The road to redemption is long, but some of Naruto's most infamous characters manage to follow this difficult path. While they cannot erase their past transgressions, they choose to either atone for their sins or find redemption in death. These arcs are popular among fans because they offer unexpected and complex character development, and these five characters, in particular, prove that anyone can have a change of heart.
Gaara is the son of the Fourth Kazekage from the Hidden Sand Village in the Land of Wind. Like Naruto, he is a jinchūriki who suffers from a dark and lonely childhood. Being the One-Tail (Shukaku) jinchūriki as a young child, the villagers saw him as a monster wielding dangerous and demonic power.
When he is first introduced in the series, he and his two siblings are a guest team from the Hidden Sand who arrive in Konoha to participate in the Chūnin Exams. During the Chūnin Exam arc, Gaara shocks audiences with his infamous "Sand Coffin" jutsu, using his sand to mercilessly suffocate and kill his opponent. Gaara is framed as a villain during this arc when the Sand and Sound Villages plan to invade Konoha and use Gaara and Shukaku's power as their trump card to bring down the village.
In the meantime, Gaara attempts to kill Rock Lee during their exam fight before Guy Sensei intervenes. He even goes to see Rock Lee at the hospital to finish him off, until Naruto and Shikamaru stop him. He still kills several Grass and Sound shinobi before the final exam, solidifying his bloodlust and utter disregard for human life. When the invasion begins during his and Sasuke's fight, it moves to the surrounding wilderness where Naruto stops Gaara -- despite his One-Tails' transformation. After discovering that Naruto is also a jinchūriki with a similar upbringing -- who managed to find friends to protect like Sasuke and Sakura -- Gaara begins to rethink the meaning of his existence.
As Gaara turns over a new leaf, he tells Kankurō that meeting Naruto brought him the clarity he needed to redefine his ties to others, which previously brought him nothing but pain. Gaara declares he'll clear his own path to redemption to become more like Naruto, who he now looks up to. When Gaara soon becomes the young Fifth Kazekage, his own villagers are afraid of him but Gaara aims to win them over and be cherished by others.
Gaara achieves this goal after protecting the Sand Village, sacrificing his own life to save them from the Akatsuki before later being resurrected. His village and the entire shinobi world grow to admire and respect him, appointing him the Commander-in-Chief of the Allied Shinobi Forces in the Fourth Great Ninja War.
Nagato was only a child in the Hidden Rain during the Second Great Ninja War when he's gifted the power of a god from Madara Uchiha's Rinnegan, hoping to retrieve his eyes in the future. After watching Leaf shinobi wrongfully kill his civilian parents, Nagato awakens the Rinnegan's power for the first time in order to kill them and avenge his parents. Fighting to survive in war-torn lands, he finds Konan and Yahiko, who are also war orphans. They then find the Legendary Sannin, hoping to be taught ninjutsu, which Jiraiya agrees to and raises and trains the three war orphans for several years.
After Jiraiya leaves them to their own devices, the three orphans form the Akatsuki to rid the world of pain and violence. However, their well-intentioned group is manipulated by Obito, leading to Yahiko's death. Realizing that peace is a naïve and unobtainable objective, Nagato adopts his "Pain" persona with the mission to bring about pain to the world in order to make them desire peace. He later uses the Six Paths of Pain to kill Jiraiya and annihilate the Hidden Leaf with "Almighty Push."
As students of the same master, Nagato and Naruto have a heart-to-heart about their different ideas of peace. Suddenly convinced that Naruto is the one who'll bring about the peace he always longed for, Nagato sacrifices his life with the "Samsara of Heavenly Life Technique" to revive everyone in the Hidden Leaf -- achieving redemption by death.
After suffering the death of his family and entire clan as a young child, Sasuke fixates on his hate for his older brother, Itachi. Desperate to bring down the one who took everything from him, he tells Team 7 he'll restore his clan and destroy a certain "someone." This thirst for revenge causes Sasuke to pursue Orochimaru and the power he's offered him despite multiple attempts from his sensei, teammates and classmates to stop him from leaving. He's branded a rogue shinobi, allowing his hatred to consume him until he becomes unrecognizable.
