11 Boxing Rappers (and Vice Versa)

Rappers want to box. Boxers want to rap. Why? No idea. But as Eminem strikes a deal to star in the new boxing flick Southpaw, Marky Mark’s The Fighter scores two Golden Globes, and Floyd Mayweather hangs with 50 Cent, we salute our 11 favorite pugilistic poets.

11. Mark Wahlberg
Nominated for a Best Actor Golden Globe for The Fighter, Wahlberg estimates he lost $500,000 making the film because he kept paying trainers even when it looked like the flick wouldn’t be made. If that sounds like a lot consider this: he spends much of “Good Vibrations” preparing to get in the ring, suggesting he’s had them on retainer for nearly two decades. Behold a routine so grueling it forces Wahlberg to use a cane.

 

10. Floyd Mayweather
He is a master of time management. When not coming up with increasingly convoluted reasons for ducking Manny Pacquiao or being arraigned for his latest set of criminal charges, “Money” lives a hip-hop lifestyle that includes being in a pool with ladies, standing around near bottles of Grey Goose, and, er, that’s it.

9. Roy Jones Jr.
While he’s lost six of his last 11 fights, at one point boxing was so easy for Roy that he added challenges including shifting between weight classes, playing semi-pro basketball on the day of a bout, and making a rap that offers a weirdly thorough recounting of his career (it’s less a song than a resume).

8. Eminem
After 8 Mile proved a surprise Oscar-winning blockbuster, Slim Shady turned his back on film…until they offered him a chance to lace up the gloves. A collaboration with the Sons of Anarchy creator, Southpaw will presumably feature Em as a lefty and has been called a “metaphorical” sequel to his earlier effort (yay, figurative language!). Happily, he already seems to be in full-on Manny Pac mode, as this clip demonstrates.

7. LL Cool J
He always seemed like he had a gym membership, and with the video for “Mama Said Knock You Out” James Todd Smith got in the ring and suggested to those who believed his career had peaked that they were perchance mistaken. Sure enough, his classic single would soon land him the ultimate in street cred: starring in a TV show opposite Chris O’Donnell.

6. Kool Moe Dee
LL Cool J and Kool Moe always had a bit of a rivalry and “Death Blow” was Dee’s counterpunch to “Mama Said.” But while LL looked like he could step in the ring with Tyson, Dee seemed far more interested in the Tyson who makes that delicious chicken, which may be why this fighter is oddly reluctant to remove his robe (or sunglasses).

5. Will Smith
What a transformation. Long before he played Muhammad Ali and became heavyweight champion of the world, the Fresh Prince was just a young man with so little strength that he was nearly killed by his parents (the video documents the savage beating, as well as earlier humiliations such as being denied Adidas).

4. Muhammad Ali
Pre-Grandmaster Flash and the Furious Five, the former Cassius Clay was dropping rhymes to attain honorary rapper status. Our favorite? Before a Liston fight, he prognosticated: “I predict that he will go in eight to prove that I’m great. And if he wants to go heaven, I’ll get him in seven. If you want to lose your money, bet on Sonny.” Ali acted too, starring on the big screen in 1977’s The Greatest. Most interesting thing about the film? As shown in this scene with Robert Duvall, Ali is oddly unconvincing despite playing himself.

3. 50 Cent
Okay, Curtis Jackson has yet to get in the ring, but he does work out obsessively and endlessly start beef with people (not to mention he’s been stabbed and shot enough times that punches may not even register on his pain spectrum), earning him the right to ride a Segway around Floyd Mayweather’s pad.

2. Cassidy
Cassidy’s been dropping albums since 2004 in a career that’s involved everyone from R. Kelly to Carmelo Anthony (he’s on the Denver Nugget’s label), but time hasn’t dulled his edge. He wants to fight anybody. Well, not really. He specifically makes a point of ruling out battling rappers who are “tall”. That said, if you’re “around my size”, watch out.
1. J.O.E.
You may not have heard of him, but he’s a pugilist, a wordsmith, and, above all, a gentleman who does a mean chicken dance. A Canadian-born brawler plying his trade in Asia, Joe Pineault is also the only rapper we know to reference Frodo in a lyric.  

 

 

 

 

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