Jiraiya

was one of the legendary Sannin, along with Tsunade and Orochimaru, who was trained by the Third Hokage. He was a self-proclaimed super-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 teacher of the Fourth Hokage, Naruto Uzumaki, Nagato, Yahiko and Konan. 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 travelled 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 made a prophecy concerning Jiraiya: that he would someday choose whether one of his students saved or destroyed the world. During the Second Great Shinobi World War, 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. 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. During which, he grew close to the three children, and even wrote a book that was inspired by one of them, Nagato. Eventually, however, he left 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 that 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, the Tale of the Utterly Gutsy Shinobi, that had failed as a seller. However, Minato, now the Fourth Hokage, thought the book was excellent. He and Kushina Uzumaki who was pregnant at the time, 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 an 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 had failed to save either of the previous Hokages from dying, as well as him having to conduct more "research". After he found Tsunade, and began to suspect that she might 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 called 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 disliked being referred to as the by Naruto in front of others.

Jiraiya's perversion had been used against him on occasions, as seen when Naruto got Jiraiya to start training him after a simple display of the Sexy Technique (Though Naruto hit a roadblock when Jiraiya wanted him to use the technique around him when training). When two Akatsuki members later tried to distract Jiraiya, they used 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 did not typically express interest in him. His peeping habits had 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 retained a rather healthy fear towards his former teammate, and usually attempted 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 ghost-wrote one of Jiraiya's Icha Icha novels. The book was found to be very popular. This indicates 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 was 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. Jiraiya 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 he watched Naruto tried to walk over the surface of shallow water; Jiraiya quickly discerned that there was something within Naruto that was disrupting the chakra's circulation through his body.

Despite Jiraiya's flamboyant behavior and prowess as a shinobi, he was a strong believer in peace; his hope being to one day end the hatred that plagued the ninja world. Jiraiya also held a great deal of faith in the next generation of Konoha, and saw them as the answer to this hate.

Chunin Exam arc
Jiraiya first met Naruto Uzumaki while he was "researching" at the hot springs in Konoha. After Jiraiya knocked out Ebisu for catching him in the act, Naruto demanded that Jiraiya begin training him in Ebisu's place. He refused, until Naruto used his Sexy Technique. When they started training, Jiraiya removed Orochimaru's Five Elements Seal from Naruto's stomach, which allowed him to tap into the Nine-Tailed Demon Fox's chakra. To teach him how to take advantage of the Nine-Tails' reserves, Jiraiya taught Naruto how to use the Summoning Technique, but was met with very poor results. To this end, Jiraiya decided to force Naruto to use the Nine-Tails' chakra by pushing him off a cliff. Naruto survived by summoning Gamabunta.

When Orochimaru began his invasion of Konoha, Jiraiya summoned Gamahiro to stop Orochimaru's snakes. He later mourned the Third Hokage's death, but did not attend the funeral.

Search for Tsunade arc
With the Third's death, the village elders, Homura Mitokado and Koharu Utatane, requested that Jiraiya become the next Hokage, which he quickly turned down. Instead, he volunteered 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 Uchiha and Kisame Hoshigaki 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 did 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 escaped. After that, Naruto and Jiraiya resumed their search for Tsunade, Jiraiya teaching Naruto the Rasengan along the way to keep him occupied.

Orochimaru found Tsunade before Jiraiya did, and asked that she heal his arms. When Jiraiya eventually found her as well, he suspected that they were in contact, and threatened Tsunade not to help Orochimaru. In response, Tsunade drugged his sake when they went to a bar, making it difficult for him to move or use chakra. After he discovered that this was so he wouldn't interfere in her attempt to kill Orochimaru, Jiraiya came to help her. In his drugged state, he struggled to fight Orochimaru, but was able to recover to the point that he could summon Gamabunta to fight Orochimaru's Manda. The healthy Tsunade proved too much for Orochimaru and Manda, defeating the two and causing them to flee. Tsunade then accepted her post as the Fifth Hokage, and they returned to Konoha.

