Artists Wanted, the collaborative project of a group of New York artists and creative organizations devoted to using their "networks and infrastructure to bring undiscovered talent to the forefront," each year hosts the "Power of Self" self-portrait competition. The contest's top prize comes with the (delightfully confounding) promise of "one year of your life paid for," along with a video documentary about the winner, and a party. This year, the Portland, Oregon-based figurative painter Stephen O'Donnell nabbed the top honor for his historicized paintings of himself in fancy (and often female) dress. ARTINFO spoke to the artist, who says that he'll use his winnings spend the next year "making some art, dammit!"

You say you're interested in the portrait historié, the historicized portrait. What kind of subjective additional meaning is introduced in your restaging of history? What emerges in the gap between your historical sources and your paintings?

I really don't think that much about meaning in my work. It's there, certainly. But I really want it to be discovered, individually, by the viewer. And I include myself in that group! My work forms at such a subconscious level. For the most part, the only understanding I have of some idea that comes to me is, "that's what I want to see." I let my own desire for an image be the reason for making it. I let the "why" sort itself out later.

View Slideshow: A Q&A With the "Power of Self" Prize Winner Stephen O'Donnell, the "Perverted Norman Rockwell" of Portland

As someone whose work is so literal — you always know exactly what I'm showing you — I think it would be disastrous if I was consciously trying to "say something." I think it's one of the few things that makes my work contemporary at all, some need for the viewer to assess why I painted what I did, to try and figure it out on some level. Because I try so hard not to steer the direction of the artistic choices I make, I feel it must end up coming from a pretty deep place, and I have to say I really enjoy discovering my own work, after the fact.

Tell me a little bit about the significance of painting portraits of yourself in drag. About gender in your work, and about how your visions of gender and of history work together, or in tension with one another.

You know, honestly, I'm not trying to make any sort of statement about gender, not trying to add any historical perspective to the discussion. Why do I do it? The answer is so simple and so complex at the same time. The simple reason is that it's fun. Female costume is usually more interesting, more elaborate, more colorful. It makes the work more theatrical, takes the image farther from the standard self-portrait genre, the "portrait of the artist."

It's more complex than that, I know. The extreme subtleties of gender and sexuality are something that I don't think any of us can truly comprehend, no matter how society tries to codify it all so neatly. I'm not sure many of us can even really, completely, understand our own specific gender identity or sexual response. A lot of me responds to the world as a woman; a lot of me feels like a woman. But I couldn't say I'm transgender. Nor would I say I'm cross-dressing if I've done drag or painted myself in women's clothes. Though I think I'd make a spectacular female, in this life of mine I'm a big, hairy guy. And I'm OK with that. I don't want to alter anything about that. I can totally understand the need of a transgendered person to match up the inside and the outside but, for me, the duality is what makes me me.

As a way of being more closely, if temporarily, female, doing drag is occasionally fun, but it's damned uncomfortable. Painting myself the way I do, as a man in woman's clothes — I never really try to make the illusion that I'm female — is a more permanent (and more physically comfortable) way of expressing that side of myself. The closest I can get to representing a whole self.

Can you list a few of your influences? Artists whom you admire or emulate?

It would be an appalling lie to say that I'm not really influenced by or emulate the artists I admire; everything I see and love has a tremendous effect on me. But as for my actual painting style, it's hard to find what and where I draw from. I'm self-taught, so I had to find my own route to the way I do things — how I apply paint, how I choose color. I have very little understanding about how a celebrated so-and-so might have accomplished this-or-that artistic miracle.

But artists that thrill me? At one time or another, or always: Vermeer, Winterhalter, de Hooch, Maurice Quentin de La Tour, Ingres, Caspar David Friedrich, Sargent, Serov, Gerard, van Dyck, Veronese, Bronzino, and so many others.

You say you draw inspiration from "often very bad" classical paintings. What's the appeal?

