I usually never cry in anime, ie Elfen Lied, i didn't cry - i'm not heartless i swear! but in Naruto.. wow.. D:
1. When Kushina is dying and says her last words to Naruto telling him how to be a good man when he's older, and then after the flashback shes all like -aishiteru- (tears we're shed)
2. Zabuza's and Haku's death, only because it was the first death and i was like D:
3. Jiraiya's death... no explanation needed
4. Itachi's death didn't make me cry, only because i knew it was going to happen (someone spoiled it..) but when in the manga, he's saying goodbye to Sasuke, i bawled my eyes out.