What was the saddest 아니메 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 보컬로이드 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 베개 for almost an hour.

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

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

when 나루토 parents died

Airi Yūnami's death in the Qualidea Code anime.