in the manga, when kisame died (i saw the anime first so i was expecting all the other emotional moments before that), and itachi's flashback before edo tensei was released.
from the anime, loads of moments- zabuza and haku's deaths, gaara's flashback, naruto after defeating gaara, chouji's death, hiruzen's death from part 1. part 2 gaara's death, asuma's death, jiraiya's death and naruto's reaction after, nagato's flashback, obito's death, kakashi's death, naruto going 8-tails. itachi and minato/kushina's deaths i didn't really feel anything though