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. It came in the summer of 2011, as he was strolling through the West Village with his girlfriend, the actress Paz de la Huerta.

“Paz says, ‘I think that’s a paparazzi guy,’” Mr. Olson explained while obsessively drumming an unlit cigarette against a notebook as we sat in a beautiful, airy Soho loft (it’s pal Curtis Kulig’s, the street artist). “I’m like, ‘Fuck ’em. If they want a picture, I’ll give ’em a picture. And we started kissing.” Later, gossip blogs would home in on the fact that Mr. Olson  was holding a skateboard. “They’re like, ‘Who’s this old guy trying to relive his youth?,” Mr. Olson recalled. “I’m like, ‘Bitch, I’ve skateboarded since I was a little kid. And I’ll skateboard until I die.”

He’s been living off his art for over a decade, and it’s the latest stage in a miraculously itinerant life. Permanently restless, Mr. Olson hops between coasts, between gigs, between girls. Not caring about much more than making rent, and taking care of his son, he has crammed a few lifetimes worth of experiences into one. Ask his friends how he’s managed to pull this off and they’ll answer, with just a touch of awe, that it’s obvious—somehow, he stayed 17 forever.

Mr. Olson is a solidly built, grizzled, prominently jawed man. He’s handsome now, but was likely exceptionally—swooningly—handsome in his younger days. His best asset is his hair, which is thick and greasy and grayed, and which separates into two autonomous zones: a midskull-to-back-of-skull section, and another tuft on the edge of his forehead. He tugs on it constantly, and it juts out in wild, wondrous angles.

When The Observer first met up with Mr. Olson, he was in town working on an art piece called “Hanging.” The centerpiece is Mr. Olson himself, in bare feet and a loose black suit, slung up in a noose. Underneath, he explained as we looked through photos on his iMac, will be a slice of demographics—“some Hasidics, some Africans, whatever”—looking up at him. Below it’ll say “We all come from the same bang.”

Much of Mr. Olson’s persona can be traced back to his beginnings as an L.A. skate kid. He rolled with a crew from Orange County, unofficial rivals of the famous Dogtown kids to the North. As Dogtowner-turned-filmmaker Stacy Peralta put it, “He was the first vertical skateboard champion. He would show up to contests with the least amount of practice. But then he’d get this intense focus and would go out there and be flawless. And he never did the same thing twice.”

In 1979, Mr. Olson won the Skateboarder of the Year award. The fledgling industry was working hard to legitimize itself at the time— but Mr. Olson had just gotten into punk rock. Oblivious to any chances of winning, he’d shown up to the banquet in a white blazer, pants nicked from a bondage shop, and a polka dot tie that he pretended to hang himself with. Also, he was coked out. “I went up to get the award,” Mr. Olson recalls, “and all the photographers are like, ‘Speech!’ I was so gakked out on blow. I couldn’t talk.”

He was in his late teens at the time. He had dropped out of high school, and was being paid by the skateboard maker Santa Cruz to travel the country, “just hanging. Skateboarding. And fucking people up.” And then, like that, it was gone. The skate parks integral to blooming the sport were being shuttered, a reaction to insurance claims and the early-’80s recession. “Skateboarding fucking died,” Mr. Olson says. “And it’s, ‘O.K.—what are you gonna do with your life?” He’s never really answered that question once and for all.

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