Brandon Teena – Hilary Swank
It would be frowned upon today for a cis actress to take on the role of a transgender character. For her 1999 biopic Boys Don’t Cry, Hilary Swank transformed into Brandon Teena. She was unknown at the time.

In real life, Hilary Swank is a movie star with beautiful hair. For her audition, she disguised herself as a boy and showed up. She then lived as a guy for a month, cut her hair, and wrapped her chest before reclaiming the award.