Hilary Swank – Boys Don’t Cry

Hilary Swank transformed her look into an androgynous one for her Oscar-winning role as Brandon Teena in the 1993 film, Boys Don't Cry. Years before transgender transformations became as talked about as they are post-Caitlyn Jenner, Hilary adopted male mannerisms in order to walk and talk differently, cut off her hair, lost weight and strapped down her breasts to play the movie adaptation of the true story of a young woman who was discriminated against when she posed as a young man.