Cruel Intentions (1999)

Kathryn and Sebastian are step-siblings, from upper Manhattan, and the social leaders at their NY prep school. The step-siblings enjoy many of the same things including risky behavior, getting exactly what they want, and revenge. The two siblings often find themselves at odds with each other, which leads to a bet regarding sexual conquests and a hefty wager.

Cruel Intentions is a drama movie featuring Sarah Michelle Gellar and directed by Roger Kumble.

It is possible to buy Cruel Intentions on Amazon Video, Apple iTunes, Google Play Movies, Microsoft Store, Redbox, Vudu and YouTube.