Tale of Jiraiya the Gallant

The, known as in the anime, is an arc from Part II of the series. This arc sees Jiraiya's investigation of Pain's identity. It spans through volumes 40 to 42, or more specifically, covers chapters 368 to 383 in the manga and episodes 127 to 133 of the Naruto: Shippūden anime. This arc is preceded by the Itachi Pursuit Mission and followed by the Fated Battle Between Brothers.

Jiraiya vs. Pain
Jiraiya told Tsunade that he was going to personally gather information regarding the Akatsuki in the most probable place: Amegakure. Seconds after Jiraiya successfully entered the village, he was detected by Pain. Wandering around the village, Jiraiya speaks to the inhabitants about their leader, Pain. Unsuccessful in gathering information he captures two ninja of the village, who tell him about their mysterious new leader Pain, who single handedly defeated Hanzō, the former leader of Ame. Before acting further, Jiraiya summoned Gerotora and instructed him to store himself in Naruto should anything happen to him, speculating that Madara Uchiha was responsible for the Nine-Tails attack on Konoha in the past. Meanwhile Pain knowing that an intruder had infiltrated the village, orders Konan to search for the intruder. She then transforms into multiple origami papers to seek the intruder out. Konan locates Jiraiya, and informed Pain, who then changes bodies in a secret chamber.

Konan then went ahead and attacked Jiraiya, who fought, evenly matched, with her for a short time. Jiraiya then spoke about this history with Yahiko, and Nagato. When Pain arrives, they discuss Pain's personal ideology, and Akatsuki's goals. Pain, who is convinced Jiraiya is to die anyway, reveals his reasoning behind collecting the tailed beasts which was to create a kinjutsu which could wipe away entire nations, so that the world would "mature" and develop aversion for war. Finishing their talk, Pain summons a crustacean to attack Jiraiya, who defeats it and summons Gamaken. Having no other choice left, Jiraiya and Gamaken begin their battle against Pain. Camouflaging himself, Pain summons multiple creatures to defeat Jiraiya. Realising that he is up against a powerful foe, Jiraiya uses a barrier and prepares to enter Sage Mode. Due to the predicament Gamaken has, he sustains deep wounds from the battle. As Jiraiya has his technique ready to use, Gamaken leaves the battle and enters Sage Mode after summoning Fukasaku and Shima.

Jiraiya soon finds Pain, who summons two of his other Paths to enter the battle. Jiraiya blinds one of the new Pains with a kick to the face, and Fukasaku suspects that all three Pain's share the same eyes and vision after they countered all their attacks, while Jiraiya realises that each of the bodies has only one specific purpose. Jiraiya stalls for time while Fukasaku and Shima prepare a powerful genjutsu to defeat the bodies and are successful in doing so. Jiraiya had a flash back to when he first met the Toad Sage, who had told him that he would be a pervert, travel the world, write a book, and would train the destined child who would either save or destroy the world. Leaving the bodies behind, another Pain attacked Jiraiya from behind and severed his arm off. Being confronted by the full attendance of the six paths of pain, Jiraiya was able to discover that all of Pain's bodies belonged to ninja he once knew, amongst them being his old student, Yahiko, functioning as Pain's Deva Path.

With this information, Jiraiya was able to discover the truth, but his throat was crushed by the Asura Path, before he was stabbed by the other Six Paths of Pain. Pinned down to the ground, Jiraiya was unable to tell Fukasaku of what he had learned. As Jiraiya laid dying, he remembered a conversation he had had with Minato and Kushina about how they wanted to name their son after the character in his book, thereby making him Naruto's godfather. Remembering this forced himself back to life with his own willpower, and writes a message on Fukasaku's back. Thinking to himself, he decides that Naruto was the Child of the Prophecy, and that it was up to him to decide his future. The Asura Path then shot his fist at Jiraiya and Fukasaku and destroyed the slab of concrete that Jiraiya was lying on. Jiraiya then drifted off into the water to his death while thinking about what he'd name his next book. He then decided to name it "The Tale of Naruto Uzumaki" and said it had a nice ring to it. Meanwhile, Pain deduced that Jiraiya was dead, but Fukasaku had got away.