Hip-Hop 50: Why Will Smith's comic jab at Mike Tyson never hit its mark - ESPN

Editor's note: In honor of hip-hop turning 50, ESPN tapped the culture's top voices to write about their favorite athlete name-drops in hip-hop history.

«Some fool asked why I ran away/ I said, 'A good run is better than a bad stand any day'/ My career is over as far as fightin'/ But I don't know what made me think I can beat Mike Tyson» — The Fresh Prince on «I Think I Can Beat Mike Tyson» (1989)

In 1989, it was inconceivable to think any sane human being could beat Michael Gerard Tyson in any kind of fight (cough, cough...Mitch Green), let alone a professional boxing match. Yet, in the delusional mind of Will Smith — better known then as hip-hop wunderkind, The Fresh Prince — he thought he could shoot a fair one with the best fighter on the planet.

Well, on wax, at least.

As one half of DJ Jazzy Jeff & The Fresh Prince, Smith's nutty display of hubris was the impetus behind «I Think I Can Beat Mike Tyson,» the lead single off of the duo's aptly titled third album, «And In This Corner...»

In the late '80s, the Philadelphia natives honed in on a satirical musical style thanks to tracks like the Grammy Award-winning (the first ever in the newly formed «Best Rap Performance» category) «Parents Just Don't Understand.»

Smith's lightheartedness and witty wordplay made the burgeoning genre digestible to a mainstream audience intimidated by some of hip-hop's more politically direct artists. Although, to keep it a buck, this «safe rap» led to the genre gaining broader appeal and opened the door for the cultural transformation to follow.

Since transcendent personalities of the era were usually the subject of Smith's lyrics, it made sense that Tyson — fresh off a title defense against Carl Williams that ended in a 93-second