A trusted friend becoming an enemy can make an anime’s central conflict especially personal. The heroes in these six series must face people who once shared their dreams, fought beside them or even saved their lives—and, in some cases, still hope they can be brought back.

In Naruto, Naruto Uzumaki and Sasuke Uchiha start as teammates on Team 7. Sasuke’s determination to avenge the Uchiha clan eventually takes over, and he leaves the Hidden Leaf Village to seek power from Orochimaru. After learning the truth about Itachi and the massacre, he turns his anger against the village itself. His changing loyalties become a major part of Naruto: Shippuden and lead to a final battle with Naruto at the Valley of the End.

Guilty Crown’s Gai Tsutsugami is initially someone Shu Ouma admires: a confident leader of the resistance group Funeral Parlor. The two also share a connection to their childhoods. After Gai sacrifices himself while helping stop Mana’s resurrection, his return brings a reversal: he abandons his former allies and becomes an antagonist. Gai helps advance a plan involving Mana and the Apocalypse Virus, later explaining that he wanted to free her from her fate, despite the harm caused along the way.

In Cowboy Bebop, Spike Spiegel and Vicious once worked together in the Red Dragon Crime Syndicate. Their relationship falls apart after Spike falls in love with Julia, who is involved with Vicious. Spike tries to leave the syndicate and build a new life with her, while Vicious stays and becomes one of the organization’s most dangerous members. Their shared past makes their eventual confrontation more than a clash between enemies.

Gungrave follows childhood friends Brandon Heat and Harry MacDowell, who join the Millennion crime syndicate after losing members of their gang. Brandon becomes an enforcer, while Harry advances through the organization using his ambition and intelligence. Their friendship lasts for years, but Harry’s pursuit of power leads him to target Millennion’s leader, Big Daddy. Brandon refuses to support the plan, and Harry shoots him, leaving him for dead.

Satoru Gojo and Suguru Geto are once the strongest pair at Tokyo Jujutsu High in Jujutsu Kaisen. They share the belief that their abilities should be used to protect ordinary people, but the death of Riko Amanai and the suffering Geto witnesses on his missions change his outlook. He comes to blame non-sorcerers for the world’s suffering, massacres a village and leaves the school. Geto pursues a world inhabited only by sorcerers, setting him against Gojo. Their confrontation in Jujutsu Kaisen 0 is made more painful by Gojo’s memories of their friendship.

In Devilman Crybaby, childhood friends Akira Fudo and Ryo Asuka have sharply different personalities. Ryo takes Akira to a dangerous gathering, where Akira merges with the demon Amon while retaining his human heart and becoming Devilman. Though Ryo appears to help him fight the demonic threat, he reveals Akira’s identity to the public, fuelling the fear and chaos engulfing humanity. Akira later discovers that Ryo is Satan, and the former friends end up on opposite sides of a war that destroys the world.

Sources: Comic Book Resources.