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Annette Bening vs. Hilary Swank (1999)
Poor Annette Bening fell to Hilary Swank twice, it turned out (as there was a rematch five years later). But it really was a difficult choice between her "American Beauty" performance and Swank's transformative "Boys Don't Cry" Oscar winner. Indeed, "Beauty" managed to win a number of other awards, including Best Picture, Best Director, Best Actor and Best Original Screenplay. Bening even won the Screen Actors Guild Award. Obviously, it was close.