Jiraiya

was one of the legendary Sannin, along with Tsunade and Orochimaru, who was trained by the Third Hokage. He was a self proclaimed mega-pervert, and wrote a popular adult book series called Icha Icha, a favorite of Kakashi Hatake. He was also known as the, because of his signature toad summonings. He was the Fourth Hokage's teacher, then Naruto Uzumaki's. Jiraiya had the kanji for "oil" on his forehead protector.

Background
As a child, Jiraiya and his former teammates, Orochimaru and Tsunade, were students of the Third Hokage. Jiraiya's relation with his team mirrored that of the future Team 7, with Jiraiya being quite similar to Naruto. After leaving the Third's tutelage, he traveled the world and discovered the residence of the toads, a species he proved to have a natural affinity for. During this time, the Great Toad Sage makes a prophecy concerning Jiraiya: that he will someday choose whether one of his students saves or destroys the world. During one of the great ninja wars, Jiraiya and his former teammates fought Hanzo of Amegakure. Hanzo was so impressed that they could survive in a fight with him that he gave them the title of Konoha's in exchange for letting them live.

Once the battle was over, Jiraiya encountered three orphans from Amegakure; Konan, Yahiko, and Nagato. While Orochimaru suggested they kill them to spare them the cruelty of the world, Jiraiya decided to look after them for a time and taught them ninjutsu before leaving them so that they could pursue their own goals. Although news of their exploits reached him from time to time, he thought them to have died during an undisclosed incident.

Once becoming a Jonin capable of leading a squad, Jiraiya became the teacher of Minato Namikaze and two other unknown Genin. Years later, when Orochimaru betrayed Konoha and fled the village, Jiraiya pursued him, trying to convince his friend to come back. Orochimaru refused, and attacked Jiraiya. While he tried to find a reason for Orochimaru's defection, he eventually realized that his friend wasn't coming back. Feeling he was responsible for Orochimaru's escape, Jiraiya left Konoha so he could follow Orochimaru's movements as well as the organization Orochimaru eventually joined, Akatsuki. In doing so, Jiraiya was unable to fulfill the Third's wishes of taking on the role of Hokage, knowing that tracking down Orochimaru was more important.

A few years before Orochimaru's defection, Jiraiya finished his first book that had failed as a seller. Minato, now the Fourth Hokage, however thought the book was excellent, he and Kushina Uzumaki decided to name their son after the main character in his book, Naruto, thus making him Naruto's godfather.

Personality
Despite the fact that he left Konoha for many years, Jiraiya had maintained a strong allegiance with his hometown. During Orochimaru's invasion of Konoha, he helped fend off the invading forces in order to protect the village. When Konoha found itself in need of a new Hokage after the Third Hokage's death, Jiraiya volunteered to look for Tsunade so that she could become the Third's successor after turning down the position himself. His reason for refusing the position was, among other things, that he felt unworthy to take the role since he failed to save either of the previous Hokage from dying. After he found Tsunade and began to suspect that she may be assisting Orochimaru, he made it clear that he would kill her if she betrayed the village. However, once it became clear that Tsunade was still loyal to Konoha and later accepted the title of Hokage, Jiraiya served as her most trusted adviser, loyal confidante, and personal spy into the dealings of Akatsuki and Konoha's enemies.

Jiraiya was a self-proclaimed super-pervert with no equal and a frequent voyeur, going so far as to create the Transparent Escape Technique to allow him to spy on naked women without being caught (doing "research" as he calls it, even as a child). He never actually hid his perversion and even seemed proud of it, as seen when he told the Third Hokage about it when he was still a child. Despite this, Jiraiya didn't like being called the by Naruto Uzumaki in front of others.

Jiraiya's perversion has been used against him on occasion's, as seen when Naruto got Jiraiya to start training him after a simple display of the Sexy Technique. When two Akatsuki members later tried to distract Jiraiya, they use a hypnotized woman to catch his eye and keep him busy. While their effort initially succeeded, Jiraiya eventually saw through their plot due solely to the fact that women do not typically express interest in him. His peeping habits have also caused him great injury on one occasion; when caught spying on Tsunade in his younger years, she proceeded to break both of his arms, six of his ribs, and ruptured a number of organs as punishment. As a result of such injuries, Jiraiya now retains a rather healthy fear towards his former teammate and usually attempts to suppress his perverted ways when in Tsunade's presence.

