Cruel Intentions - (1999) Director: Roger Kumble Stars: Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon 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.
In 2001 Reese Witherspoon played Elle Woods in the sleeper hit Legally Blonde. Pretty, pink and not quite so blonde. Elle Woods went on to become one of the most memorable screen lawyers of the new millennium and even inspired a musical.