Skateboarding and Hip-Hop were destined to intersect. Both were born of the streets, masters in rhythm and maestros of flow. While the sport first appeared as an offshoot of surfing in the '40s and '50s, it took hold of American youth culture in 7'0s-era California. Meanwhile, an underground movement called Hip-Hop was brewing in New York — with rapping, beatboxing, DJing, breakdancing, and graffiti — being shared at block parties, and later in clubs.

Of course, not everyone in the skating world appreciates Hip-Hop and some in Hip-Hop might be oblivious to the skateboarding scene, but in the great Venn diagram of life, these sets overlap. Meet the special union of those who kick-flipped the script.

50:50 Grinders: Skater-Musicians & Musical-Sk8rs

EAZY-E

Eazy-E was captured riding a skateboard on the Venice Beach Pavillion in 1989 by photographer Ithaka Darin Pappas, who was a freelancer hired by Priority Records. He was assigned to shoot N.W.A. on a Yo! MTV Raps interview with Fab Five Freddy. “I would go to their video shoots with them and worked with them about once a month from ’88-’90,” says Pappas. “The first time I worked with them was a photo shoot at my apartment, which ended up being the press photograph for Straight Outta Compton.” The Venice shoot took place on February 24 in ’89, recalls Pappas. “They started the morning in Compton and I was told to meet them at the beach and to get some portraits. Kriss Kross was there, the D.O.C. was there, they were hanging out doing a promo thing. Then we go down to the Pavillion where people would rollerskate and skateboard. While Freddy was interviewing Dre, Eazy just wanders off about a hundred yards north to a bunch of skaters, grabs somebody’s skateboard, skates for 5-10 minutes, then comes back. Then he grabs someone else’s board and skates away again. It was obviously something he had practiced somewhere. For who he was and what he was representing it was such a courageous thing to do in a public place. Maybe not everybody was happy about that—it might have been ‘too crossover’ or ‘sellout’ but I think he was just being himself.”

Pappas says it was extra surprising because a few weeks earlier while in a van with the guys on the way to another shoot, he had suggested if they ever wanted to go surfing sometime, he could hook them up with friends’ boards and uncrowded surf spots, “and they just chuckled, like, ‘cracka please.’”

Pappas was careful with his film, trying to stay on target, but grabbed a few candid photos of the moment. “It was accidental grassroots promotion. Maybe people who liked Hip-Hop but never thought of skating paid attention or maybe people skating who never liked Hip Hop thought about it. Some people in my inner circle didn’t think rap was even going to be around that long. But the kids around that day were well aware of who he was and they were stoked.”

Those photos appeared in an article in Thrasher Magazine later that year and Priority made some shirts with the group image. Years later Pappas’ photos resurfaced when N.W.A. was inducted in the Rock-n-Roll Hall of Fame and again in Vikki Tobak’s book and exhibit, Contact High: A Visual History Of Hip- Hop.

Mike Miller shot the photo of Eazy-E holding a pentagram-emblazoned Natas Kaupas skateboard, which appears in his book West Coast Hip Hop: A History in Pictures. He says he met the rapper in 1992 while skateboarding at Ruthless Records. Eazy's son, Eric “Lil Eazy-E” Wright Jr., said in a press release: “I learned how to skate from him!”

Such rare images cement Eazy-E’s place in history as Hip-Hop's first skateboarder.

LIL WAYNE

Grammy-award-winning rapper Lil Wayne took up skateboarding in 2010 after leaving Rikers Island, then started ripping it up at parks and forming his own SQVAD UP Skate team. His private skatepark shows up in his Skate It Off video, with dancers SheLovesMeechie and Toosi echoing the fluidity of skate body language in their breakdance-like moves.

Danny Fuenzalida, the Chilean Miami-based pro skater sometimes seen skating on stage behind and around Lil Wayne, met him through a mutual friend—Young Weezy’s skate trainer Adam Ziegler (RIP) in Miami in 2010. After sessioning with them at all hours of the night, Fuenzalida was invited to come along and film the rapper’s Rebirth tour of Africa and Australia, where Wayne opened for Eminem. “I didn’t know we’d be skating on stage,” says Fuenzalida, “so I had an out-of-body experience when they told me that’s what I’d be doing. There were 65,000 people watching.” On their last show in Australia, Fuenzalida skated up a quarter pipe onstage and aired a Mellon Grab, causing Lil Wayne to yell an approving “Ooooh!” mid-set. “Afterwards his manager told me no one had ever made Wayne stop rapping mid-show. I said ‘All it took was a Mellon Grab.’” One night while driving around lost in South Africa with police escorts, they found the skate park someone had tipped them off to. “When we got there I told Wayne it wasn’t the best skate park but the best skaters don’t come from the best skate parks. They make the best with what they have. We started skating just as the sun was rising,” he recalls. Fuenzalida later visited Lil Wayne’s home in Miami, where they shredded his rooftop mini ramp and custom wooden bowl.

“He loves all aspects of skateboarding and is a true sports fan,” Fuenzalida attests. “It was cool to see him at his crib watching legendary videos like Dango the Good Life, Transworld videos and other classics from our area. He knew a bunch of skaters and was always into seeing the young blood rip it up.”

