The 50 Best New York City Movies

11. The Squid and the Whale (2005)

Director: Noah Baumbach
Leading Actors: Jesse Eisenberg, Jeff Daniels, Laura Linney
NYC Neighborhoods Featured: Park Slope, Brooklyn

Like a mad earnest Woody Allen, Noah Baumbach focuses on brainy, white, artist types who excel at hurting each other. He doesn't write jokes so much as write barbs for the characters to stick in each other, and if you laugh from discomfort, know that you're not alone. The Squid and the Whale takes viewers to Park Slope circa 1986, where one marriage is falling apart, and two young brothers will deal with that dismantling in very different ways, neither positive. Not only does it encapsulate Park Slope before Brooklynland (or whatever we're supposed to call it), The Squid and the Whale pins down the squirming weirdness of budding male sexuality in a way that no contemporary film has come close to touching. —RS

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