Boys Don’t Cry

Swank’s acting career began with small television roles in the early 1990s, including a stint on the popular series “Beverly Hills, 90210” and her breakthrough came in 1999 when she was cast as Brandon Teena, a transgender man, in the film “Boys Don’t Cry” Swank’s powerful and poignant performance earned her critical acclaim and numerous awards, including her first Academy Award for Best Actress.