Hilary Swank as Brandon Teena/Teena Brandon in Boys Don’t Cry

By besting Annette Bening, Hilary Swank prevented American Beauty from taking home the triple crown of best picture, best actor, and best actress. The young Swank was a relative newcomer to movies whose only major screen appearance prior to Boys Don’t Cry was as Pat Morita’s new student in the sequel film The Next Karate Kid(1994). Boys Don’t Cry, though far from a box-office smash, received praise and awards from critics and film festivals around the world in 1999, particularly for the performances of Swank and costar Chloë Sevigny (AAN). This modest true-life drama tells the fascinating yet tragic story of Teena Brandon, a young Nebraska woman whose gender identity crisis led to her brutal rape and murder, as well as the slaying of two other innocents, in 1993. Swank joined Linda Hunt (The Year of Living Dangerously, 1983) in the small group of actors who have earned Oscars for gender-bending performances.

Hilary Swank, in full HILARY ANN SWANK (b. July 30, 1974, Lincoln, Neb., U.S.)

Hilary Swank as Maggie Fitzgerald in Million Dollar Baby

Swank was a bit of a surprise winner of the best actress Oscar for her performance in Boys Don’t Cry (1999), but she was a bit of a sure thing to win for her turn as a strong-willed boxer in Million Dollar Baby (AA). As Maggie Fitzgerald, a waitress who decides to become a professional boxer, Swank imbued the character with warmth and courage and conveyed the intense vulnerability of a young woman literally fighting to make something of her life. A former competitive swimmer and gymnast, Swank got ready for the physical aspects of the role by gaining 19 pounds of muscle, the result of a diet and training regime that included over four hours a day in the gym.