Mike Tyson's Best Film And TV Appearances, Ranked

Will Smith puts his money where his mouth is in the 1989 song "I Think I Can Beat Mike Tyson." Like his other hit Fresh Prince and DJ Jazzy Jeff songs "Parents Just Don't Understand" and the Freddy Krueger-centric "A Nightmare on My Street," "Mike Tyson" is a story song, opening with Smith watching old Tyson fights late at night. Convinced that he could beat the champ, Smith calls up Tyson's manager Don King (as himself) and sets a fight for two months away in Atlantic City. Smith prepares for the fight, with "DJ Jazzy Jeff" Townes as his trainer, while no one in his neighborhood thinks he can win, not even his barber or his grandma. In the ring, Smith thinks he's doing all right at first, but one single punch from Iron Mike lays him out. 

The video features Smith parodying another famous Philadelphian, Rocky Balboa, as he wheezes up the steps of the Philadelphia Museum of Art and trains by punching a slab of beef. He and Townes also dress up as old men and comment on the action, baldly ripping off a similar scene from "Coming to America." Tyson appears in just two scenes, appearing to rough Smith up at a rowdy pre-fight press conference, and then fighting Smith in the ring. Dressed in a "Free James Brown" t-shirt, Tyson dances around and throws punches toward the camera, while Smith takes several exaggerated pratfalls to the canvas before showing up at the end of the video with his face covered in gnarly bruises and welts.

Tyson's second career of popping up unexpectedly on shows like "Franklin and Bash" or "How I Met Your Mother" is likely due to his surreal turn in the 2009 megahit comedy "The Hangover." When a weekend bachelor party in Vegas turns unexpectedly debauched, three groomsmen (Bradley Cooper, Ed Helms, Zach Galifianakis) have to piece together what they did the night before and find their missing groom (Justin Bartha). Somewhere in that wild night they kidnapped a full-grown tiger, and the next morning have to face the wrath of its owner, Tyson, introduced air-drumming to Phil Collins' "In the Air Tonight."

The tiger-centric subplot is a reference to the era in Tyson's life when he owned apparently three large cats at the same time. It takes advantage of his well-known eccentricities while using his reputation for violence both in the ring and out as subtext. At the same time, the film fawns over him like the megastar athlete he once was. "He's still got it," Helms marvels after Tyson knocks Galifianakis unconscious with a single punch. It's a strange balance, and for those who might not be so quick to overlook the fighter's sexual assault conviction or other crimes, it makes for uneasy viewing. The film's success spawned two direct sequels and made movie stars of its three leads — and of Tyson, in a way. At the very least, it showed audiences that Tyson could laugh at himself, and perhaps showed filmmakers that he was willing to take direction.

Amazingly, Rocky Balboa and Mike Tyson never faced each other. Apollo Creed (Carl Weathers), Rocky's foe turned friend, was famously based on Muhammad Ali, and although 1990's "Rocky V" featured a showboating Don King-like promoter (Richard Gant), the "Rocky" films were mostly in hibernation during Tyson's peak years, and by the time Sylvester Stallone re-entered the ring for 2006's legacy sequel "Rocky Balboa," Tyson was more or less retired. When offered to fight in an exhibition match with current heavyweight champ Mason "The Line" Dixon (real-life boxer Antonio Tarver), a 60-year-old Rocky takes stock of his legacy and tries to reconnect with his adult son (Milo Ventimiglia).

Tyson's cameo here is brief, with little audible dialogue, as he and Dixon argue ringside before the big fight at the end of the film. What's most interesting about the moment, though, is how the film engages with the world of real life boxing circa 2006, in a way that the previous "Rocky" films never really did. The fight between Rocky and Dixon is presented as an HBO broadcast, with actual boxing commentators Jim Lampley, Max Kellerman, and Larry Merchant calling the fake action, and actual celebrities and professionals like Tyson lining the front rows. It may not be the biggest or funniest moment on this list so far, but it's the first time Tyson's presence is justified as something more than a gimmick or meme come to life.

