I consider myself somewhat of a connoisseur of oddball cinema and by far the wildest, most Surreal film I've ever seen is a little Filipino horror movie called THE KILLING OF SATAN. If David Lynch, David Cronenberg, Alejandro Jodorowsky, Salvador Dali and Luis Bunnuel all got together and dropped the brown acid from Woodstock they couldn't have made a stranger movie. Well worth hunting down.
A handful of movies already mentioned, especially Last Year At Marienbad and Eraserhead. I'll throw in The Discreet Charm of the Bourgeoisie, and The Honeymoon Killers.
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