Jimmy Kimmel and Tom Brady have shared some of the most unforgettable moments in late-night television history. Whether it’s Tom Brady reading brutal Mean Tweets, hilariously breaking Matt Damon’s window with a perfect spiral, or explaining why he willingly earned less than many other NFL quarterbacks, every appearance has showcased a different side of the seven-time Super Bowl champion.
For football fans, Brady is known as the Greatest of All Time (GOAT). For Jimmy Kimmel’s audience, however, he’s also one of the funniest celebrity guests ever to visit Jimmy Kimmel Live!. Their chemistry, humor, and willingness to laugh at themselves have produced countless viral clips that continue to attract millions of viewers in 2026.
If you’re searching for Jimmy Kimmel Tom Brady interview, Tom Brady Mean Tweets, Matt Damon sketch, or their funniest television moments, here’s the complete story.
The Famous Mean Tweets That Became an Internet Sensation
One of the biggest reasons Jimmy Kimmel and Tom Brady became such a popular pairing was the legendary Mean Tweets segment.
The concept is simple but brilliant: celebrities read harsh—and often hilarious—tweets about themselves on camera.
Tom Brady had already become one of the NFL’s most polarizing stars because of:
- Deflategate
- His championship success with the New England Patriots
- Endless debates about whether he was the greatest quarterback ever
- Countless internet memes
Recognizing how much attention Brady received online, Jimmy Kimmel dedicated a special Mean Tweets edition almost entirely to him around multiple Super Bowl appearances.
Some of the funniest tweets Brady read included jokes about:
- His famous chin dimple.
- His emotional reactions during games.
- Internet memes comparing his appearance.
- Friendly jokes directed at teammate Sony Michel.
One tweet involving Brady’s dog even made both Brady and Kimmel pause before joking that bringing pets into online insults crossed the line.
The segment quickly exploded online, collecting tens of millions of views and proving something many fans hadn’t realized—Tom Brady was more than willing to laugh at himself.
His relaxed personality surprised many viewers who only knew the intensely competitive quarterback seen every Sunday.
Tom Brady’s Perfect Throw That Broke Matt Damon’s Window
Perhaps no Jimmy Kimmel sketch involving Tom Brady is remembered more fondly than the famous Matt Damon window stunt.
Jimmy Kimmel has maintained a long-running comedy feud with actor Matt Damon, ending countless episodes with the joke:
“Apologies to Matt Damon—we ran out of time.”
During Brady’s appearance promoting The TB12 Method in 2019, Kimmel decided to involve the NFL superstar in the ongoing comedy rivalry.
Wanting to prove Brady still possessed incredible throwing accuracy during the offseason, Kimmel challenged him to throw a football through a second-story window at what was presented as Matt Damon’s house.
Brady delivered exactly what fans expected:
A perfect spiral smashed directly through the window.
Seconds later, Matt Damon appeared yelling in mock outrage before quickly transforming into an excited football fan upon realizing Tom Brady was responsible.
The sketch became comedy gold.
Among its funniest moments were:
- Damon acting furious before admitting he admired Brady.
- Brady apologizing while humorously calling Damon by the wrong name.
- Damon eventually keeping the football as a souvenir despite pretending to be angry.
The sketch perfectly combined sports, comedy, and celebrity culture while showcasing Brady’s surprisingly natural comic timing.
The Interview Where Tom Brady Explained Why Winning Meant More Than Money
Another unforgettable Jimmy Kimmel interview came shortly after the Patriots won Super Bowl LIII.
Instead of focusing solely on football, Jimmy Kimmel asked one of the questions NFL fans had debated for years:
Why wasn’t Tom Brady the highest-paid quarterback in football?
Despite being the league’s biggest star, Brady consistently accepted contracts below market value.
His answer became one of the interview’s defining moments.
Brady explained that for him:
Winning had always been the priority.
He then added one of the night’s funniest lines by joking that his then-wife, supermodel Gisele Bündchen, already earned plenty of money.
The audience immediately burst into laughter.
The interview also offered fascinating insight into Brady’s legendary preparation.
He discussed:
- Training throughout the entire year.
- Treating football as a full-time profession every day.
- Constantly working to improve even after multiple championships.
