He may have courted controversy over the years, but the man is a natural-born entertainer - both in and out of the ring.
Whether you're a boxing fan or not, Tyson has probably made you laugh at some point in your life. But which are his funniest moments which have brought a smile to people's lips?
From the appearance on Jimmy Kimmel where he ended up singing karaoke in front of a live crowd to THAT television commercial with his arch-rival Evander Holyfield, we look back at some of Iron Mike's most hilarious gaffes.
1. Fluffing his lines
By the age of 24, Tyson was on top of the world, and an ad man's dream. He just wasn't very good at it.
During a trip to Japan to promote his upcoming fight against Buster Douglas, Tyson hilariously forgot his lines, and struggled to hide his amusement.
In the clip, he can be heard saying: "Hi I'm Mike Tyson, coming to you from Tokyo, Japan, and we're having a... [pauses] Oh, s---."
2. Fluffing his lines again (part 2)
In fact, he once got so annoyed with himself after forgetting his lines, he ended up taking his frustration out on poor old Don King.
His former promoter just happened to be in the wrong place at the wrong time when Tyson hilariously 'lost' his temper.
3. Laughing at his opponent
Mitch Green gave it a good go despite the odds being heavily stacked against him but, with Tyson openly laughing in his face, it's fair to say it didn't exactly go according to plan for the four-times Golden Gloves champion, who lost by unanimous decision.
4. Rematch with Razor Ruddock
This was Tyson at his best - nobody could sell a fight quite like him. Speaking ahead of his fight with Donovan 'Razor' Ruddock, Tyson ramped up the trash talk, and promised to make his opponent 'my girlfriend'.
"I dare you to talk to me like that," said Tyson, before adding: "You should get up and kneel to me now and I'll spare you the night of the 28th."
Ruddock fired back: "The doctor said you come in and you come ready, you understand, because I'm going to come ready."
To which Tyson replied: "I don't know why you talk to me like that when you know I'll kill you for it."
Ruddock added: "That's what I like about you Mike, you talk tough.
"Mike Tyson is Mike Tyson, he's an ignorant little kid, you know what I mean.
"And [if] he's gonna [sic] be like that, I don't want to bring myself down to his level so I don't even really want to trash talk.
"I'm going to go in there and we're going to fight and that's the bottom line."
But Tyson would have the final word, saying: "Oh man I can't wait till the 28th. I'm going to make you my girlfriend. You are sweet. I'm going to make sure you kiss me good with those big lips."
Bit weird, that...
5. Lip Sync Battle vs Terry Crews
Mike Tyson and Terry Crews famously brought their 'A Game' in an unforgettable showdown on Spike’s Lip Sync Battle.
While Crews got the crowd going by channelling his inner White Girls for Vanessa Carlton's 'A Thousand Miles', Tyson countered with a rousing performance of Salt-N-Pepa’s 'Push It'.
Those dance moves alone are enough to get you crying with laughter.
6. Making Dana White move out of his seat
Triumphantly, he sits back in the seat and places a travel pillow behind his neck - much to the amusement of those around them.
7. Falling off a hoverboard
Mike Tyson on a hoverboard - what could possibly go wrong?
His daughter can even be heard saying: "Daddy, I don't want you to fall."
Famous last words...
8. Singing Hotline Bling
Tyson, in all his lisped glory, singing along to Drake's 'Hotline Bling' in a way that only he could.
9. Mike Tyson vs Steve Harvey
On 'The Steve TV Show', Tyson took on Harvey in a game of 'Rock 'em Sock 'em Robots'.
Harvey may have beaten Tyson three rounds to one, but Tyson was clearly the crowd favourite.
10. Unboxing a Strawberry Shortcake doll
And finally, the reason we're all here - an unboxing video unlike any other.
"I accidentally ripped a little bit of her hair out," Tyson can be heard saying. "Please forgive me Shortcake."
He then proceeds to brush her hair with a little comb in the most awkward way imaginable.
Check out the video below:News Now - Sport News