Boys Don't Cry (1999)

Peter Sarsgaard, Hilary Swank, Chloë Sevigny, Brendan Sexton III

Based on actual events. Brandon Teena is the popular new guy in a tiny Nebraska town. He hangs out with the guys, drinking, cussing, and bumper surfing, and he charms the young women, who've never met a more sensitive and considerate young man. Life is good for Brandon, now that he's one of the guys