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There are plenty of warped perspectives on the world that are represented in the Criterion Collection; questions about Life and God and the Universe which raise eyebrows and set our minds to work unraveling what we've just seen. These are my favorites.
It starts out in one place and ends somewhere completely different, both literally and figuratively. A synopsis of Kiarostami's best piece to date (in my opinion) makes it sound as though it would alienate its viewers with the warped storyline and shifting characters, but the male/female archetypes are so universal that it instead becomes immediately accessible to anyone with a brain.
One of the most quoted lines from the movie is "Exterminate all rational thought," which should also double as advice for the viewers themselves, because going into this movie with any sort of expectations is just foolish.
Whatever you do, don't turn away from the movie screen.
A mixture of documentary, improvisation and Chekhov's "Uncle Vanya," this might not seem like it fits in with the rest of the movies on this list at first, but watching it is certainly an experience both awesome and strange.
In my opinion, this is the lesser of Bruce Robinson's two Criterion movies. However, that's not to say it isn't brilliant. Full of beautiful prose, powerful acting and full-on insanity, this is the story of a man and his boil, and the epic struggle between them.
Another partial documentary, a slightly dramatized depiction of a true story acted out by most of the actual people it happened to, Abbas Kiarostami gives us a piece that's at once very confusing and thoroughly engrossing.
A surprising number of Terry Gilliam films deal very heavily with insanity or other forms of brain malfunction, and this is perhaps his best work on the subject. (SPOILERS) Set in a bleak English future where bureaucracy reigns supreme, one man tries to turn around and go against the current, and fails miserably.
These three films off of Robert Downey Sr.'s Eclipse set, when watched all at once without stopping, will cause temporary insanity. Babo 73 is the closest thing to a live-action political cartoon I've ever seen, with comical politicians stomping around and yelling obscenities at one another, giving preposterous speeches and crying out phrases about America full of both humor and truth. Chafed Elbows is a shockingly raunchy comedy told mostly in still photographs, made an even stranger experience by the fact that all the female characters are played by the same woman. Putney Swope is surely Downey Sr.'s masterpiece; the hilarious and endlessly watchable story of an advertising agency led by the title character. The ads (which are in color) are enjoyable to watch, even just by themselves, and the movie is full of entertaining asides thrown every which way.
One of Godard's best works, this movie meanders throughout the relationship between a man and a woman, not often making sense, but always having fun (the movie has fun, not the characters).
Christopher Nolan's first film, while not his best, acts as a harbinger of his later cerebral work such as Insomnia and Memento.