The Untold Story: Why Did Will Smith's Humorous Jab at Mike Tyson Miss the Target?

“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 first-round TKO — would be used as comedic fodder.

Name-dropping in hip-hop was, and still is, a show of reverence and a testament to your place in the zeitgeist. Tyson’s reign occurred during a particularly potent cultural shift, a time when a new generation of African-American artistry began wrapping its arm around the necks of the industries of film (Spike Lee’s magnum opus, “Do The Right Thing,” three generations of comedians — Redd Foxx, Richard Pryor and Eddie Murphy — starring in “Harlem Nights,” Denzel Washington’s Academy Award-winning performance in “Glory”), television (the debut of “The Arsenio Hall Show”), music (Prince, Bobby Brown, Whitney Houston and Janet Jackson topping the Billboard charts) and sports (Michael Jordan and Bo Jackson). Even amongst those all-timers, Tyson wore the crown and was arguably the face of this wave.

Hailing from the gritty environs of Brownsville, Brooklyn, he was a full-blown pop culture phenomenon.

For many of us ’80s babies (more specifically, one young, impressionable, richly melanated eight-going-on-nine-year-old from the streets of Flatbush, Brooklyn, who’d one day write these words you are reading right now) Tyson was for us what Muhammad Ali for our parents and Joe Louis were for their parents. Many African American boys across the country saw themselves in Tyson.

His origin story was one of despair, poverty and dejection at every turn and that resonated for an inner-city population fighting to stay afloat during one of the most tumultuous times of the 20th century. He faced circumstances similar to those who looked up to him, kids who were front row to a brutal kind of trauma undeveloped minds should never witness.

As a preteen, my own bubbling adolescent rage would erupt due to living in a verbally abusive household with no outlet.

This happened whenever someone tested my quiet nature and slightly overweight stature.

I’m sure I wasn’t the only one to get comparisons to Tyson. Fighting was not only a rite of passage, but a necessity in my neighborhood. Showcasing power, toughness and a willingness to scrap earned you cool points. That’s what we saw when we saw Tyson step into the ring. Yes, Marvin Hagler was marvelous and Sugar Ray Leonard’s skills were sweet, but Iron Mike was the standard. That’s why we loved him — especially Brooklynites.

We’re a prideful bunch in Kings County. Maybe it’s our underdog disposition, birthed by generations of the blue-collar ethic our elders exhibited in stark contrast to our silver spoon neighbors across the bridge.

Whether right or wrong, we stick with our guys. That’s why we cheered him on. That’s why we begged our parents to stay up late and watch his fights on pay-per-view and HBO. That’s why we made Mike Tyson’s Punch-Out!! one of the highest selling video games when it dropped in 1987.

That’s why we swore he was unbeatable, which Smith admitted to at the end of the song.

Sean A. Malcolm is a 21-year media industry veteran who was once the Editor-In-Chief of KING Magazine and has written for the likes of Rolling Stone,The Players Tribune, AFROPUNK, Viacom and many others.