But over the last two decades, the “Baddest Man on the Planet” has successfully transitioned into one of pop culture’s most unexpected, charismatic, and downright hilarious screen presences.

To celebrate his milestone 60th birthday, we are looking back at the best movie and television roles of Mike Tyson’s eclectic Hollywood career. From face-punching comedies to martial arts showdowns, here is where Iron Mike shined brightest on screen.

1. The Hangover (2009)

  • The Role: Himself (and his tiger)

You can’t talk about Mike Tyson’s acting career without starting here. Tyson’s cameo in The Hangover didn’t just steal the movie; it completely revitalized his public image. Playing a hyper-intense, air-drumming version of himself who is deeply protective of his pet Bengal tiger, Tyson delivered pure comedic gold. His sudden knockout punch to Zach Galifianakis’s character, Alan, remains one of the most iconic movie moments of the 2000s.

2. Ip Man 3 (2015)

  • The Role: Frank

If you thought Tyson could only play himself for laughs, Ip Man 3 proved he has genuine action-movie chops. Playing Frank, a corrupt American property developer with ties to the local triads, Tyson went toe-to-toe with martial arts legend Donnie Yen. The three-minute, blistering fight scene between Tyson’s raw heavyweight boxing style and Ip Man’s Wing Chun technique is beautifully choreographed and remarkably intense.

3. Tyson (2008)

  • The Role: Himself (Documentary)

For a deeper, more vulnerable look at the man behind the myth, James Toback’s critically acclaimed documentary is essential viewing. Premiering at the Cannes Film Festival, Tyson eschews traditional talking-head sports docs to let Mike tell his own story. It is a raw, stylized, and deeply intimate psychological portrait of a man grappling with his troubled childhood, his meteoric rise to fame, his prison stint, and his inner demons.

4. Mike Tyson: Undisputed Truth (2013)

  • The Role: Himself (One-Man Show)

Taking his life story to the stage, Tyson starred in a raw one-man Broadway show that was ultimately captured and directed by filmmaking icon Spike Lee for HBO. Part stand-up comedy, part tragic confessional, and part motivational speech, Undisputed Truth showcases Tyson’s undeniable charisma and narrative grip. It takes a unique kind of star power to hold an audience captive on a bare stage for 90 minutes, and Tyson pulls it off with a split-decision victory.

5. Rocky Balboa (2006)

  • The Role: Himself

Before The Hangover made him a fixture of mainstream cinema, Sylvester Stallone gave Tyson an epic meta-cameo in Rocky Balboa. Right before the titular character steps into the ring for his final exhibition match against Mason “The Line” Dixon, Tyson appears ringside, aggressively taunting the current champion to get inside his head. It was the ultimate passing-of-the-torch moment between real-world boxing history and cinematic sports royalty.

Honorable Mention: Mike Tyson Mysteries (2014–2020)

We couldn’t close this out without shouting out Adult Swim’s brilliant animated comedy. Voicing a fictionalized, mystery-solving version of himself alongside a talking pigeon (voiced by the late Norm Macdonald), Tyson proved he was more than willing to lean entirely into the absurd.

Whether he’s knocking out sharks or singing off-key, Mike Tyson has proven that his second act in entertainment is just as memorable as his first. Happy 60th birthday, Iron Mike!