Based on the 18th-century French novel Les Liaisons Dangereuses, the story follows two horny and borderline incestuous step-siblings, Sebastian Valmont (Ryan Philippe) and Kathryn Merteuil (Sarah Michelle Gellar), who go to a prep school for Manhattan's wealthy elite. Kathryn makes a bet with Sebastian that he can't seduce and deflower the new headmaster's daughter, Annette (Reese Witherspoon).
The cast talked about how Witherspoon (who happened to be celebrating her 43rd birthday), was brought on to the film. She was dating Philippe at the time, but Kumble maintained that beyond that, they knew she would make a good addition to the cast. "I thought we were all just going to dinner as friends, and then Roger and Ryan asked me to do the movie. I remember a lot of coercing," said Witherspoon.
"It had nothing to do with “Oh, let’s cast [Ryan’s] girlfriend,” Kumble added. "The world hadn’t seen Election, but we knew how talented Reese was. He just happened to be going out with her at the time."
The cast and crew also made sure to note that Annette's character didn't quite feel like a fit for Witherspoon, as she seemed a bit one-dimensional. The actress spent time with Kumble, who also adapted the screenplay, to make Annette a character with more agency, instead of just someone who lets herself get manipulated by the other characters. "We drank a lot of wine," said Philippe. "We were wooing her! She loved the movie for me, but it wasn’t a great part at the time for her. She helped Roger turn it into one."
"It’s true, she came and sat with me for a week, and we worked on the dialogue together," said Kimble. "Annette was the character most removed from me. There’s no way the movie would have its success if it weren’t for [Reese’s] talent as a writer."