on Gisele's New Boyfriend: "Tom, you have to give credit where credit is due. You wouldn't have that many rings if it wasn't for Gisele. You wouldn't have that many rings if it wasn't for the guy who deflated your balls. But you wouldn't have a Brazilian jiu-jitsu instructor if it wasn't for Gisele." This joke perfectly blended the Deflategate scandal with his divorce.
2. Kevin Hart on Brady's Looks: Hart repeatedly hammered Brady on his appearance and perceived lack of charisma, suggesting he only became a superstar because of his talent, not his looks, a classic roast trope.
3. Julian Edelman on Robert Kraft and Brady: Edelman, surprisingly, delivered a joke that was considered by some to be one of the most offensive of the night, further pushing the boundaries of what was acceptable.
4. Jeff Ross on Deflategate: Ross delivered a simple, yet effective jab: "Tom, you’re the only quarterback in the NFL who has two rings that are not on his fingers. They’re on his balls."
5. Tom Brady's Retort to Jeff Ross: In his closing remarks, Brady didn't hold back, delivering a series of brutal, highly personal attacks on the roasters, including Jeff Ross, proving he could dish it out as well as he took it.

The "Greatest Roast of All Time: Tom Brady" will be remembered not just for the laughs and the spectacle, but for the conversation it started about the emotional price of fame. The event proved that even a seven-time Super Bowl champion has a breaking point when his family is involved, turning a comedy special into a surprisingly poignant lesson on celebrity and parenthood.