Sasuke Retrieval arc
After Naruto failed to stop Sasuke Uchiha from defecting to Orochimaru at the end of Part I, Jiraiya encouraged him to give up on Sasuke, remembering his own experiences with Orochimaru. Naruto refused, prompting Jiraiya 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 information on Akatsuki. Jiraiya would soon return to inform Kakashi and Yamato about Naruto's four-tails transformation, a form so powerful that it nearly killed Jiraiya before he managed to stop 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 returned to Konoha to congratulate Naruto on defeating Akatsuki's Kakuzu. In order to keep Naruto from participating in Team 7's new Sasuke-related mission, Jiraiya offered to train him again, and took Naruto to Yugakure. Jiraiya and Naruto also had a discussion over the meaning of 'home': "Wherever someone is thinking of you, that is the place you can return to." In light of Naruto's need to learn some high-ranked, long-distance techniques, Jiraiya introduced Naruto to the concept of synchronized, collaboration jutsu and began by demonstrating a synchronizing jutsu, the Water Release: Water Pistol technique, in collaboration with Gamariki.

When Naruto and Gamariki proved unable to synchronize, due to their conflicting personalities, Jiraiya confronted Naruto with the fact that, unless he can work with a summoned toad, a collaboration jutsu would stay out of his reach. Naruto compensated by summoning toads that he did get along with, and, after giving up on trying to work with Gamariki, finally began on working with a synchronized jutsu with Gamatatsu, while Gamakichi guided the process.

Jiraiya openly applauded Naruto's progress, and expressed how pleased he was at his dedication to his goals and beliefs. After receiving a message about Akatsuki, Jiraiya was forced to leave Naruto to continue training by himself, though not before convincing Tsunade to let Naruto go on the mission.

Hunt for Uchiha arc
After learning about the defeat of Orochimaru at the hands of Sasuke, Jiraiya informed 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, amongst others who his parents were, he left to infiltrate Amegakure and see what he could find out. He captures two Rain villagers while there, and sent one to Konoha to be interrogated. After hearing that the Akatsuki leader, Pain, killed Hanzo in battle, Jiraiya decided to leave the key to the Nine-Tails' seal to Naruto, before going out to see what else he could learn.

Jiraiya went looking for, and eventually found, Konan and after incapacitating her, questions what happened to her Yahiko and Nagato. Suddenly Pain appears and Jiraiya recognizing him as his former student, Nagato, because of his Rinnegan eyes. Fearing that his student would destroy the world, as was warned against in the prophecy, Jiraiya tried to kill Pain. He entered Sage Mode, and summoned Shima and Fukasaku to help him, but had difficulty with the battle when Pain summoned additional bodies (the Preta path and the Human path). Although they were able to defeat three of Pain's bodies, they were outmatched when Pain's Asura path destroyed Jiraiya's left arm, and was joined by the remaining five paths, three of which had been revived. Doing the most that he could, Jiraiya managed to kill and capture the Animal path, and orders Shima to take it to Konoha, before heading out one last time to see if he could figure out the secret behind 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, he was able to discover the truth, but his throat was crushed, leaving him unable to tell Fukasaku what he had learned. As his life waned, he mused over his death calling it unworthy and flashes back to his life and his failures, failing to win Tsunade's heart, failing to stop Orochimaru from leaving Konoha, failing to protect both his master Hiruzen and his student Minato Namikaze, but then remembers how Minato called his book a success and decided to name his son after the protagonist of the book, Jiraiya realizes that it was he who named him Naruto.

Seeing that the students way should also be the teachers way, Jiraiya realized that Naruto, not Nagato, was the child foretold of in the prophecy. Knowing that Naruto would someday save the world, he forces himself back to life and inscribed a coded message into Fukasaku's back and sent him to Naruto. The Asura path sees the coded message on Fukasaku, he attacks him with a rocket hand destroying the rock Jiraiya was lying on making him fall into the water. As Jiraya dies he compares himself to the "Frog at the bottom of the well... Drifts off into the Great Ocean" calling it a more honorable death and realizing that he needed a title for his next book. Finding the "Tale of Uzumaki Naruto" perfect he dies with a smile while sinking into the watery depths of the battlefield.

Naruto Shippūden the Movie 2: Bonds
Most of Jiraiya's appearances in this movie were more spiritual than actually appearing. When Naruto was sent on a mission without Kakashi or Yamato, Jiraiya gave Naruto, through Sakura, a small package. After Naruto transformed into his four-tailed form, the package was revealed to be a small seal charm, to force Naruto back to normal. Jiraiya then appeared again as a hallucination, pushing Naruto to fight on. At the end of the movie, Jiraiya finally made a physical appearance by saving his apprentice from certain death by summoning Gamabunta to cushion his fall.

