Jiraiya

was one of Konohagakure's legendary Sannin. He was known as the because of his special affinity for toads. Famed as a hermit and pervert of stupendous skill, Jiraiya travelled the world in search of knowledge that would help his friends, the various novels he wrote, and, posthumously, the world in its entirety - knowledge that would be passed on to his godson and final student, Naruto Uzumaki.

Background
As a child, Jiraiya and his former team-mates Orochimaru and Tsunade, were students of the Third Hokage. Jiraiya's relationship with his team practically mirrored that of the future Team 7, with Jiraiya being quite similar to Naruto, being the clumsy and reckless member of the team. At various times, he would try to impress Tsunade, only to embarrass himself. Jiraiya at some point discovered the residence of the toads. This happened, in the anime, when still the Third's student; after seeing the Third perform the Summoning Technique, Jiraiya tried to use it himself. Since he did not have a contract, Jiraiya was reversed summoned to Mount Myōboku. There, he learned to have a natural affinity for their variety of ninjutsu techniques. He was also trained in senjutsu. After leaving the Third's tutelage, he travelled the world, where he was later called upon by the Great Toad Sage who made a prophecy concerning Jiraiya: that he would someday choose whether one of his students saved or destroyed the world.

During the Second Shinobi World War, Jiraiya and his former team-mates fought Hanzō, the leader of Amegakure. Hanzō was so impressed that they could survive in a fight with him, that he bestowed upon them the title of Konoha's, and that they accept the title in exchange for letting them live. Once the battle was over, Jiraiya and his team-mates encountered three young 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 while and teach them ninjutsu. During the time he spent with them, Jiraiya grew close to the three children, and even wrote a book that was inspired by one of them, Nagato. Eventually, he left them so that they could pursue their own goals. Although news of their exploits reached him from time to time, he thought they had died during an undisclosed incident.

Jiraiya later became the teacher of Minato Namikaze and two other unknown genin. Jiraiya took particular interest in Minato, taking him as an apprentice, and among other things teaching him the Summoning Technique and senjutsu. At some point, he also told Minato about the prophecy the Great Toad Sage had given him, believing that Minato could be the Child of the Prophecy.

Later, Jiraiya's first book, The Tale of the Utterly Gutsy Shinobi, failed to be a best-seller. Minato, now the Fourth Hokage, thought the book was excellent, and praised Jiraiya, saying that the protagonist resembled him greatly. It was then that Minato revealed that he and Kushina Uzumaki, who was pregnant at the time, wanted to raise their child to be a great shinobi, like the one in the book, and for that reason they decided to name him "Naruto", after the main character. Jiraiya jokingly pointed out that it would make him Naruto's godfather, and asked if they were sure that they would want that. Minato replied that Jiraiya was a good example for them all and that he could not think of a finer shinobi than him.

Years later, when Orochimaru betrayed Konoha and left the village, Jiraiya pursued him, trying to convince his friend to come back (similar to Naruto's efforts to bring Sasuke home). Orochimaru refused, and attacked Jiraiya. While he tried to find a reason for Orochimaru's defection, Jiraiya eventually realised 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 those of "Akatsuki", an organisation which Orochimaru had eventually joined. In doing so, Jiraiya was unable to fulfil the Third's wishes of him taking on the role of Hokage, feeling that tracking down Orochimaru was more important.

Personality
Although he left Konoha for many years, Jiraiya was still loyal to his 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 be the Fifth Hokage, 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 Hokage from dying, as well as him having to conduct more "research". After he found Tsunade, and began to suspect that she might be helping Orochimaru, he made it clear that he would kill her if she betrayed the village, a proof of his loyalty to Konoha. 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 confidant, and a spy into the dealings of Akatsuki and Konoha's enemies.

Jiraiya was a self-proclaimed super-pervert with no equal (although he meant it as a joke), 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 tried to distract Jiraiya, they used a hypnotised 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 team-mate, and usually attempted to suppress his perverted ways when in Tsunade's presence. Despite these perverted tendencies, Jiraiya was in love with Tsunade nonetheless and even as he died, he lamented the fact that he was never able to win her heart. However, despite his one-sided affections for his team-mate, Jiraiya didn't let his feelings cloud his judgment and resolutely stated that he wouldn't hesitate to kill Tsunade should she betray Konoha and help Orochimaru.

