The 10 Best Woody Allen Movies

1) Annie Hall

Annie Hall

By 1977, Woody Allen had established himself as one of the kings of film comedy, with a string of hits like Bananas, Sleeper, and Love and Death. These were fairly absurd pictures with silly comedic set pieces strung together with goofy plots. They’re funny but not particularly lasting. You laugh and enjoy them and then move on with your life. Annie Hall was different. It had probably just as many laughs as his previous efforts but there was something more to it. The laughs were deeper, not necessarily in the chest the way deep laughter can be, but more like in the brain. They were funny and you thought about the jokes after and you were like actually, that’s really true too.

It was one of the first great demonstrations of how comedy can so seamlessly transition into thoughtful commentary about love and relationships, and death, and knowledge, and purpose. The fact that it’s one of the most acclaimed comedies of all time also demonstrates the difficulty of this task. The character of Annie Hall, portrayed by Diane Keaton who was the bomb in the 70s, is one of the all-time greats, and her relationship with Alvy is one demonstrating remarkable maturity in its unfolding even by today’s standards (maybe especially). But there are few movies that show just how truth and meaning can be found through the eyes of a comedian—observations that play into Alvy’s closing monologue, riffing off a classic joke to make a poignant remark about relationships in general. This is undeniably one of Allen’s, and cinema’s, finest works.

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