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It seems wrong to me to just point at one and say 'saddest', since there are all different kinds of sad. Haibane Renmei is probably my pick for heartwarming sad. Ima Sokoni Iru Boku wins for the oppressive kind of sad that tries to make you hang yourself because the world is a bleak and endless hellscape, and I think Mahoromatic wins for whatever you call the kind of sad where a warm, fluffy kitten curls up in your lap, stretches, yawns, and then dies (I'll go with 'wtf sad' for lack of a better name). Kanon wins my vote for shamelessly-just-trying-to-make-you-sad sad, and I think I'd go with Mai Hime for death-march sad.
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