Some time after leaving Konoha, Jiraiya became the author of a series of adult novels called Icha Icha. The novels were based on his personal experiences 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 cheque book 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 included traditional kabuki poses accompanied by dramatic self-introductions, keeping with his hermit theme, even when he was a child. He became annoyed if he was interrupted for whatever reason while trying to strike a pose, which happened frequently. His summon Gama however was the only toad he ever summoned that posed along with him. Although he was generally light-hearted and gregarious, Jiraiya could be very serious in a demanding situation, such as fighting Orochimaru, and later, Pain. He was also quite perceptive, as demonstrated when he watched Naruto try 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 eccentric behaviour 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, and saw them as the solution to this hate.

Appearance
Jiraiya was a tall man with waist-length, spiky white hair usually tied back into a pony tail, with two shoulder-length bangs that framed both sides of his face. He also had red lines that ran down from his eyes and wore a horned forehead protector with the kanji for, which denotes his affiliation with Mount Myōboku. He also had a noticeable wart on the left side of his nose. Jiraiya wore a green short shirt kimono and matching pants; under which he wore mesh armour that showed out of the sleeves and legs of his outfit. His outfit was completed with hand guards, a simple black belt, traditional Japanese geta (wooden sandals), a red haori with two simple yellow circles on each side, and a scroll on his back. He also had a tattoo in his left palm which resembles one that Gama has in his as well.

Jiraiya was also seen sporting different attires. As a child, he wore pale grey robes with a design of red flames on the edges, with a green ribbon showing a curled gold design tied in a loose bow around his waist. In childhood, the length of the red lines that ran down his eyes extended to just over half his face, but became longer in time. Underneath it, he wore the standard black mesh shirt with red lining, and wore puffy black pants that are tighter around the ankles as well as black sandals to go with the outfit. During the Second Great Shinobi War against Hanzō, he wore the wartime variant of Konoha's flak jacket and its standard forehead protector. He was also shown wearing what appeared to be a rubber frog suit during a flash back to when he was training the Ame Orphans.

Abilities
While untalented in childhood, though sheer hard work and dedication, Jiraiya eventually obtained power rivalling that of his peers in Orochimaru and Tsunade, the former of which is considered to be a genius. Being one of the three famed Sannin, Jiraiya was an extremely powerful shinobi, easily considered Kage-level, becoming a legend before he died. Jiraiya was even initially chosen for the position of both Fourth and Fifth Hokage by his teacher the Third Hokage and the Konoha Council, though he turned it down both times. 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 being beaten to a pulp by her for doing so), and when he used the toad key to weaken the seal that held the Nine-Tails' seal on Naruto's stomach, which resulted in Naruto's four-tailed form. The latter only happened because he was trying to reseal the demon chakra rather than harm Naruto.

Jiraiya's strength was so great that Ebisu asserted how only a Sannin like Jiraiya was powerful enough to kill Orochimaru during his Invasion of Konoha. Even powerful members of the S-rank criminal organisation Akatsuki were either easily subdued like Konan, while others like Itachi Uchiha and Kisame Hoshigaki, a Mangekyō Sharingan user and former member of the Seven Ninja Swordsmen of the Mist respectively, opted not to face the Sannin in battle, fearing that the very best they could do together against Jiraiya would end in a stalemate, even with reinforcements. Kisame even admitted that he was no match for Jiraiya, saying he was "on a whole other level". Minato Namikaze also acknowledged his master's power, skills, and mindset, and wished to fight him. Even Nagato — the ex-leader of Akatsuki and a former student of Jiraiya who possessed the legendary Rinnegan — was initially overwhelmed despite outnumbering Jiraiya. This caused the younger opponent to marvel at Jiraiya's abilities, as defeating the Sannin still cost Nagato one of his strongest tools, stating that he would not have defeated Jiraiya had he had prior knowledge of Nagato's "secret". Even Obito vehemently refused Kabuto's suggestion to also revive Jiraiya using the Impure World Resurrection, with Obito telling Kabuto "not to push his luck".

Taijutsu
While not being his preferred combat method, Jiraiya was still very proficient with taijutsu, capable of stopping some of the individual dogs that split from the Giant Multi-Headed Dog just using his legs. His natural strength, while nowhere close to his team-mate Tsunade, was very impressive. In the anime, there is one such occasion where this is shown, when Jiraiya intervened in a fight between a young Gamabunta (who was still bigger than himself) and an unknown snake of equal size where Jiraiya grabbed and tossed the snake a great distance away with ease. Also in the anime, Jiraiya, as a child, was able to lift a large boulder several times his size. Jiraiya has showcased a high level of durability over the course of his life; taking a direct kick to the face from Might Guy, as well as surviving a direct blow from Nagato's Giant Ox, which ploughed him through several steel pipes, without getting injured. Even at the brink of death he still managed to figure out Pain's secret and engrave it on Fukasaku's back, so he could deliver the intel to Konoha.

