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I've really enjoyed Garden State recently, and American Beauty is one of my favourite films of all time. Are there any other similar bittersweet films out there about the human condition that someone can recommend. Eternal Sunshine of the Spotless Mind has already been suggested to me, and I'll be picking it up soon.
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For more on marking an answer as the "Best Answer", please visit our FAQ.You may also want to take a look at Bill Murray's new film - Broken Flowers (see http://www.imdb.com/title/tt0412019/)
...or practically anything directed by Cameron Crowe.