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As a man of few words, I'll keep this short. I comment on The AV Club, here are my Top 11 Criterions, let's go. Runners-up include The Last Temptation of Christ, The Three Colors Trilogy, 12 Angry Men, and Harold and Maude.
The tagline for Lolita applies here as well; "How did they ever make a movie out of Fear and Loathing in Las Vegas?" But Terry Gilliam did, and the result is a masterpiece. The edition Criterion put out is one of the most comprehensive I've seen. The only thing missing was Where The Buffalo Roam, to show how a Hunter S. Thompson film can go so horribly wrong.
More Gilliam! Certainly his best film, as well as one of Criterion's finest packages.
A movie you either love or don't get. I'm firmly in the former category.
The Python film with all the silliness, but with an actual plot this time. For that reason, it's more cohesive than Holy Grail, and equally as funny.
The audacious debut of both Charlie Kaufman and Spike Jonze, as well as one of my favorite comedies. It also has one of the bleakest endings I've ever seen for a comedy outside of Billy Liar.
"These are O.R. scrubs. O.R. they?"
Wes Anderson's most successful mixture of comedy and genuine emotion.
Terrence Malick is one of cinema's greatest genuises. Even if you find his movies boring (I sure as hell don't, but there are others), you can't deny their beauty.
Spalding Gray + Steven Soderbergh: a match made in Heaven. Now if only you guys will release Swimming to Cambodia and King of the Hill any time soon...
One of the most innovative DVDs of all time that happens to highlight one of my favorite bands of all time. This got much play in my house when MCA passed away.
I wish I was the first person to make this incredibly easy joke, but Aki Kaurismäki beat me to it.