THE HOUSE IS BLACK (1962)

A 22-minute short film directed by a poet about a leper colony in Iran, which is somehow one of those works of art that might mean basically anything or everything.

UN CHIEN ANDALOU (1929)

Probably the best known surrealist avant garde movie, co-created by none other than Salvador Dalí. He wanted it to piss everyone off, and was annoyed that people seemed to like it.

LE VOYAGE DANS LA LUNE (1902)

This might be the earliest movie we ever discuss on this site. Should you watch it? Spoilers: probably.