Glencoe native Lili Taylor has made a career playing complicated women. Recently seen onscreen in The Notorious Bettie Page and Off Broadway in Landscape of the Body, the 39-year-old indie film actress is perhaps best known for starring as the radical feminist Valerie Solanas in I Shot Andy Warhol. This month, she plays an alcoholic, opposite Matt Dillon, in the movie Factotum, which is loosely based on the seedy, wandering life of the writer Charles Bukowski. Chicago spoke to Taylor, who lives in Manhattan, about her theatre roots, why she is drawn to damaged characters, and why she’ll likely return to Chicago this summer.

Lili Taylor

Q: You filmed Factotum in Minneapolis. Did you enjoy being back in the Midwest?
It seemed very familiar to me, even though I had never been before. The shoot itself was invigorating, like working on an independent film. We didn’t have much money; I think that helped.

Q: How does it feel to be a woman in Charles Bukowski’s world?
It’s painful because of his troubled relationships with the feminine and his struggles with women.

Q: What was it like working with [Academy Award nominee] Matt Dillon?
Although we hadn’t done any projects together in the past, we’d crossed paths in New York many times. I felt comfortable with him. As an actor, he’s honest, authentic, and he listens.

Q: Other famous New Trier grads are Liz Phair, who graduated with you in 1985, Virginia Madsen [1979], and Hal Sparks [1988]. What was in the water?
At one point, New Trier was one of the wealthiest public schools, and we all benefited from that. It had a good drama program because the school could afford great acting teachers. That was also when Steppenwolf was [outgrowing] Highland Park, and people were excited about theatre.

Q: Did you know Liz Phair?
A: Are you sure she was in my class?

Q: Yes.
No, I didn’t. That’s funny.

Q: You studied at the Piven Theatre Workshop in Evanston around the same time as John and Joan Cusack. What was the vibe at that time?
A: I didn’t have classes with John and those guys but I knew of them and could feel them around. I think we were all inspired by the fact that something collective was happening, that everyone was participating in this “thing” that was bigger than each of us.

Q: You entered college at the Theatre School at DePaul. Why didn’t you finish?
A: I got kicked out! I wanted to take a paid acting job, and it was against the rules. I would have only missed one class. Everybody said yes except for one teacher.

Q: How did your parents react?
A: Oh, they totally supported me. My dad even disguised his voice and called the school to question why they made me leave! [Laughs.] I found that out years later when I ran into one of my former teachers. Needless to say, my family was pissed off.

Q: Would you ever consider working here?
A: It’s not totally official, but it does look like I will be working [in Chicago] in July, on a movie called Quebec by [local screenwriter] Steve Conrad.

Q: You just finished a two-month run Off Broadway with the play Landscape of the Body. How did it feel to get back on the stage?
A: I try to do one play a year. I love theatre. It feeds the soul more than film. I realized about five years ago that I needed to carve out room for theatre in my life or it would just keep getting forgotten. It’s an easy thing to let go of, since, in the industry’s value system, film is viewed as more important.

Q: What inspires you to take these soul-baring roles?
A: I feel like the woman’s story just hasn’t been told. We’re getting a late start. We haven’t had a forum to tell our tale through the ages, so we have a lot of catching up to do.

Photograph: Nick Ruechel
Stylist: Naila Ruechel
Fashion assistant: Mengly
Clothing: Dries Van Noten top over DKNY tank
Necklace: Copperlace