The rich teenage Machiavellis in Cruel Intentions don't use swords or guns to enact vengeance, but their schemes and manipulations prove that you don't need to draw blood to inflict damage. Stung by a recent breakup, Kathryn Merteuil (Sarah Michelle Gellar) takes her ex's new gal under her wing, ostensibly to help her academic prospects but with the, ahem, cruel intention of destroying her social standing. She enlists her playboy stepbrother Sebastian Valmont (Ryan Phillippe) to help her plot against her enemies, and the pair leaves a swath of battered reputations in their poisonous wake. Inspired by Pierre Choderlos de Laclos's classic novel Les Liaisons dangereuses, Cruel Intentions proves that while social mores may have changed since the days of the French aristocracy, people haven't stopped resorting to underhanded, devious double-dealing.