Film: Sideways
Previous best supporting actress wins for role: Broadcast Film Critics Assoc.; Chicago Film Critics Assoc.; L.A. Film Critics Assoc.; National Society of Film Critics; New York Film Critics Circle; San Francisco Film Critics; Seattle Film Critics; Southeastern Film Critics
Previous Oscar nominations/wins: None
Character Bio: Madsen turns in a stunning tour de force performance as Maya, a kindhearted waitress who is terribly smitten with Miles, Sideways‘ sad-sack writer and wine enthusiast. We don’t know much about her, at first. She is recovering from a bitter divorce and studying horticulture. But from the intricate, heartfelt way she equates a bottle of wine to life, how it evolves and gains complexity and then “tastes so f***ing good,” we know this is a woman has a rich interior life, stories to tell, and a lot of love to share.