Re: saddest chapters in naruto/shippuden
I'm gonna go old school. I'm going all the way back to pre-Shippuuden. When Haku talks his one dream in life to be Zabuza's tool/instrument, and nothing more, and Naruto breaks the ice mirror prison, prompting Haku to realise he's failed and asking Naruto to kill him. As well, as Naruto showing his power to awaken in people the ability of emotion by making Zabuza cry over Haku and asking while dying to lie next to Haku as snowflakes fell. Touching.
Another old-school one was when Lee fought Gaara, and Gai initially learning the he would never be ninja again.
In Shippuuden, Jiraiya's death hit me hard, as did Kushina's telling of Naruto's birth and the surrounding events, as well as Hinata's confession followed by her apparent death.
For some reason, Sasuke's tragedies haven't hit me as hard, not sure why. They seem more the ninja way than tragic. I'm not sure if anyone else feels the same way, or has an explanation.