a short movie but very nice, funny and sad: Hotarubi no Mori e
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Angel Beats! is a series, but it's only one season. It's got a lot of action, much comedy, and the waterworks really get turned on toward the end of the series. It will make you cry, but without leaving you depressed. Angel Beats! also happens to be on Netflix at this time, if you don't do CrunchyRoll.
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I think a lot of anime listed by others aren't really sad. A lot of them are really good anime with dramatic elements, maybe a sad moment here and there. but I wouldn't count them as overall sad.
Of course, if you're not actually picky about how sad it is and just want to watch good anime, there's no problem.
(I think Grave of the Fireflies is hard to beat for top of the list. It was so depressing I couldn't even finish it T.T)
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Nobody mentioned my favourite anime yet, but it was the reason I started watching other romantic/drama/sad animes.
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Dokuro-chan is a short series that has a few really sad moments..
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My goal is to watch a sad anime movie per day until Sunday. I already watch The Silence Voice, Maquia: When the Promised Flower Blooms, and I am currently downloading Grave of the Fireflies. I did google top 10 sad animes, but I want to hear what would you recommend (I need 4 more Anime titles).
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