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It's a Halloween movie for most, but I consider Ghost Story a good "bleak winter film." It has a lot of winter scenes, the ghostly stuff makes you feel cold and damp, and it's just a good...ghost story. Complete with moral and everything.

Fargo is another favorite winter film.

My main winter 'entertainment ritual' is reading The Wendigo by Algernon Blackwood on the first really cold and windy night, though.

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Does Fargo count as bleak though? The tone is so whimsical, and the character of Marge is so uplifting.

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It is funny, but it's also about greed and murder, so...Maybe?

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I'm struggling with the prompt because there are so few films that I think are truly bleak. Most things I'd think of as being in a "bleak" winter setting have positive elements somewhere. Although I do agree that The Shining is bleak (mentioned by @138930193-aine in another comment).

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The bleakest movie I've ever seen is A Serbian Film, and I wouldn't recommend it.

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Everyone involved in that film deserves a bat to the skull.

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