6. Unforgiven (1992)
If you don’t count Cimarron (and really, why should you?) this marked the first time a Western won for Best Picture. And what a Western! Not since The Searchers had the genre so harrowingly laid bare the battered psyche of the frontier “hero.” “I got scars,” says Clint Eastwood’s William Munny. That’s one way of putting it. By turns rip-roaring, terrifying, beautiful, and deeply moving.
5. The Apartment (1960)
The Academy so often rewards cheap feel-good movies that it feels like a real triumph whenever they decide to go with something smart. And “smart” is the word for Billy Wilder’s The Apartment: even its very funny jokes—and bittersweet-happy ending—leave a sting. 1960 was a watershed year in movie history, a moment that marked a turn into modern cinema. The win for The Apartment suggests that even its first audiences recognized this and were ready for it (even if many of the next eight Best Picture winners appeared to go backward).
As witty, if not necessarily as funny, as anything Oscar Wilde ever wrote, and at times quite a bit nastier. It remains one of the wisest and most cynical movies ever to be made in and about Hollywood, even if it’s technically a New York movie. And it absolutely nails the ending. Makes a great double bill with its West-Coast doppelganger Sunset Boulevard, which it narrowly beat for Best Picture.
It seems to me another small miracle that this loose, free-wheeling, free-associative 99-minute-long comedy—which is still, for my money, Woody Allen’s best achievement—picked up most of the major categories (Picture, Director, Actress, Screenplay) at the 1978 ceremony. (Star Wars swept the technical categories.) Annie Hall’s wins are a victory for all those films and filmmakers that opt for lightness instead of heaviness and quiet humor instead of grand tragedy. In every way the antithesis of the bloated prestige picture.
2, 1. The Godfather (1972) and The Godfather, Part II (1974)
But if grand tragedy is what you’re going for, this is how to do it right. Is it cheating to lump these together in order to avoid having to choose between them? Arguably, they’re not two different movies so much as two halves of a single, complexly woven story. They’re also, again arguably, the finest films ever to come out of the studio system, poised delicately between the formal perfection of classical Hollywood and the intimate rawness of New Hollywood.