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i take it saddest here means only saddest not emotional
well there are many sad moments in many animes now and then, but for me the most saddest would be
Chrono Crusade :ending and other few scenes in the anime as well
Clannad/Clannad Afterstory: many moments in both the anime, and of course Tomoya and Ushio scene in the snowfield
Naruto/Shippuden:
Lee's past,Gaara vs Lee
Neji's past,Neji vs Kidomaru
Itachi's truth, when sasuke learns about itachi from the masked guy(obito)
..................and there are many other moments from this name
these would be it ..for now.
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