The Departed.
It Happened One Night (1934): Before 1944 there was no limit on the number of films AMPAS could nominate for Best Picture. Indeed, the year Frank Capra's screwball swept the ceremony, 12 films were up for the trophy, including Imitation of Life and the Claudette Colbert Cleopatra--you know, the kind of fare the Oscars would typically flip for throughout the years. Oddly, this being only the seventh ceremony, good taste prevailed. Things quickly returned to normal, though ...
The Bridge on the River Kwai (1957): Through the '50s and '60s no BP short-list was complete without some ponderous, butt-numbing epic, either in the style of Cecil B. DeMille or by DeMille himself. The exception is David Lean's first epic--an uncommonly intelligent and well-acted extravaganza that exists mostly to invert the genre's cliches, not reiterate them.
Tom Jones (1963): In a year populated by torturous big-budget follies (Cleopatra, How the West Was Won) and well-meaning but stiff socially conscious tracts (Lilies of the Field; America, America), the award mysteriously went to Tony Richardson's bawdy romp, which brought a loose French New Wave style to the costume pic in a way that really ought to happen a lot more.
Annie Hall (1977): The first of two times the Oscars actually picked the right movie out of all the movies released that year. Good work, 1977.
Unforgiven (1992): The second time. Had Clint never wowed the Academy with Mystic River, Million Dollar Baby or his Iwo Jima diptych, he would still have the trophy awarded to his true masterpiece--a stark and disturbing meditation on violence and vengeance, not to mention the first (and most effective) time its maker reflected critically on his bloody career. Best last line ever: "I was building a house."
The Departed (2006): After trying twice to appease AMPAS, Marty finally won when he deserved to.
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