From becoming the youngest heavyweight champion in history to going to jail and owning pet tigers - Mike Tyson has had a crazy life.
The boxing legend’s wild journey is perfectly encapsulated by his strange relationship with Jackass star Steve-O who has had several bizarre run-ins with ‘Iron’ over the years.
Tyson first met the MTV daredevil, who celebrates 15 years sober in 2023, at a Hollywood party and they struck up an immediate friendship over their shared love of cocaine.
"I have so many f***ing crazy Mike Tyson stories, man. Oh, my God. I’ve done f***ing cocaine with Mike Tyson, dude,” Steve-O told GQ in 2016.
“We spent three hours locked in a bathroom together. There was this house party in the Hollywood Hills. And I remember I was distinctly not invited, but I showed up and rang the doorbell.
“Mike Tyson opened up the door. I said, ‘Hey, is it cool if I come in?’ And he said, ‘You got any coke?’ And I told him, ‘Yeah, dude, I got a bunch.’ And I did. I had like a whole eight ball in one pocket, half an eight ball in the other pocket.
“Yeah, I was packing. So, we locked ourselves in this bathroom.”
After spending a wild night with Tyson, Steve-O didn’t see him again until they were both checked into a psychiatric hospital when their partying caught up with them.
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The 48-year-old says most of his second meeting with Tyson was spent trying to convince one of the most prolific KO artists in boxing history to punch him in the face.
"The next time I spent real time with Mike Tyson, one-on-one conversing, was when we were locked up in the psychiatric ward together,” Steve-O added.
“I was talking him into holding out his fist with his elbow locked and letting me run into it with my face to try to give myself a black eye. I was trying to talk him into filming that with me when we got out. But I couldn’t talk him into it.”
However, Steve-O ultimately got his way when they came together again for The Roast of Charlie Sheen in September 2011.
After breaking his nose while filming Jackass 3D, he convinced Tyson to hold his fist out and allow him to run into it in a hilarious reset attempt.
Steve-O ended up breaking his nose again before someone from the audience put it back into place and apparently did a great job as it’s been fine ever since.
“Then came the Comedy Central Roast with Charlie Sheen, and we talked Mike into doing the thing and holding his fist out, and I dove into Mike Tyson’s fist and landed on it with nothing but my nose. Super broke my nose. Like, really crazy broke it.
“I let this kung fu a***hole set my nose on the spot, and it just turned out that he did a f***ing magnificent job. He basically fixed my nose perfect. Everything I was hoping to get that [doctor] dude to do, I got done by Mike Tyson and a f***ing kung fu weirdo.”
Both men have seriously calmed down in recent years and don’t see each other a lot but Steve-O says it’s always a good time when he bumps into Tyson.
He concluded: “I don’t see him a whole lot, but whenever I do, it’s great, man. He’s just the nicest guy. He really is.”
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Steve-O is currently taking his ‘Bucket List’ tour around the world.
Meanwhile, Tyson appears content in retirement after a comeback fight against Roy Jones Jr in 2020. The 56-year-old has a popular podcast and recently opened a coffee shop in Amsterdam.
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