When Did Naruto Tobi And Obito Join Akatsuki?

I still get a little fired up whenever this topic pops up in forums, because it's one of those fandom myths that won't die. To be clear: Sasuke Uchiha never officially joined the Akatsuki in canon. He has encounters and temporary alliances with Akatsuki-affiliated people (most notably with Tobi/Obito after Itachi's death), but he never took a ring, never got formally inducted, and never became an Akatsuki member the way Itachi, Pain, or Konan did. If you trace the timeline in 'Naruto'/'Naruto Shippuden', Sasuke leaves Konoha, trains with Orochimaru, forms Team Taka (originally called Hebi), fights Deidara, and then learns the truth about Itachi. After that revelation he aligns himself with Tobi for a while — more of a strategic pact than a membership. I love rewatching those arcs because his moral trajectory is so messy and compelling; it’s easy to see why people blur alliance and membership, but canon keeps them distinct.

The relationship between Tobi and Obito Uchiha is quite fascinating, and honestly, it blew my mind when I first put the pieces together! Tobi initially appears as this mysterious and almost goofy character in 'Naruto,' throwing everyone off with how he presents himself—especially in the early arcs. But once you dive deeper, you realize that he is actually Obito, who was presumed dead after the events of the Second Shinobi World War. The reveal of their connection adds layers to both characters and enriches the narrative in ways that I truly appreciate. Obito’s transformation from a hopeful and idealistic young man to a villain shrouded in darkness is striking. It’s tragic, really. After witnessing the death of Rin and feeling abandoned by Kakashi, he adopts the persona of Tobi, embracing the chaos and nihilism he once fought against. The duality of his character—between Obito’s remnants of hope and Tobi’s villainous ambitions—creates such a compelling arc. This struggle is so relatable; many of us have moments where we grapple with our past and present selves. I see Obito as a reflection of how pain can shape us in unexpected ways, leading us down dark paths. It’s also worth noting how Tobi's role in Akatsuki raises questions about the meaning of teamwork and trust. Tobi, as a manipulative leader, alters allies like Pain and Itachi's roles, leveraging their strengths for his own ends. It mirrors the loss of unity that Obito faced when he lost his team. In a way, their connection is a great reminder that even the strongest bonds can fracture under pressure, often leading us to take unexpected routes. Whether you see Obito as a tragic hero or Tobi as an effective antagonist, I think there’s no denying the complexity and richness they bring to the 'Naruto' saga. Just amazing storytelling, if you ask me!

I dug through my old volumes and relived a chunk of the war arc to answer this — the clashes between Naruto, Tobi (the mask persona), and the man behind the mask, Obito, are spread across a long stretch of the Fourth Shinobi World War in 'Naruto'. The story peels back the mystery slowly: the identity reveal and flashbacks showing Obito’s past are centered around the late 500s to early 600s chapters, which set up why Tobi acts the way he does. From there, the actual battlefield confrontations where Naruto faces Tobi/Obito in person happen in several bursts throughout the 600–700 chapter range. You get big combat sequences when Obito becomes the Ten-Tails’ jinchūriki and Naruto (with allies) tries to stop him, plus emotional one-on-one moments where Naruto attempts to reach Obito rather than just land blows. If you want to read the arc as scenes, look through the chapters covering the identity reveal (around the high 500s), the middle war-campaign fights (early-to-mid 600s), and the redemption/ending battles (mid-to-late 600s). Those spans will show most of the meaningful encounters and their emotional beats — I still tear up reading Naruto try to bring him back.

Looking back, the relationship between Madara and the man behind the Tobi mask shifted from savior-and-protégé into a toxic, complicated power play. At first, Obito was broken—crushed physically and emotionally—and Madara slotted into that gap, offering care, a purpose, and a grandiose plan: the Infinite Tsukuyomi. Madara fed Obito a narrative about reclaiming the world and fixing loss, and Obito clung to that belief as both comfort and mission. In those early stages the dynamic felt paternal but manipulative; Madara provided tools, ideology, and a way to heal—on his terms. Later the roles blurred. Obito began to perform Madara, adopting his name and myth to terrify and direct others. That impersonation gave Obito agency, but it was also a mask for lingering insecurity. When Madara literally returned to the stage, their balance changed: Obito went from acting as the mastermind to being overshadowed, then subordinated, even betrayed by the idol he’d tried to emulate. In the final arc the relationship unraveled completely. Obito finally rejected Madara’s absolute vision after confronting Naruto’s compassion and the consequences of blind control. Watching him step out from under that shadow and choose atonement felt painfully human to me—one of the series’ rawest transformations.

