Pretty in Pink

Molly Ringwald faces some tricky teenage dilemmas in John Hughes’ quintessentially ‘80s rite-of-passage.

Andie (Ringwald) is an outcast at her Chicago high school, hanging out either with her older boss (Annie Potts), who owns the record store where she works, or her quirky classmate Duckie (Jon Cryer), who has a crush on her. When one of the rich and popular kids at school, Blane (Andrew McCarthy), 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.

Named after a song by The Psychedelic Furs, this boasts one of the most acclaimed soundtracks in cinema history, and made a hit out of “If Your Leave” by Orchestral Manoeuvres in the Dark.