During his quest, he attempts to kill his former teammates without hesitation and successfully kills Itachi to fulfill his life's goal. He joins the Akatsuki after Obito reveals the truth about his clan and village, plunging him further into darkness.
After discovering that Itachi purposely annihilated the Uchiha clan in order to protect the overall Hidden Leaf, Sasuke resents the Hidden Leaf and embarks on a new mission to destroy it. However, the Fourth Great Ninja War begins and he is given the opportunity to speak with the resurrected Hokages of the past. He starts to question the meaning of clan and village, and which one is ultimately more important.
Realizing that Madara and Itachi both chose to protect the Hidden Leaf from the shadows and do its dirty work, Sasuke decides to do the same and reunites with his former team to save the shinobi world. After the war, Sasuke embarks on a solo journey around the world to atone for his past sins, which leads him to redemption.
Orochimaru has always been driven by his goal to learn all the world's Jutsu and secrets, putting his pursuit of knowledge above the lives of others. As a Leaf shinobi, he grows up to become one of the Legendary Sannin along with Tsunade and Jiraiya. The three teammates serve in the Second Great Ninja War, where Orochimaru shows little regard for the value of life -- to the point he suggests killing war orphans.
He causes many to suffer or die in his twisted experiments to research and create new jutsu. He's not only responsible for the death of the Third Hokage and well over a thousand people he used as lab rats, but he also plays a major role in Sasuke's descent into darkness, forcing his power and curse mark onto him against his will.
With his immeasurable crimes and wrongdoings, Orochimaru is painted as a villain for nearly the entirety of the Naruto series. The evil depiction fans had come to expect is precisely why his redemption is arguably the most shocking among the cast. During the Fourth Great Ninja War, Orochimaru uses four White Zetsu to perform the Impure World Reincarnation Jutsu to resurrect the four previous Hokage. This allows Sasuke to ask questions about the clan and village, with the answers offering the clarity needed for him and Orochimaru to suddenly join the war effort.
Now aiding the Allied Shinobi Forces, Orochimaru finds the injured Kage and offers Tsunade life-saving treatment. Given his unexpected change of heart to fight in the war, Orochimaru's past transgressions are mostly overlooked, allowing him to live freely under Yamato's supervision.
Obito is a member of the Uchiha clan who serves as a child soldier in the Third Great Ninja War alongside Kakashi, Rin and Minato. When Rin gets kidnapped on their mission, Obito convinces Kakashi to risk the mission and save her from the kidnappers. During their rescue mission, the cave begins to collapse and Obito sacrifices himself to protect Rin and Kakashi. Crushed under a boulder with seemingly no chance of survival, he gifts Kakashi his left Sharingan and accepts his death because he was able to save Rin, who he always loved. However, Madara Uchiha finds him and saves his life using White Zetsu and Hashirama Senju's cells to restore his broken body.
Obito eventually leaves Madara because he's told Rin and Kakashi are in danger but arrives just in time to see Rin sacrifice herself on Kakashi's chidori, thus avoiding being used as a weapon against the Hidden Leaf. Obito misinterprets the scene and believes Kakashi killed her. He begins to view the world as cruel and unforgiving and later goes by Tobi, wearing a mask to manipulate the Akatsuki in Madara's place. He shares Madara's goal of creating the Infinite Tsukuyomi so he can live the life he always wanted as the Hokage alongside Rin. This completes his transformation into a main Naruto antagonist, starting and perpetuating the Fourth Great Ninja War.
After fighting and talking things out with Kakashi, though, he has a drastic change of heart, helping Team 7 takedown Kaguya by using his Rinnegan to travel between dimensions. He again sacrifices himself and dies from overexerting his power, reuniting with Rin in the afterlife where he finally finds peace and redemption.