Sad backstories crop up often in the world of anime, but in Naruto it seems like just about everyone has a tale of misery and woe.
What are some of the saddest Naruto backstories? Let's start with the title character, Naruto himself. After losing his parents, he was totally ostracized by his village, which made him so miserable that he was able to see himself in Gaara, a character whose equally tragic backstory led to him becoming incredibly violent. There's also Sasuke Uchiha, whose brother Itachi slayed their whole clan, and Itachi himself, who did it for absolutely heartbreaking reasons.
This list doesn't even come close to covering all the tragic backstories in Naruto. If you didn't see one of the ones that hit you hardest in the feels, know that it was probably a contender.
Itachi spent his early childhood enduring constant warfare. That trauma made him deeply vulnerable and desperate to maintain peace at all costs. When Danzo approached him with just about the most horrifying plan possible, he was on board. He was given a choice - wipe out his entire clan by himself and save himself and his little brother, or be destroyed along with them. While he could have warned his family and prepared them to fight back, he was petrified of more war and convinced that doing so would only result in more casualties.
In order to make sure Sasuke would be able to develop the Mangekyo he'd need to protect himself and face later enemies, Itachi encouraged his only remaining family member to hate him so much he'd come and destroy him. So he couldn't even take solace in the one remaining bond he had.
Even the most basic facts about Kakashi's childhood are traumatic - he's been a child soldier since he was five years old, and has been involved in devastating battles his whole life. His father Sakumo was shunned by the village for making a mistake, which led to Sakumo taking his own life and leaving Kakashi orphaned. His teammate Obito supposedly passes away during a mission, a tragedy that he feels responsible for. Then he's actually forced to take his other teammate Rin's life in order to stop the Three-Tails that was implanted in her from rampaging. Oh, and his jonin instructor Minato was destroyed by a villain who turns out to be his former teammate.
It's amazing that Kakashi is not just functional, but actually seems pretty cheerful throughout most of the series. But that laid-back attitude is most likely a coping mechanism rather than a sign of genuine healing.
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While Gaara was still in utero, his father implanted the One Tails into his developing body in the hopes of turning him into a Jinchuuriki. This resulted in his premature birth, and his mother Karura's demise.
As Gaara got older, he struggled to control the One Tails. Because of this, everyone in his village was terrified of him and treated him like a monster. At first, he was able to deal with it because he felt like his uncle Yashamaru loved him, and felt that the sand that protected him was infused with his mother's love. But that only lasted until Gaara's father Rasa ordered Yashamaru to try and assassinate Gaara - and also ordered him to pretend that neither Yashamaru nor Karura had ever loved him if he failed.
Yashamaru failed, so he told Gaara that lie, and then took his own life. Totally bereft of any and all human connection, Gaara became the monster everyone told him he was.
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Living in a small nation can be pretty difficult, especially when that small nation is used as a battleground for a war between larger nations. That's what happens to the citizens of Amegakure - and to Nagato.
Nagato lost his parents when two Konoha shinobi broke into his house in search of food. His civilian parents tried to fight the Konoha ninja in order to protect their son, but they were swiftly destroyed. Having had his eyes replaced with Rinnegan some years ago, he activated his powers and avenged his parents.
He nearly starved before banding together with two other orphans, Yahiko and Konan - but the group supported each other and tried to survive. They ended up spending a few years under Jiraiya's care, but Jiraiya left as soon as he felt like he'd taught them enough ninjutsu to defend themselves.
After that, the three orphans formed the Akatsuki as a peace-keeping organization, but it wouldn't be long before Yahiko would pass away during battle and Nagato would be severely wounded, prompting him to start believing that the only way to achieve peace is through violence.