I entered anime because of this. I have seen and enjoyed some anime before, some series on TV and some Miyazaki works rented for my kids but until on a depression I had I watched some sad (in my opinion of course) ones I didnt get caught on anime.
The fact is I watched the Kaoru death episode of EVA on a late night show. It shocked me a lot, loooong stil image while Beethoven music playing... well it really impresed me, so i get all the serie and movies at the moment and watched all in a weekend. It was some "devasting" for me, a big slap on my face. End of Evangelion battles with the Bach air playing in a sadistic combat was... I cried there. Dont know how to say it but it make me interested on how anime tells their histories so i went for more and being depressed i go for more sad ones.
Next one was Saikano and cried some more, stupid deaths on stupid situations, like real ones. An imposible love history...
And Finally Fire of the fireflyes. Few "real" movies made me cry like this anime one. So sad, so tender. Its a shame people try to bitch any of the characters and dont realize the fact that all of them are impotent over the situation they are living and just try to survive on a world that collapses over them.
So that three are on top of my "drop tears" list, for their histories and the moment I watched them.
After been "caught" by anime I saw more sad and tear ones like:
- Now and there... (impresive, so real now a day in his message. One can cry only thinking on that, will we ever learn?)
- She and her cat. (simple real live can make you sad and cry easily, right?)
- Wolfs rain.
- Voices of a distant star. (sad love history)
I can second:
- 5cm/ second
- some Aria (I love those slow simple life series)
- Fruits Basket
- Fool Moon wo Sagashite
- Ano Hana
- Haibane Renmei (nobody mentioned this one?)
then there are some just "sad" or depressing ones, but that will be another list.