A History of Rappers and Boxing


Yesterday, headlines were made and stomachs were turned with the news that Trayvon Martin-shooter George Zimmerman would be taking part in a “Celebrity Boxing” event. As if the notion of killing a teenager qualifying one as a “celebrity” wasn’t enough, it was announced that Zimmerman’s opponent would be Yonkers’ own DMX. There’s a tremendous amount of controversy surrounding every aspect of this pairing, and understandably so. However, while it may be the most uncomfortable, it’s far from the first time an MC has put the gloves on and stepped foot into the ring. Here’s a brief history of rappers dabbling in the sweet science.

See also: Top Ten Great DMX Shenanigans

DJ Jazzy Jeff and the Fresh Prince – “I Think I Could Beat Mike Tyson” 1989
We begin innocently enough with Will Smith and Jazzy Jeff being joined by Mike Tyson and Don King for a bit of fantasy-based fun in “I Think I Could Beat Mike Tyson.” At a time when Tyson was still “That Young Knock-Out Kid” and Smith was “The Fresh Prince,” it was a silly collision of two pop culture powerhouses. While it was spiritually succeeded over a decade later by Aaron Carter playing basketball with Shaq, soon the fisticuffs would get much more real.

Willie D vs. Melle Mel 1992
There’s two facts every rap fan knows about Grandmaster Melle Mel. No. 1 his work on “The Message” is the most important contribution to the art of rap and the culture of hip-hop ever committed to wax. No. 2 he’s absolutely huge. A mountain of a man, Mel’s incredible physique has taken him everywhere from combat sports to wrestling. When it came time to try his hand at boxing, he faced Geto Boy Willie D. Willie’s no stranger to donnybrooks, maintaining an actual professional fight record of 6-1. On the same hip-hop boxing event that saw Freddie Foxxx/Bumpy Knuckles knock-out Dope E of The Terrorists, Willie took Mel down.

Sticky Fingaz vs. Simon Woodstock 1998
Later that decade, MTV took their Sports and Music Festival’s cross-pollination to another level by having musicians compete against actual athletes in sports. Onyx’s Sticky Fingaz took on professional skateboarder Simon Woodstock in an admirable, but losing effort. Fingaz would fair much better against vampires in the “Blade” television series years later. Also of note is the commentary by Academy Award winner Jamie Foxx.

Vanilla Ice vs. Todd Bridges 2002
In the original “Celebrity Boxing,” one of the most polarizing hours of television ever broadcast, a pre- “anger management-era” Vanilla Ice took on sitcom star Todd Bridges. As great as it was seeing Bridges light up the small screen with an incredible effort, it was a disheartening moment for Ice loyalists hoping this would relaunch him into the spotlight. They wouldn’t have to wait long, however, as his time on the second season of The Surreal Life shortly after would transform him into the lovable well-adjusted house-flipper we adore today.

Snoop Dogg vs. Roy Jones Jr. 2008
Roy Jones Jr. is no stranger to late night hip-hop fans. His video for “Y’all Must’ve Forgot” was a staple of the glory days of “BET Un:Cut.” So, when Snoop Dogg needed someone to spar with get in better shape, he recruited Jones. Reality television makes for strange bedfellows, but predictable outcomes, in case you forgot.

R.A. the Rugged Man – “History of Boxing Freestyle” / vs. Floyd Mayweather 2009
Finally, no discussion of rappers and boxing would be complete without a mention of infamous underground MC and boxing historian R.A. the Rugged Man. A friend of Bernard Hopkins and Mitch “Blood” Green, as well as a former writer for Ring magazine, R.A.’s even landed a book deal writing about boxing for Trinity Press. While his “History of Boxing” freestyle is required listening for all fight fans, his biggest contribution to the sport might be his on-air call-in confrontation with boxing bad boy Floyd Mayweather. R.A. directly brought up Mayweather’s allegations of ducking worthwhile opponents, an event that some consider what finally got the undefeated boxing champ to begin picking better fights.

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