I love literal rap videos. Love ‘em! Nobody did literal rap like the family friendliest rapper of all time – the Fresh Prince. Will Smith and Jazzy Jeff taught us all about parents not understanding youth culture and the glories of summertime. They even took on Freddy Krueger one time. Oh how I wish there was a proper video for that one. Apparently there was one filmed, but New Line Cinema forced it to be destroyed. This move, might have saved mankind, but it deprived me the experience of watching Freddy Krueger take down Jazzy Jeff and replace him as the Fresh Prince’s DJ.

However, we are not here to discuss child molesters turned supernatural monsters teaming up with the preeminent late 80s/early 90s sitcom/music star. We’re here to talk about the preeminent early late 80s/90s sitcom/music star picking a fight with a man who would later go to prison for rape and take a chunk out of another man’s ear. In 1989, however, Mike Tyson was just known as a small, fierce boxer that could turn you into a fine paste on demand. Now, he’s known for having a facial tattoo and being in the The Hangover.

“I Think I Can Beat Mike Tyson” is Will Smith’s West Philly take on Rocky. Naturally, Smith needs to put his goofy Fresh Prince spin on things by stumbling up the Art Museum steps (also known as the Rocky Steps if you’re a tourist or monster).

Fresh Prince Beat Mike Tyson Art Museum

We sweep to West Philly, where oldhead Will Smith and Jazzy Jeff are playing checkers outside of a barber shop. Old Will Smith was clearly inspired by Red Foxx.


Will and Jeff are watching boxing in the king of late 80s living rooms when he gets it into his head that he can, in fact, beat up Mike Tyson.

Fresh Prince Mike Tyson 80s Living Room

The Fresh Prince rings up Don King in his limo, as one does when they want to get killed by Mike Tyson in a boxing ring. King looks a bit like a warlord with that style of shirt and his menacing laugh. He really should have played a Bond villain in his heyday.

Fresh Prince Beat Mike Tyson Don King

It’s time for Smith to train, which in this case involves boxing a slab of meat surrounding by bagged ice and lifting bales of hay. Is this meat locker in the back of a convenience store? Why does he want to bench press hay? What would Carlton make of all this?

Fresh Prince Beat Mike Tyson Meat Locker

One thing is certain, Carlton would love Newsie Jeff.

Fresh Prince Beat Mike Tyson Newsy Jeff

After a press conference and some head shaking, Will gets his triumphant run through West Philly. Just like Rocky! If everyone told Rocky he was a fucking idiot. Actually, no one told Rocky that because he was primarily known as a mob enforcer in his neighborhood.

Fresh Prince Mike Tyson West Philly Rocky

Finally, we’ve reached the big fight. The Fresh Prince vs. Iron Mike! You can tell Tyson is taking this bout very seriously, as he wears a t-shirt into the ring. Boxers do that all the time.

Fresh Prince Beat Mike Tyson T shirt

Smith is pummeled with all the fury of 1,000 air punches. That’s it, it’s all over. The Fresh Prince denies his terrible manager Jazzy Jeff’s encouragement of a rematch. And thus ends the video that Michael Mann must have seen this video and thought, “Yes, this is the man that should portray Muhammad Ali.” But wait! We can’t go before showing you guys this catch-all Tyson billboard that both reminds people to vote and say no to drugs. Thanks Iron Mike. You’re such a great role model.

Fresh Prince Mike Tyson TKO Drugs