Jiraiya

was one of the legendary Sannin, along with Tsunade and Orochimaru, who was trained by the Third Hokage himself. He is a self proclaimed mega-pervert, and writes popular adult book series called Icha Icha, a favorite of Kakashi Hatake. He is also known as the, because of his signature toad summonings. Jiraiya has the kanji for "oil" on his forehead protector. He was the Fourth Hokage's teacher and then later Naruto's, who calls him "Ero-sennin", or in the English anime, "Pervy Sage". He proved this in his childhood when he peeped on Tsunade in the baths, resulting in him being beaten to an inch of his life.

Despite his perversion, Jiraiya is a Kage-level ninja. In his early years, Jiraiya invented the Transparent Escape Technique to help him peek on women and not get caught, though Naruto occasionally blows his cover.

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, Jiraiya is told a prophecy concerning him and his students, which states that they will decide the fate of the world. During a war, the team consisting of Jiraiya, Orochimaru and Tsunade came to battle "Salamander" Hanzo of the Rain village. Hanzo was so impressed that they survived the attack that he gave them the title of to indicate their status as the strongest ninja in Konoha (which he ordered they refer to themselves as an exchange for fighting Konoha any further).

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. Presumably leaving the three, Jiraiya began to travel the Naruto world and write his book.

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, despite turning down the offer to fill the role, 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 Hokages 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.

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 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.

Some time after leaving Konoha, Jiraiya became an author of adult novels, his most popular work being, a personal favorite of Kakashi Hatake. The novels were based on his rejections in love that he retold in a comical way. In a filler episode of the anime, Naruto ghostwritten one of Jiraiya's Icha Icha novels and the book was found to be very popular, indicating that 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 on the Onbaa 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. Underneath all other traits, however, was an interesting philosophy that is revealed in a flashback during Naruto's Sage training. It was shown that he felt that hatred for one's companions and friends was spreading, as shown by Orochimaru and Sasuke. He then said he hoped his books could change things and asked Naruto if he could help stop the hatred if Jiraiya failed, a request which Naruto happily agreed to.

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.

Jiraiya could also become extremely serious in battle or when he was about important business (i.e like when Naruto says he wanted to give himself to the Akatsuki) and often had a serious voice in his head but he never said what he was thinking or discussed important matters with another person. He could also be quite perceptive, as seen when Naruto tried to walk over the surface of shallow water with Jiraiya as audience; Jiraya quickly discerned that there was something within Naruto that was disrupting the chakra's circulation around the boy's body, leading him to undo Orochimaru's Five-Element Seal

As mentioned above, the Kanji on Jiraiya's headband means "oil," but in Chinese, it also means "sly". So it's a bit of a double entendre for both his abilities and his personality.

Chunin Exams
Jiraiya first meets Naruto Uzumaki while he was "researching" at the hotsprings in Konoha, where he flattened Ebisu when he almost exposed him. Because he knocked out his teacher, Naruto demanded Jiraiya to train him, which he initially refused. It wasn't until Naruto used his Sexy Technique did he win Jiraiya over.

When they start training, Jiraiya removes Orochimaru's Five Elements Seal off the boy's stomach which allowed him to tap into the Demon Fox's chakra thus allowing him to use better jutsus and mold his chakra with ease. For special training for the last part of the exams 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 Fox's chakra, by pushing him off a cliff. After Naruto survives this training and summons Gamabunta, Jiraiya stays in Konoha for the events to play out. When Orochimaru and the Sand attacked Konoha, Jiraiya appeared with Gamahiro to help battle one of the Sounds summoned snakes.

The Search for the Fifth
After the death of the Third, 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, and took Naruto with him for more training. Jiraiya would train Naruto to use his father's technique, the Rasengan.

