There is a special place in American cinema reserved for a certain variety of self-doubting, sexually clumsy, hyperintellectual young man. Perhaps it was Woody Allen who first carved out a niche in film for men nursing this particular cocktail of neuroses. Whatever its origins, the archetype exists, and for a new generation of movie fans, actor Jesse Eisenberg appears to have taken awkward, unsteady hold of the baton. (Of course—these guys are never athletic.)

Born in Queens, New York, and raised in New Jersey, the 26-year-old Eisenberg began performing professionally as a teen, and even did a run on Broadway in a 1996 revival of the Tennessee Williams play Summer and Smoke. But it’s Eisenberg’s film work—punctuated by performances in Dylan Kidd’s Roger Dodger (2002), Noah Baumbach’s The Squid and the Whale (2005), and this year’s Adventureland (in which he co-starred alongside this issue’s cover girl, Kristen Stewart)—that is most responsible for his reputation as an overthinking young woman’s sex symbol. Yes, Eisenberg does self-conscious and nebbishy well. But his characters never come off as simply neurotic or tragic—instead, they’re quasi-heroic, which is a credit to Eisenberg’s knack for finding the little iron man inside each of them.

In his next film, Kevin Tyler Asche’s Holy Rollers, Eisenberg plays an Ecstasy-dealing Hasidic Jew. But he can currently be seen alongside his interviewer, Woody Harrelson, as a zombie-slaying survivalist in the horror-comedy Zombieland.

WOODY HARRELSON: You have this quality—this ability to make neuroses seem attractive and funny. I wondered, Do you feel a debt to Woody Allen?

JESSE EISENBERG: Absolutely. I think he paved the way for people who are not like Humphrey Bogart to be in movies.

HARRELSON: Do you ever feel like if you went through some sort of psychotherapy and lost your neuroses entirely that you’d be out of work?

EISENBERG: I am actually going to two therapists right now. I don’t know, I actually feel like therapy has just made me more uncomfortable.

HARRELSON: Do you pit one therapist against the other?

EISENBERG: Yeah, it’s like good cop, bad cop. One therapist kind of brings me down and makes me realize all the bad things I’ve done, and then the other one says, “Don’t worry about it; it’ll be fine.”

HARRELSON: I’d be going to the second one.

EISENBERG: I’m trying to phase out the first one, but that’s the one that’s covered by my insurance.

HARRELSON: What was growing up like for you?

EISENBERG: I grew up in Queens and New Jersey.I started doing children’s theater when I was seven to get out of school because I didn’t fit in. I had a really tough time in school. And then I missed seventh grade because I just went crazy. But acting always provided some kind of consistent outlet. It still feels like an outlet. If you’re acting, then there’s a prescribed way to behave; whereas in life there’s no prescribed way. So acting feels like a comfortable way to get through the day.

HARRELSON: I know you’re really into theater—which I am as well. Weren’t you writing a play while we were working on Zombieland?

EISENBERG: Yeah, I was trying to get a play produced, which may happen, I don’t know. I write plays, and I have a musical that’s starting to get produced now. That’s what I would love to do, but it’s so hard. The only reason people are reading my plays and musicals is because I’m in movies.

HARRELSON: You don’t feel like you have to apologize for that, do you?

EISENBERG: I don’t know. I meet people who are in movies, and the stuff that they write is terrible, but nobody tells them that because they’re famous. So I worry that my stuff might be like that, too.

HARRELSON: [laughs] Do you think much about style and clothes and all that?

EISENBERG: In my personal life, no. I have not bought clothes in years. Usually on the last day of a movie, I’ll sneak into the wardrobe trailer and take some. A few weeks ago, I took a pair of pants from a shoot and I just got an e-mail that said I had to FedEx them back, which was humiliating. People think, You’re an actor, you can afford clothes, but I just try to take the clothes from the movie, which makes the selecting of film projects that much more difficult, because you try to play characters that might wear something you’d want to wear.

HARRELSON: How did you jump from doing theater to movies? How old were you?

EISENBERG: I started doing musicals and stuff in New York when I was 14 or 15 years old. I’d come in to do plays, and then, very occasionally, for a movie audition. But I never really got into anything. Then when I was 17, I went to a performing-arts high school, and through that I got into a movie that got made. There was this series of really weird events.

HARRELSON: What happened?

EISENBERG: The first movie I got cast in was called Roger Dodger. We did a reading of it at the Nuyorican Poets Cafe and I thought, Oh, because they did a reading, the movie will definitely get made. I didn’t realize that they’ve done a reading there every Monday for the last 35 years and that maybe one of those movies actually ever made it into production. But then the director, Dylan Kidd, ran into the actor, Campbell Scott, in a coffee shop. A week before he ran into him, Campbell had gotten a letter from a rich banker saying, “I just came into a lot of money. I want to make movies, and I’ve always liked you. Is there anything you want to do?” And so the movie actually got made and got good reviews. So I started to get sent scripts after that. But I don’t think I ever would’ve tried to be an actor otherwise. I didn’t have confidence that I would actually be able to make a living from it.

HARRELSON: When we were doing Zombieland, I remember having a conversation or two with you where you said that you’re not going to do any more movies. You seemed pretty passionate about that.

EISENBERG: I meant that exactly as I said. I mean, I’m seeing two therapists now. I break pills in half in the morning and take different ones. At the time, I was in a movie that had just come out, Adventureland, and I just found that the public attention—even though it was limited—really, really screwed me up and made me feel terrible. You know, I give credence to the worst things somebody writes about me, and if somebody writes something nice, I think they’re wrong or false or lying or joking. Acting is a weird profession. It’s very disquieting, and at the time it just made me so confused. It’s only when you step away from a movie for several weeks or months that you start to put things in perspective.

HARRELSON: Yeah, I felt like quitting for a while, but that was more because I’m a world-class slacker. But what would you do if you weren’t acting?

EISENBERG: I’d like to write musicals and stuff—little, weird Off-Broadway musicals. What would you do if you weren’t an actor?

HARRELSON: I would probably just get into local politics, try to work my way up to mayor.

EISENBERG: Really?

HARRELSON: No. [both laugh] Can you imagine? I would love to do something that I didn’t really have to show up for, where I could just fax it in . . .

EISENBERG: People haven’t faxed in years.

HARRELSON: I really dated myself there, didn’t I? So what part of New York City do you live in?

EISENBERG: I live in lower Chelsea.

HARRELSON: Do you want to give your address to the readers?
EISENBERG: It’s 307 . . . West . . . Maple . . . Leaf . . . Road. The orange apartment.

HARRELSON: You live in a pretty cool building, where they differentiate the apartments by colors.

EISENBERG: Yeah, the mailman likes it, but the dogs don’t because they’re all color-blind.

HARRELSON: So what about your future plans?

EISENBERG: I’m supposed to do some movies.

Woody Harrelson is an Academy Award-nominated actor. He can currently be seen in the film Zombieland.

Photo caption: Jesse Eisenberg in New York, July 2009. Shirt and Jacket: Marc by Marc Jacobs. Scarf: Missoni. Fragrance: Marc Jacobs Men. Styling: Andreas Kokkino. Hair: Andre Gunn/The Wall Group. Makeup: Stevie Huynh/The Wall Group. Special Thanks: Fast Ashleys.