Pretty Persuasion belongs to the curious subgenre of comedies about oversexed young people who revel in their own transgressive naughtiness, ratcheting up the sex, nastiness, and emotional brutality of high-school life into a raging tsunami of bad behavior and shattered taboos. Following in the proudly disreputable tradition of Pretty Maids All In A Row, Lord Love A Duck, and Cruel Intentions, Pretty Persuasion aspires to make everyone in the audience feel as dirty and perverted as Russ Meyer or Larry Flynt, and succeeds at least on that count. When a character scrawls "We are all sinners" late in the film, she seems to be speaking for the audience most of all.
In a star-making performance, Evan Rachel Wood stars as essentially a younger version of Nicole Kidman's media-age femme fatale from To Die For, an aspiring 15-year-old actress who hides a sharp, calculating mind behind a façade of vapid, chattering self-absorption. Ensconced in a cocoon of adolescent narcissism, Wood hatches and executes a scheme to rise to tabloid stardom by fabricating sexual-harassment charges against a dorky English and drama teacher (Ron Livingston) drowning in a sea of sexual and professional frustration.
Director Marcos Siega has a background in music videos, which, along with the film's sordid subject matter, would seem to lead to the kind of manic hyper-stylization Roger Avary brought to his similarly nasty The Rules Of Attraction. But Siega instead opts for a puzzlingly antithetical approach, eschewing quick cuts, stylistic flashiness, and day-glo colors for static, claustrophobic extended takes that allow scenes to linger far too long, keeping the film's halting momentum at a slow crawl. That approach pays strange dividends, but it also does irrevocable damage to the film's pacing and comedy. Pretty Persuasion's nasty one-liners ring hollow and self-satisfied, its satirical points feel obvious and belabored, and its characters function largely as brittle, misanthropic caricatures. And yet there's something surprisingly compelling about the film's unrelenting cynicism, something strangely pure in its sustained tone of acidic, disgusted contempt. Where Pretty Persuasion fails as a comedy, it succeeds as a black little mood piece, thanks largely to the almost scary conviction and sociopathic calm Wood brings to her character. At once the film's villain, anti-heroine, and hero, she's a product of a diseased culture that has internalized all too well the warped values of her Southern California wasteland. If Pretty Persuasion lingers in the mind far longer than it should, it's probably because Wood brings such remarkable, paradoxical depth to her character's shallowness.