For another Reese Witherspoon movie, albeit much darker than Legally Blonde, Cruel Intentions is one of her earlier films. Annette (Witherspoon) is the good girl. Kathryn (Sarah Michelle Gellar) and her stepbrother Sebastian (Ryan Phillippe) are the not-so-good kids. The two take it upon themselves to corrupt Annette, but what none of them expect is for Annette and Sebastian to develop feelings for each other. Though their tentative relationship is rooted in dishonesty, perhaps they can overcome it. Though this movie is set at a hifalutin high school, it bears striking resemblance to Harvard in its opulence and its classiness.