Lawrence Kasdan was originally set to direct, but dropped out.

The Smithereens were commissioned by Cameron Crowe to write the theme song for the movie, and they came up with "A Girl Like You." Crowe thought that the lyrics were too leading (they outline the entire plot), so he rejected it in favor of Peter Gabriel's "In Your Eyes." "A Girl Like You" went on to be included in the Smithereen's next album, "11."

Jennifer Connelly was going to be cast as Diane Court but director Cameron Crowe cast Lone Skye instead after he saw her performance in "River's Edge" and felt she was more right for the part then Connelly.

Kirk Cameron was nearly cast as Lloyd instead of John Cusack.

Christian Slater, Peter Berg, Kirk Cameron, Robert Downey Jr and Loren Dean all auditioned for the role of Lloyd Dobler. John Cusack was cast instead and Loren Dean was cast as Joe, a smaller supporting role.