Written and directed by Roger Kumble, Cruel Intentions arrived in the theaters in 1999. The movie played in the theaters again to celebrate its 20th anniversary.

Based on a novel by Choderlos de Laclos, the story follows Kathryn, played by Sarah Michelle Gellar and Sebastian, played by Ryan Phillippe. It’s summer break, and Kathryn is dumped by her beau, Court Reynolds, played by Charlie O’Connell, for the innocent Cecile, played by Selma Blair.

Desperate to get even, Kathryn challenges Sebastian to ruin Cecile by taking her virginity and turning her into a tramp. The intent is to humiliate the Court by presenting him to Cecile, who is damaged goods.

Until now, Sebastian feels he has “been” with all the girls in New York City. He is bored with it all. Though this is too easy a conquest for him, he agrees to it.

He sets his sights on a greater challenge—the new headmaster’s daughter, Annette, played by Reese Witherspoon, who wrote an article in a magazine about how she intends to stay pure until she marries her boyfriend.

Sebastian bets Kathryn that he can seduce the chaste and pristine Annette before school begins in the fall. Kathryn thinks this exploit is impossible and agrees to the wager. As the stakes stand, if Sebastian succeeds, Kathryn must give him a night of unrestrained divine pleasure. A fantasy he’s dreamt about and wanted since their parents got married. If he fails, he must relinquish his 1956 Jaguar to Kathryn and suffer the shame of defeat.

The movie won several awards, including several MTV movie awards and one Teen Choice Award. Witherspoon also won the Blockbuster Entertainment Award (remember those?) for Favorite Supporting Actress in a Drama/Romance.