From the beginning of his career, Mike Tyson has been irresistible to Hollywood’s various screens: when you’re the undisputed heavyweight champion of the world with a high-pitched lisp, you’re an instant surreal punchline. Iron Mike has played along in a slew of rap videos, movies ranging from Rocky Balboa to Scary Movie 5, and TV shows ranging from Law & Order: Special Victims Unit to The Simpsons (which rendered an unauthorized version of him as Drederick Tatum). Here’s seven of our favorite Tyson cameos over the years.
1. DJ Jazzy Jeff and the Fresh Prince, “I Think I Can Beat Mike Tyson” (1989)
Back when Will Smith was a rapper rather than box-office king and show-biz patriarch, he needed a hit to follow up “Parents Just Don’t Understand.” He came up with this tall tale about having an attack of hubris and getting in the ring with Tyson (despite the opening warning of somebody who claimed he saw a Tyson fight where “he hit this boy so hard his head flew off into the 18th row!”). The then-undefeated Tyson obligingly appeared in the ring with Smith (aka “The Fresh Prince”) to dramatize beating him into a pulp.
2. Who’s the Boss? (1990)
Go to the very end of the episode to see Tony Danza bragging about his Mike Tyson impression, only to have Iron Mike himself show up at his front door.
3. Ice-T, “New Jack Hustler” (1991)
Over the years, Tyson has made cameos in lots of rap videos, flashing by in a Puffy clip or giving a pep talk to Canibus. This one set the template: with a quick shot of Tyson using a car phone (comically oversized by today’s standards), Ice-T immediately connoted money, street connections, and unbeatable hardness.
4. The Chris Rock Show‘s Presidential campaign (2000)
From The Chris Rock Show on HBO (which featured Louis C.K. on the writing staff): using press-conference footage, Rock cut together some campaign ads for Tyson touting him as a third-party alternative to Al Gore and George Bush.
5. The Hangover (2009)
The famous scene where Tyson shows up to reclaim his kidnapped tiger. In a battle of Mike Tyson versus Zach Galifianakis, Tyson wins in one punch. In the undercard of Mike Tyson versus Phil Collins, it’s Collins with a TKO.
6. Funny or Die’s “Every Little Step” (2010)
Around this time, Tyson became available for cameos in just about any project, no matter how absurd. He’s got a bunch of Funny or Die appearances in everything from “When Harry Met Sally 2” (as a law enforcement officer) to “Oscar Talk” (as a film critic opposite Leonard Maltin), but this appearance as a backup dancer for a Wayne Brady remake of the Bobby Brown video for “Every Little Step” is demented genius. Judging by the evidence here, Tyson doesn’t have a lot of moves as a dancer, but he’s light on his feet and has good rhythm.
7. Tony Awards (2013)
Not only did Mike Tyson appear on How I Met Your Mother (in the episode “Bad Crazy”), not only did Mike Tyson have a one-man Broadway show directed by Spike Lee, he brought his entire pop-culture resume together earlier this year by dancing opposite Neil Patrick Harris during the opening number of the Tony Awards.