[Blarg]

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Grave of the Fireflies
I give this answer every month when this same thread pops up.

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Excellent one and maybe I agree on that one too. Also strongly in the running is My Life as a Dog, but it's so hilarious that sometimes the real depth of sadness in it can be almost glossed over. And, again, it's one centered on kids.

House of Sand and Fog, as someone suggested, is also a very good one.

Jacob's Ladder was pretty damn downbeat too. And Nights of Cabiria was brutally sad at the end yet at the same time preposterously upbeat. A really weird mix I don't think I've seen anywhere else.

The Christmas Tree was another one that was really depressing because a kid died in it, and so was Rage, an old George C. Scott film.