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Punch Lines: Mike Tyson's Funniest (Intentional) Comedy Moments

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Punch Lines: Mike Tyson's Funniest (Intentional) Comedy Moments

Make no mistake, Mike Tyson has been a pretty funny dude throughout his career, from his comically high-pitched voice to his penchant for awesomely profane quotables ("I'll fuck you

Diet Pepsi Commercial (1988)

Complex says: OK, it's not exactly knee-slapping humor here, but this early TV ad showed the first signs of Iron Mike's lighter side. Missed opportunity, though: He should've been crushing Diet Coke cans on his head.

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"I Think I Can Beat Mike Tyson" (1989)

Complex says: What's really funny is that Mike Tyson actually had fights this easy during his career. Sidebar: Will the rap game ever be this silly again?

Bobby Brown Duet on Jimmy Kimmel Live! (2005)

Complex says: After a seven-year hiatus from (intentional) comedy, Mike bounced back with a regular guest stint on the Jimmy Kimmel Live! show. One of his most memorable moments on Kimmel was this ridiculous costumed duet with Bobby Brown. More with Bobby later...

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Winter Wonderland on Jimmy Kimmel Live! (2007)

Complex says: Another great Kimmel moment. Around this time, Mike was well into his transformation from insane psycho fighter to lovable, misunderstood tragic hero.

NME Awards Skit with The Killers (2008)

Complex says: Mike Tyson and dude from The Killers in a barbershop? Yeah, exactly.

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The Hangover (2009)

Complex says: The least overrated part in a really fucking overrated movie.

Entourage (2010)

Complex says: Could've been a lot funnier if Tyson had slapped Piven openhandedly-style, kinda like he did Robert Downey in Black and White. Ain't seen that? See it.

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"Every Little Step" with Wayne Brady (2010)

Complex says: The best Tyson comedy moment yet. Keep

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