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I find it's hard to say what's the scariest because for me they're only scariest the first time I see them. Subsequent views they're just sort of scary, the experience isn't the same. Personally, I find Cabaret chilling no matter how many times I watch it because of the way the movie shows Nazism insidiously creeping into daily life. The Pianist, for similar reason.
Other candidates: The Shining, Rosemary's Baby, Eyes Wide Shut, Vertigo, Eraserhead, The Conversation (that hotel room scene with the toilet backing up blood!).
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Ever notice how this place just basically, well, sucks.
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