Some time after leaving Konoha, Jiraiya became the author of a series of adult novels called Icha Icha. The novels were based on his rejections in love that he retold in a comical way. In a filler episode of the anime, Naruto ghostwrote one of Jiraiya's Icha Icha novels and the book was found to be very popular, indicating that either Naruto is capable of writing on the same level as Jiraiya, or that Jiraiya's writing abilities were no better than those of a child. Tsunade seemed to suspect that the latter is true, as she noted that a report he wrote as a child, accompanied by crude crayon illustrations, was poorly written. The popularity of the Icha Icha series seemed to have paid off well, as Jiraiya's checkbook revealed that he was fairly wealthy. Despite his wealth, Jiraiya was not above taking Naruto's money and spending it on sake and women, and frequently disappeared when Naruto attempted to make him pay.

Jiraiya had also been known to show off even during a fight. This showing off typically took the form of traditional kabuki poses, keeping with his hermit theme. He became annoyed if he was interrupted for whatever reason while trying to strike a pose. When the situation called for it, however, Jiraiya could become extremely serious. He could also be quite perceptive, as seen when Naruto tried to walk over the surface of shallow water with Jiraiya watching him; Jiraiya quickly discerned that there was something within Naruto that was disrupting the chakra's circulation through his body.

Chunin Exams
Jiraiya first meets Naruto Uzumaki while he was "researching" at the hot springs in Konoha. After Jiraiya knocks out Ebisu for catching him in the act and trying to stop him, Naruto demands that Jiraiya begin training him in Ebisu's place. He refused until Naruto used his Sexy Technique. When they start training, Jiraiya removes Orochimaru's Five Elements Seal from Naruto's stomach which allowed him to tap into the demon fox's. To teach him how to take advantage of the fox's reserves, Jiraiya taught Naruto how to use the Summoning Technique, but met with very poor results. To this end, Jiraiya decided to force Naruto to use the fox's chakra by pushing him off a cliff. Naruto survives by summoning Gamabunta.

When Orochimaru begins his invasion of Konoha, Jiraiya summons Gamahiro to stop Orochimaru's snakes. He later mourns the Third Hokage's death, but does not attend the funeral.

Search for Tsunade
With the Third's death, the village elders, Homura Mitokado and Koharu Utatane, requested that Jiraiya become the next Hokage, which he quickly turns down. Instead he volunteers to search for his former teammate Tsunade, asking only that he be allowed to take Naruto with him.

Just a day after setting off, however, Itachi and Kisame of Akatsuki tried to kidnap Naruto. To do so, they used genjutsu on a woman to distract Jiraiya while they captured Naruto. Jiraiya saw through the trick and intercepted Itachi and Kisame, who decided they would not want to get involved in a fight with one of the Sannin. When they tried to escape Jiraiya used Ninja Art: Toad Mouth Trap to trap Itachi and Kisame. Nobody had ever managed to escape that technique before, but Itachi used Amaterasu to burn through the walls and escape. After that Naruto and Jiraiya resumed their search for Tsunade, Jiraiya teaching Naruto the Rasengan along the way to keep him occupied.

Orochimaru finds Tsunade before Jiraiya does, and asks that she heal his arms. When Jiraiya eventually finds her as well, he suspects that they were in contact and threatened Tsunade not to help Orochimaru. In response, Tsunade drugs his sake when they go to a bar, making it difficult for him to move or use chakra. After he discovers that this was so he wouldn't interfere in her attempt to kill Orochimaru, Jiraiya comes to help her. In his drugged state he struggles to fight Orochimaru, but is able to recover to the point that he can summon Gamabunta to fight Orochimaru's Manda. The healthy Tsunade proves too much for Orochimaru and Manda, defeating the two and causing them to flee. Tsunade then accepts her post as the Fifth Hokage, and they return to Konoha.

Sasuke Retrieval
After Naruto fails to stop Sasuke Uchiha from defecting to Orochimaru at the end of Part I, Jiraiya encourages him to give up on Sasuke, remembering his own experiences with Orochimaru. Naruto refuses, prompting Jiriaya to take him away for two-and-a-half years of training to make him strong enough to bring Sasuke back, and to protect himself from Akatsuki.

