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Midnight Cowboy (1969)
What is it? Tragi-comic drama about a naive country boy (Jon Voight) who moves to the Big Apple planning to make a living as a male prostitute, and his friendship with cynical, sickly con artist Ratso Rizzo (Dustin Hoffman)
Why did it win? We like to think that it's because the Academy were collectively embarrassed over the whole Oliver! thing the year before and were going as far to the other extreme as possible. After all, Hello, Dolly! was right there among the nominees and they didn't go for it, so the era of the musical had belatedly, finally come to a close (until Chicago in 2002, but that's another story).
Did it deserve to win? Well, on one hand this is the only X-rated film ever to win Best Picture, and as such it deserves a big cheer. On the other, this was the year of Butch Cassidy and the Sundance Kid, a defeated nominee, and the not-nominated Wild Bunch and Easy Rider, not to mention The Prime of Miss Jean Brodie and They Shoot Horses, Don't They?
Worth a look? Yes, but it's kinda heavy. Line up Butch and Sundance for right after. And then turn that off as soon as they get to Bolivia for the ultimate feelgood ending.
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