Abilities
Being one of the three Legendary Sannin, Jiraiya was an immensely 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 herself, (and beating beaten to a pulp by her for doing so), and when he used the toad key to weaken the Nine-Tails' seal on Naruto's 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 it would end in a stalemate or worse. Kisame even said that he was no match for Jiraiya. Even Pain marveled at Jiraiya's abilities, noting that Jiraiya would likely have won against Pain if he had had prior knowledge of Pain's six separate bodies.

Jiraiya was often described as a perfectionist. He had the ability to improvise or expand the limit of a jutsu to the point where even an academic or E-rank technique could 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 Sage", due to his natural affinity for toads, and his utilization of a number of toad-related techniques. Many typically dealt with summoning toads. 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. He also had the Hiding in a Toad Technique, where he hid in the belly of a small toad, which could enter most areas undetected.

Sage Mode and Associated Techniques
His most powerful ability, however, was to enter Sage Mode, a transformation that allowed him to use natural energy to greatly enhance all of his abilities. In order to enter Sage Mode, Jiraiya had to summon the elder toad couple Shima and Fukasaku. In addition to maintaining Jiraiya's natural energy while he fought, they added their own abilities to him to help him in battle. Sage 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 his other jutsu. An example would include the Super Great Ball Rasengan, a massive variant of Rasengan even larger than his own body. As Jiraiya was not adept with genjutsu, he relied on Shima and Fukasaku to help him in that aspect.

Jiraiya didn't like Sage 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. He 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. Examples would include 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, that kept the Nine-Tailed Demon Fox sealed within him, also allowed its chakra to mix with his own. He later created a method of suppressing the Nine-Tails' influence over Naruto through the Chakra-Suppressing 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 a Japanese folklore. 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. As the character was about to die, he made a reference to the 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 commented that, of the student-teacher relationships in Naruto, Jiraiya and Naruto's is the one he likes the most.

Trivia

 * Jiraiya was trained by the Third Hokage, trained the Fourth Hokage, and trained with the Fifth Hokage.
 * Jiraiya's belief in peace is ironically based on Nagato's belief when he was a child.
 * Jiraiya appears in all of the Naruto: Ultimate Ninja games but in the first one he just appears in one of Naruto's ultimate jutsu.
 * Jiraiya also shares his blood type with his former teammates, Tsunade and Orochimaru.
 * Two of Jiraiya's students Minato and Nagato became leaders of their own villages at different points in time.
 * According to the Naruto databook:
 * Jiraiya has completed 1839 official missions in total: 58 D-rank, 345 C-rank, 684 B-rank, 614 A-rank, 138 S-rank. With this rating of mission completed by Jiraiya, this gives him the most amount of mission completed in all of the Naruto.
 * Jiraiya's registration number is 002301.
 * Jiraiya's favorite word is "free".
 * Jiraiya's favorite past times are sneaking a peek into the Women's Bath House, and writing books.
 * Jiraiya and Naruto have a lot in common. Both were repeatedly rejected by the female member of their squad (Tsunade and Sakura) in the beginning of their relationships, but grow up to be good friends with them. Also, they both failed to stop their other squad mate, who at the time was their best friend, from leaving Konoha (Orochimaru and Sasuke). They are also the members of their respective squad that failed to retrieve a bell in the bell test to became ninja as delivered by their teachers (Third Hokage and Kakashi).
 * Jiraiya's relationship with Tsunade has been hinted to be on the verge of romance, though both refused to admit it. Reactions from both of them over certain events and statements have shown this, again relfecting the parallel's between Naruto/Sakura and Jiraiya/Tsunade.

Quotes

 * (First thing he said to Tsunade) "Nice to meet you. I'm Jiraiya! You can send me a love letter later!"
 * "I'm not a little pervert ... I'm a big one!"
 * "Wherever someone thinks of you, that's where home is."
 * (To Pain) "When people get hurt, they learn to hate.. when people hurt others, they become hated and racked with guilt. but knowing that pain allows people to be kind. PAIN allows people to grow...and how you grow is up to you."
 * (To Pain) "I wanted you to rise above that pain, to conquer it, not use it to lead the world to ruin."
 * "The true measure of a shinobi is not how he lives, but how he dies."
 * "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 the master's too! Right, Naruto?!"
 * (To Orochimaru) "Because it's no fun to train a genius!"
 * (To Naruto in the uncut dub) "You think that old trick will work on me i'm a goddamn sage"
 * "There, that ending ... was a little better. The frog at the bottom of the well drifts off into the great ocean. Heh heh ... yep ... pretty damn honorable ... pretty damn honorable"
 * (Last words) "The Tale of Naruto Uzumaki ... perfect."