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When Mike Tyson won his first heavyweight boxing title in 1986, he became the youngest champion (20 years, four months) in the history of the sport. But it didn’t take long for Tyson’s personal demons to get the better of him.

By 1990, he’d lost his championship belts, divorced from his wife Robin Givens, and fired his trainer. Two years later, he was convicted on rape charges and sentenced to six years in prison. At that point, Tyson looked like he’d lived the entire Raging Bull story in less than 10 years.

In 2003, the man who’d earned over $400 million in his career filed for bankruptcy, at that point some $23 million in debt. And a younger generation began to know him as just an ex-boxer with substance abuse problems and money issues.

But the legend of Tyson’s days as the king of Las Vegas — complete with a 550-lb pet tiger — remained fresh in the minds of many. So when Todd Phillips got the green light to shoot The Hangover (2009), a Tyson cameo struck the director as a great idea.

Tyson struggled with a cocaine addiction during the ‘Hangover’ shoot

Boxer turned actor Mike Tyson arrives on the red carpet for the premiere of the Warner Bros. film, “The Hangover Part II.” | MARK RALSTON/AFP/Getty Images

There’s no question Tyson’s cameo was part of The Hangover’s success. When the idiotic main characters find him waiting in their Vegas hotel room, the story really kicks into gear. And it builds on the legend of Tyson, who gamely sings “In the Air Tonight.”

But that small role was no walk in the park for the former heavyweight champ. Looking back on the shoot (and that of The Hangover Part II), Tyson admitted being on drugs, barely able to get through his lines.

“I was a mess. I was overweight,” he told In Depth’s Graham Bensinger in 2012. “I was a pig, high on cocaine. They had to know I was messed up. I couldn’t talk. I had the cocaine talk.”

It wasn’t exactly a huge payday for Tyson, either. While The Hangover franchise easily topped $1 billion, he made a total of $300,000 for his two appearances. However, no one could have seen that sort of box office coming — including Tyson himself.

Tyson thought ‘The Hangover’ would be ‘low-budget, not a serious movie.’

Bradley Cooper and Mike Tyson arrive at the premiere of Warner Bros. “The Hangover Part II” on May 19, 2011. | Alberto E. Rodriguez/Getty Images

In the Hollywood Reporter’s The Hangover oral history, Tyson recalled knowing little about it prior to the shoot. “Somebody had told me something about a movie, but I wasn’t coherent as to what he was talking about,” he said in 2013. “They made it sound like it was low-budget, not a serious movie.”

He even met co-stars Justin Bartha (Doug) and Zach Galifianakis (Alan) at a club before the shoot began. “They said, ‘We’re going to be shooting a movie with you in two weeks.’ I didn’t even know. I said, ‘Really?!’ I was a little wasted at the time.”

As for the backlash the studio got for casting a convicted rapist in a profile-raising appearance, Phillips shrugged it off in a THR interview. “We didn’t cast him because he was a convicted rapist,” Phillips quipped.

“We didn’t cast him as a sensationalistic thing, either,” Phillips added. “We cast him because the story took place in Las Vegas. I had heard Mike Tyson had seven tigers when he was living in Las Vegas. It’s a true story, and it just sort of made sense. He played Mike Tyson in the movie.”

Also see: When Joe Pesci Couldn’t Stop Saying the F-Word on David Letterman