Part II
After taking Naruto back to Konoha, Jiraiya went off to search for info on Akatsuki. Jiraiya would soon return to inform Kakashi and Yamato about Naruto's four tail transformation, a form so powerful that it nearly killed Jiraiya before he stopped it. It was later revealed that Jiraiya himself released it (not expecting Naruto's loss of control) with a special key passed down from the Fourth Hokage, capable of unlocking Naruto's seal.

Three-Tails Arrival arc
In the anime, Jiraiya returns to Konoha congratulate Naruto on defeating Akatsuki's Kakuzu. In order to keep Naruto from participating in Team 7's new Sasuke-related mission, Jiraiya offers to train him again. He begins teaching him how to use synchronizing jutsu with Gamariki. When Naruto finally begins synchronizing with Gamakichi and Gamatatsu (after giving up on trying to work with Gamariki), Jiraiya openly applauds Naruto's progress and expresses how pleased he is at his dedication to his goals and beliefs. After receieving a message about Akatsuki, Jiraiya is forced to leave Naruto to continue training by himself, though not before convincing Tsunade to let Naruto go on the mission.

Infiltration of Amegakure
After learning about the death of Orochimaru at the hands of Sasuke, Jiraiya informs Tsunade that he had found the location of the Akatsuki Leader, somewhere in Amegakure. After a chat with Tsunade revealing much of Naruto's history, he left to infiltrate Amegakure and see what he could find out. He captures two Rain villagers while there, and sends one to Konoha to be interrogated. After hearing that the Akatsuki leader, Pain, killed Hanzo, Jiraiya decides to leave the key to the demon fox's seal to Naruto before going out to see what else he can learn.

Jiraiya goes looking for and eventually finds Pain, recognizing him as his former student Nagato because of his Rinnegan eyes. Fearing that his student will destroy the world as was warned against in the prophecy, Jiraiya tries to kill Pain. He enters Hermit Mode and summons Shima and Fukasaku to help him, but has difficulty with the battle when Pain summons additional bodies. Although they are able to defeat three of Pain's bodies, they are outmatched when the three bodies are revived and joined by three others. To do what he can, Jiraiya captures one of the bodies and sends it to Konoha before heading out one last time to see if he can figure out the secret behind Pain.

Jiraiya is able to discover that all of Pain's bodies belonged to ninja he once knew, amongst them being his old student Yahiko. With this information he is able to discover the truth, but his throat is crushed and he is unable to tell Fukasaku what he has learned. As his life wanes he realizes that Naruto, not Nagato, was the boy foretold of in the prophecy. Knowing that Naruto will someday save the world, he inscribes a coded message into Fukasaku's back and sends him to Naruto before dying, sinking into the watery depths of the battlefield.

Abilities
Being one of the three Legendary Sannin, Jiraiya was an extremely powerful ninja, being considered Kage-level. He stated that he had only been brought to the verge of death twice in his entire life, once when he was doing "research" on Tsunade, and when he used the key weaken the demon fox's seal on Naruto stomach. His strength was so great that even Itachi Uchiha and Kisame Hoshigaki, two of Akatsuki's most powerful members, opted not to face him in battle fearing that the best they could do was kill each other. Kisame even said that Jiraiya's skills and power outclassed his own. Even Pain marveled at Jiraiya's abilities, noting that only Jiraiya could come as close to defeating him in battle as he had.

Jiraiya is often described as a perfectionist, and has the ability to improvise or expand the limit of a jutsu to the point where even an academic or E-rank technique can make him an extremely formidable opponent. The Transparent Escape Technique, created to help him spy on women, eventually proved to be very useful in espionage and reconnaissance. By his own admission, however, he was not cut out for using genjutsu.

Toad Techniques
Jiraiya was known as the "Toad Hermit" due to his natural affinity for toads and his utilization of a number of toad-related techniques. Many typically dealt with summoning toads, and he had risen to a level of ability that allowed him to summon Gamabunta. He could even summon the nearly indestructible esophagus of a great, fire-breathing toad with Summoning: Toad Mouth Bind. Once the technique had been used to cover the area, Jiraiya could control it as he pleased and used it to trap most ninja.

