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without a doubt, the most bizzarre that i've seen, is 'the holy mountain' [1973], by alejandro jodorowsky. this one wins out for a number of reasons.
1] it doesnt progress quite like anything i've seen before; it starts out with a string of several disconnected 10-15 minute character introduction sequences.
2] at times it's clear where it is going, but it never fully makes sense.
3] the characters themselves: they include:
-the leader of a cult of neuters. he is trying to create "the sanctuary of a thousand testicles".
-the owner of a toy company that produces toys demonizing the "enemies of the nation."
-the son of a wealthy industrialist, whose father makes all of his business decisions by feeling the sex of his dead, stuffed wife. if it is wet, then yes. if dry, then no.
-an art dealer who sells marqui de sade-esque human funiture and human art objects.
-a mute jesus christ lookalike
anyway, you get the idea. each of the characters is basically a criticism of something: hippies, government, business, christianity, etc.
3] a reenactment of the conquest of the americas, using frogs and lizards. [frogs in conquistador getups and lizards in incal-warrior garb being exploded on camera.]
4] a plot that involves a group of villians attempting to overcome their weaknesses so they can kill the gods of "the holy mountain", and steal their immortality. the feats that they are driven to in this quest include drowning a thalidomide baby, and being suffocated by a bull's semen.
5] a joke ending.
yeah, i'm having a hard time thinking of something weirder than this on such a large scale. maybe if jodorowsky had been successful in his attempt to film 'dune' without getting the rights i'd chose that instead.