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It's been a long time since I last felt this feeling from an anime, because I have this feeling from a VN more often (and manga for a time). But, I do have saddest moments I can still remember. The Big 3 of sad moments in anime for me:
1. Air.
"Goal~"
2. Saikano.
Akemi. And the rest of the anime after the elope.
3. KimiNozo
"The Gift of Mayauru."
This one made it into the list recently.
4. Angel Beats
"I want to be a bride."
Clannad didn't make it because I finished the VN first.
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