"PRETTY Persuasion" is neither terribly pretty nor particularly persuasive. Populated by characters that are either over-the-top cartoonish (James Woods as a scenery-chewing father) or drawn with all the depth of stick figures (almost everyone else), there is only one reason to watch this latest entry in the high-school-as-Dante's-ring genre -- Evan Rachel Wood.

Wood is intriguing as Kimberly Joyce, the ultrabright, Machiavellian high school sophomore who manipulates everyone around her to achieve her twin goals of fame and revenge. She enlists her best friend, Brittany (Elisabeth Harnois), and Randa (Adi Schnall), a new Muslim student at their tony Beverly Hills high school, in a plot to accuse their English teacher (Ron Livingston of "Office Space" fame) of sexual misconduct. TV reporter Emily Klein (Jane Krakowski, who has film and Broadway credits but is still best known for her turn on "Ally McBeal") uses the story to boost her career.

The movie tries hard to be shocking with lots of sex, talk about sex, casual slurs and other "my, aren't we daring" devices. And it isn't without laughs, such as when Kimberly is explaining to Randa how she's such a good person that she actually talks to one kid whose parents aren't famous. Turns out she doesn't even know the guy's correct name.

Wood's Kimberly holds your gaze. She glides from self-absorbed to petulant to seductive to conniving without ever breaking a sweat. Kimberly's home life is a mess. Her dad is apparently addicted to pills and phone sex lines. Her stepmom isn't much older than she is. Her brother was killed by friendly fire in Iraq (her consistent use of air quotes whenever she mentions "Operation Iraqi Freedom" is an amusing touch). She is alone with only the delicate alliances of high school and whatever sense of self-worth she can muster, which at first seems to be plenty as she comes across like a younger version of Linda Fiorentino's character in 1994's "The Last Seduction." So Kimberly goes through life using and abusing people -- all of whom are portrayed to varying degrees as deserving of such treatment.

Had it stuck with being a teen amorality play and just ridden Wood's effortless magnetism (which you may recall from the far superior teen angst film "Thirteen" or TV's "Once and Again"), "Pretty Persuasion" might have been more satisfying in spite of its wearyingly smug self-awareness. Instead it crashes into a somber wall of seriousness, pulling back from the provocations and dark comedy of the first hour and undercutting the strength of Wood's blithely evil performance with an attempt at humanizing her. It just rings false, like having Hannibal Lecter take up vegetarianism. Especially when such an attempt at tacking on meaning leaves you no choice but to notice the movie's ludicrously simplistic, not to mention misogynistic, message: Men are dumb and ruled by sexual desire, and all women are potential lesbians but they are mean to each other over boys because they can't live without them.

The result is that you feel as used and empty as one of Kimberly's pawns for having sat through it.

PRETTY PERSUASION (Unrated, 149 minutes) -- Contains profanity, sexual situations, violence and drug use. At Landmark's Bethesda Row, Cineplex Odeon Shirlington and Cineplex Odeon Dupont Circle.

James Woods, with Evan Rachel Wood, who gives a deft performance as the conniving Kimberly Joyce in "Pretty Persuasion."