Bracketed by Clueless’ updating of Emma and the forthcoming 10 Things I Hate About You, a high school version of The Taming of the Shrew, writer-director Roger Kumble’s Cruel Intentions—Les Liaisons Dangereuses transposed to the contemporary Manhattan preppie set—illustrates the wisdom of using the classics as a basis for teen movies. Bolting training wheels onto road-tested novels and plays affords young performers more substantial vehicles than the jerry-built rigs cranked out by hack screenwriters. One can only speculate how far this trend will go. I wouldn’t be at all surprised if, a few miles down the road, Leonardo DiCaprio were signed to play the title role in Grotty Old Dude, a Valleyspeak King Lear.

Cruel Intentions’ miscalculations are glaringly evident. Kumble’s 20-ish cast is too old to portray preppies, yet too young to be fully persuasive as Choderlos de Laclos’ cynical degenerates, and his film’s synthetically moralistic climax rings hollow. Nevertheless, the movie can be recommended as a nastily entertaining divertissement, though not to those with delicate sensibilities. Like a defrocked Campfire Girl, it is wicked in word, thought, and deed.

Previous versions of this story include Roger Vadim’s now-campy Les Liaisons Dangereuses (1959), Stephen Frears’ icily amoral Dangerous Liaisons (1988), and Milos Forman’s relatively decorous Valmont (1989). Kumble’s screenplay follows the plot of de Laclos’ 1782 epistolary novel with surprising fidelity. In a series of intrigues too complicated to summarize, stepsiblings Kathryn Merteuil (Sarah Michelle Gellar with black hair) and Sebastian Valmont (Ryan Phillippe) enter into a wager about lady-killer Sebastian’s ability to seduce two virgins—doltish Cecile (Selma Blair), who has unluckily attracted the attention of one of Kathryn’s paramours, and serious-minded Annette (Reese Witherspoon), who has published a saving-myself-for-marriage manifesto in Seventeen. Should Sebastian fail, Kathryn will take possession of his 1956 black Jaguar. If he succeeds, Kathryn must offer up, in Howard Stern’s delicate formulation, all three inputs. Subplots include additional straight and gay sexual encounters involving Cecile’s cello teacher (Sean Patrick Thomas) and Sebastian’s jock classmate (Eric Mabius).

Looking like a depraved Margaret O’Brien, Gellar clearly relishes her image-shattering role as the superficially goody-goody prep-school class president (self-dubbed “the Marcia Brady of the fucking Upper East Side”) whose crucifix conceals a coke spoon and a cache of blow. Recovering from his entrapment in the lamentable 54, Phillippe gives a credible performance, though he strikes me as slightly deficient in looks and erotic charisma to play a world-class seducer. (He fails to erase memories of French matinee idol Gérard Philipe, in Vadim’s version, but he easily outclasses the creepy John Malkovich in Frears’ adaptation.) Blair proves to be an awfully good sport as the butt of the screenplay’s cruelest japes. Although cast as the film’s least flamboyant character, Witherspoon once again challenges Christina Ricci for the crown of Hollywood’s most expressive junior-division temptress. Her subtly shaded Annette impressed me more than the effusive histrionics of this year’s Oscar-nominated actresses. Christine Baranski and Swoosie Kurtz attack their cartoonish parts as, respectively, Cecile’s outraged mother and Sebastian’s bromidic shrink with excessive theatricality, but they aren’t on screen long enough to do much damage.

Glamorously photographed and expensively mounted, Cruel Intentions—terrible title!—does not intend, in Vladimir Nabokov’s phrase, “to uplift the spiritual organ of man,” and its obligatory closing-reel comeuppance for its licentious protagonists feels clumsily forced. Still, given the choice between this unwholesome escapade and noble-minded trash like October Sky and At First Sight, you’d be foolish to take the high road.

In Ross McElwee’s Sherman’s March, the most popular movie in the history of the much-mourned Biograph Theater, the filmmaker, armed with a lightweight sound-recording camera, retraces the path of Civil War Union General William Tecumseh Sherman’s bloody march to the sea while trying to find a successor for his recently departed girlfriend. His totally unscripted 1986 personal documentary is a triumph of independent filmmaking that works on multiple levels: as a picaresque comedy, an exploration of contemporary Southern womanhood, and a meditation on the possibility of love in the nuclear age. Its 157 minutes zoom by, filled with handsome images, surprising encounters, wry humor, and poetic insights.

In 20 Dates, writer-director Myles Berkowitz plunders (without credit) McElwee’s premise, but his 88-minute neodocumentary seems to drag on forever. The recently divorced Berkowitz, who has struggled unsuccessfully for a decade to make his directorial debut, decided to film his dates with 20 women, bringing along a cameraman to record these amorous adventures. He hoped that if his experiment succeeded, he would simultaneously redeem his failures as both artist and lover.

Obviously, this gambit paid off, because Fox Searchlight has picked up 20 Dates for national distribution, and Berkowitz is presently engaged to marry Date 17, a pretty young Brentwood, Calif., shopkeeper. If only the audience for his movie were as lucky. There are enough laughs in this partly improvised, partly staged docu-comedy to fill a half-hour short, but the material is too thin and repetitious to sustain a full-length feature. Prolonged exposure to the 30-ish, darkly handsome Berkowitz’s abrasively vapid personality becomes so grating that one wants to warn his prospective victims to buy their own dinners. Running commentary by screenwriting guru Robert McKee and the project’s unseen, toilet-mouthed producer does little to enliven the tedium. Muddily photographed and amateurishly edited, 20 Dates amounts to little more than Sherman’s March for Dummies.CP