Boys Don't Cry (1999)

Based on true events, Boys Don’t Cry (1999) tells the story of Brandon Teena (Hilary Swank), a female-to-male transgendered teen that chooses to live life as a male. When Brandon is discovered to be missing a penis, he becomes a target of redneck attacks, forcing him to movie to a nearby city where he befriends ex-convicts John Lotter and Tom Nissen (Peter Sarsgaard and Brendan Sexton III) and becomes one of the guys. When Brandon ends up in jail, his I-have-a-vagina-secret comes out to his newfound friends, leading to a series of violent confrontations. During "the infamous scene", Sarsgaard shows a quick flash of his rump as he pulls up his underwear. It’s a bright spot in a dark situation that is just a small foreshadowing of Peter’s future, fantastic nude scenes that will actually make boys (and girls) cry.