5 Zabuza - The part when he cried when Naruto talked about Haku.

4 Chiyo - When Naruto told Kankuro that Chiyo just passed out, he didn't even know that what she used was a tensei ninjutsu. :| Also when Ebizo said he was expecting her to say she was just playing dead.

And when Gaara asked everyone to pray for her...

((
3 Death of those in HQ - There's nothing worse than knowing you're about to die in a matter of seconds and you couldn't do anything. But still they faced it instead, and sent their last strategy for those in the battlefield. But really, that chapter's last page...

That's the saddest page in any chapter of this manga.
2 Itachi - That poking part, and when he said that there won't be next time, those got me.

1 Jiraiya - He didn't let his death to be in vain, and even in his death he considered himself to be a failure compared to his teacher and student. And in his last moments, it showed that he loves his godson Naruto.
If this thread is for the Top 10, I would put Naruto's parents' death at 6, Danzo's at 7, Kisame's at 8, Deidara's at 9 and Uchiha Clan at 10.
I would've included the moment when Edo Itachi was about to go (Chapter 590), but Edos were dead people that were brought back to life right?