Actors Who Played Opposite Gender Roles Flawlessly

Boys Don't Cry: Young female-to-male transgender Brandon Teena (Hilary Swank) leaves his hometown under threat when his ex-girlfriend's brother discovers that he's biologically female. Resettling in the small town of Falls City, Nebraska, Brandon falls for Lana (Chloë Sevigny), an aspiring singer, and begins to plan for their future together. But when her ex-convict friends, John (Peter Sarsgaard) and Tom (Brendan Sexton III), learn Brandon's secret, things change very quickly.