There are countless painful moments in Naruto Shippuden that make you cry your heart out. If I start talking about them it will lead to a never-ending discussion. But for the sake of answering this question, I would stick to a few and only those that move me a lot. I am a die-hard Naruto fan who has grown up with those characters and the anime has very well shaped my teenage years. Here are the moments as follows:
This was the moment that I realised that I want to watch the complete anime and that it is definitely a great show that is worth investing my time in. After Haku’s death, Naruto broke the tough act put by Zabuza who pretended that Haku was nothing but a weapon for him. While Naruto shouted about how Haku gave his life for Zabuza and why it meant nothing to him, it was not just Zabuza who cried. It was me too.
As usual, it was Naruto’s words that made Gaara’s death so painful because he talks about the reality of hatred and negligence that he was subjected to by the world as he was a jinchuriki. The pain felt by everyone was so great that Lady Chiyo gave her life to revive Gaara. Nothing is more effective than Naruto’s talk no jutsu. The most powerful jutsu in this world falls short when weighed against it.
This is one single death that I am not able to accept. While Sakura and Sasuke have their masters watch them become fine shinobis, Jiraiya is not there to see how far Naruto has come. He should have been there to see him become the hero of the hidden leaf, save the world, and become Hokage.
What’s sad is that the one who killed him was Jiraiya’s own apprentice, Pain. While it was sad, it was also reassuring that Naruto is the child of prophecy and he will one day save the entire world from the cycle of hatred and bring peace.
The Truth About Itachi
This was a very cathartic experience for me. When you realise that we as viewers hate him because of the sacrifice he made, that he was so noble to bear all the hatred spewed against him just to keep the leaf village and his brother safe, you cannot help but cry. You also feel a kind of relief that it was not him but the Konoha leaders, especially Danzo who was responsible for the Uchiha massacre.