(1999) Before watching this black comedy from writer/director Roger Kumble, the storyline drawn from Les Liaisons Dangereuses by Pierre Coderlos de Laclos, first see Valmont for greater appreciation of what evil intentions their adult models perpetrated compared to these unsupervised teens' cruelty.
In 1990s New York City, handsome, rich, and pampered Sebastian Valmont (Ryan Phillippe) does a number on his shrink, Dr Regina Greenbaum, finishing up her last therapy session with the young man before going on a tour for her book Great Parenting, when she gets a call from her distraught daughter Marci that nude photos of her have been posted on the Internet. He keeps an account of his joyful conquests at the miserable expense of his trophies in a journal.
Valmont's stepsister, ravishing in her pulchritude and popularity (class president at Manchester Prep), Kathryn Merteuil (Sarah Michelle Gellar), wanting revenge against Court Reynolds, offers Sebastian the opportunity of "uncharted pooty," freshman flesh, newly arrived and naïve Cecile Caldwell (Selma Blair): "boldly go where no man has gone …" Instead, Sebastian has other plans, a bigger challenge - after reading a manifesto of waiting for love before making love in Seventeen by virtuous and virginal Annette Hargrove (Reese Witherspoon) - to diddle Manchester's new headmaster's blonde baby girl before the beginning of classes.
Annette wagers Sebastian that he'll fail in his quest, betting herself ("You can put it anywhere") against his 1956 Jaguar Roadster. Visiting his aunt, Helen Rosemond (Louise Fletcher), Valmont makes first acquaintance with Annette, already well-informed (won't reveal the source) of his reputation; her boyfriend Trevor is off backpacking in Europe.
Initially Valmont suspects jock Greg McConnell of having ratted on him to Annette since they're childhood chums from Kansas; Sebastian's gay pal Blaine helps set up the fudge-packing Gregster for blackmail. Meanwhile, Cecile has been receiving affectionate attention (love letters she's kept hidden in her dollhouse) along with cello lessons from Ronald Clifford (Sean Patrick Thomas). After teaching Cecile what it's like to get to first base, Kathryn first informs Mrs Caldwell of her daughter's romance with the African-American music tutor and then encourages Ronald to write another epistle of love.
However, Sebastian feels a pang of conscience in this scheme to ruin the girl's innocence. Nevertheless, he takes over from Kathryn by running Cecile all around the bases. But with his roadster on the line, he takes Annette for a drive where she coaxes him into laughing; infatuated with her, he's still put off by her "holier than thou" attitude. Annette also finds herself attracted to his charm but wary of his manipulations: "I don't trust myself with you."
Watching Sebastian's rapacious resolve beginning to crumble, Kathryn reminds him: "You and I are two of a kind."
Remember Dr Greenbaum's book title, Great Parenting? For the most part the parents of these teens are absentee; not until the funeral at the conclusion do Mr and Mrs Valmont appear on the screen.
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