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AIR, without a doubt. Also, Azumanga Daioh. The series itself wasn't sad, but I baw'd like crazy at the very last episode. It's unbelievable.
A few years ago I would have said SaiKano, but looking back, I thought that series was trying way too hard to be depressing. Utter hopelessness and end-of-the-world scenarios really don't affect me, whereas bittersweet themes with a glimmer of hope such as those found in AIR do. Oh well.
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