Cruel Intentions (1999)

Directed by Roger Kumble

Slaking a thirst for dangerous games, Kathryn challenges her stepbrother, Sebastian, to deflower their headmaster's daughter before the summer ends. If he succeeds, the prize is the chance to bed Kathryn. But if he loses, Kathryn will claim his most prized possession.

The success of any serious version of Liaisons Dangereuses depends on the subtle working-out of the intricacies of that plot, which should have the fascination of the operation of an elaborate machine, and especially on the genuine depth of feeling unleashed when the hero-cad discovers the penalty for toying with someone else's emotions.

Bob Graham (SFGate)