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The skateboard culture has been obsessed with the Vans shoe since the California brand saw its start up in the early ’70s. Built by the hands of a brotherly duo, the shoe was iconic for its waffle sole that held an impeccable grip on skateboard decks — a market untapped at the time.

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After nearly a decade of remaining relevant solely in the skate game, the checkered slip-ons got their break when Sean Penn’s surfer-dude role as Jeff Spicoli in Fast Times at Ridgemont High sported a pair in the 1982 film.

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The recent news of the passing of skate shoe maverick James Van Doren, who started the company along with older brother Paul and two friends, has prompted us to look beyond how Vans has served as a skate shoe to how the V logo has saturated the urban market as a shoe of choice.

From The Pack dedicating an entire track to the waffle sole shoe, to Lil Wayne sitting courtside in a red pair, in celebration of Van Doren’s legacy, here are some of Vans’ run-ins with hip-hop!

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In the first line of Lil Wayne’s “Bill Gates” song, the rapper leads with the line “Skinny ass jeans, fresh pair of Vans” and  then later continues “Dress like a skater, ride on you like Shaun White.”

The rapper lives true to the lyrics as he is frequently pictured in his skinny jeans, dressed like a skater in Vans. Two claps for Lil Wayne rapping what he’s living.

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Chris Brown wearing a pair of Vans is not headline news, but when CB wears a pair of Vans to a Nike sponsored event, that shows the brand’s power.

We are sure that the R&B crooner has his fair share of Nikes lined up, but Chris sported a pair of Vans Vault Chukka del Barcos in 2009 to celebrate LeBron James And Nike Celebrity Basketball Game.

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When super producer Pharrell Williams didn’t have his feet in a pair of Bape or BBC shoes, he was almost always spotted in a pair of Vans.

Laced Vans seemed to be Pharrell’s preferential style, and when one of Williams’ fans made a shoe to immortalize him and Spongebob Squarepants onto a pair of black leather Vans Eras, the speculation was solidified.

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When Lupe Fiasco kick pushed and coasted onto the music scene, the rapper made it no secret that he was an avid skateboarder and a hip-hop enthusiast. Years later, the rapper proved that he didn’t lose his skater roots when he collaborated with Vans for the OTW collection.

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The most hip-hop moment that Vans has encountered was when rap group The Pack made their break with the song “Vans” and were discovered by Too $hort.

The California natives rapped: “I wear checkered vans the same color as snow. When Uno spit crack, the same color as coke. Got my vans on, but they look like sneakers. You wearin coke whites, but my vans are cleaner.”

Talk about product placement!