Ninjutsu
Jiraiya was well-versed in a variety of ninjutsu types. He could grow and sharpen his hair for offensive and defensive purposes. Jiraiya was taught how to use the Rasengan by Minato, and had since developed a larger variant.

Jiraiya was often described as a perfectionist. He had the ability to improvise or expand the limit of a technique to the point where even an academic or E-rank technique could be used formidably in battle. He is highly skilled in stealth, espionage, and reconnaissance, even having his own personally made technique known Transparent Escape Technique to aid him in such missions (although he mainly uses it to help him spy on women).

Apart from his fighting abilities, Jiraiya was very proficient with barrier based techniques. Examples would include Barrier: Canopy 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.

While he had basic knowledge on how to recognise and counter genjutsu, he was not skilled at using it, and relied on his partners to use illusions.

Nature Transformation
In terms of element ninjutsu, Jiraiya had proficient knowledge if not skill in multiple types. He could use Earth Release to create deep swamps to immobilise his opponents as large as Orochimaru's gigantic snakes even when on low chakra or beings as physically strong as Human Path. His proficiency in Fire Release is great enough to unleash oil enhanced blasts of flame. Not only that, he could create even larger blasts of fire with the help of Gamabunta, creating the Fire Release: Toad Oil Flame Bullet which could cover an entire valley in flames. When in Sage Mode he could create entire lakes of burning oil with the help of Fukasaku and Shima. He was also at least knowledgeable enough to teach others how to manipulate the nature of their chakra. His knowledge of all five elements allowed him to teach Nagato each of them (albeit it was feat Nagato could only accomplish thanks to his Rinnegan). He also and proficiency in Water and Wind Release plus Yin and Yang Release.

Toad Techniques
Jiraiya was known as the "Toad Sage", due to his natural affinity for toads, and his utilisation 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 œsophagus 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. Due to his training with toads, he even gained the ability to spit oil from his mouth.

For spying and infiltration, Jiraiya had the Toad Flatness — 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. Kakashi noted that Jiraiya was a specialist when it comes to infiltration and espionage tactics.

Fūinjutsu
Jiraiya had been shown to be very skilled and otherwise 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. Jiraiya easily recognised the Five Elements Seal that Orochimaru had placed on top of Naruto's seal and how it was distorting Naruto's chakra and easily removed it with Five Elements Unseal.

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 utilise the Fire Sealing Method to contain even Itachi's Amaterasu within a scroll for future study.

Chakra
Like Naruto, Jiraiya naturally possessed exceptionally large amounts and strong levels of chakra and stamina. Its potency was able to make Naruto back down from chasing after Itachi and Kisame with a single glare and chakra spike. Even with his ability to mould chakra weakened by Tsunade's poison, he could create a swamp which sank one of Orochimaru's massive snakes (two in the anime) and kept it completely immobilised throughout the battle. Though by Jiraiya's own admission, the technique had failed to some extent.

He has also shown an extremely high level of chakra control as well. He could use the Rasengan in a single hand, or two at once as well as effortlessly displaying each stage of the technique to Naruto. Even after being stabbed five times by the Six Paths of Pain's Chakra Disruption Blades, he was able to use the Finger Carving Seal despite Nagato's disruptive chakra circulating through his body.

Senjutsu
Jiraiya's chakra reserves were large enough to learn the Mount Myōboku teachings of senjutsu — an alternate combat style that utilises natural energy in unison with his chakra to greatly increase his overall abilities. The pinnacle of his skill is to enter Sage Mode, a transformation that allowed him to harness natural energy inside of himself to immensely augment his physical parameters. This form enhanced his strength to the point of destroying the Human Path's eyes with just a kick to the face, while also sending him several metres away. Likewise, his speed was enhanced to the point where he could leap down from a high vantage point and form an attack, before his sandals — which had fallen before he jumped — had even reached the ground.

Due to the limited nature of using Sage Mode on his own as one must remain absolutely still to gather the necessary natural energy, while before entering it, Jiraiya will summon the elder toad couple Shima and Fukasaku and have them fuse to his body and absorb the energy for him. 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, webbed hands and feet and sharp teeth, all of which made him unappealing to girls. This appearance is due to Jiraiya not having complete mastery over the technique.

