Boys Don't Cry (1999)

Okay, so when you’re not lucky enough to be born with a penis, what’s a girl to do? Get a crew cut, wear jeans, and walk and talk like a dude! Least ways, that’s how it used to be back in the 20th century. The R-rated biopic Boys Don’t Cry (1999) — not to be confused with the same-named song by The Cure from 1979 — follows the true story of Brandon Teena, who was born Teena Brandon. Slender yet busty babe Hilary Swank was named Best Actress for her starring turn at the Academy Awards. Suffice it to say, Mr. Skin also had a statuette for her in his pants! While on screen, Hilary was able to pass as a guy. Her character even becomes quite the ladies’ man when she hooks up with real-life lass Lana Tisdel (portrayed by Oscar’sBest Supporting Actress nominee Chloë Sevigny). Roseanne’s Becky Conner (Alicia Goranson) is also on hand to make flesh fans start using their hands! Throughout the course of the ill-fated saga, Hilary can be seen binding her bare boobs and wearing boy’s briefs. If that’s not erotic enough, Ms. Sevigny struts her stuff in a pink brassiere and white panties. But soon she reveals her breasts and same-sex preferences for Brandon! No wonder, both Swank and Sevigny won Best Actress prizes at the Chicago Film Critics Association Awards, the New York Film Critics Circle, and the Independent Spirit Awards. The real Brandon didn’t have a happy ending. But maybe you can.