Cruel Intentions (1999)

97 min - Drama, Romance, Thriller
Kathryn makes a bet that her step-brother, Sebastian, won't be able to bed Annette (a virgin, who wants to wait until love). If he loses, Kathryn gets his Jaguar, if he wins, he gets Kathryn.
Director: Roger Kumble
Writers: Choderlos de Laclos, Roger Kumble
Stars: Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, Selma Blair
Filmillion already knows film "Cruel Intentions"
and it guessed it 33 times.
Movie Fact
Titanic (1997)
The following actresses were considered for the role of Rose: Nicole Kidman, Madonna, Gwyneth Paltrow, Jodie Foster, Sharon Stone and Cameron Diaz.
All movie descriptions including art are taken from LinkedMDB