Swank garnered critical acclaim for her portrayal of Brandon Teena in the 1999 biographical independent film Boys Don't Cry, which earned her the Academy Award for Best Actress and the Golden Globe Award for Best Actress in a Motion Picture — Drama.
Most of her television and film roles have included portraying boyish characters, a thing she is so good at.
In 2007, Swank starred in and executive produced Freedom Writers, a drama about a real-life teacher who inspired a California high school class.