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Well the OP said sad, depressing, or painful, so:
Hanbun no Tsuki ga Noboru Sora: sad
Kimi ga Nozomu Eien: sad
SaiKano: depressing
Romeo x Juliet: Er ? semi-painful?
Elfen Lied: sad/painful
Byousoku 5 Centimetre: painful/depressing
Mushishi: sad
Chrno Crusade: sad
And also, I still consider the first 130 some off episodes of Naruto one of the best, maybe 9/10 on my list.
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