Linda Hunt
Linda Hunt was the first to win, for The Year of Living Dangerously (1983). Hilary Swank's award-winning performance in Boys Don't Cry (1999) was for a character who was a pre-operative transsexual, biologically female. Julie Andrews in Victor Victoria (1982) played a woman dressed as a man impersonating a woman. And Gwyneth Paltrow's Oscar-winning character in Shakespeare in Love (1998) was a woman dressed as a man.