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).
Does Fargo count as bleak though? The tone is so whimsical, and the character of Marge is so uplifting.
It is funny, but it's also about greed and murder, so...Maybe?
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).
The bleakest movie I've ever seen is A Serbian Film, and I wouldn't recommend it.
Everyone involved in that film deserves a bat to the skull.