Tobi's alliance with the Akatsuki is like a dark, twisted tale woven into the rich tapestry of 'Naruto.' Initially, Tobi presents himself as quite the goofball, often infuriating while trying to play off as subordinate. But deep down, the truth is far more sinister and layered. He allies with the Akatsuki to execute plans that align with his ultimate goal: to gather the tailed beasts and eventually cast the 'Infinite Tsukuyomi' using the moon. It's a plan that’s chilling in its ambition, essentially aiming to put the entire world under a genjutsu to create peace, albeit in a nightmarishly oppressive way. In joining Akatsuki, Tobi manipulates the members for his advantage. Early on, he uses them as pawns, showcasing a level of chessmaster-like strategy that makes his approach fascinating yet terrifying. Moreover, Tobi’s complex identity as Obito Uchiha adds depth. He appears to genuinely believe that his actions could bring about peace, twisted as it might seem. This duality of being both a humorous character and a tragic villain adds so much complexity to the story. It reflects real-world struggles surrounding ideals of peace, making his character so compelling. The amalgamation of past trauma and misguided desire for redemption drives Tobi's character arc and gives fans so much to think about. His partnership with the Akatsuki isn’t just plot exposition; it's a commentary on ideologies of power and control disguised as a quest for peace. That duality is what keeps fans like me hooked and debating over cups of ramen!

Whenever I rewind the Fourth Shinobi War arc I still get tripped up by how messy loyalties look on paper — so here’s the clean, canon-only version from my point of view. There is no point in the official storyline where 'Naruto' formally joins the 'Akatsuki' as a faction or signs an alliance with 'Tobi' while Tobi is acting as the Akatsuki leader. Tobi (who is later revealed to be Obito) was the hidden force behind much of Akatsuki’s direction, and for most of the series he’s working against Naruto and the Allied Shinobi Forces, not side-by-side with them. What does happen, and why people get confused, is that allegiances shift during the war. Several members of Akatsuki had already died earlier or were reanimated with Edo Tensei by Kabuto, and a handful — most notably Itachi while under Edo control — end up turning the tide by breaking Kabuto’s control, which allows many reanimated shinobi to return to the afterlife rather than fighting for Madara/Tobi. That’s not Naruto joining Akatsuki; it’s more like individual former-Akatsuki souls being taken out of the conflict or briefly working against their original group under different circumstances. The closest thing to an actual cooperation between Naruto and Tobi is late in the war when Obito (no longer the anonymous masked Tobi puppet) undergoes a redemption arc. After Naruto’s relentless attempts to reach him and Kakashi’s involvement, Obito rejects Madara’s plan and begins to help the Allied forces. He fights alongside them against the Ten-Tails and later against the threat that follows, but that’s Obito the individual switching sides, not an institutional alliance between Naruto and the Akatsuki organization. It’s an emotional, personal turn of events — one enemy becomes a repentant ally in the final battles, sacrifices and all — and it’s portrayed as Obito’s redemption rather than a negotiated pact. So if you want a one-liner to tell friends: there’s no canonical moment where 'Naruto' and the entire 'Akatsuki' ally with 'Tobi' as a bloc. What you see is fractured: some former Akatsuki members are neutralized or helped to stop fighting, and Obito/Tobi ultimately defects and aids Naruto near the climax. To me that ambiguity is part of why the war arc feels so charged — loyalties are personal and messy, which makes the payoffs hit harder.