In addition to maintaining Jiraiya's natural energy while he fought, they added their own abilities to help him in battle. Sage Mode greatly increased Jiraiya's physical power, as shown by his ability to send Pain's summons flying and use the extremely powerful collaboration ninjutsu Sage Art: Goemon. This form allowed Jiraiya to use stronger versions of his other techniques. An example would include the Ultra-Big Ball Rasengan, a massive variant of Rasengan even larger than his own body. Though unseen, this version is supposedly strong enough that if it exploded, it'd have destroyed an entire mountain. As Jiraiya was not adept with genjutsu, he relied on Shima and Fukasaku to help him in that aspect.

Intelligence
While he would normally come off as goofy, Jiraiya had repeatedly shown himself to be a shrewd man. His intelligence enabled him to track Orochimaru and Akatsuki through the years, and he headed his own spy network all over the Five Great Shinobi Countries for this purpose. He was very knowledgeable in various techniques, able to quickly recognise them and know how to counter them. He also demonstrated being a capable teacher, as even Itachi acknowledged Naruto's growth under Jiraiya's tutelage for three years. Jiraiya was also very skilled in information gathering, as he would constantly relay any important intelligence he acquired to his allies.

Chūnin Exam Arc
Having spent years gathering information on Orochimaru and Akatsuki, and having considered the possibility they were after Naruto with the goal of obtaining the Nine-Tails, Jiraiya returned to Konoha with the goal of preparing Naruto for the upcoming threat. 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 become his trainer 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.

Invasion of Konoha Arc
When Orochimaru began his invasion of Konoha, Jiraiya summoned Gamahiro to stop Orochimaru's snakes. He later mourned the Third Hokage's death, but decided not to 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 team-mate, 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 Summoning: Toad Mouth Bind 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.

Pre-Shippūden Filler Arcs
Jiraiya appeared in a few episodes and was a major character in the Land of Rice Fields Arc, in which he travelled with Naruto and Sakura in search of Orochimaru's hideout. The trio were unable to locate Sasuke, but managed to free the Fūma clan from Orochimaru's control. He later appeared in Please, Mr. Postman!, and was present in Departure to take Naruto away for his training.

Kazekage Rescue Arc
Jiraiya and Naruto return after two and half years of training and goes to Tsunade about how much progress Naruto has made. He later meets up with Kakashi with information about Akatsuki and gives him a seal to Naruto's transformation. Before Naruto's departure to retrieve Gaara, Jiraiya warns Naruto to refrain from using his inner power.

Sasuke and Sai Arc
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-tailed form, 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 Arc
In the anime, Jiraiya returned to Konoha to congratulate Naruto on defeating Akatsuki's Kakuzu and Deidara. 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 synchronised, collaboration jutsu and began by demonstrating a synchronised technique, the Water Release: Water Gun technique, in collaboration with Gamariki.

When Naruto and Gamariki proved unable to synchronise, due to their conflicting personalities, Jiraiya confronted Naruto with the fact that, unless he can work with a summoned toad, a collaboration techniques 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 on a synchronised technique 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.

Itachi Pursuit Arc
His meeting with Tsunade and Shizune, is cut short when Naruto and Sakura enter the office. Surprised that his master had returned to the village, Naruto informs him that he finally mastered the collaboration technique with Gamakichi and Gamatatsu, impressing him. After discussing on how to capture Itachi Uchiha, Jiraiya and Tsunade got to the front gate to see the Eight Man Squad off. After Deidara's death, 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 captured two Rain villagers while there, and sent one to Konoha to be interrogated. After hearing that the Akatsuki leader, Pain, killed Hanzō 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 eventually found Konan, and after incapacitating her with his oil, questioned what happened to her, Yahiko, and Nagato. Suddenly Pain appeared and Jiraiya recognised him as his former student, Nagato, because of his Rinnegan. Fearing that his student would destroy the world, as was warned against in the prophecy, Jiraiya tried to kill Pain. After summoning Gamaken to protect him from various summons, 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 with a powerful genjutsu, Jiraiya was handicapped when Pain's Asura Path ambushed Jiraiya and somehow severed his left arm. The Asura Path was joined by the other five paths, with the first three having been reanimated. Doing the most that he could without his arm, Jiraiya managed to kill and capture the Animal Path, and ordered Shima to leave and 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, Jiraiya was able to discover the truth, but his throat was crushed by the Asura Path and he was pinned down to the ground by the other paths, leaving him unable to tell Fukasaku what he had learned. As his life waned, he mused over his death, calling it unworthy compared to the Hokage and flashed back to his life and his failures, failing to win Tsunade's heart, failing to stop Orochimaru from leaving Konoha, and failing to protect both his master Hiruzen and his student Minato Namikaze. But when he remembered how Minato called his book a success and decided to name his son after the book's protagonist, Jiraiya realised that it was he who named him Naruto.

