No matter how much someone loves skating, you can’t skate 24 hours a day. Some literally spend days at a time playing video games online with their buddies, some go the opposite direction and spend their free time chasing down pro-friendly ladies, while others wash away their time with countless adult beverages. However, some skaters choose to use their time more wisely and get involved with making music, and with the influence rap has had on skateboarding over the years, it’s no surprise that many skaters have taken up rhyming as a pastime, some with better results that the others. For better or for worse, here are ten of the most well-known skaters to try their hand at it.
1. CHRIS GENTRY, Big Brother, Crap, 2001
Long after the Beastie Boys broke white boys rapping open to the mainstream, and a few years after Eminem proved it was here to stay, we had Chris Gentry doin’ his thang in the opening montage for Big Brother magazine’s video Crap. Chris Gentry’s rapping had long been entertaining fellow skaters at trade shows, afteparties, and the such, but this was his chance to display his skills front and center on a skate-video soundtrack. As far as how good his performance was? Well, let’s just say there may be a reason the video was called “Crap.”
Only could find this one on VHS.
2. QUIM CARDONA, Eastern Exposure 3, 1997
Quim kicks off the credits section to this East Coast classic by freestyling a little “a capella with a hurt patella,” or without music but with a hurt kneecap for all you hip-hop laymen out there. In the clip, Quim comes off very proper, showing that he’s obviously spent a decent amount of time practicing. In fact, he freestyles so well that he almost makes up for countless other embarrassing moments provided by rapping skateboarders everywhere. Almost.
3. JEREME “JR BLASTOFF” ROGERS, All Over The Internet, 2008
In the fall of 2008, Jereme Rogers created an Internet feeding frenzy when a link to his MySpace Music page was posted on every skateboarding Web site that exists. As someone growing up as a sponsored skater, it seems only natural that JR Blastoff rhymes about life on the streets, guns, and slangin’ drugs for money (and of course, the saving graces of God). But between the whispering delivery and the auto-tune, if I were you, Jereme, I wouldn’t quit my day job. Oh wait… you already did.
4. TONY FERGUSON, Plan B, Virtual Reality, 1993
Opening his classic Plan B section, Tony Rone busts out a freestyle in Vancouver about being an amateur skateboarder. Getting only two lines in before the Souls Of Mischief take over, Ferguson’s raps come across as much better than many of his fellow rapping skaters, perhaps showing us that keeping it short and sweet is the way to go (wrap that shit up before you have the chance to embarrass yourself).
5. HAROLD HUNTER, Zoo York, Mixtape 2, 2002
Although providing the soundtrack for your own section is almost always a bad idea, when you’re the Ol’ Dirty Bastard of the skateboard world, it all sort of seems to make sense. And that’s exactly what Harold Hunter does for a montage including his section in Zoo York’s second Mixtape video. Featuring clips of a makeshift rap video to go along with it, the rapping definitely isn’t the best out there, but in retrospect, it’s just all part of the legend of Harold that will never die.
6. JOEY SURIEL, City Stars, Street Cinema, 2001
Another skater opening up his section with a short freestyle, Suriel doesn’t come off quite as proper as Tony Ferguson as he rhymes to the camera while busting out some dance moves from inside his car. Rapping about his various sponsors, Suriel also manages to fit in the phrase “word, ya heard?” three times in seven seconds. Word. We heard.
7. TERRY KENNEDY, Baker, Baker 3, 2005
Taking inspiration from growing up in the hood, TK provided the track for his Baker 3 section along with his rap group, Fly Society. Rapping about the prerequisite money and chains, TK has actually enjoyed some success as a rapper, which has helped push lots of his signature product such as multi-colored print hoodies and strappy hig- top shoes. So you know he means it when he says, “I’m a skateboard ni–a, gettin’ paid like a skateboard ni–a.”
8. PAT WASHINGTON AND HENRY SANCHEZ, Gold Wheels, Got Gold?, 2002
Another skate section mixed with a video for the accompanying rap song, Sanch and PW Esquire spit their rhymes Bay Area style as they share a section in this video for Stevie William’s wheel company. As mentioned before, providing your own rap song for a skate section is almost always a bad idea, but PW and Sanchez actually manage to pull it off. Sanchez comes off a little bit sketchy, but Pat Washington has been spitting rhymes for a “hot minute” now, and it shows.
9. RON ALLEN, Girl, Mouse, 1996
Providing the track for Mike York’s section and even shouting him out in it, uncredited O.G. H-Street skater Ron Allen’s rap skills were so good that he had skate kids everywhere searching their asses off for the track long before you could find songs upon the button click of a mouse (pun intended). The Mouse performance along with an amazing freestyle at the end of a ’94 video for his company Fun gives hope that perhaps skaters actually can rap.
10. DARREN HARPER, Get Familiar, 2006
“Who changed the channel to BET?” is a question that a lot of people seemed to be asking after the drastic change to the rap video style of Darren Harper’s closing section in Chris Hall’s video Get Familiar. Although Harper doesn’t actually rap in this song, he still deserves an honorable mention as clips of his gigantic pop are intermingled with shots of him profilin’ and flossin’ beside his R&B friend singing about the dangerous life they’re living. And judging by the clips, unlike other rapping skaters claiming a dangerous life, these guys aren’t faking it.