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.
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.”
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.
The second time The Observer saw him was a few days later, at another beautiful loft that belongs to a friend of his, the photographer Michael Halsband. Framed prints of Halsband’s work—Rolling Stones tour shots, Peter Tosh profiles, his famous Warhol-Basquiat boxing photo—were stacked unceremoniously on a counter, and the place was lined with artifacts: mandolins, surfboards, amps, stacks of LPs, vintage cameras, a Roland TR-808. When I walked in the actor James Ransone—a.k.a. Ziggy from The Wire—and his brother Dave were posing for the “Hanging” piece, in front of a white background, in matching white T-shirts and leather jackets.
Mr. Olson shouted out instructions—“Zip up your jackets. O.K., now unzip them”—and the shoot quickly transitioned into a casual round of bullshitting about last night’s parties. On the way out Mr. Ransone asked Mr. Olson what he was up to later. Steve was noncommittal, mumbling something about the Standard before clapping him on the back and out the door. Three minutes later, the next batch of cool kids walked in: an Asian model-looking dude with gorgeous chick hair, a pair of identical tall black twins in Supreme hats.
Mr. Olson was all smiles with these guys too, doling out some minimal directions—“the scarf stays”—before regaling us with a story about the time he rejected the advances of a future A-list movie star at his buddy’s son’s bar mitzvah. The kicker: “So my friends are like, ‘She’s beautiful. You should blaze her.’ I’m like, her? She’s boring. The chick I’m blazing is beautiful.”
Next up was Mr. Olson’s pal Armand, a 40-something Spanish-American oil painter dressed in all black, and his equally elegantly attired mother. Before he stepped 10 feet into the apartment Mr. Olson had already squeezed Armand’s cheeks and complimented his haircut and effusively praised his work, and Armand was nearly blushing. Meanwhile, Armand’s mother and Halsband engaged in an impassioned conversation about quinoa-based diets, yoga, natural soy sauce alternatives, and the high-quality level of those complimentary pens you get at TD Bank branches.
Forty-five minutes later, after we’d all forgotten why we were there, Armand asked for an explanation of the piece. Mr. Olson explained that it’s “to wake up the people. They’ve been sleeping. In piles and piles of money.” He grinned. After some back and forth (“Drop your chin, Armand” “But I have a lot of chin”), Mr. Olson got the pair arranged just like he wanted: Armand staring up, Armand’s mother staring dutifully at
Armand. It was a great shot.
Mr. Olson took the leap into art full time after landing one last big commercial gig, for the early aughts search engine Excite.com. He played a character called Mr. Lucky who, with the help of the site, always managed to narrowly avert disaster. It got Mr. Olson’s face all over New York: in TV spots, on the tops of cabs, on a giant Times Square billboard. And it got him paid. Feeling “independently wealthy” for the first time in his life, he tried hawking his wares. He remembers his first success, a piece he sold to “some rich woman” for $5,000. “I’m like, O.K.! This is a scam!” He cracks up. “I said, ‘Fuck it, I’ll make art.’ That allows me to do any of the things I want to do: make a record, make a movie, take photos.”
On that note: he’s going into the studio soon to record his first solo album. It’s called Steve Mr. Olson’s Drag City Racing, and it’ll feature Steve Jones from the Sex Pistols and Bruce Slesinger from the Dead Kennedys. It’ll be fun, Mr. Olson explains: “We want the girls to dance.” He also just shot an indie drama, Johnny Christ, in which he plays the beaten-down patriarch of a Southern country family. He was put up for the role by Jack Nicholson’s daughter Jennifer, one of his best friends. And he’s now writing a screenplay based on The Swimmer, the 1968 John Cheever adaptation starring Burt Lancaster. He wants to do it as The Skater.
But if you insist on thinking of him as that guy who made out with Paz de la Huerta, well, he’s cool with that. “I’ve known Pazzy forever,” Mr. Olson says. “She’s a genius. She’s one of the talents out there. Everyone’s like, ‘Oh, she’s crazy.’ Yeah, well, we all are.”
Mr. Olson and Ms. de la Huerta met the first time at a party in Malibu. She recalled seeing “this vibrant handsome man laughing hysterically” and being smitten right away. (Her friend had a crush on him too, so “I let her have him.”) They reconnected in New York, and now spend their time together “listening to good music, dancing, and being romantic.” Ms. de la Huerta called Mr. Olson “gentle and kind” and his art “tactile and sexy.” They’re taking it easy right now: he sees her when he’s in the city, she sees him when she’s in L.A.
And what about the tabloid spotlight? Does that get to him?
Mr. Olson scoffed. “I’m 50. I’ve dated broads like that before.”
Care to say who?
“One was a big actress. An Academy Award winning chick. Ah, we don’t have to go there. That’s pathetic.”
And did he get shit from his friends for the Paz photos?
“I got mad jabs,” he says. “Like, ‘What a sellout.’ Why, ’cause me and baby are hanging out? But Peralta hit me up too. He was like, ‘I’m so psyched you had your skateboard.’”
At our first meeting, he had indulged in a bit of self-examination. “Everyone’s always like, ‘Oh, you live this lifestyle.’ Yeah, but you have to work hard, and you have to live with less. Rent and, fuck, the phone bill, the gas bill. That’s about it.” Now, he says, his parents like to introduce him as “our son, the bohemian.” “I’m not a bohemian. I’m a hustler.”
But any introspection is fleeting, and worn lightly. After Mr. Olson wraps up with Armand and his mom, the two of us rolled outside so Mr. Olson could smoke. A buttoned up 20-something brunette walks by; Mr. Olson made eye contact, and she smirked back. “I love girls that smile,” he said.