A lot of the appeal for me is that they're so instructive. I can learn a hell of a lot from their mistakes. In so many ways, my work isn't modern. I'm almost wholly pre-Impressionist in my sensibilities. So the technical and pictorial issues that the classical, academic artists faced are the same ones that I struggle with. I can't learn how to do what I want to do in my painting by observing a Picasso or a Rothko — there is absolutely no correlation — but I can gain so much by noticing a poorly done bit of drapery or mistaken perspective in a painting by some very earnest and probably forgotten artist. Also, often the reason they aren't really remembered or respected is because they're "too" something that makes them unappealing to a modern audience: too feminine, too hierarchic, too psychologically un-challenging. And that's just the kind of work I like!

Tell about your interest in figurative, highly realist image-making. What role do you think classical figuration plays in the contemporary art world?

As a person whose visual world is almost entirely pre-twentieth century, there isn't really any art for me that isn't figurative and narrative. So it isn't just an interest or a choice for me, it's where I "live." I know figurative art wasn't really "the thing to do" for a long time, but it's certainly come back strongly in the last few decades. How classical it's allowed to be is another question. Making things that look like real things is still pretty suspect, I'm thinking. And "ugly" is still more valued than "pretty," but maybe things are shifting.

How does your art relates to illustration. I know that's a bit of a dirty word in the art world, but some of your work seems very akin to certain classical allegorical illustrations.

Do you mean the narrative aspect of my work because, yeah, I'm sort of something like a perverted Norman Rockwell. I actually often think of myself as a genre painter, with my little tableaux, my little stories. And genre painting died a horrible death way more than a century ago, but I just really love all those old archetypes. I don't think I'll ever do a battle scene, and I gravitate most to the genre-portrait — I don't know if I'm coining a phrase, there — but I love all the various forms of story-based imagery. Right now, I'm working on a subversion of the classical Orientalist nude: re-making Ingres' "Grande Odalisque" with a male figure, altering much of the detail to better fit the character of the friend whose portrait it is. And I'm working hard, in upcoming work, at re-imagining the classic Dutch Interior blended with a French eighteenth-century aesthetic.

You've got a lot of animals and people whose hair, either styled or wild, seems very important. What's your interest in this?

Well, that's funny! I don't know. Mostly, I've just been representing periods where the "do" was a pretty important article. If I were to delve into my subconscious, hmm.... When I was younger I got a lot of attention for my flowing locks. Now they're thinning a bit, which is distressing. I'm expressing my loss? How about that! But hair is also really fun to paint. And it can be so useful — compositionally, for movement, and as an element of humor.

You also have a performance art practice, where you perform as a '30s starlet. Tell me about how that relates to your painting.

Well, Madeleine Prévert might think it odd that you called her a "starlet." She'd quickly correct you, letting you know that she's a great lady of the musical theatre, a seasoned and consummate professional — though still remarkably youthful. Now, her daughter Prudence, who insists on being billed as Penny, would no doubt be thrilled to be called such. She's longing to break into American films, much to her mother's chagrin. Oh, don't get me started! Yes, my wife, writer Gigi Little, and I have performed as a mother/daughter musical act. Only a few times so far. You might go too far in calling it performance art, but we both enjoy being seriously creative in a field completely different from our regular practices. We're both so focused on what we normally do, that it's very freeing to stretch in another direction, even briefly.

It only really specifically relates to a body of work I did a few years back that mixed gender-bent classical mythology with '30s-style Art Deco. The first performance of Mlle. Prévert came about because of that. But I think doing any of the creative things I enjoy feeds all the others, really. Being able to design costumes or interiors or architecture to include in my paintings is terrifically satisfying. And I love music and often sing, loudly, while I paint. Not to be too frantically poetic, but I can think of the parts my artistic life as petals of a flower, all overlapping, touching. All separate but relating to each other and making a whole.

When I was growing up, I always felt I had to choose one thing to focus on, one thing to be, to the exclusion of all the other things I loved to do and wanted to be; it's one of the biggest reasons I rebelled and avoided making art for so long. It felt unnatural to have to make a choice. Now I know that I can be and have all of those things — use all of it. And oddly, it's made it so much easier to really focus on making art, the thing I'm probably most designed to do.