Top 5 Saddest Naruto Moments

[zinescience]

jiraiya's death
itachi
pain
asuma
grandmal chiyo's death

 

[Lana Del Taka]

in no particular order:
1.Chiyo's death
2. Uchiha massacre and Itachi crying
3. when Sasuke was about to kill Karin. (most people will disagree)
4.Jiraiya's death
5.Konan's death/Kisame's death

 

[Valen]

Jiraiya's death wasn't sad

Just badass

 

[Amaterasuice]

1. Itachi's death/uchiha clan truth
2. Itachi forcing poor 7 yr old Sasuke to watch his family be slaughtered in his illusion.
3. Sasuke leaving the village
4. Jiraiya's death
5. Asuma's death

And number six: Sasori being trolled.....twice

 

[Rogerr]

1.Karin being introduce to the anime
2.Itachi's death/suffering
3.Naruto meeting Kushina
4.Neji's death
5.Hinata's life is pretty sad to.