Dr. Martens, the iconic shoe brand closely aligned with decades of rock culture, premieres a new installment of the Dr. Martens Music And Film Series. Waterparks fans may remember hip-hop artist De’Wayne Jackson when he opened for the rock-pop trio on tour last fall. DM commissioned filmmaker Erik Rojas (tiLLie, Chase Atlantic, Waterparks) to deliver the artist’s essence in “De’Wayne: Tough As You.” 

In the clip, De'Wayne Jackson can be best described as neither tough or benign but rather remarkably human. He affably discusses his obsession with hip-hop as a child when he used to listen to his father’s music collection and write down the raps of his favorite artists as a way to inspire his own writing in his tweens.

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“At 14, I pretty much stopped going to school,” the rapper says. “Everything else was secondary to me. I was always the different guy, and I figured that if any place would accept me and understand me, that must be where everybody else is.”

From then on, Jackson discusses some serious dues, paying both physical (living in his car) and emotional (missing several years’ worth of holidays with his fam because he didn’t have the cash to travel back). His refusal to sugarcoat that experience is refreshing but very much real, as he kept his eyes squarely on the prize. While most of us would just go back to the comfort of our parents’ basements watching muckbang videos on YouTube, Jackson talks the journey to getting discovered by Benji and Joel Madden.

Director Rojas captures the ambition, the hustle and the reality in Jackson’s Dr. Martens mini-doc. In addition to the inspiring interview, there’s footage of Jackson and his band slamming down his latest single “Top Gun,” as well as him cavorting on the set with Waterparks’ Awsten Knight

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But if there’s one thing you take away from Jackson—well, besides his sweet sing-rap flow, the urgency of “Top Gun” or the dude’s infectious enthusiasm—it’s a life lesson that everybody needs to heed: “Whatever happens, you can’t give up on yourself.” He pauses with a disarming smile and a laugh. “Can’t do it!”

Check out the Dr. Martens' presentation, “De’Wayne: Tough As You” below.

You can keep tabs on all of Dr. Martens’ upcoming events here. As for Jackson, he just released his latest single “Top Gun,” which you can stream here. He’ll be performing at a sold out show with Anti-Flag and the Bombpops in Los Angeles Friday. You can keep up with future plans on his Twitter and Instagram.