Seeing that the student's way should also be the teacher's way, Jiraiya realised that Naruto, not Nagato, was the child foretold of in the prophecy. Knowing that Naruto would someday save the world, he forced himself back to life and inscribed a coded message into Fukasaku's back and sent him to Naruto. When the Asura Path saw the coded message on Fukasaku, he attacked him with a rocket hand, destroying the rock Jiraiya was lying on, making him fall into the water. As Jiraiya died, he compared himself to the "Frog at the bottom of the well… Drifts off into the Great Ocean", calling it a more honourable death and realised that he needed a title for his next book. Finding the title "Tale of Naruto Uzumaki" perfect, Jiraiya died with a smile while sinking into the watery depths of the battlefield.

Konoha History Arc
Jiraiya and Naruto have left Konoha to begin their three-year journey. As they walk, they talk about Naruto's need to overcome Sasuke's Sharingan. During a genjutsu practice, Naruto tries to disrupt his inner chakra flow, but instead, creates a wave of chakra around him thus hitting Gamariki in the physical world. To overcome this part of the training, Jiraiya takes Naruto to the Genjutsu Tree Village. After realising that the village was taken over by a man named Kandachi, Naruto and Jiraiya decide to liberate the village. As the final battle with Kandachi continued, Jiraiya and Naruto got trapped in the Conch King's Water Release Genjutsu: Mystic Fog Prison but later managed to escape thanks to Tanishi's Chilli Pepper Bomb. At the end of the battle, Naruto defeats Kandachi with his Big Ball Rasengan.

Adventures at Sea Arc
Decades earlier, Jiraiya encountered the leader of the Nadeshiko Village, as he trespassed into her village to do "research" for his next novel. After he escaped, she pursued him and challenged him to a duel for his hand in marriage. This match was however postponed, as neither party was making headway against the other. Jiraiya promised that their students instead should one day seek each other out and fight if the two never met again. This promise fell to her student Shizuka and Jiraiya's last pupil Naruto Uzumaki.

Legacy
Although the next arc played out after his death, Jiraiya still had a great impact on the events that happened during it. With the message that he left on Fukasaku's back "the real one isn't among them" allowed Konoha to learn the nature of Nagato's Paths of Pain technique which ultimately helped Naruto Uzumaki in defeating Nagato's paths before facing him in person. Having inherited their mentor's ideals of peace being gained by ending hatred, Naruto convinced Nagato to redeem himself in the end.

Soon time after, Naruto created a memorial to Jiraiya in the woods near Konoha, adorned with symbols of high importance: A rock with the kanji for, Jiraiya's first novel The Tale of the Utterly Gutsy Shinobi, and Konan's bouquet of "never-dying flowers of hope". Later on, Kabuto revealed that he attempted to retrieve Jiraiya's body to bring him back through Summoning: Impure World Reincarnation, but it was far too deep in the ocean for him to reach without being crushed by the water pressure. However, he noted that Tobi should still have enough DNA on the Six Paths of Pain's weapons but was refused.

Later during the Fourth Shinobi World War, Tsunade noted that Jiraiya would not have died if Orochimaru had changed. Orochimaru countered that even if he had lived Jiraiya would have changed instead of dying without changing. Betrayed by Nagato and defeated by Naruto, Obito comes to the conclusion that with the two as the disciples of Jiraiya, the Sannin was the one who defeated him in a sense.

Naruto the Movie: Ninja Clash in the Land of Snow
Jiraiya had a brief appearance in the flash back when Naruto was thinking about his friends.

Naruto Shippūden 2: Bonds
Most of Jiraiya's appearances 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. In the end, Jiraiya finally made a physical appearance by saving his apprentice and Amaru from certain death by summoning Gamabunta to cushion their fall.

