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The young man known as Jiraiya was selected to study as a Genin under Sandaime Hokage. More of a klutz than his teammates Orochimaru and Tsunade, Jiraiya was a bit jealous over their abilities. As Jiraiya grew his skills did as well, soon all three teammates were highly regarded for their skills. Jiraiya devoted himself to the village and to his friends.

As the years passed, Orochimaru dedicated himself to bizarre experiments. When Sandaime Hokage found out, Orochimaru fled. Jiraiya had a hard time believing the revelation and he took off after his friend to get him to return. They battled and Jiraiya returned to the village as a failure with his teammate gone for good. This colored his perceptions of priorities and he soon decided to leave Konoha behind.

Traveling the world he began to write a series of erotic novels, which gained him quite a bit of additional fame. In his travels he would often spy on women to get material for his books. Years passed and his travels took him back to Konoha to look upon its fine women. One such peeping session was interrupted by Ebisu and Naruto. Jiraiya took to Naruto seeing a bit of himself in the clueless wonder.

In the following weeks he would train Naruto to better use his chakra and how to summon toads. This would greatly help Naruto in his fights ahead. When Orochimaru launched an invasion of Konoha, Jiraiya did what he could to help but he did not make it in time to save the life of his former sensei Sandaime Hokage. With the village lacking a leader the Hokage advisors turned to Jiraiya. He declined but he and Naruto went and found Tsunade for them.

During this trip they battled Orochimaru once again and managed to convince Tsunade to return to the village as Kage. In the following weeks Uchiha Sasuke left the village to train with Orochimaru and Naruto gave chase. He returned after failing in his mission. Thinking of his own failure, Jiraiya told Naruto to give up but the young man refused.

Several months later Jiraiya and Naruto left the village to further his training and be better prepared to face Akatsuki. Jiraiya helped Naruto learn more about Genjutsu and also how to better use the Kyuubi chakra. In one such incident, Naruto was driven into a four-tailed Kyuubi state. He was nearly unstoppable but Jiraiya finally ended the wild destruction. Though he was given a huge scar on his chest for his troubles, Jiraiya chose not to tell Naruto what exactly happened, as the young man lost control of himself and his mind in that state. After two and a half years their training came to an end so they returned to Konoha.

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During the invasion of Leaf Village by Sand and Sound, Jiroubou served as one of the corners of the barrier which contained the battle between Orochimaru and the Third Hokage. Later when the Four Sounds were going to deliver Uchiha Sasuke to Orochimaru, the five Leaf Genin led by Shikamaru followed in pursuit.

Jiroubou managed to entrap the group in a mud dome prison. He stayed behind to feed off the chakra of the Genin, while his teammates continued on. When they managed to escape, Akimichi Chouji stayed behind to battle Jiroubou as the rest chased after Kidoumaru, Tayuya and Sakon. It was then revealed that like Sasuke, Jiroubou had been given a cursed seal by Orochimaru. Utilizing special Akimichi clan soldier pills, Chouji was able to stand on somewhat equal ground with the powerful Jiroubou. When Chouji was able to use his massive multi-size jutsu, Jiroubou was forced to use his curse seal level two form. Though this gave Jiroubou ten times the strength, Chouji was able to ingest the last of three special soldier pills and gain enough power to strike Jiroubou with enough force to apparently kill him.

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Juugo was the original source of Orochimaru's cursed seal experimentation. Juugo possessed the ability to morph and strengthen his body. Unfortunately these abilities were not under his control, when he began to change he lost control and became a simple killing machine. For this reason he sought out Orochimaru in the hopes the skilled ninja could help him. Orochimaru took Juugo to his northern base and used his genetic structure to synthesize a enzyme he could implant in others. This enzyme would be implanted with the curse seal and allow the wearer to draw out more of their power.

Juugo was put under heavy lock and key alongside numerous other prisoners who were experimented upon with his curse seal. For many long years Juugo remained imprisoned. When Sasuke finally defeated Orochimaru, he began to gather subjects within Orochimaru's sphere of influence to assist him in his plans. His new team included Mist ninja Suigetsu, Karin a prison guard and Juugo. At some point in the past Orochimaru had Suigetsu fight Juugo, however Juugo never revealed his strange abilities in the fight. At some point in the previous years Juugo also met Kimimaro, and saw the man as nothing more than a copy-cat. Suigetsu and Karin were both unsure about having Juugo join and when he was initially freed, he was in his crazed state and lashed out against Sasuke. Suigetsu arrived and began to battle Juugo much to Sasuke's dismay. Sasuke sought to sway Juugo with words and used his high killer intent to make the two men back down. Juugo returned to normal and fled back to his cell, fearing that his freedom would allow his murderous tendencies to go wild.