This actress has 2 Oscar wins represented in the five best Hilary Swank movies list. Not only is she the third youngest woman to win 2 Academy Awards, she also has 39 various other awards under her belt.
- "Million Dollar Baby." In this Oscar winning best Hilary Swank movie, Maggie Fitzgerald is a waitress that becomes a boxer. When Frank refuses to train her, Maggie continues to train on her own and gets pointers from an ex-fighter at the gym. After seeing her determination, Frank takes her under his wing and trains her to be one of the best woman boxers.
- "Amelia." Swank plays Amelia Earhart who, at 35, earns the Distinguished Flying Cross for flying over the Atlantic Ocean. Her love for flying began at 23 and ended with her disappearance over the Pacific Ocean when she was 37.
- "Boys don’t Cry." Swank plays Brandon Teena who was actually born Teena Brandon. After fleeing his hometown, he tried to rebuild his life. Only it was found out he was a woman, not a man. After that, he returned to his hometown to try and clear up some legal issues.
- "P.S. I Love You." As a tourist in Ireland, Holly falls in love with a local. They marry shortly after since she was smitten with Gerry from the moment she laid eyes on him. He dies just before her thirtieth birthday leaving her devastated, alone, and unsure of who she has become.
- "Freedom Writers." In this best Hilary Swank movie, she plays teacher Erin Gruwell who tries to teach inner city kids who know nothing but violence. Trying to teach the kids tolerance when all they know is drive-by shootings and death seems pointless to some but Erin perseveres, showing that these kids are teachable and worth the chance.
Although she has been acting since 1990, this best Hilary Swank movies list doesn’t get started until 1999 with “Boys don’t Cry”. The best Hilary Swank movies can leave us utterly happy for the characters in one scene and crying in the next.