Before they could reach Tsunade, Orochimaru contacted her in an effort to have his dead arms fixed by Tsunade's medical jutsu. Tsunade, deciding to meet Orochimaru herself, drugs Jiraiya's sake and heads out on her own. When Jiraiya, Naruto, and Shizune catch up with her, she is already in battle with Kabuto. Jiraiya goes into battle with Orochimaru, trapping Orochimaru's snake with his Underworld Swamp jutsu. Although the weakened jutsu fails to envelop the snake completely, it is still more than large enough to immobilize it. After Naruto takes Kabuto out of battle with a now-perfect Rasengan (made with the help of a clone, an innovation he came up with mid-battle), Tsunade joins Jiraiya in the battle against Orochimaru. With their ultimate summons, Gamabunta and Katsuyu, the two take on Orochimaru and his snake Manda. The healthy Tsunade proves too much for Orochimaru and Manda, defeating the two and causing them to flee. With Tsunade now accepting her post as the Fifth Hokage, they return to Konoha.

Sasuke Retrieval
Jiraiya apparently witnessed Naruto's brief fight with Sasuke on the rooftop. He then debated with Kakashi about teaching Sasuke the Chidori, which Sasuke could have killed Naruto with. In turn, Kakashi said it was irresponsible of Jiraiya to teach Naruto the Rasengan. Jiraiya was planning on having a talk with Naruto about his and Sasuke's unhealthy rivalry, but as Naruto walked past him he couldn't bring himself to say anything for whatever reason. Jiraiya wasn't in Konoha during Sasuke's defection and reappears only after Naruto returns after failing to bring him back. Jiraiya reveals that Sasuke and Orochimaru are very similar, in that both only lust for power and both will do anything to get it. In fact, Naruto's battle with Sasuke was very similar to Jiraiya's fight with Orochimaru when he tried to bring Orochimaru back, trying to remind his friend of their past friendship. When Jiraiya called Naruto a fool for even considering trying to rescue a friend like that, Naruto tells him he would rather be a fool than to give up on Sasuke. Taken aback, Jiraiya tells him that once he is better, he will take him to train for three years so he will be strong enough to bring Sasuke back, and protect himself from the Akatsuki.

Part II
After taking Naruto back to Konoha, Jiraiya went off to search for info on the Akatsuki. Jiraiya would reappear later to inform an injured Kakashi and the current leader of Team 7, 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.

Hunt for the Three-Tails
Hearing about Naruto's victory over the Akatsuki, Jiraiya returns to congragulate his student. After Naruto reveals his disappointment at how dangerous it is to use his Rasen Shuriken, Jiraiya offers to train him again. In truth, this was actually offered in order to make sure Naruto would not know of the recognaisance mission of Orochimaru's hideout carried by Kakashi and rest of Team 8, excluding Kurenai, because of his desire to encounter Sasuke. After they arrive at a hot springs resort, Jiraiya notes to himself that while Naruto is still so childish, he has indeed grown since they last met, and may actually succeed where Jiraiya failed. He then begins teaching him how to use synchronizing jutsu, together with his summon Gamariki. While Naruto continues his attempts to synchronize with partner, Jiraiya continues his usual antics of spying on women in the hot springs.

Defection from Otogakure
In this manga arc Jiraiya appeared again to inform Naruto and Sakura that Sasuke has killed Orochimaru and was most likely going off to kill Itachi, before doing more research on the Akatsuki.

Infiltration of Amegakure
Jiraiya later returned to Konoha once more to inform 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 headed out to the Rain country. He infiltrated the village using a particular frog with a jutsu that warped in size and began interrogating two ninja he abducted in that same frog. There was no initial response, but he was immediately spotted by Pain's rain jutsu. Upon learning that Pain singlehandedly defeated Hanzo, he summoned the frog containing the key to Naruto's seal, and informed it to go to Naruto if he died. Rather than wait for Pain to come to him, Jiraiya prepared to do battle (to forcibly extract the information).

After fighting with Pain for some time, he claimed to have discovered his true identity. However, Pain's thorn-headed body was able to attack Jiraiya by surprise, allowing Pain's other bodies to thrust their four black blades into his stomach. As he died, Jiraiya recalled his view on how the measure of true shinobi is not just how they live, but how they die. He recalled his life as one full of failure, since Tsunade turned him down every time he asked her on a date, he wasn't strong enough to stop Orochimaru, and failed to help Minato, as well as the Third. However, he always thought that his failures were building character, and that he would be granted one, final adventure. However, he failed to stop Pain. He thought that his story was pathetic, and that writing it was a waste of time. However, he remembered how Minato actually enjoyed the story, and that he and Kushina decided to name their son Naruto, after the character in Jiraiya's story, making Jiraiya Naruto's godfather. He then realized that his point in life was encouraging others to do their best, and to never give up. He forced himself back to life with willpower, and transferred the information about Pain to one of his toads. He believed that Naruto was the child of prophecy he heard in a prediction by the Toad Sage. As Jiraiya's toad escaped to Konoha, Jiraiya sunk to the watery depths of the battlefield, while stating that this ending for him was a lot better than he thought he could achieve. His death was later confirmed by the toad Fukasaku.

