Ethan Hawke was at this point unhappy with the direction his career was taking. He recalled that his career was in a lull after the buzz from Sociedade dos Poetas Mortos (1989) had faded. Winona Ryder was a fan of his work and stipulated in her contract that her involvement in this movie was dependent on Hawke starring opposite her. She chose Hawke after seeing him in Noites Calmas (1992).
Lisa Loeb's song "Stay" was included on the soundtrack after actor and director Ben Stiller was given a tape of the song by Ethan Hawke, who was a personal friend of Loeb.
Before filming began, Janeane Garofalo was fired from the production because actor and director Ben Stiller did not like her attitude during rehearsal. Garofalo was rehired after Winona Ryder stepped in on her behalf. Garofalo stated later that she has a really poor work ethic and hates to rehearse.