On the phone from Los Angeles, Justin Oswald is talking up an art installation he's got on tap for the weekend.

"My friend called me up and asked me to be a dirty Santa and I said, 'Yes, sign me up,'" he says in excitable tones. "I am so there."

Truth be told, the bearded and barrel-chested Oswald is so kind of everywhere in Portland, and all over the West Coast and the world. He has pads in Portland and Los Angeles, but he considers Stumptown his real home. A Viking-looking aesthete with a shock of curly red hair, Oswald's an iconoclastic one-man band: an artist, entrepreneur, traveler and the former owner of Portland's infamous First Thursday art party destination Gallery 500. You can't miss him at a party, because Oswald usually is the party—so much so that he was approached by a producer interested in featuring Oswald in a new reality show. Oswald turned it down: "Too much of it involved drinking."

Back in town from L.A., the 27-year-old has decided not only to officially call Portland home again, but to invest in the city's creative community. Like many people involved in philanthropy, he says he chooses to keep his finances private. Then again, The Oregonian reported in 2005 that Oswald, the great-great-grandson of catsup czar H.J. Heinz, spent $100,000 sprucing up the Gallery 500 space—so he's not hurtin'. WW caught him on the eve of a fundraiser he's helping put on for p:ear, a local nonprofit arts center for homeless youth. The party's theme? Alter Egos, appropriately enough.

i]WW[/i] : So, what is it exactly that you do?
Justin Oswald: People get pissed off when I don't give a straightforward answer. It usually comes down to "self-employed." I have a company with [designer] Ryan Glasgow... called Jorg—Justin O. and Ryan G…it's pronounced "George." We do product design, and we're doing some sunglasses, which haven't hit the market yet, and Ryan's doing a modular home and I'm trying to help him with that. It really started the year before I shut down the gallery [in 2005], and then I took off to Africa for six or seven months. Right before that I started doing p:ear [he's a board member for the nonprofit].

And your art-production-jewelry company, Tits-and-Bling—what the hell is that?
It was a kind of a spinoff from a collector in New York…Marcia May, who died a year and a half ago. She was this amazing woman who had a tit on the table [in her apartment]. And I had all these dreams of having a cocktail party and being comforted by this tit underhand. Everyone should have a tit on the table. And I just started making all these Table Tits [a silicone and gold art piece modeled on a real woman's breast]. And bling.…I mean, what goes better with tits than bling? I went to Lloyd Center, which is this awful ghetto mall, and they have this kiosk where they make bling dog tags, where you can photo engrave a picture. I got one of these machines, and now I can make my own personalized dog tags.

How did you find the perfect breast for your Table Tit?
I molded so many women... I found the woman with the tit I was looking for, not the perfect tit—I'm a fan of smaller tits myself—but hers was perfect for the Table Tit. It wasn't too big, but it wasn't too small, it could be a nice centerpiece. You wouldn't believe the perfect tits I would see, but then, when you mold one, it's not right. The one we [finally] reproduced, it has a gold base with my signature on it. I have been talking to a woman at Barney's [a high-end department store] about selling them for $500 a pop [Note: Oswald, who uses local artists to craft the breasts out of silicone, has yet to sell one of his Table Tits ].

Back when you ran Gallery 500, i]WW'[/i] s Richard Speer called you "the Prince of the Portland arts scene's next generation." Do you miss that life?
It was a hell of a lot of fun, but the art world is all about parties…it was a good time when we did it. It's nice not being host all the time. One of the things I was into at the gallery was making an egalitarian environment: From ages 21 to 60, everybody got the same attention.

Why get involved with p:ear?
What it really comes down to is it's a great place for kids to go and feel safe. There's a show every month, and artists, and a place where a kid can be a kid…I don't know if they'd want me to call them "kids." It's very arts-focused and it has a strong social justice angle I really like. Maybe you could say I'm maturing a bit.

OK, what's next for Justin Oswald?
I've got a roller derby team, Guns N' Rollers. Last year I was their only sponsor, and I'm buying them all new jackets—they better get off their ass and get first place, for chrissake! Oct. 20 is the next big game at the Expo Center.

Why stay in Portland?
The quality of life is amazing, everyone is real and hands-on, everything's accessible. Nobody's so high on the horse that they can't come down and talk to you. I would hate to see Portland change too much, I like the way it is.


p:ear presents

Alter Egos: Super Villains and Heroes Masquerade

at Someday Lounge, 125 NW 5th Ave., 228-6677. 8 pm Saturday, Oct. 13. $7-$10.