Cruel Intentions

Cruel Intentions (1999) is a drama directed by Roger Kumble that you can watch online on iFILM. Sebastian Valmont and his stepsister Kathryn Merteuil are Manhattan prep-school royalty with money, looks, and nothing left to prove — except to each other.

Kathryn proposes a wager: Sebastian must seduce Annette Hargrove, the headmaster's daughter who has very publicly pledged her virginity. Win, and he gets something he's wanted far longer than he'll admit. Lose, and Kathryn takes his most prized possession. Ryan Phillippe plays Sebastian, Sarah Michelle Gellar is Kathryn at her most calculating, Reese Witherspoon brings surprising steel to Annette, and Selma Blair rounds out the cast as the easily manipulated Cecile.

The screenplay transplants the 1782 French novel Les Liaisons Dangereuses — aristocratic scheming under Louis XVI — into the Upper West Side of late-1990s New York. Made for around $10 million, the film earned over $76 million worldwide. Stream Cruel Intentions (1999) online on iFILM.