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The Oscars’ Biggest Losers

By Ben Steverman - 2012-02-23T21:37:15Z

Photograph by DreamWorks/Everett Collection

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Woody Allen

Woody Allen won two Oscars in 1978, for directing and writing "Annie Hall." (He lost a best actor nomination for the film.) He won again in 1987 for writing "Hannah and Her Sisters." Otherwise, Allen has lost when nominated 18 times, often for directing and writing the same movie. Losses include "Manhattan," "Broadway Danny Rose," "Crimes and Misdemeanors" and, most recently, "Match Point" (left).