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.

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.

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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 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.

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