Boys Don't Cry (1999)

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 and dating hometown beauty Lana. However, he's forgotten to mention one important detail. It's not that he's wanted in another town for GTA and other assorted crimes, but that Brandon Teena was actually born a woman named Teena Brandon. When his best friends make this discovery, Brandon's life is ripped apart.