Most painful moment in naruto

YoItsJo

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Jiraiya's death and the last clash between Sasuke and Naruto at the Valley of the End... If you're talking any kind of pain.
If physical... What you said, OP, or maybe Hinata versus Pein all in all, just because she probably wasn't used to that.
 

kmrasengan

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when pain asura path( i think) crushed jiraya troat and when kankuro was slowly dying from poison and suffering until sakura came (guess she isn't that useless) or when naruto suffered the thousand years of death by kakashi
 
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