Ahh I am always a sap for emotional moments in Naruto.
I cried when....
CHoji almost died
Naruto met his dad
Naruto met his mom
his parents story
JIraiya died
Konan died
Itachi died (twice >_>)
Gaara's Speech to the Allied Shinobi force
Lee was told he couldn't be a shinobi anymore (i felt his devastation)
Asuma died
Obito died (as a good guy xD)
The story between Madara and Hashirama
Sai's story and his encounter with his edo tensei
and plenty more I need to remember....
oh yeah the story arc about the sannin when they were young and knowing jiraiya is dead while watching it
Oh that is without a doubt the most emotional moment in Naruto. I also found the moment when Naruto met his father & when Itachi & Dr.Snake aka Sasuke reunited to fight pretty emotional too. But then again I find everything emotional so I don't really count lol.
When J Man died for sure.
When Itachi died, I was depressed. Just a little depressed.
When Haku died for sure.
When Lee got up unconsciously against Gaara I got emotional.
I was also saddened at Kakashi's "death".