- The difficulty of throwing truly perfect passes despite completing many throws during games.
His honesty helped viewers better understand why he remained successful for so many seasons.
Jimmy Kimmel Covered Every Major Chapter of Brady’s Career
Over the years, Jimmy Kimmel’s show became one of the places where fans could watch Tom Brady discuss the biggest moments of his football journey.
Those conversations followed Brady through several remarkable career milestones, including:
- Winning multiple Super Bowls with New England.
- Leaving the Patriots after two decades.
- Signing with the Tampa Bay Buccaneers in 2020.
- Capturing his seventh Super Bowl championship.
- Retirement announcements and eventual return before retiring permanently.
- Beginning his broadcasting career with Fox Sports.
Even during the COVID-19 pandemic, Brady remained one of Kimmel’s favorite discussion topics.
Jimmy regularly joked about Brady continuing to dominate the NFL despite getting older, especially during Tampa Bay’s championship run.
As Brady transitioned from quarterback to television analyst, Kimmel continued inviting him back to discuss football from an entirely different perspective.
Their conversations naturally evolved alongside Brady’s career.
Why Jimmy Kimmel and Tom Brady Have Such Great Chemistry
Not every athlete becomes an entertaining late-night television guest.
Tom Brady, however, consistently proved to be an exception.
Several qualities made him especially enjoyable on Jimmy Kimmel Live.
He Doesn’t Take Himself Too Seriously
Although Brady is known for his competitive nature, he willingly laughs at jokes involving:
- His appearance.
- His fashion choices.
- Internet memes.
- Past controversies.
He Has Excellent Comic Timing
Brady’s appearances showed that he could comfortably participate in comedy sketches alongside experienced entertainers.
Whether breaking windows, reading Mean Tweets, or exchanging jokes with Jimmy Kimmel, he demonstrated impressive natural humor.
He’s Willing to Share Personal Stories
Away from formal football press conferences, Brady often opened up about:
- Family life.
- Training routines.
- Nutrition.
- Parenting.
- Competition.
- Life after football.
That honesty allowed audiences to connect with him beyond his achievements on the field.
Where to Watch Jimmy Kimmel and Tom Brady’s Best Moments in 2026
Many of Jimmy Kimmel and Tom Brady’s most memorable appearances remain available through official platforms.
Fans can watch highlights including:
- Tom Brady Reads Mean Tweets
- Tom Brady Breaks Matt Damon’s Window
- Tom Brady Full Jimmy Kimmel Interview (2019)
- Super Bowl discussions.
- Career interviews.
- Comedy sketches.
Complete episodes and official clips are available through ABC, Hulu, and the Jimmy Kimmel Live! YouTube channel, where many segments continue attracting millions of views years after their original broadcast.
Why Their Interviews Still Stand Out in 2026
Years after Brady’s playing career ended, his appearances with Jimmy Kimmel remain some of the most rewatched sports interviews on late-night television.
Unlike traditional athlete interviews focused entirely on statistics or championships, these conversations revealed Brady’s personality.
Viewers saw:
- A quarterback comfortable laughing at himself.
- A fiercely competitive athlete discussing success with humility.
- A father sharing personal stories.
- A celebrity willing to participate in outrageous comedy sketches.
Jimmy Kimmel’s relaxed interviewing style allowed Brady to move naturally between serious football discussions and hilarious comedy moments, creating interviews that appealed to both sports fans and casual viewers.
Final Thoughts
The partnership between Jimmy Kimmel and Tom Brady produced some of the funniest and most memorable moments in modern late-night television. From the wildly popular Mean Tweets segments to the unforgettable sketch where Brady shattered Matt Damon’s window with a perfectly thrown football, every appearance demonstrated why Brady became one of Jimmy Kimmel’s favorite recurring guests.
Beyond the laughs, their interviews also revealed Brady’s mindset about winning, discipline, family, and life after football, giving fans a rare opportunity to see the legendary quarterback away from the pressure of the NFL.
Whether you’re revisiting the viral Mean Tweets, enjoying the Matt Damon comedy sketch, or watching Brady explain why championships mattered more than salary, Jimmy Kimmel and Tom Brady remain one of television’s most entertaining host-and-athlete duos—a partnership that continues to delight audiences well into 2026.