Naruto Shippūden 3: Inheritors of the Will of Fire
Jiraiya met with a group of Sunagakure shinobi and talked with Gaara. Later, he took a message from Gaara to a ravine, where Suna and Konoha forces were ready to battle. He stayed there and talked to Tsunade after Suna withdrew from the war.

Naruto Shippūden 4: The Lost Tower
Jiraiya called Minato aside to show him he learned to perform the Rasengan. Unfazed, Minato simply congratulated him and left, much to Jiraiya's confusion.

Naruto 6: Road to Ninja
In the Genjutsu World, Jiraiya died trying to procure the Red Moon Scroll which the Great Toad Sage foretold will help defeat the Masked Man.

Creation and Conception
Jiraiya is named after the character of the same name from a Japanese folklore. The Jiraiya in this story is vastly different than his manga counterpart in terms of personality and relationships, however both individuals 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 shares the same blood type with his former team-mates, Tsunade and Orochimaru, as well as his former apprentices, Naruto Uzumaki and Minato Namikaze.
 * In a special episode, The Top 5 Ninja Battles!, Jiraiya was intended to have an interview, but Orochimaru popped up next to him instead.
 * Despite no canonic source ranking him, in the anime, he was revealed to be a jōnin.
 * Studio Pierrot's Settei sheets of Jiraiya show that he was 153 cm when he was part of Hiruzen's genin team, they also show that his sandals add 7 cm on to his height.
 * According to the databook(s):
 * Jiraiya's hobby was sneaking a peek into a Women's Bathing House.
 * Jiraiya wished to fight Naruto Uzumaki.
 * His favourite food was garlic pickled with Japanese basil and karaage-fried chicken, while his least favourites were kiwifruit and gratin.
 * Jiraiya completed 1,839 official missions in total: 58 D-rank, 345 C-rank, 684 B-rank, 614 A-rank, 138 S-rank. With this rating of mission completion by Jiraiya, he has the most completed missions of all characters in the entire Naruto series.
 * Jiraiya's favourite phrase was.
 * Jiraiya is tied with Itachi Uchiha as having the highest stats total in the databook.
 * Jiraiya's last words were based off of a Japanese proverb 'I no naka no kawazu taikai o shirazu' which translates literally to 'A frog in a well does not know the great ocean'.
 * Although Jiraiya is always seen using his trademark horned forehead protector with the kanji for, he is briefly seen using the standard Konoha's forehead protector during a flashback with Kakashi regarding's Tsunade bust size.
 * It's unknown if this was a continuity error made by Kishimoto, since old Jiraiya always uses his horned forehead protector, and only used Konoha's when he was young.

Quotes

 * (To Tsunade) "Yo! I'm Jiraiya! You can send me the love letter later!"
 * (To Nagato) "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 Naruto) "I'm not a pervert… I'm a super pervert!"
 * (To Orochimaru) "You're wrong, that's not what makes a shinobi. You never did get it, a real ninja is one who endures no matter what gets thrown at him… Let me explain something to you, there is only one thing that matters if you are a shinobi, and it isn't the number of techniques you possess. All you do need, is the guts to never give up."
 * (To Naruto) "Even I can tell that hatred is spreading. I wanted to do something about it … but I don't know what … but I believe… that someday the day will come when people truly understand one another!! If I can't find the answer, it will be up to you to do it!!"
 * (To Naruto) "They say wherever someone is still thinking of you, that place is your home."
 * (To Naruto) "I think we all have to acknowledge you. Gamatatsu, Gamakichi, Sakura, Tsunade… and I… we all admit you've worked really hard. But I wonder what's pushing you forward."
 * (To Tsunade) "Now my job is to help the next generation, and set a good example for them. And for that I'll gladly lay down my life, and I'll be smiling the whole time. It's what makes us old guys cool, you see."
 * (To Naruto) "Never go back on your word… and never give up. That's your ninja way… and as your mentor… I have no business whining! Because… the student's ninja way should be the master's too! Isn't that so, Naruto?!"
 * (Last words) "The true measure of a shinobi is not how he lives but how he dies. It's not what they do in life, but what they did before dying that proves their worth. Thinking back of it, my story is one full of failures. Tsunade rejected me every time. I couldn't save my friend, I failed to protect my student… and my teacher. Compared with the Hokage who came before me, my accomplishments have all been petty and insignificant. I wanted to die like them…"
 * (Last words) "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 honourable… pretty damn honourable… I guess it's time to put down my pen. Right… I need a title for the next book… let's see… Ah, got it… "The Tale of Naruto Uzumaki"… perfect."