From least saddening to most saddening. .
5: Konan's death was fairly sad, for me atleast. She had watched the deaths of both her closest friends. Unable to do a thing. One of their deaths she could easily say she caused. Yahiko's. In vain, she tried to protect both her friends and defeat "Madara".
She even knew that if she were to use her collection of paper bombs, it would kill her too. She was willing to die to help out Naruto and the world, but Obito survived and then choked her to death. While making her give up the information on Nagato's rinnegan. She sort of died, losing everything. . Failing. It was sad.
4: Zabuza and Haku I am grouping up here. They were the first antagonists we saw, and were great! They had such chemistry too. Haku, loving Zabuza as a father and Zabuza openly calling and using Haku as a tool. Haku had so much love for Zabuza that he gave his own life for him.
Hell, he wanted to die the moment he thought his usefulness had run out. But he then charged into the chidori and was impaled for Zabuza. Zabuza then, hestiated, but tried to chop Haku in half to defeat Kakashi. Only later did we see that Zabuza had a deep affection for his student, and it was too late to go and tell Haku this.
So Zabuza, without being able to use his arms, charged a mob full of thugs with only a kunai and torn them up. Ignoring a majority of them to simply get to Gato. He would have lived, but in the end thought that life with such grief was not worth it. He wished he could have seen Haku again, as he lay next to his corpse, but we all know that Zabuza would probably not see his student in the after life...
3: Kisame is the next on this life. His death touched me, in many ways. And is my favorite death in the entire series. Kisame, at the time of his death, was all alone. Itachi, his friend, had long since passed away. Samehada the sword he used had left him for Killer Bee. He was alone, captured.
So, Kisame decided to bite his own tongue off. AFTER surviving a deadly punch with little chakra left, courtesy of Gai. With his chakra, again surpressed, he broke out of the wood that was binding him and summoned up a water prison to hide in. What did he do next? he thought of his 'friend' Itachi. His words, and realized that he would never get to see his own dream come true. That a world where he could belong in, where he wouldn't be the play thing for his superiors wouldn't occur. .
To both get information out, and protect it. . Kisame let his own sharks devour him. A bitter sweet ending for the shinobi. Ironic too, we just found out that in Kiri protecting information seemed to be a regular job for him.
2: Of course it's Itachi next. Even to those who dislike his character, as I do, Itachi had a pretty sad death. He had kept his body moving through many different drugs just to die at the hands of the one he loved. Itachi was forced to injure, hurt, lie to again . . His precious little brother. To try and restore honor to his clan's name.
Itachi had put in as much as he could into the fight, and was hoping Sasuke was now strong enough. Having to experience tremendous pains, from his body giving out on him during the battle. . And then there was the fact that he removed Orochimaru and his curse mark from Sasuke. Wiping him free of that part of his life.
Even in the end, he had tapped Sasuke on the forehead and gave him a bit of his chakra to try and protect him further. He died as traitor, alone, hated by his dearest brother. And yet he found a way to die with a smile on his face. Like Kisame, it was a very bitter sweet moment. Once we found out the exact details of Itachi's life, that is.
1: Jiraiya of course had the best death, for emotional reasons. The legendary teacher of Minato, Naruto, and we would soon find out Pein. . I doubt there is anyone who could say they disliked Jiraiya. Sure, they didn't care for him. But it's hard to say you dislike him. He was a pervert, but a kind man. He was a father figure to Naruto, taught him, passed down his own special brand of "Will of Fire".
He even had a very tender moment with Tsunade before he left, and we all knew that something was going down....
When he arrived in Amegakure, he was quick to wreck shit up. Capturing two enemy ninja and sending them back to Konoha. It wouldn't be long before he met up with Konan. One of his dearest students whom he thought had died. He seemed rather happy, to me. Despite her being apart of Akatsuki. She seemed like she had some compassion left for him too, the way her face was looking and all.
He fought Pein shortly after that. Believing he was fighting Nagato himself. Jiraiya AGAIN seemed to not mind his student being apart of Akatsuki, as long as he was alive... Sort of goes to show you how much he loved those three Ame Orphans. He soon realized, as the battle went on, that he needed more help. So he then had to work to summon both Ma and Pa and acquire Sage Mode.
He trapped and defeated a few Pein's, only for another one to show up. He managed to get the Animal Path back to Konoha. . . But he was faced with shinobi he all knew. Most of which were enemies. He was greeted to the sight of Yahiko's corpse, the Deva Path. And then he hears that Yahiko had been dead for years? That was a heart breaker for him. In this fight, he even lost his hand! He was being demolished by what he thought was his student.
He even learned the truth in the end and sent a message back to Konoha. His sheer will had kept him alive long enough to do this. And then, that moment when he was gathering his last thoughts as he slowly drift down to the bottom. . Where he admits he was a failure, how he lived a sad life that he covered up with his novels and perversion. . .
It was very touching. And, he did have the best scene afterwards. It would be in my top ten best scenes, not only emotional scenes, in Naruto. When Tsunade tells Naruto of Jiraiya's death. His death affected the manga even more, though. It was a build up to the fight between Pein and Naruto.
That build up over shadowed the Sasuke vs Killer Bee fight, for me. And when Pein did invade... And killed even more of Naruto's comrades. Faced Tsunade. . And then when Naruto came and Pein refered to Jiraiya as "Jiraiya-sensei". . .
The Pein invasion Arc, in my opinion, was so great because of that lingering emotion from Jiraiya's death. How Naruto would react, him avenging his dead sensei. . .
It was just amazing.
Honorable mention goes out to: Hiruzen, Kimimaro, Asuma, and Minato and Kushina.
