Pretty in Pink (1986) DVD

Andie Walsh is a bright, sensitive girl with a second hand wardrobe and three men in her life. 

First there is her father. He doesn't work and has been going steadily downhill since his wife left him. There is Ducky Dale (marvellously played by Jon Cryer). He's a pal of Andie's and he's got an intense, unrequited crush on her. The there's Blane McDonough, a cute, rich preppie. He and Andie come from opposite sides of the tracks. So when they fall in love, the differences between them (he drives a BMW and she's ashamed of where she lives) bring barriers to their romance. 

The soundtrack features hits from a host of artists including The Psychedelic Furs, John Lennon, New Order, Nik Kershaw, OMD, Echo and the Bunnymen, INXS, Otis Redding, The Smiths, Suzanne Vega and Talk Back.