Cruel Intentions 1999, Rated R Columbia/Tristar Home Video

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Starring Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon. Released to DVD on August 3, 1999.

Sarah Michelle Gellar stars in Cruel Intentions as Kathryn, a rich and emotionally manipulative teenager living in New York City with her step-brother Sebastian (Ryan Phillippe), an equally rich and emotionally manipulative teenager. Ala Dangerous Liaisons, the two make a bet: if Sebastian can successfully bed the virginal daughter of their schoolmaster, Annette (Reese Witherspoon), Sebastian will have the opportunity to sleep with Kathryn. If not, Kathryn will get possession of Sebastian's prized car. Apparently, the new 'in' thing to do in Hollywood is to create teen versions of dramatic adult films that, themselves, were often based on Shakespeare--a sort of Cliff Notes movie for the teenagers--and, on this platform, Cruel Intentions is as 'in' as you can get. As a whole though, these actors need to keep their WB jobs.