For nearly 40 years, Mike Tyson has been considered one of the greatest heavyweight boxers of all time, as well as one of the sport’s most controversial icons. During that time, Tyson joined the ranks of legends like Muhammad Ali and Sugar Ray Robinson, who became not only boxing legends but also cultural phenomena. With that pop culture prominence has come multiple surprising cameos in movies, TV shows, and landmark wrestling events.
With Tyson being in the news quite a lot lately due to his upcoming fight with Jake Paul on Netflix, we decided now would be a great time to go back and look at the boxer’s best big-screen appearances and even more from beloved TV comedies. Let’s take a look!
The Hangover (2009)
Todd Phillips’ The Hangover helped further propel the careers of Bradley Cooper, Ed Helms, and Zach Galifianakis upon its release in June 2009 and instantly became one of the best 2000s movies. One of the reasons for this was Mike Tyson’s scene-stealing performance. In the movie, “Iron Mike,” plays a version of himself that is very close to the real thing, which adds a wild, dangerous, and unpredictable dynamic, especially when he gives the core trio another obstacle to overcome as they look for their missing friend.
Tyson would also appear in The Hangover Part II in a smaller yet just as memorable way in the final stretch of the movie. Like, how could you forget that over-the-top ending sequence?
Ip Man 3 (2015)
The Ip Man movies, starring martial arts legend Donnie Yen as the titular Wing Chun master, has given audiences all kinds of impressive fights and other great moments over the years. Ip Man 3, which was released in 2015, features what could be one of the best fight scenes in the series, as well as a great Mike Tyson appearance.
Tyson plays a boxer and corrupt American property developer named Frank who challenges Ip Man to a fight about halfway through the movie. The contrast between the styles – boxing vs. Wing Chun – creates an incredible dynamic and one of the most grueling three-minute fights ever captured on film.
Law & Order: Special Victims Unit (2013)
Mike Tyson provided one of his most emotional and unforgettable small-screen appearances during a 2013 episode of Law & Order: Special Victims Unit. During the episode titled “Monster’s Legacy,” Tyson took on the role of Reggie Rhodes, a victim of child abuse who later murdered one of his attackers after dealing with years of trauma from the attacks. Though he’s only featured for a short while, Tyson makes the most of his time and provides a heartbreaking and gut-wrenching performance that’s up there with the best SVU guest appearances.
The Last O.G. (2020)
Tracy Morgan’s TBS comedy series, The Last O.G. had some great guest stars throughout its four-season run, and one of the best was Mike Tyson. Appearing in a pair of episodes, the boxer took on the role of Triple O.G., an over-the-top gangster who gave Morgan’s Tray Leviticus Barker some unorthodox yet much-needed advice. Again, he wasn’t on the show all that much, but he did give audiences some outrageously hilarious moments.
How I Met Your Mother (2013)
There were a lot of actors you may have forgotten were on How I Met Your Mother, and that includes Tyson. During the 2013 episode titled “Bad Crazy,” he, playing himself, saves the day by helping Robin (Cobie Smulders) take care of a baby. What’s so great about the concept is how the premise plays against type for Tyson and instead treats him like a kind, gentle, and misunderstood giant.
Entourage (2010)
Entourage was a show that was known for its outrageously funny celebrity cameos, and Mike Tyson could very well have one of the best. In the 2010 episode, “Bottoms Up,” the boxing legend approaches Ari Gold (Jeremy Piven) with an idea to repair his reputation: a new and improved version of The Brady Bunch. Though the attempt to get Jessica Simpson to sign on for the project blows up, we can still imagine just how great that would have been, especially in the show’s universe.
Mike Tyson Mysteries (2014 – 2020)
Though it may not be the best Adult Swim show, Mike Tyson Mysteries was one hell of an animated experience. Unlike other entries on this list, Tyson wasn’t just a cameo on the show, he was the main attraction of all 70 episodes. Playing a parody of himself, the show followed Tyson and his crew solving a variety of mysteries in a similar fashion to Scooby-Doo and other Hanna-Barbera classics. If you haven’t already, this is a must-watch with some immensely hilarious moments.
Who’s The Boss? (1990)
Who knows if we’ll ever get the Who’s the Boss? revival series, but if we do, hopefully, Mike Tyson will come back for another great cameo. Back in 1990, Tyson showed up as himself at the very of the the episode titled “Sam Accelerates,” which saw him confront Tony Micelli (Tony Danza) after he heard someone had been making fun of him. The scene then turned into what could be the best freezeframe of the show as the credits rolled.
Rocky Balboa (2006)
We never got to see Mike Tyson fight Sylvester Stallone in a boxing match, but we did get to see the iconic bruiser show up for a brief moment in Rocky Balboa. No, Tyson doesn’t confront the aging “Italian Stallion,” but he is seen jawing off at Mason “The Line” Dixon (Antonio Tarver) before the climatic fight. It was brief, but the cameo did add a nice flash and sense of realism to the big bout.
Webster (1987)
Way back, when Tyson was still making a name for himself in the boxing world, he showed up on an episode of Webster. In 1987, “Iron Mike” crossed paths with Emmanuel Lewis’ beloved titular character and other members of the cast as he was caught in the middle of a family feud.
WrestleMania XIV (1998)
There have been so many celebrity appearances at WrestleMania over the years, and Tyson’s involvement in the 14th annual Showcase of the Immortals is one of the most well-known and impactful of them all. In March 1998, Tyson served as the special outside enforcer and helped Stone Cold Steve Austin defeat Shawn Michaels and claim his first WWE Championship in the process. More than a quarter-century later, the image of Iron Mike turning on the Heartbreak Kid to help the Texas Rattlesnake is one wrestling fans remember fondly.
Surely, we haven’t seen the last of Mike Tyson in movies and TV shows. Perhaps we’ll see much more from him as he gets ready to fight Jake Paul in one of the most anticipated boxing matches in recent memory.