I couldn't stop thinking about how cleverly they hid their faces while reading through 'Naruto' again, and honestly, it hits different seeing the layers. Obito's decision to vanish under a mask came from a poisonous mix of grief and purpose. After Rin's death, he didn't just want to run — he wanted to erase the man who failed her. Wearing a mask let him become someone else: a myth, a leader, a threat. He could push Madara's 'Eye of the Moon' plan without the baggage of being the boy who grew up in the shadows of Kakashi and Minato. That anonymity also protected him from being hunted as a supposedly dead Uchiha, which made it easier to operate behind enemy lines. Tobi, the goofy persona, was a brilliant misdirection. Acting silly made people underestimate him, and that allowed him to pull strings inside the Akatsuki. Later, adopting Madara's identity gave him instant authority — people respond to legends. So it wasn't just costume drama; hiding his identity was emotional armor, a tactical advantage, and a story engine all at once. It still breaks my heart and fascinates me at the same time.

I got lost in this world the first time I read through 'Naruto' again and really paid attention to the Kakashi Gaiden, and the way the Sharingan threads through the story is gorgeous. Obito was born into the Uchiha clan, so the Sharingan is part of his bloodline: it’s a kekkei genkai tied to Uchiha genetics. He awakened his Sharingan as a kid during missions and intense emotional moments, which is how many Uchiha first activate it. That’s why both Obito and later the masked Tobi possess those eyes — the origin is simply his lineage. The twist is the eye swap. During that mission when a boulder crushed Obito, he gave his left Sharingan to Kakashi as a last gift. Kakashi then grew up with an Uchiha eye despite not being Uchiha himself. Obito survived, was rescued and manipulated by Madara, and continued on as the masked man using his remaining ocular power. Later events involve surgical work, Hashirama-derived modifications, and other implants, but the core reason Obito/Tobi had the Sharingan is Uchiha heritage and the trauma/experience that awakened it. I still get chills reading that scene where he gives Kakashi his eye.

I get a little giddy talking about this one — the best place to start is the 'Kakashi Gaiden' bits in 'Naruto' because that’s where Obito’s childhood, Kakashi’s borrowed Sharingan, and Rin all properly show up. Watch episodes 119–120 of 'Naruto' first; they’re short but emotionally huge and give you the core of who Obito used to be. After that, the really full reveal of Tobi’s identity and the deeper Obito backstory is in 'Naruto Shippuden' during the Fourth Great Ninja War flashback sequences. The crucial episodes that fill in his descent, Madara’s manipulation, and his relationship with Rin and Kakashi are concentrated around episodes 344–348 and then continue into the mid-350s where the war and the past interweave. Those episodes show both the painful choices and the world-warping decisions that explained why he became the masked man. If you want the most coherent watch order: do 'Naruto' 119–120, then jump to 'Naruto Shippuden' around the 340s–350s cluster. The anime pads things a bit with war arcs, but those flashbacks are the heart of his story — heartbreaking and kind of haunting, honestly.

That turning point that rips the bond apart for me is brutal and simple: it’s Rin’s death and everything that spiraled from that moment. I get cheered and crushed at the same time every time I think about the scene where Obito watches the person he loved die, and he believes Kakashi did it. Back during the Third Great Ninja War, Obito was literally crushed under a boulder and presumed gone, only to be saved by Madara. That rescue twisted his grief into something poisonous. Seeing Rin killed — a death staged in a way that made it look like Kakashi had betrayed them — cracked whatever hope he still had in the system. From there he embraced Madara’s dream: a world under the Moon’s eye where pain could be erased. What cements the enmity between 'Naruto' and Obito, though, isn’t only that backstory; it’s what Obito becomes. He masquerades as the masked man, wrecks villages, drags the world into the Fourth Great Ninja War, and supports the Infinite Tsukuyomi. Those actions put him squarely against everything Naruto stands for: bonds, stubborn hope, and fighting to fix the world rather than erase it. When they finally clash, it’s less a simple hero-villain duel and more two philosophies colliding. Naruto refuses to let Obito’s despair dictate everyone’s fate. I always walk away from that arc with a heavy heart — Obito made choices that hurt so many, but you can still feel the tragic human inside. It’s one of the messiest, most emotional enemy-pal dynamics in 'Naruto' for me.