It is also possible to rent "Cruel Intentions" on Apple TV, Amazon Video, Redbox, Vudu, Google Play Movies, YouTube, Microsoft Store online Synopsis Slaking a thirst for dangerous games, Kathryn challenges her stepbrother, Sebastian, to deflower their headmaster's daughter before the summer ends. Cruel Intentions. Sarah Michelle Geller, Ryan Phillippe and Reese Witherspoon star in this steamy, stylish look at Manhattan's posh youth and their wanton games of sexual manipulation. 1 h 37 min 1999. R. Drama · Romance · Alienated · Cerebral. This video is currently unavailable. to watch in your location. Customers also watched. Released March 5th, 1999, 'Cruel Intentions' stars Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, Selma Blair The R movie has a runtime of about 1 hr 38 min, and received a user Synopsis. 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. Watch Cruel Intentions 2 (2001) - Free Movies | Tubi. Remind Me. You'll be notified via email when this becomes available. content unavailable. Cruel Intentions 2. 2001 · 1 hr 27 min. R. Drama. In this prequel to the 1999 film, 16-year old Sebastian moves to New York where he first meets his manipulative and beautiful stepsister, Kathryn. wMfJN.