Steve Olson: Irresistible Man-child, Dater of Movie Stars, Professional…Well, We Don’t Know Exactly

At the age of 50—after helping to birth professional skateboarding; after hustling orange juice futures and working as a Hollywood stunt man and having his face plastered across Times Square billboards; after dating runway models and Oscar-winning actresses—Steve Olson had himself his first tabloid flare-up.

For a little while, he sold commodities—silver, orange juice, Deutsche marks, whatever. And then Mr. Olson targeted his next big score: SOS, a clothing line he founded under Santa Cruz. Nordstrom wanted to seal a deal for distribution of the brand, but his issues with the cooked books and shady ways of Santa Cruz led him to pull the plug on the deal. There were millions to be made, Mr. Olson said. But “I didn’t give a fuck about the money. I walked away with my integrity.” Pause. “Which means absolutely nothing.” Pause. “Ish.”

Sign Up For Our Daily Newsletter

By clicking submit, you agree to our <a href="">terms of service</a> and acknowledge we may use your information to send you emails, product samples, and promotions on this website and other properties. You can opt out anytime.

See all of our newsletters

And that’s when the skate movie Thrashin’ came along. These days, the Josh Brolin-starrer is known as another misdirected attempt by Hollywood to cash out on a subculture. Back in the mid-’80s, it was an excuse to coalesce the fragmented L.A. skate scene. “The director was an idiot, the fucking script is stupid,” Mr. Olson says. “But all your boys doing some movie? It was so much fun.” He recalls meeting the producer, “this little guy, at this club. He’s dancing around like ‘I wanna make your life story! We’re gonna make you movie stars!’ And I grab him, pull my switchblade out, put it to his throat and say, ‘You’re annoying.’ And he’s in shock, trembling. And I go, ‘I’m acting …’” They cast him as one of the Daggers, a member of the villain, Hook’s, gang; he also did the stunts for the guy who played Hook.

On the set of Thrashin’, Mr. Olson met a photographer who set him up with advertising casting agents. All of a sudden, he was in demand. “It was stupid things: ‘Oh, hang out with this chick and pretend like you’re trying to fuck her.’” He landed jobs for Reebok, Chevy and Harper’s Bazaar. He also got Hollywood auditions, but never quite bought in. At the audition for a TV version of Teen Wolf he rolled around on the floor like a feral creature, growling at the casting agent. She told his rep to never, ever send her Mr. Olson again. Meanwhile, the commercial money was coming easy, with some jobs paying up to $50,000.

And then he had a son, Alex, who went as far as anything could toward coaxing Mr. Olson into adulthood. The younger Mr. Olson is a professional skateboarder, too. He rides for the company Girl, and has traveled the world shooting videos.

Mr. Olson modestly cuts down his involvement in Alex’s career. They’ve shot magazine covers together and gone on skate tours across Europe. Mr. Olson couldn’t be prouder. He tells a story about the premiere of the Fully Flared video, during which he hid in the back to watch Alex’s segment: “I knew I would be totally psyched and emotional about seeing that my kid had made something of himself.” Mr. Olson had Alex as a result of a drunken one-night stand, and now can’t help but beam when he talks about him. It seems in line with his catch-as-catch can approach to the world, which always seems to produce a happy ending.

Steve Olson: Irresistible Man-child, Dater of Movie Stars, Professional…Well, We Don’t Know Exactly