For spying and infiltration, Jiraiya had the Toad Flat - Shadow Manipulation Technique, which allowed him to hide himself as a shadow and even attach to the shadow of another ninja to control them, and the Hiding in a Toad Technique, where he hid in the belly of a small toad, which could enter most areas undetected.

Hermit Mode and Associated Techniques
His most powerful ability, however, was to enter Hermit Mode, a transformation that allowed him to use natural energy to greatly enhance all of his abilities. In order to enter Hermit Mode, Jiraiya had to summon Shima and Fukasaku, generally referred to as Ma and Pa. In addition to maintaining Jiraiya's natural energy while he fought, they added their own abilities to the mix to help him in battle. Hermit Mode greatly increased Jiraiya's physical power, as shown by his ability to send Pain's summons flying. This form allowed Jiraiya to use stronger versions of this other jutsu, such as the Super Great Ball Rasengan, a massive variant of Rasengan even larger than his body.

Jiraiya didn't like Hermit Mode because it gave him a more toad-like appearance, with longer marks along the sides of his face, a goatee, a larger nose with warts, and webbed hands and feet, all of which made him unappealing to girls.

Ninjutsu
Jiraiya was well-versed in a variety of ninjutsu types, being capable of spitting oil from his mouth or breathing fire. He could create deep swamps with Earth Release: Swamp of the Underworld and could grow and sharpen his hair for offensive and defensive purposes with Needle Jizō. Jiraiya was taught how to use the Rasengan by Minato, and had since developed larger variants.

Apart from his fighting abilities, Jiraiya was able to use barriers, such as Barrier: Dome Method Formation, which allowed him to detect all movements within a wide radius and block attacks, and Barrier: Toad Gourd Prison, which allowed him to trap an enemy inside the belly of a small toad-shaped gourd, the inside of which contains a landscape with a lake of stomach acid.

Sealing Techniques
Jiraiya had been shown to be very knowledgeable with Sealing Techniques, and had used a number of them throughout the series. When first meeting Naruto, he quickly deduced that the seal on Naruto's stomach kept the Nine-Tailed Demon Fox sealed within him though also allowed its chakra to mix with his own. He later created a method of suppressing the demon fox's influence over Naruto through the Demon Fox Chakra Seal, which activates by simply coming into contact with Naruto's body. In addition, he could utilize the Fire Sealing Method to contain Itachi's Amateratsu within a scroll for future study.

Creation and conception
Jiraiya is named after the character of the same name from. The Jiraiya in this story excelled in summoning a giant toad (the toad itself was sometimes called "Jiraiya") and toad magic. In that story, Jiraiya and Tsunade were a married couple. There, his name is written as "児雷也" meaning "Young Thunder" which in turn comes from the name from the Chinese story.

Masashi Kishimoto originally planned to draw Jiraiya with a different design and with a different style of hair. He also intended for Jiraiya to summon Toads that were of a similar size to humans. However, this idea was deemed a failure. During an interview, he comments that, of the student-teacher relationships in Naruto, Jiraiya and Naruto's is the one he likes the most.

Trivia

 * Jiraiya was also the only Sannin that did not try to hide his age.
 * Jiraiya was trained by the Third Hokage, trained the Fourth Hokage, and trained with the Fifth Hokage.

Quotes

 * "I'm not a little pervert..., I'm a big one!"
 * "Never go back on your word... and never give up, no matter how bad it gets that's your ninja way... and I'm supposed to be your teacher... I can't go out like this! Because I... the student's ninja way should be master's too! Right, Naruto?!"
 * (First thing he said to Tsunade) "Nice to meet you. I'm Jiraiya!! You can send me a love letter later!"
 * (To Pain) "I wanted you to rise above that pain, to conquer it, not use it to lead the world to ruin."
 * "There, that ending... was a little better. The frog at the bottom of the well drifts off into the great ocean. Hehe... yep... pretty darn honorable... pretty darn honorable."
 * "The true measure of a shinobi is not how he lives, but how he dies."
 * "Wherever someone thinks of you, that's where home is."