Tyson remains a formidable physical presence, and in the 2010s he put his fists back to work in a string of international and/or direct-to-video action movies. The first of these, and one of the best, was 2015's "Ip Man 3," the second sequel to Donnie Yen's iconic 2008 biopic of the eponymous Wing Chung master. Loosely based in fact, the series is more than anything a showcase for Yen's prodigious stunt work, as the forces of midcentury Chinese history compel Ip to continuously defend his home and family with deadly force. "Ip Man 3" takes place in 1959, as Ip protects his son's school from a ruthless American real estate developerOur House Fils and boxer named Frank (Tyson), while dealing with his wife's cancer diagnosis and the training of his most famous student, Bruce Lee.

Tyson's villain turn here is more of a glorified cameo; his role could have been excised without much damage to the rest of the film. But he shines in his big fight scene with Yen, as Frank, impressed with Ip's abilities, challenges him to a three-minute round with the fate of the school at stake. Director Wilson Yip keeps the action tight around his actors, emphasizing the bone-crushing, wall-breaking ferocity of Tyson's fists. The contrast of Ip's graceful, lightning-fast movement against Frank's tank-like momentum is the film's conflict in miniature.

When Tyson does comedy, it is almost always as "himself," and there is often the sense that the audience is laughing at him as much as they are with him. An unusual exception to that rule came in 2012, when Funny or Die cast him as Republican presidential hopeful Herman Cain in a series of video sketches that were only marginally more unhinged than Cain's own campaign. The best of these was "Cain Time Live," Cain's new Fox News series in the vein of Bill O'Reilly or Glenn Beck. Cain sits behind a desk, shouting ridiculous conservative talking points at the camera and changing the title of the show whenever the mood strikes. "We should put all the poor people in a tomb, like mummies," he declares before thinking it through: "But then who will work for us?"

At less than two minutes, the video doesn't overstay its welcome, and ends with an effective, if left-field, dig at filmmaker Tyler Perry. Tyson is no political satirist, and he's no Phil Hartman or Jay Pharoah; his transformation into Cain is no more than putting on a suit and glasses, Clark Kent-style. But there's an infectious energy to his performance that is often missing when he is just playing a slightly exaggerated version of himself, whether it's a cutaway moment when he protests to a baby doll, "But I work alone!" or simply shouting "Cain!" Now, years after these shorts were produced, it feels like a road not taken for Tyson's career.

"What the hell is Mike Tyson gonna do on stage?" That question is rhetorically posed by Tyson at the start of his one-man show, "Undisputed Truth," which premiered on Broadway in 2013. Directed for the stage by Spike Lee, who also filmed a version for HBO, and written by Tyson's wife Kiki, the show is a multimedia tour through the fighter's life, narrated at a breakneck pace across 90 minutes. In the version filmed for HBO, Tyson performs in front of a warm, supportive local audience — banners naming all the neighborhoods in Brooklyn hang from Broadway's Longacre Theatre — and uses his bully pulpit to exalt his mother Lorna Mae and his trainer Cus D'Amato, both of whom died at the start of his career, while dragging ex-wife Robin Givens and Desiree Washington, the woman who accused him of rape, through the mud. The script, which was later published in memoir form, plays to Tyson's strengths as a storyteller, and his charisma, for better or worse, carries the audience through the show's touchiest moments.

2022 brought new attention to the show thanks to the Hulu miniseries "Mike." This unauthorized look at Tyson's life by "I, Tonya" writer Steven Rogers and director Craig Gillespie uses a performance of "Undisputed Truth" as its framing device as Tyson (Trevante Rhodes) narrates his life from the stage. The stage show is not officially credited as a source material for the series, even though large swaths of its scripts, particularly in the early episodes, appear to have been taken from it. Tyson has denounced the miniseries and Hulu for stealing his story, comparing them to slave traders on social media.