Pretty in Pink(1986)

Andie Walsh (Molly Ringwald) is just your average high schooler. She's a good student and she has a job at a music store with a cool co-worker named Iona (Annie Potts), but her love life is a little rough. She has a quirky friend named Phil "Duckie" Dale (Jon Cryer) who wants more than friendship, but her eyes are focusing on the handsome and rich Blane McDonnagh (Andrew McCarthy). She thinks he isn't noticing her, but he is, much to the chagrin of his snotty friend Steff (James Spader), who objects to her poor financial state. Andie and Blane see their friendships tested in the quest for love, but eventually, love proves itself to be the great uniter, even among different social strata.

This is one of the best romance movies of the 80s, as well as Molly Ringwald's final collaboration with John Hughes. Look for supporting parts by Gina Gershon and Andrew "Dice" Clay, who plays a nightclub bouncer with a distinctly Diceman flavor.