Ever since his 1996 debut as a grown-up child-abuse survivor seeking payback in Barry Levinson’s Sleepers, it seems like Billy Crudup has been on the cusp of movie stardom. But while he received an Independent Spirit Award Best Actor nomination for his role in the cult hit Jesus’ Son and generated a lot of buzz as a beautiful but self-absorbed rock idol in Almost Famous, genuine stardom has eluded him.

Crudup has enjoyed more success in the theater, where he received an Outer Critics Circle Outstanding Debut award in 1995 for his Broadway bow in Tom Stoppard’s Arcadia and a 2002 Tony Best Actor nomination for his titular role in The Elephant Man. Perhaps it is fitting, then, that Crudup’s latest movie role—that of the 17th-century cross-dressing actor Edward "Ned" Kynaston in Sir Richard Eyre’s Stage Beauty— might just offer the 36-year-old actor his greatest chance at movie stardom yet.

At a time when women were forbidden to take the stage, Kynaston became a star in woman’s roles, equally as renowned for his beauty as for his talented turns in roles such as Othello’s doomed Desdemona. Stage Beauty, adapted by Jeffrey Hatcher from his play Compleat Female Stage Beauty, takes place at the juncture when King Charles II (played in the film by Rupert Everett) lifted the ban on female performers, effectively ending Kynaston’s career and sending the sexually fluid actor into a deep identity crisis.

It is a role that Crudup, fine-boned and delicately pretty, seems born to play. But it also presented challenges to a performer who never had to consider gender questions before, as he attests in this conversation at the Toronto International Film Festival.

Q: So what was it like to get in touch with your feminine side?

Billy Crudup: It was alarming. I was not attracted to myself as a woman at all, quite frankly, and that was fairly disappointing. The interesting thing about this role is that Ned’s interested in the theatrical expression of being a woman; he’s not interested in being a woman. So, for me, the focus was on the superficial expression of femininity. The reason he was interested in it was that, for him, it was a way to not be lonely; it was the only way he knew how to get attention, so there was a kind of desperation involved with it that didn’t allow me to be too frivolous with the experience.

Q: Do you think, for Ned, it was the idea that the furthest extreme he could take the deceit was to convince the audience that not only was he a woman, but the most beautiful woman on stage?

BC: Absolutely. The interesting thing about Ned is that he continued, despite his success, to be unsatisfied with his work. I think what that shows—what the film attempts to say—is that he was, first and foremost, somewhere deep in his heart, an artist who wanted to express himself in the most beautiful way. His attention to detail and the facade was actually getting in the way of that. I think the extent to which people accepted his beauty points to his level of artistry. But, for him, I think it was finding a way to channel that talent toward the play, for a change, rather than toward the pose.

Q: Is there a little bit of an extra thrill in getting to play in Othello and getting to play Desdemona, a role you would not normally be asked to play?

BC: You hit the nail on the head there. Othello happens to be one of my favorite plays, a play that I’ve done several times and that I’ve seen I don’t know how many times. It’s probably the most accessible of Shakespeare’s plays for me; I just find it gripping and I am always so overwhelmed and pained by the ending and Othello’s inability to get past himself. Desdemona is a beautiful role; she’s a beautiful creation, this gracious, loving woman. Unfortunately, I didn’t get to do my Desdemona. I got to do Ned’s Desdemona, who was only interested in the pose of tragedy, but I loved being able to work on Othello. Not to mention the fact that it was a text that I was familiar with, which made it a little easier. It’s a gorgeous play.

Q: What would your Desdemona be like?

BC: Well, if played wrong, she becomes this sort of unrealistic archetype. She’s so gracious with Othello; she’s so forgiving of him, that she could become a bit of a doormat. I think I would try to explore the conflict that she’s going through in trying to tolerate his behavior as she would have been expected to under the circumstances, and, at the same time, be able to express her love and kinship for him in a way that doesn’t completely subordinate her own desires and passions.

Q: You are not an action-hero hero. You possess a kind of androgyny. Did you immediately connect to that when you were offered the part, because the type of cross-dressing roles Ned plays were ones you might have played as a 17th-century actor? Or did you have to be convinced?

BC: I guess my perception of myself is fluid and undergoes a lot of restructuring. There have been times in my life that I have felt, I suppose, more delicate than others. When I read the script, I think I felt like this was going to be difficult. It wasn’t just because I was being asked to play a woman, it was because Ned was meant to be so good at it, so convincing. I had never explored that part of myself and didn’t really know how to go about constructing that artifice. It was important for the audience to believe the supposition of the audience of the time, which was that I was very convincing as a woman. That was a little bit scary, frankly.

Q: When Patrick Swayze made To Wong Foo, he hired a professional female impersonator to guide him. Did you do anything similar?

BC: I did not. One of the reasons that I didn’t enlist the help was that the style that [17th-century actors] would have cultivated would have been much different than the female impersonators that we experience today. My guess is that Kynaston would have been interested in the archetypical poses, the postures of tragedy—the five gestures of feminine supplication or something like that is the perfect example and reduction of how he thought about character in big, broad strokes. There was no realistic attempt to become a woman. It was an attempt to display femininity, which is a very different exercise.

Q: How did you prepare to play the part?

BC: I lost some weight, because it’s more useful to fit into the corsets and Desdemona is sort of a delicate figure—or my perception of her was. I felt that that would exaggerate the sort of delicate quality that Ned supposedly wields so well. It helps with the androgyny. I don’t mean that quite as superficially as it sounds. One thing that is interesting about Ned is he is having trouble tracking down his own sexuality. He’s having trouble tracking down his own identity. It’s not just who he’s in love with and whom he shares his bed with—it’s who he is inside, what parts of himself is he most comfortable being expressive with. I think part of the movie is about how we, with great, broad strokes, define people as male or female so succinctly and matter-of-factly when we share so many qualities that are similar with the other sex and when there are so many places on the continuum between male and female and beyond that are worth noting and expressing. Ned is somewhere in between.