"Some Kind of Wonderful" (1987)

Working-class guy (Eric Stoltz) likes uber-popular girl (with a jerky uber-popular boyfriend), but his tomboy best friend (Mary Stuart Masterson) isn't happy about it, as she loves him. Hey, did you hear high school has a rough social hierarchy? LESSONS LEARNED: Guys nicknamed "Skinhead" really could have hearts of gold; true love fosters only after grand romantic gestures. Also, high-school social order sucks.
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