Crying with anime.

[izinagi54]

ummm
3 animes have ever brought me to tears

ninja scroll when that one plant women died
naruto :naruto shippuden movie one, jman nagato suffering
finally sonic the hedgehog anime

 

[Sabuto Hayashi]

AnoHana's bittersweet end brought me close.
Surprisingly, some of the sadder stories on Gintama can be pretty emotional too, despite the comedy value. xd

As many have already said, Jiraiya's death was hard-hitting also.

 

[IKSOKRIPS]

My tears come when they say their last words:

Hiruzen's death - "When the tree leaves dance, one shall find flames. The fire's shadow will illuminate the village, and once again, tree leaves shall bud anew."

Jiraiya's death - "There, that ending… was a little better. The frog at the bottom of the well drifts off into the great ocean. Heh heh… yep… pretty damn honourable… pretty damn honourable… I guess it's time to put down my pen. Right… I need a title for the next book… let's see… Ah, got it… "The Tale of Naruto Uzumaki"… perfect."

 

[-Ibrahim-]

Jmans death was a little sad, but not as sad as Naruto crying over Gaara. That was epic as hell, that entire arc was just amazing.

 

[Totsuka No Tsurugi]

CLANNAD is the best tear jerker anime
followed by ano hana