It's the rare leading lady who can impersonate a boy and still come off sexy. Tall, with rangy, lean limbs and torso and a striking face that is equal parts strength and sensuality, Hilary Swank burst into the A-list portraying a woman who passes as a man in Boys Don't Cry (1999). Boys Don't won Hilary an Oscar and exposed her bush and hips in a graphic depiction of what boys sometimes do. The film's harsh realities were further softened with some nuanced lesbian make-out scenes with an equally unclothed Chloë Sevigny. It was a nice slice, but boys have certainly been crying ever since—Hil's hills have since remained under wraps. She won her second Oscar in 2005 for her portrayal of a female boxer in Million Dollar Baby (2004). And though audiences may have to wait awhile to see her box or million dollar boobies again, Hilary was kind enough to bare her butt in 2006 in The Black Dahlia.