Jiraiya

Jiraiya graduated the academy at 6 years old and became the student of The Third Hokage and the teacher of Minato, the would be Fourth Hokage.

Jiraiya is the author of a series of adult-themed novels, the very books Kakashi adores so much. He uses his books as justification for peeping on women and paying for their services, saying he's "researching" for his next novel. He is also rather wealthy due to the success of his novels.

Young Sannin

Growing Up

His Destiny

During this time in the Rain village, he'd meet three Rain orphans: Konan, Nagato, and Yahiko. They asked the Sannin for some food and Jiraiya gave them his. The orphans started following the Sannin and Konan used the wrapper from the food to fold Jiraiya a flower, but their presence started to annoy Tsunade who told them to go away. Orochimaru at which point suggested that the kindest thing they could do was to kill them since their lives as orphans in a war-torn country will consist of nothing but misery, but Jiraiya was outraged at the comment and told Tsunade and Orochimaru to return to the Leaf village without him. Jiraiya then took the orphans under his care for 3 years to teach them how to survive on their own, and even decided to teach them ninjutsu.

Training the Rain Orphans

Jiraiya's Genin Squad

Some time later Jiraiya trained a group of genin, one being Minato. The two were very close and both shared admiration for the other. Jiraiya later left the Leaf village to explore the world and write his book, and Minato became the 4th Hokage while he was gone. When Jiraiya wrote his first book it was basically a story about his life, but in the book he called himself Naruto. Jiraiya gave Minato a copy of the book and Minato greatly enjoyed it, as he told Jiraiya his opinion of it he told Jiraiya that he and Kushina Uzumaki want their son to be just like Jiraiya and said they were going to name their son "Naruto." He was also asked to be Naruto's godfather.

Naruto meets Jiraiya

When the Sand and Sound villages attacked the Leaf village, Jiraiya made a grand (albeit late) entrance by crushing one of the giant snakes with his giant frog. After the 3rd Hokage's death, Jiraiya was offered the position of Hokage by the village elders, but turned it down saying that he'd be horrible. They wouldn't take no for an answer, saying that only one of Konoha's three legendary ninjas could be the next Hokage... which got Jiraiya to go out looking for Tsunade who left the village many years ago and has since become hard to find. He had Naruto travel with him so that he could look for Tsunade and train Naruto at the same time.

Facing Akatsuki

Old Friends

He and Naruto found Tsunade when they went into a restaurant. Tsunade was very surprised to see him, but even more surprised to find out that she is to be the next Hokage... which she turns down, saying that only a fool would want to be a Hokage, which greatly annoyed Naruto who demanded retribution and Tsunade decided to teach him a lesson so they went outside where Naruto lost... badly. Realizing that Orochimaru came to her trying to make a deal, Jiraiya asked her out for sake so they could talk in private and Jiraiya showed both great concern for the choice she was thinking of making, and warned her what he'd do if she helped Orochimaru. However, Jiraiya was too trusting of his good friend (and maybe a little too drunk) to notice Tsunade slip a drug in Jiraiya's drink and run off. Jiraiya returned to Tsunade's apartment the next morning, hardly able to stand or throw a kunai straight (as noted since he tried to throw one at Shizune).

Sannin Battle

Master & Apprentice

After the two and a half year time skip, Jiraiya taught Naruto how to utilize his Shadow Clones strategically, create a more powerful version of the Rasengan, improved his taijutsu, and how to combat genjutsu. He may have taught him much more, since Tsunade made the comment that Jiraiya packed Naruto full of power. He also unsuccessfully tried to further teach Naruto how to control the Kyuubi's chakra, getting injured trying to subdue Naruto after he acquired four tails.

Teacher and Student, on Equal Grounds

The Wager

Jiraiya captured two Rain ninjas inside of one of his frogs and attempted to interrogate them. One refused to talk so Jiraiya turned him into a frog, at which the other was quick to tell Jiraiya what he knew. Turns out the Rain village was in a civil war, half siding with Hanzo and the other siding with Pein. Although it's unknown when or how, Pein assassinated the elderly Hanzo and proceeded to kill Hanzo's family, loved ones, and associates. He also informs Jiraiya that no one knows what Pein looks like and some doubt he even exists, and Pein's announcements and orders are even given through word of mouth. Jiraiya then leaves him and summons a toad that has information about the seal on Naruto containing the Kyuubi and Jiraiya wants him to stay with Naruto.

Questioning Konan

Hermit Mode

Feeling Froggy

The Frog Song

Pa suggested a tactical retreat and him and Jiraiya started discussing what they knew about Pein while hiding. They realized that with those bodies' abilities and teamwork, they're forced into a corner and knew Jiraiya'd win if he could separate them, but Pa thinks they he should use genjutsu. Jiraiya isn't very good at using genjutsu and Pein knew this so Ma and Pa attempt to do their most powerful genjutsu, one based on using sound. Pein(s) realized it was a genjutsu but chased after where the sound was coming from anyway and found Jiraiya, but he was surprised by Jiraiya's Shadow Clone who used a giant fire blast. Hungry Ghost attempted to absorb it, which Jiraiya knew it would, but it's very cloud-like and kept him blinded while Jiraiya used a miniature Swamp of the Underworld to capture Human, leaving only Jiraiya and Beast. Beast attempted to summon, but Jiraiya kicking him in the chest and sent him flying. By this time, Ma and Pa's genjutsu took effect, placing Pein(s) in a clear water-filled box surrounded by 4 metal frog statues wearing armor and holding swords. Jiraiya told him that "I wanted you to rise above the pain and conquer it, not use it to lead the world to ruin." In reality the three laid out on the ground incapacitated while Jiraiya stabbed each of them in the heart with giant swords.

Battle of Gods

Ma and Pa started coughing from singing, Jiraiya apologized to them and they started leaving... but then one of Pein's other bodies appeared behind Jiraiya and sent him flying through a wall, tearing off Jiraiya's left arm in the process. Two more of Pein's bodies appeared and pulled the swords out of the three fallen and were brought back to life, Pa deduced that one of the bodies have the ability to resurrect the others. Jiraiya demanded to know who he is, but Pein replied that the name "Pein" refers to all six of them.

Though much of the resulting battle went unseen, it's shown that Jiraiya hid in a summoned frog's stomach, but was somehow followed by Beast Pein whom impaled Jiraiya in his right forearm and shoulder with a black spike that extended from his arm, this Pein however died in combat but the spike that he stabbed Jiraiya with made him lose control of his chakra and the Rinnegan appeared ominously around him, but Pa quickly pulled it out. Jiraiya thought that only Nagato had the Rinnegan, but the one body is Yahiko and wondered if Yahiko stole Nagato's eyes... but that wouldn't explain how the other five bodies have the Rinnegan as well. Looking at the the Beast body, noticing it's headband fell off, Jiraiya realized that he fought him before due to a scar on it's forehead... and now that it came to his attention, he realized that he has met all of the other bodies before. He sent Ma with the Beast body to Tsunade while him and Pa left the frog's stomach to see if his suspicion is true.

Into the Ocean