What woman won an Academy Award for Best Supporting Actress for portraying a man in a drama?
Linda Hunt won Best Supporting Actress for Year of Living Dangerously (1983) for playing a man – she was the first female actress to win an Oscar for playing a gender-switched character role – a character of the opposite sex. Hilary Swank’s Best Actress Oscar for Boys Don’t Cry (1999) also played a member of the opposite sex, although she was a pre-operative transsexual, biologically female. HONORABLE MENTION: Hilary Swank — Brandon Teena (Hilary Swank) was a female-to-male pre-operative transsexual. His birth name was Teena Renae Brandon. Boys Don?t Cry received overwhelmingly positive acclaim from critics, especially the two lead performances from Swank and Sevigny, and considering its reasonably low budget, and independent production, it was a box office success, with most of the success coming from word of mouth and critical views. Swank was awarded the 1999 Academy Award for Best Actress, and Sevigny was nominated for the Academy Award as Best Supporting Actress.