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

Editor’s Note: In celebration of hip-hop’s 50th anniversary, ESPN reached out to culture’s top voices to write about the names of their favorite athletes in hip-hop history.

“Some idiot asked why I ran away/ I said, ‘A good run is better than a bad stance’/ My career as a fighter is over/ But I don’t know why I thought I could beat Mike Tyson” – The Fresh Prince on “I Think I Can Beat Mike Tyson” (1989)

In 1989, it was unimaginable that any sane person could beat Michael Gerard Tyson in any match (cough cough…Mitch Green), let alone a professional boxing match. But in the delusional mind of Will Smith — better known at the time as hip-hop prodigy, The Fresh Prince — he believed he could score fair with the best fighter in the world.

At least on wax.

As one half of DJ Jazzy Jeff & The Fresh Prince, Smith’s zany display of hubris was the impetus for “I Think I Can Beat Mike Tyson,” the lead single from the duo’s aptly titled third album, And In This Corner. .”

In the late 1980s, the Philadelphia-based artists developed a satirical style of music with tracks such as the Grammy-winning song “Parents Just Don’t Understand” (the first ever in the newly formed Best Rap Performance category).

Smith’s light-heartedness and witty wordplay brought the burgeoning genre to a mainstream audience intimidated by some of hip-hop’s more politically outspoken artists. However, this “safe rap” to keep it small led to the genre’s broader appeal and opened the door for the cultural shift that would follow.

Since transcendent personalities of the era were typically the subject of Smith’s lyrics, it made sense that Tyson – fresh from a title defense against Carl Williams that ended in a 93-second TKO in the first round – would be used as comedic fodder.

Dropping names in hip-hop was, and still is, a mark of reverence and a testament to your place in the zeitgeist. Tyson’s reign came at a time of particularly profound cultural shift, as a new generation of African-American artists began to gravitate towards the film industry (Spike Lee’s major work, Do The Right Thing, Three Generations of Comedians). – Redd Foxx, Richard Pryor and Eddie Murphy – Leading roles in “Harlem Nights”, Denzel Washington’s Oscar-winning performance in “Glory”), television (the debut of “The Arsenio Hall Show”), music (Prince, Bobby Brown, Whitney Houston and Janet Jackson topped the Billboard charts) and sports (Michael Jordan and Bo Jackson). Even among those all-time players, Tyson wore the crown and was arguably the face of that wave.

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

For many of us ’80s babies (more specifically, a young, haunting, utterly melancholic eight- to nine-year-old from the streets of Flatbush, Brooklyn, who would someday write those words you’re reading right now) Tyson was, for us, what Muhammad Ali was to our parents and Joe Louis to their parents. Many African American boys across the country saw themselves in Tyson.

Its origin story was a tale of desperation, poverty, and despondency that resonated during one of the most turbulent times of the 20th century for inner-city residents struggling to survive. His circumstances were similar to those who looked up to him, children facing brutal trauma in the front row that an undeveloped mind should never witness.

As a teenager, I erupted in the simmering youthful anger of living in a household where I was verbally abused and had no opportunity to express myself.

It always happened when someone challenged my calm demeanor and slightly overweight build.

I’m sure I wasn’t the only one drawing comparisons to Tyson. Fighting wasn’t just a rite of passage, it was a necessity in my neighborhood. You earned cool points by demonstrating strength, tenacity, and dedication. We saw that when we saw Tyson enter the ring. Yes, Marvin Hagler was great and Sugar Ray Leonard’s skills were great, but Iron Mike was the standard. That’s why we loved him—especially Brooklynites.

We’re a proud bunch in Kings County. Perhaps it’s our misfit disposition, bred through generations of the working-class ethic of our elders, in stark contrast to our silver-spoon neighbors across the bridge.

Right or wrong, we’re sticking with our boys. That’s why we cheered for him. So 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 best-selling video games when it was released in 1987.

So we swore he was unbeatable, which Smith admitted 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.