1.When ash was turned to stone and only through pikachu (and the other pokemon's) love, could he be turned back. (the first movie)
2.When ash tried to make pikachu leave him and stay behind with a group of wild pikachu. (I really did start to cry).
3.When ash released his butterfree.
4.When misty said goodbye in that song she sang.
8.When Max had to leave Jirachi
cute-mew said:the saddest moment ever was when poor little mirage mew had to sacrifice his life to beat mirage mewtwo, POOR MEW
(in the master of mirage pokemon special)
that's all I can think of that hasn't been mentioned, , this thread makes me get emotional j/k