What was the saddest anime moment you've seen?

I've seen many but this one - Nagisa's death in Clannad After Story - is the saddest...

I don't think Vocaloids are anime... But the Kakuri series makes me really really sad...

They're so many heartbreaking moments, it's impossible to just pick one, but I'd say Tengen Toppa Gurren Laggan's ending scene ( the weeding one) was extremaly traumatising and soo unfair to me, I cried in my pillow for almost an hour.

So many... so many... I'm torn between 3.
The ending of Angel Beats!
The ending of Code Geass.
The ending of K.

Both times Itachi died (Naruto) has to be close to the saddest.

when naruto parents died

Airi Yūnami's death in the Qualidea Code anime.