Hilary Swank

Hillary Swank was only 24 when she won the Oscar for Best Actress for her portrayal of transman Brandon Teena in the 1999 film ‘Boys Don’t Cry’. Directed by Kimberly Peirce and based on a real-life story, the movie explores the life of Brandon, who is abused and eventually killed for his gender identity.

Swank, 49, won her second Oscar for Best Actress in 2005, this time for her role as female boxer Maggie Fitzgerald in Clint Eastwood’s ‘Million Dollar Baby’.