At 23, Justin Oswald is a bit like the young Henry VIII: auburn-haired, robust, eclectically artistic and, it is rumored, rich. "He's an heir to the Hellmann's mayonnaise fortune," an informant told me the other night. "No, no," said a woman within earshot. "French's mustard." "You're all wrong," pronounced a third person. "He's piss-poor. Tends bar to make ends meet."

The Gatsbian aura surrounding Oswald is only part of his enigma. Simultaneously soft-spoken and larger-than-life, he has pushed the First Thursday envelope with the daring and occasionally inspired shows over which he presides at Gallery 500, and is luring a younger crowd to the traditionally staid art walk with the gallery's hopping opening-night parties.

When I met Oswald at Carlyle for Sapphire and tonics, he was wearing buckskin clogs so tacky they were trendy, and he was in the mood to talk--not about the subject of his income but the object of his passion, contemporary art.

WW: Gallery 500 is just over a year old now. What makes it different from other galleries in town?

Justin Oswald: It's comfortable. It doesn't have this snooty-asshole environment. We integrate a lot of different worlds. I opened it when I was still going to Lewis & Clark, so we had a big Lewis & Clark crowd--still do, a lot of teenagers mixed in with the more established collectors.

What's your take on the difference between the art scenes in your native L.A. and here?

I like Portland better than L.A. It would be a lot easier to have a gallery in L.A. Here, you really have to work at it. I called up New York artist Tony Oursler the other day and asked him to do a show, and when he found out I was in Portland, he was like, "Who the fuck are you? Have you spoken with my agent?" It was a total reality check. But Portland's small enough that you can--I don't want to say "take it by storm"--but you can make an impact.

You obviously like to take risks in your shows. You had the condom show by Laudir Fiero, the 8-foot interactive vagina by Amy Harwood....

Right. I like to do things that are original. I don't want to be the 18-millionth person to do something.

I think there's a similarity between what you're doing at Gallery 500 and what's happening over at Haze Gallery.

Well, you know, I've shown my own artwork there, my stretched canvases, and Jack Shimko and Leah Empkin are friends of mine from Lewis & Clark, and Randy Calvert and I bonded at a Ted Nugent concert one night, so we're all on the same page. Those guys aren't afraid to tell me I'm full of shit.

What's coming up at Gallery 500 in February?

Anastasia Schipani is coming up from San Francisco with some larger-than-life pieces that are all about love, death and passion. They draw blood, seriously. She's an eccentric woman, really into bullfighting and Spanish culture, but also influenced by Japanese erotica. Hell of a mix, if you ask me.

Anastasia Schipani's works.