Pretty in Pink (1986)
starred Molly Ringwald, Andrew McCarthy, James Spader,
and Jon Cryer. In this movie, Andie Walsh (Ringwald)
is a low income high school student trying to fit in at
her richy-rich high school with the help of her bud,
Duckie (Cryer). When a rich boy asks her out
(McCarthy's character), things are turned upside down.