I'm not sure about the most tearjerking moment for me, but the ending of Doctor Horrible's Sing-Along Blog has me misty-eyed by the end... Damn you Neil Patrick Harris...!
That 2-part Doctor Who episode with the 10th doctor, that was set just before the outset of WWI. Specifically, one of the last scenes where they see the boy in the present who is now an elderly man at a war memorial Remembrance ceremony. There are a few scenes in those episodes that are tear-jerking, but for me the one at the end especially.
Grave of the fireflies, most harrowing things I've seen.
Second, is boogie on youtube. Go through his serious stuff playlist. That guy is so clever and a really awesome guy, and his serious stuff has made me completely depressed. Go check him out if you haven't already.
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