Beastie Boys

The Platinum-selling Rock-n-Roll Hall of Famer Beastie Boys have long repped the skate aesthetic and lifestyle—from mentions of boards and threads in their lyrics to the iconic photo of Mike D. and Ad Rock sitting on a deck together with MCA leaping in the air behind them. Glen E. Friedman, the photographer behind that pic, has preserved and bridged counterculture since the 80s. Not only did Friedman shoot the gods of skating’s early days, but his work graces many of the most important record covers from Hip Hop’s Golden Era, including Run-DMC, Ice-T, Public Enemy, Slick Rick, LL Cool J and more, making him one of the most prolific photographers of the time. As punk singer/spoken word artist Henry Rollins has said of him: “The bottom line is that he was there at the beginning of so much cool stuff in so many different areas it’s not funny.”

Innovators & Collaborators

Streetwear companies evolved out of both scenes and eventually major brands came calling, willing to pay for cred. Cultures once considered “sub” partnered up. Aesthetics Skateboards made a limited edition Tribe Called Quest deck that’s highly coveted on the secondary market. Pro skater Jimmy Gorecki skated for Pharell’s Ice Cream sneaker company (a collab with Reebok). Listen Skateboards did a deck with Lupe Fiasco for his hit “Kick, Push”… the list goes on and on. Here are a few of the major players.

DGK

DGK (Dirty Ghetto Kids) is a multi-million dollar skate brand that has embodied the spirit of Hip-Hop since its inception. Founder Stevie Williams, a pro named one of the "30 Most Influential Skaters of All Time" by Transworld Skateboarding, says he was merely following his heart. He grew up in Philly, breakdancing to Schoolly D, Cool C, Steady B, EST and Will Smith, but the punk and metal soundtracks to the old skate videos were an issue. “When I was young, I used to want to watch the skateboard videos at home but I had to turn the volume button down because my mom would be thinking I'm worshipping the devil or some shit,” he says. At the age of 14, Williams ran away to California and by the age of 15 in 1994, he earned his first pro sponsorships with Chocolate Skateboards and DC Shoes.

Williams chose a Jeru the Damaga graphic for his signature deck, and later, largely inspired by Hip-Hop entrepreneur JAY-Z, launched his DGK brand in 2002. Its name and success flick a middle finger to childhood taunts. “They called me Dirty Steve and my homies, too… so we used ‘Dirty Ghetto Kids’ as a crew name and didn’t nobody know I was going to turn that shit into a company.” He sees himself as a lifestyle specialist riding in on a wind of cultural intersection. “The suburban kids can go into the hood and feel comfortable. And the inner city kids can go into Neiman Marcus and Louis Vuitton and all these other stores that wouldn't really allow us, or just vibe us.” At some point, the world caught up with Williams’ vision of a diverse Hip-Hop skateboarding brand. “Right when it crossed, DGK was there. Because it represents the inner city kid that chills in the suburbs, and also represents the inner city kid that shows up in the suburbs and put them niggas on to hip hop. And it also represents the suburban kids coming into the city wanting to learn and be a part of their culture, and people like DGK fuck with them because they skateboard. It's weird.”

The brand has collaborated with the likes of Beanie Siegel, Rick Ross, Lil Wayne, Dr. Dre, Smif-n-Wessun and more. Williams sees the Hip-Hop skate connection as more “mental than physical,” both pushing inspiring messages about rising above one’s circumstances.

ZOO YORK

The New York-based skateboard and apparel company founded in 1993 by skaters Rodney Smith, Eli Morgan Gesner, and Adam Schatz borrowed their name from a 70s-era graffiti hangout dubbed “Zoo York” by Marc André Edmonds (AKA: ALI), founder of the Soul Artists collective. With links to Phat Pharm and Supreme, the -90s kids formed a brand behind the name, legendary for The Zoo York Mixtape, a video of streetskating footage, DJs and rappers, all backed by a laidback soundtrack. The original and follow-up vids feature appearances by the likes of Busta Rhymes, Wu Tang Clan, Fat Joe, Diamond D, and K-Terrible freestyling on Columbia University/WKCR’s Stretch Armstrong and Bobbito Show intercut with team members pulling off sick tricks.

R. B. Umali, Director of Video Production for Zoo York at the time, says, “Skateboarding, Hip-Hop, punk rock, and graffiti all went hand in hand back in those days. We were all fans. Eli was good friends with Stretch and Bobbito. Real heads like us listened to their weekly radio show religiously and the Stretch & Bobbito show became the soundtrack for the Mixtape video.” For the next decade, Zoo York and Element were two of the biggest skateboard companies worldwide.

LRG

Orange County-based streetwear brand LRG (Lifted Research Group) was founded in 1999 by friends Jonas Bevacqua and Robert Wright, who used their backgrounds in Hip-Hop and fashion to push polos, hoodies, baseball jerseys, cargo pants, woven button-downs and other urban casual wear using the company motto: "underground inventive, overground effective."

One of their first collaborations was with Questlove and Black Thought and since then they’ve worked with the likes of Kanye West (in his pre-College Dropout years), Madlib, Just Blaze, Drake, Waka Floca, Rae Kwon, Migos, and Master P’s No Limit Records, among others. Tyrone Romero, former team manager/marketing manager says “People spend more money on the Hip-Hop side than skateboarding, so there was a conflict at the beginning about paying skaters to wear our clothes versus not paying a celebrity.” The brand eventually reached beyond niche skateboarding magazines to more crossover outlets like Complex and XXL, he says, “still all cool and street-oriented.”

* HEADER CREDIT: Skateboarder in Brooklyn (Photo by: Godong/Universal Images Group via Getty Images)