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10 Shocking Moments From The Tom Brady Roast: Why Kim Kardashian Was Savagely Booed And Her Post-Show Regret

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The Tom Brady roast, officially titled "The Greatest Roast of All Time: Tom Brady," was a landmark event in live comedy and celebrity culture, airing on Netflix on May 5, 2024. It quickly became a lightning rod for controversy, not just for the savage jokes directed at the NFL legend, but for the unexpected and brutal treatment of celebrity roaster Kim Kardashian, who was met with a chorus of boos and later slammed the experience as "sexist." This article, updated for December 2025, dives deep into the full, uncensored details of the event, the key players, the jokes that went too far, and the lasting impact on all the stars involved. The live special was intended to celebrate Tom Brady’s legendary career, but it quickly devolved into a full-contact comedy special where no topic—from divorce and dating rumors to career failures and controversial pasts—was off-limits. Kim Kardashian's surprise appearance was meant to be a high-profile moment, but it turned into one of the most talked-about and uncomfortable segments of the entire night, solidifying the event's status as a cultural phenomenon.

The Titans of the Roast: Kim Kardashian and Tom Brady Profiles

The roast brought together two of the most recognizable figures in American pop culture and sports history. Understanding their backgrounds provides context for the intensely personal nature of the jokes.

Kimberly Noel Kardashian

  • Born: October 21, 1980, Los Angeles, California.
  • Career: Media personality, socialite, businesswoman, and aspiring lawyer. She first gained major media attention in 2007 following a leaked sex tape with Ray J.
  • Key Ventures: Star of the reality TV show Keeping Up with the Kardashians (2007–2021) and The Kardashians (2022–present). Founder of SKIMS (shapewear/clothing) and KKW Beauty (now SKKN by Kim).
  • Family: Daughter of Kris Jenner and the late Robert Kardashian. She has three famous sisters (Kourtney, Khloé, and Kendall) and a brother (Rob).

Thomas Edward Patrick Brady Jr.

  • Born: August 3, 1977, San Mateo, California.
  • Career: American former professional football quarterback, widely considered the greatest of all time (GOAT).
  • Key Accomplishments: Played 20 seasons for the New England Patriots, winning six Super Bowl championships (XXXVI, XXXVIII, XXXIX, XLIX, LI, LIII). He later won a seventh with the Tampa Bay Buccaneers (LV). He is a five-time Super Bowl MVP.
  • Personal Life: His highly publicized divorce from supermodel Gisele Bündchen in 2022 was a major focus of the roast.

The All-Star Roasters and the Most Savage Jokes

The roster for the Tom Brady roast was a mix of comedy legends and NFL icons, ensuring a relentless barrage of deeply personal and career-focused insults. The event was hosted by comedian Kevin Hart, who set the tone for the night.

The Full Lineup of Roasters

The stage saw appearances from some of the biggest names in comedy and sports, all eager to take a shot at the seven-time Super Bowl champion. Key roasters included:

  • Kevin Hart (Host)
  • Jeffrey Ross (The Roastmaster General)
  • Nikki Glaser (Comedian)
  • Tony Hinchcliffe (Comedian)
  • Drew Bledsoe (Former Patriots Quarterback)
  • Randy Moss (Former Patriots Wide Receiver)
  • Rob Gronkowski (Former Patriots Tight End)
  • Julian Edelman (Former Patriots Wide Receiver)
  • Bill Belichick (Former Patriots Head Coach)
  • Kim Kardashian (Media Personality)

The Jokes That Landed (and the Ones That Didn't)

The most shocking jokes centered on Tom Brady's divorce from Gisele Bündchen, his career longevity, and his brief retirement. Nikki Glaser, in particular, was praised for her brutal and hilarious set, which heavily targeted Brady's personal life.

  • Gisele Bündchen's New Boyfriend: Multiple roasters, including Kevin Hart and Jeffrey Ross, joked about Brady losing his wife to her jiu-jitsu instructor, often implying the instructor was a better 'receiver' than his former teammates.
  • Brady's Performance: Jokes were made about Brady’s mediocre 8-9 record in his final season, with one joke suggesting, "If you get a chance to go 8-9 and all it costs you is your wife and kids, you gotta do what you gotta do."
  • Kim Kardashian's O.J. Simpson Joke: When Kim took the stage, she used a family joke to try and win over the hostile crowd. She quipped about her father, Robert Kardashian, being O.J. Simpson's lawyer, saying: "I know you guys are really nervous about me being here... I promise I won’t leak anything, unless Tom asks me to."

The Kardashian Controversy: Booing, Sexism, and Post-Show Regret

Kim Kardashian's appearance was arguably the most controversial segment of the night, overshadowing even the most savage jokes aimed at Brady.

The Crowd's Savage Booing

From the moment Kevin Hart introduced Kim, the live audience began to relentlessly boo her. The noise was so loud that Hart had to intervene and ask the crowd to calm down. Despite the hostile reception, Kim attempted to proceed with her prepared material, which included a joke about the long-standing rumors that she and Tom Brady had been dating.

  • Addressing Dating Rumors: Kim directly addressed the speculation about her and Brady, saying, "I know there were rumors that me and Tom might be dating. We never dated. I would never date a man that my sister’s ex-boyfriend’s sister’s best friend’s brother’s ex-girlfriend put a restraining order on." This convoluted joke was a reference to her dating history, but failed to stop the booing.

The Sexist Joke That Went Too Far

The situation worsened when comedian Tony Hinchcliffe took the stage and, in a joke widely criticized as sexist, told Kim to "shut up" after she was booed, suggesting she didn't belong on the stage. This moment highlighted the difference between the celebrity and comedy roast cultures.

Kim’s Vow: Never Again

The experience profoundly affected Kim. In the aftermath, she publicly declared that she would never participate in a comedy roast again. She specifically lashed out at the nature of the jokes directed at her, stating that all the comedians seemed to do was "call the girls whores," implying the humor was lazy and misogynistic.

The Lasting Impact and Brady's Regret

The roast was a massive success for Netflix, earning an Emmy nomination for Outstanding Variety Special (Live) in 2024. However, the fallout revealed that the jokes had a deeper emotional toll than anticipated.

Tom Brady’s Confession

In the months following the event, Tom Brady admitted he had regrets about the roast, specifically how the jokes about his divorce and family affected his children. He acknowledged that while he was prepared for the insults, he hadn't fully considered the impact on his kids, who were watching.

The Comedy Climate Debate

The event sparked a wider conversation about the limits of comedy in the modern era. Kevin Hart, the host, defended the roast format, suggesting that the "full-contact" nature of the special was "necessary" for the current climate of sensitivity, even as he sided with Brady's regret over the family jokes. Dana White, who was in attendance, commented that the crowd was "not a Kardashian crowd," offering a simple explanation for the intense booing Kim received.

Ultimately, "The Greatest Roast of All Time: Tom Brady" will be remembered as a cultural flashpoint: a spectacular, savage night of comedy that successfully skewered a sports icon, but also exposed the brutal, sometimes sexist, nature of the roast format when applied to a global reality star like Kim Kardashian.

kim kardashian tom brady roast
kim kardashian tom brady roast

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