Pretty persuasive: fresh from edgy roles in Once and Again and Thirteen, Evan Rachel Wood tackles her darkest character yet--not to mention Jane Krakowski--in Pretty Persuasion.

Even for a young actress as well-versed in hard-edged, hot button-pushing cinema as Evan Rachel Wood--her fearless performances as an innocent girl gone terribly to seed in 2003's Thirteen horrified parents everywhere--her work in Pretty Persuasion as Beverly Hills prep school sophomore Kimberly Joyce was, she says, "definitely the hardest thing I've ever done."

Her first challenge arrived on the first day of filming when Wood, who will be 18 in September, had to fake an orgasm on camera. Contrast that with her last day of filming, when she had to give a fake orgasm on camera to Jane Krakowski, who plays an ambitious (and closeted) TV journalist making her career covering a sex scandal involving Kimberly, her two closest friends, and a nebbishy English teacher played by Ron Livingston. Director Mareos Siega had a standing rule that if anyone felt at all uncomfortable doing anything in front of the camera, everyone behind the camera had to do it too. Since Krakowski had to be in her underwear, "we shot that scene staring at a crew in their boxer shorts, pretty much laughing the entire time," Wood recalls with a giggle. "It was a big party."

When Wood first received the script (which she says was then titled The Movie That Will Never Get Made), she was being offered the role of Kimberly's best friend, Brittany, who's much like Wood's previous roles: good-hearted girls who find themselves at the edge of some acutely adult decisions. Wood first caught audiences' attention, in fact, on ABC's woefully short-lived Once and Again as the sweetly sad Jessie Sammler, who was just in the first furtive throes of a lesbian relationship when the series was canceled in 2002.

Kimberly, by contrast, has "bad intentions all over the place," Wood says. "There's no good bone in her body, really. They've all been shattered." With an I.Q. off the charts and a bracing command of racial epithets inherited from her blinkered and bigoted father (James Woods), Kimberly is "too smart for her own good," says Wood. More important, furious with the world for reasons both clear (her older brother was killed in Iraq) and clouded in the murk of adolescent rage, Kimberly decides to use her sexuality as an indiscriminate weapon to achieve the fame and fortune to which she feels righteously entitled.

Hence her seduction of Krakowski. Though she concedes that in the movies younger girls rarely hit on older women, Wood says she handled her scenes with Krakowski "like I approached the other seductions" of straight men in the film. "Seriously, the only difference is that there's lip gloss involved and that it's slippery," she says. "[Kimberly] has no boundaries. I don't think she's bisexual; I think she will pretty much do anything to get what she wants. That's one of the reasons I did [the film], to show that it's kind of sad that it's that easy to manipulate somebody with sex."

Rife with political incorrectness on other scores, Persuasion actually doesn't go after gays. "I wouldn't want to do anything that would be really making fun of [being gay]--no, no, no," Wood is quick to say. "People ask if I'm purposefully looking for [projects] where I have to kiss a girl or have some kind of homosexual experience, and I don't. If I kiss a boy on-screen, then I don't see why I can't kiss a girl. Because there are people out there who kiss girls. So why not do it? It's just acting."

And if fans think Persuasion pushes envelopes, just wait till next year, Wood says, when they see her starring alongside Annette Bening and Joseph Fiennes in the film adaptation of out writer Augusten Burroughs's seminal autobiography Running With Scissors, which Wood calls "the craziest thing I've ever done."

With a career that has repeatedly called upon her to say and do things that could make a 30-year-old blush, the real question is, How does Wood weather watching these films with her parents? "It sucks! They're both actors, so they get it. They know that it's just acting. [But] they are still my parents." She laughs nervously. "I try not to think about it."