Itachi Uchiha

Deep tear-troughs run beneath Itachi's black eyes, the most telling feature of a tall, fair-skinned man whose looks closely mirror Sasuke's and win him many admirers. He keeps his jet-black hair in a low ponytail, with centre-parted bangs reaching his chin that lengthen over the years. Off duty in Konoha he wore a black, clan-crested shirt, tan trousers with a rear pouch, and sandals over bandaged ankles; on missions he donned full Anbu gear and a weasel mask topped with a red triangle. Once in Akatsuki he took to the group's red-clouded cloak, a scratched-out Konoha headband, a ring inscribed for vermilion, pale nail polish, and a triple-ringed necklace. Reanimated years later, his skin turns chalk-white and cracked, his hair grey, his eyes empty of pupils.

Scarred by the deaths he witnessed as a small child, Itachi grew into a pacifist who disliked fighting and ended battles as quickly and gently as he could, leaning on genjutsu over force. Humble despite staggering talent, he studied the history of the wider world rather than just his clan, which let him judge situations without prejudice and worry over where the shinobi system was heading. He held that his own needs came second to the greater good, and he uniquely bore Naruto no resentment, seeing the jinchuriki as the Nine-Tails attack's true victim. Above all stood his devotion to Sasuke, whom he raised more than trained, forever putting off lessons with a poke to the forehead.

To spare his brother, Itachi shouldered the clan's massacre and cast himself as a hateful villain, hiding his real reasons so that Sasuke would grow powerful enough to kill him and claim the glory. The mask concealed genuine anguish; he wept as he struck down his parents and granted Izumi a peaceful dream-death through Tsukuyomi, yet he turned a merciless cruelty on those who harmed the people he loved. Reincarnated after death, he found his scheme had failed and finally dropped the act, showing dry humor and open warmth. He urged Naruto to save Sasuke, admitted his error of manipulating rather than trusting his brother, and told Sasuke in their final moments that he would love him no matter what.

The first son of Mikoto and Fugaku, Itachi was a once-in-a-generation talent: he cleared the Academy at the top of his class, awakened his Sharingan around age eight, and rose to Anbu captain by twelve. When his father steered the Uchiha toward a coup against Konoha, Itachi judged that such a revolt would ignite another world war and quietly turned informant for the village's leaders. The theft of his best friend Shisui's eye by Danzo Shimura and Shisui's subsequent suicide awakened his Mangekyo Sharingan and left him Shisui's remaining eye to guard. Facing Danzo's ultimatum, he chose to wipe out his own clan rather than let a war consume Sasuke too, carrying out the killing alongside the masked man he took for Madara Uchiha, executing his parents personally before casting himself as the enemy his brother would chase.

He left Konoha branded a traitor but secretly tasked with infiltrating Akatsuki to keep it away from the village, partnering first with Juzo Biwa and later with Kisame Hoshigaki. A terminal illness took hold, and he clung to life through medicine and sheer will so that he could fall by Sasuke's hand. A master of the Sharingan and of the Mangekyo techniques Tsukuyomi, Amaterasu, and the near-invincible Susanoo, he finally died in their long-awaited duel, letting Sasuke win. Kabuto Yakushi later dragged him back through the Impure World Reincarnation during the Fourth Shinobi World War, but a hidden crow bearing Shisui's eye triggered Kotoamatsukami and broke Kabuto's control, freeing Itachi to fight beside Naruto and Killer B, help defeat Nagato, and ultimately end the reincarnation on his own terms.