We're in Pierre Choderlos de Laclos territory again with Cruel Intentions, a modern-day update of his Les Liaisons Dangereuses. Kathryn (Sarah Michelle Gellar) and her stepbrother Sebastian (Ryan Phillippe) rule Manhattan's preppie set with their ability to seduce even the most innocent and morally upright. Egomaniacal Kathryn wants him to deflower and ruin Cecile (Selma Blair), for whom she has been dumped by a former beau. The preening Sebastian, meanwhile, has his sights set on Annette (Reese Witherspoon), his headmaster's daughter, who prides herself on her virginal status. The two amoralists make a wager: If Sebastian has his way with Annette, the long-desired Kathryn must then give herself to him. If he fails, he must give her his cherry 1956 Jaguar and suffer a decided loss of reputation as irresistible Don Juan.

Doing a teen revision of this probably seemed like one of those achingly clever ideas that pitched like a dream to the big boys. However, to the film's detriment, every bit of the original's nastiness is retained but none of its wit or elegance. Like Jawbreaker, it's but one more in the disturbing vein of misogynistic 'edgy' comedies that Hollywood seems to think are what their target youth audience craves. There's that central all-powerful bitch who gleefully wreaks havoc on her rivals, while we in the audience are meant to anticipate and savor her garish downfall. ('Blow me,' Sebastian tells his evil stepsister at one point. 'Eat me,' she ripostes, not to be outdone.) The filmmakers go wholly awry when they try to show Sebastian's change of heart. He goes with goody-good Annette to a senior citizens' home and just charms the Depends off the old geezers in a way to make her fall and him even more creamily self-satisfied than ever.

This dreck just might have squeaked by had any of its cast possessed the requisite charisma. Phillippe meets every requirement for being a coverboy on any glossy journal, but his combination of smirky good looks and uncertain histrionics call to mind Robert Taylor, that emptiest of matinee idols, more than anyone else. Gellar works overtime to convey delectable bitchery, but isn't accomplished enough to overcome a basic, telling lack of beauty and charm. Her eventual comeuppance arrives too late (we've long since lost any interest here) and is ineptly staged, to boot. (Overaged actors impersonating schoolkids giving the villainess grief in the last reel are fast becoming a '99 movie clich.) Blair has a few rambunctiously funny moments as dim-witted Cecile, but is made to push for laughs. Witherspoon comes off unflatteringly as the chaste Annette. (Let it not be forgot that Stephen Frears' Dangerous Liaisons benefitted enormously from the presence of two of the most beautiful women of our time, Michelle Pfeiffer and Uma Thurman, both of whom could act, as well.) There's a nasty gay subplot involving some closeted and not-so- hunks who, despite their beefy physiques, are really nothing more than shameful reworkings of the old Clifton Webb-George Sanders vicious aunties of yore. Also stereotyped are the two minority characters, one a clueless black dupe who does stud service for Kathryn, and the other an Asian maid who massages her feet. Swoosie Kurtz and Christine Baranski bring momentary tart relief to the leadenly obvious shenanigans. (You yearn for them to just shuck off this worthless tripe and reprise their legendarily dazzling turns when they shared the stage in John Guare's House of Blue Leaves some years back.)

--David Noh