1962: La jetée (The Pier)

Is this even a film? Well, it's a 27-minute sequence of nonmoving b/w pictures with an omniscient narrator's voiceover and a little classical music, dealing with a man that, after the nuclear war is over, is a prisoner in a POW camp and is sent back and forth in time by the Germans, who finally managed to win a world war.

Does it work? I'll quote someone else: "This is experimentalism how it should be done, not as a chore for the viewer but as something that the viewer can enjoy at least as much as its creator. So the visual style is challenging? Put some interesting plot in it. The plot is strange, mundane or cryptic? Do it in a visually interesting way."

Though a critic's favourite, today La jetée is probably best known as the film that inspired 12 Monkeys. Both films are about equally good (8) and would make a nice double feature.