7. Hilary Swank
In 1999, Hilary Swank played a transgender teen in Boys Don’t Cry. The film was based on the real life story of Brandon Teena who was beaten, raped and murdered by his friends after they found out that he was a biologically a she. Hilary won an Oscar for Best Actress, and Chloe Sevigny who played Brandon’s girlfriend in the film was nominated for Best Supporting Actress. They were both also nominated for Golden Globes, and Hilary took home that win as well.
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