Mike Tyson‘s life has gone in directions few people could predict. In a recent interview with motivational speaker Tony Robbins, the legendary boxer discussed one of his most beloved pop-culture moments, when he threatened Bradley Cooper for kidnapping his pet tiger.

Tyson’s scenes in The Hangover went viral instantly. But he nearly said no to the opportunity. Tyson’s cameo revived his image to the point that he got his own TV show years down the line. 

Controversy followed every chapter of Tyson’s life

For reasons both laudable and criminal, Mike Tyson’s presence in the culture has been consistent for over 30 years. He was the dominant force in boxing in a time when the heavyweight title still mattered to mainstream sports fans. Tyson was the youngest boxer to win a heavyweight title at the age of 20, won his first 19 professional fights by knockout, and he eventually became the first person to hold the WBA, WBC, and IBF titles at the same time in the late 1980s.

Tyson’s exploits in the ring earned him the nickname “The Baddest Man on the Planet”. Rarely has a moniker felt more appropriate. But the same impulses that led him to exert exhilarating violence to the acclaim of fans worldwide also had disturbing consequences. Tyson was convicted of raping an eighteen-year old in 1992 and spent three years in prison. Two years after getting released, he tried to bite off one of Evander Holyfield’s ears. 

Tyson’s numerous demons and financial troubles grew more apparent in the years after as he receded slightly into the foreground. He retired from professional boxing in 2006, but he didn’t stay out of the public eye for long. 

‘The Hangover’ made him likable for a new generation

The tenth highest grossing film of 2009 was Todd Phillips’ Vegas bro comedy The Hangover. Audiences loved the movie’s raunchy humor and outlandish situations. One of the most enduring scenes from The Hangover involves Tyson playing a heightened version of himself in a surprise cameo. 

These scenes popularized him for a generation of moviegoers who only had a vague understanding of Tyson’s life and his actions. For many, he was just a former boxer who bit a dude and took care of pigeons. Nothing quite softens a person’s image like badly singing a Phil Collins song and concussing Zach Galifianakis. 

No one expected to see Tyson in the movie, much less Tyson himself. He stated in a 2010 interview that he only took the role to fund his cocaine habit. That didn’t stop him from striking up a rapport with the rest of the cast, as seen on this behind the scenes clip from the film: 

Tyson also appeared in the other two Hangover movies, but the less said about those sequels, the better. But with his value as a cultural figure back on the upswing, he gained access to many more opportunities on screens big and small. 

Tyson’s career decisions after the movie are fittingly strange

Tyson parlayed his resurgent fame into several similar roles. None of them got close to the wattage of his part in The Hangover though. Most of Tyson’s appearances come in two guises: either in low-rent action movies like Kickboxer: Retaliation or Grudge Match — he shares a screen with Evander Holyfield — or comedies where the crux of the joke is that Tyson actually showed up on the set of How I Met Your Mother or Scary Movie 5. (He also sung Salt-N-Pepa’s “Push It” on an episode of Lip Sync Battle.)

His most substantial work during this time is Mike Tyson Mysteries, an animated show in the style of ’60s and ’70s classics Jonny Quest and Scooby-Doo, Where Are You! The show follows Tyson, an alcoholic talking pigeon voiced by Norm McDonald, Tyson’s adopted daughter, and the ghost of the Marquess of Queensberry, who’s considered one of the forefathers of modern boxing. Reviews were mostly positive, but the show ended after its fourth season. 

That still isn’t enough to make Tyson go away. He’s recently agreed to an eight-round exhibition march against Roy Jones Jr. in September. The idea of two men in their fifties punching each other should be concerning, especially during a pandemic, but money and ratings have made one thing clear: a lot of people still want to watch Tyson do anything.