Mike Tyson was arguably the best boxer of his generation. However, his standing in pop culture might be even stronger. The world’s youngest Heavyweight Boxing champion had his own Nintendo game, brawled with the WWE’s Steve Austin, and even had his own cartoon on Adult Swim. However, his most iconic moments outside of the ring are in his brief, but memorable film roles.

Lace up your gloves (and protect your ears) as we take a look at some of the prolific pugilist’s best movie appearances.

5. ‘Rocky Balboa’

Yes, when Sly Stallone decided to return to the ring as the people’s champ in 2006’s Rocky Balboa, it only made sense that Tyson would cameo. Iron Mike’s role here is brief but electric. As Balboa’s opponent Mason “The Line” Dixon steps up to the ring, Mike Tyson engages him from the spectator seats. Though Mike is mostly inaudible here, it’s clear he’s antagonizing Dixon (played by real pro-boxer Antonio Carver) for taking an exhibition fight rather than “The Baddest Man on the Planet”. Heightening the tension is the fact that Stallone directs the scene to look like real-life footage from a pay-per-view event.

4. Mike Tyson Finally Gets a Proper Fight Scene… ‘Ip Man 3’

Mike Tyson had made several cameos in films leading up to 2015’s martial arts movie, Ip Man 3. However, this one sticks out because the boxer finally gets to be in a scene that showcases his skills in the sweet science. Ip Man 3 is the second sequel to Donnie Yen’s 2008 biopic of the legendary Wing Chun master. Based on true events, the series showcases Yen’s remarkable stunt work, as he fiercely protects his home and family against the backdrop of midcentury Chinese history. Tyson’s character challenges Ip to a three-minute round of no-holds-barred fighting with the fate of a beloved school at stake. The clash of styles here is terrific, and it shows Tyson is willing to pull punches for cinematic glory.

3. ‘Black and White’

This is another role in which Tyson plays a version of himself. However, it’s not in the ring. Iron Mike also gets to showcase that he can handle a lot of dialogue. Released in 1999, Black and White showcases a pre-Marvel Robert Downey Jr. as he portrays a character creating a documentary about well-known figures such as Mike Tyson. However, Tyson takes offense to Downey’s remarks, leading to a memorable scene where he takes out the future superhero with a simple chokehold.

2. ‘Grudge Match’

2013’s Grudge Match was an epic boxing movie that brought together two legendary film boxing veterans, Sylvester Stallone (the Rocky films) and Robert De Niro (Raging Bull). However, Tyson’s pivotal moment happens after the credits. In the post-credits scene, Mike joins Evander Holyfield on a couch, providing insightful commentary on the match. The highlight of the scene occurs when Kevin Hart playfully urges the two boxing legends to face off in their own bout. Tyson even takes a moment to express remorse for his past actions, including the infamous ear-biting incident. Hart jokingly reminded Holyfield to protect his ears after extending the invitation to participate.

1. ‘The Hangover’

2009’s The Hangover follows three groomsmen (Bradley Cooper, Ed Helms, Zach Galifianakis) at a wild Vegas bachelor party. But their night takes an unexpected turn, leaving them to piece together the events and find their missing groom (Justin Bartha). Amidst the chaos, they unknowingly kidnap a tiger and face the consequences when its owner, Tyson, confronts them. This unforgettable scene includes a memorable air-drumming moment to Phil Collins’ iconic “In the Air Tonight.” Of course, he eventually knocks out Galifianakis out with a single punch. Ed Helms is impressed rather than concerned, exclaiming, “He’s still got it!”