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This is a REALLY hard one. Treasure of the Sierra Madre is one of the few John Huston films I think actually lives up to its reputation; blew me away the first time I saw it, in no small part to Bogart's grim performance. He should've won his Oscar for this, not The African Queen. But Caligari is so steeped in the German Expressionst style, which is pretty much my absolute favorite thing ever in films. It does have that unfortunate frame story, though, that kind of takes away some of the bizarre power of the film. I guess I'd say Sierra Madre is the better-crafted and more wholly successful of the films, but I think I gotta go with my gut and say I like Caligari more.
I agree with faithx5 that Caligari is great. However, I also agree that Bogart deserved and Oscar for Treasure of Sierra Madre. His performance just drew me into the film like not many actors/actresses have before. It's in my top 50 so Sierre Madre wins.
Beyond the scenery Caligari doesn't really have much going for it. I mean, I understand it was made 28 years before Sierra but that doesn't make Sierra any less good.