Cruel Intentions Publication date 1999 Topics Trailer, Movie, Drama 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. Addeddate Watch Cruel Intentions (1999) free starring Ryan Phillippe, Sarah Michelle Gellar, Reese Witherspoon and directed by Roger Kumble. Free SD HD 4K Stream Subs HD Ads Something wrong? Let us know! Cruel Intentions - watch online: stream, buy or rent Currently you are able to watch "Cruel Intentions" streaming on Amazon Prime Video or for free with ads on Tubi TV. Where can I watch Cruel Intentions for free? The film tells about Kathryn Merte, the manipulative, cold-hearted daughter of social climber Tiffany Merte-Valmont. Tiffany has just married again, and Kathryn is not getting along well with her new stepbrother Sebastian. Together they negotiate the tricky paths of sexual…. Cruel Intentions 2. Roger Kumble. Cruel Intentions. Trailer. IMDB: 6.8. 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. 'Cruel Intentions 2' is currently available to rent, purchase, or stream via subscription on DIRECTV, Microsoft Store, Google Play Movies, Amazon Video, Vudu, YouTube, and Apple iTunes . Watch Cruel Intentions (1999) free starring Ryan Phillippe, Sarah Michelle Gellar, Reese Witherspoon and 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. Learn More. Purchase Cruel Intentions 3 on digital and stream instantly or download offline. Meet Cassie (Kristina Anapau, Cursed), Jason (Nathan Wetherington, The It Factor) and Patrick (Kerr Smith, The Forsaken), three amoral college students who, through a series of sexual wagers, take malicious pleasure in ruining the lives of their fellow BSdDUpS.