I'm very sensitive so quite a few of the deaths and a couple of flashbacks made me cry. Minato and Kushina's death and farewell to Naruto were the saddest to me, followed by Itachi's death and farewell to Sasuke(both of them, especially the second. His parting words to Sasuke had me in tears again) Gaara's(Naruto's also, but not quite as much) past was very sad to me because the hurt of having no one and being told that no one loves you...I can't even imagine how painful that must have been. Obito's death(his death for real, at the end) would probably be next. Gaara's death was sad...but I knew ahead of time that he would be brought back to life so it didn't have as big of an impact, I found lady Chiyos death very sad though.