Pretty in Pink

Andie is an outcast at her Chicago high school, hanging out either with her older boss, who owns the record store where she works, or her quirky classmate Duckie, who has a crush on her. When one of the rich and popular kids at school, Blane, asks Andie out, it seems too good to be true. As Andie starts falling for Blane, she begins to realizes that dating someone from a different social sphere is not easy. (Paramount Home Entertainment)