Abilities
Being one of the Sannin, Jiraiya was an extremely powerful ninja. He stated that he had only been brought to the verge of death twice in his life, once when he was doing "research" on Tsunade and when he used the toad key to "twist" Naruto's seal unleashing his Four-Tailed Transformation. His strength was so great that Itachi and Kisame, two of the most powerful members of Akatsuki, opted not to face him fearing that it would end in a draw or worse. Kisame even said that Jiraiya's skill and power far outclassed his own. Another example of his extreme power was shown when he was battling Pain, the leader of the Akatsuki and an extremely powerful ninja. In his Hermit Mode, he was shown on equal footing with him and only lost because he let his guard down after he trapped three of Pain's bodies. Pain had also mentioned that if he hadn't brought out the rest of his bodies and surprised Jiraiya then he may have lost.

Toad Techniques
Jiraiya was known as the "Toad Hermit" due to 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.

Hermit Mode and 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 the Two Great Toad Hermits, 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, such as War of Words Binding, a highly effective tracking technique with a wide range, and War of Words Decapitation, a powerful mid-range cutting technique. Hermit Mode greatly increased Jiraiya's physical power, as shown by his ability to send Pain's giant Bull Summon flying. In this form, Jiraiya could utilize special techniques, such as Hermit's Art: Goemon, an fire-wind-oil combination attack with Shima and Fukasaku that covered a wide range, Hermit's Art: Hair Needle Barrage, a technique where his hair blasted at the opponent like a barrage of needles, and Super Great Ball Rasengan, a massive variant of Rasengan even larger than his body. Shima and Fukasaku were also capable of using one of the most potent Genjutsu in the Naruto world, Demonic Illusion: Toad Confrontation Singing, a sound-based Genjutsu which does not activate until the two toads have sung a special song in harmony, but will instantly paralyze all opponents who hear it once activated. He didn't like this form 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. Because of this and the fact that Shima and Fukasaku had to be on his shoulders when using it, he didn't always stay in Hermit Mode.

Ninjutsu
In addition to calling upon toads for aid in battle, Jiraiya had a large number of techniques he could use independently. His Earth Release: Swamp of the Underworld created a powerful swamp on a surface of his choice, which could be as large as a lake, and was highly difficult to escape. He had an affinity for fire and could utilize a number of fire techniques. He could also use Toad Oil Bullet, another toad related technique with his mouth. Jiraiya had also been shown to use his hair for techniques, and could grow and sharpen it to surround him as a shield with Needle Guardian or used it to bind and impale opponents with Wild Lion's Mane Technique. For spying and infiltration, Jiraiya had the unseen Transparent Escape Technique, 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. 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. He was not, however, suited for Genjutsu, and thus could not effectively utilize it in battle.

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

 * Even though Tsunade is the only remaining Sannin, Jiraiya is the only one that is actually dead as Orochimaru is only sealed.
 * Jiraiya was also the only sannin that looked closer to his actual age.
 * In an anime filler after the Hidan & Kakuzu Arc, Jiraiya appeared in Konoha and told Naruto that they'll train together once more after Naruto's arm has been healed (due to the severe bone damage made by his Fuuton: Rasen Shuriken).
 * Jiraiya has had training with or under three hokages (that being the Third, Fourth, and Fifth Hokages).

Quotes

 * "The true measure of a shinobi is not how he lives, but how he dies."
 * "I'm not a little pervert..., I'm a big one!"
 * "Never give up..., that was the decision I had to make..., Naruto..., you are the "destined child". I know it..., the rest is up to you!"
 * "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?!
 * "'The Tale of Uzumaki Naruto'... perfect."