Jiraiya is one of Naruto's most beloved characters. As a Toad Sage and one of the Legendary Sannin, Jiraiya held an impressive reputation known throughout the Hidden Villages. After fighting in the Second Shinobi War and passing on the Will of Fire as a sensei in Konohagakure, he spent most of his life (outside of his occasional expert espionage work) traveling and writing his popular Make-Out novels. While doing "research" for his latest novel he caught Naruto's attention. Naruto recognized his incredible abilities and harassed Jiraiya into training him. He reluctantly agreed, and the show's best student-teacher relationship was born.

Fans learned a lot about Jiraiya through his relationship with Naruto. It's through these interactions that fans became emotionally attached to his character. He not only trained Naruto's father Minato, but inadvertently named Naruto and declared himself his godfather. Jiraiya was a kindhearted and powerful shinobi that helped Naruto become the unstoppable force he is today, and fans will be forever grateful.

10/10 "A Sage Doesn't Go Back On His Word."

Jiraiya begins training Naruto

Naruto's first impression of Jiraiya set the tone for their relationship. Despite Jiraiya's questionable private activities, Naruto was impressed by his strength and demanded that Jiraiya train him. He eventually gave in and agreed to train Naruto.

Naruto was overjoyed and wanted to confirm his concession. Jiraiya put his mind at ease by telling him "a sage doesn't go back on his word." He gave Naruto his first lesson in that moment and helped him control his chakra enough to be able to walk on water.

9/10 "My Duty Is To Be A Model For 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."

Jiraiya Last Dinner With Tsunade

Tsunade knew tracking the Akatsuki alone was dangerous, but Jiraiya was a master of espionage and worked better alone. Still, they both knew this mission was different and it could claim his life. As they discussed the risk Jiraiya was prepared to take, they reflected on their lives. Tsunade apologized to Jiraiya for always getting "the short end of the stick."

Jiraiya didn't regret tracking Orochimaru for years, passing up becoming the Hokage to recruit Tsunade, or preparing to find the Akatsuki's leader alone. He believed in leading by example and was proud to put his life on the line for the sake of his loved ones and his village.

8/10 "There Is Only One Thing That Matters If You Are A Shinobi, And It Isn't The Number Of Jutsu You Possess. All You Need Is The Guts To Never Give Up."

Jiraiya, Tsunade, and Orochimaru Showdown

The Legendary Sannin Battle brought former friends and teammates, Tsunade, Orochimaru, and Jiraiya together after spending several years apart following different pursuits. The three former Team Hiruzen members displayed their incredible skills and showed fans how they received their titles. Jiraiya and Tsunade fought to stop Orochimaru from continuing on the sinister path that caused innumerable deaths and endless suffering.

As they fought, they exchanged words and detailed their conflicting philosophies. Orochimaru measured a shinobi's worth by the jutsu or genjutsu they possessed, he believed a shinobi should endeavor to "use and master all the jutsu of the world." Jiraiya responded by informing his former comrade that he was still misguided. Jiraiya understood that a shinobi's ability had nothing to do with becoming a ninja – a ninja is simply "one who endures."

7/10 "A Ninja's Life Is Not Measured By How He Lived, But Rather What They Managed To Accomplish Before Their Death."

Jiraiya smiling At Tsunade

As a writer, Jiraiya valued an epic tale. He was constantly trying to augment his storyline. As he died, he thought about his failures: his rejection from Tsunade and his inability to save Orochimaru. Jiraiya always tried to better the situations he came across.

As a sensei, Yahiko, Nagato, Konan, Minato, and Naruto were pupils he held dear. He helped them reach their greatest potential and wanted to see them improve the world. As a shinobi, he took it upon himself to embark on dangerous journeys to try to save his friend Orochimaru and track formindable enemies to ensure Konohagakure's safety. He stated he wanted to obliterate his failures and die like a Hokage. In the life he led and in his last moments, he did just that.

6/10 "A Place Where Someone Still Thinks About You Is A Place You Can Call Home."

Naruto falls asleep on Jiraiya

Naruto and Jiraiya had similar plights. They wanted to save their friend Sasuke and Orochimaru, respectively. While recovering at a local hot spring, Jiraiya watched Naruto with admiration. While he "gained a sense of helplessness and regret," for not being able to save Orochimaru, Naruto lived with regret for 3 years, but didn't give up on Sasuke.

Naruto asserted that he needed to continue to train in order to become strong enough to bring Sasuke home. Jiraiya responded by illustrating that Sasuke would always have a home with him because he's never forgotten him.

5/10 "Rather Than Rule The World Through Pain... I Wish You Moved Past The Pain And Harnessed Your Power To Bring About Peace In A Positive Way."

Jiraiya with young Nagato

Jiraiya was shocked when he learned that his former student Nagato was the Akatsuki leader he'd been tracking. He was sad to see that the young, sensitive child that cried about wanting to protect his friends, became a ruthless villain. When Jiraiya finally obtained the upper hand in his intense battle with Pain, he expressed the disappointment he felt for the path his former pupil decided to take.

Jiraiya thought about the night he consoled Nagato as a child, he told him that understanding pain creates kindness and it "makes [them] human." He trusted that Nagato would understand this better when he grew up. Unfortunately, it took more time, several deaths, and Konoha's destruction for Nagato to learn this lesson.

4/10 "You Should Bet That I'm Going To Die. Knowing Your Luck You'll Definitely Lose."

Jirayiay says goodbye to Tsunade

Jiraiya's ominous joke to Tsunade foreshadowed his death. Before he left for his fatal mission, he spent time with Tsunade discussing their lives and reminiscing about the past. Tsunade's sadness and worry was obvious as she knew her friend might die.

Tsunade is a habitual gambler with bad luck. For her, winning is a bad omen. In an attempt to ease her mind and make her smile he told her to bet against him to ensure his safe return. Tsunade was surprised to hear him talk about his death so casually and his laughter made her feel uneasy. Tsunade finally displayed the love and affection Jiraiya always wanted from her.

3/10 "To Me It Feels As Though I'm Looking At My Grandson."

Jiraiya Last Words To Tsunade

Tsunade and Jiraiya discussed several things before he left, Naruto was one of them. Tsunade expressed her belief that Naruto would become Hokage and Jiraiya mocked her because Naruto had obviously won her over. Tsunade responded by reminding him that he set high standards for him as well by teaching him the Rasengan.

Jiraiya chocked up teaching Naruto Minato's signature move to nostalgia. He then told Tsunade that if Minato were his son he'd be proud of him. As such, Naruto's success and growth made Jiraiya feel as though he's watching his grandson excel. In teaching Naruto, "the will of the Leaf from the past to the future," was passed on.

2/10 "Never Give Up That Was The True Choice I Was Supposed To Make."

Jiraiya's Death

Though Jiraiya could've escaped with his life, remembering the Great Sage Toad's words encouraged him to stay and continue to fight Pain. The Great Sage Toad told Jiraiya that he would have to make a choice that would decide the ninja world's fate. He wanted to confirm Pain's identity to give his comrades the chance to defeat him.

When he confirmed his theory he was already dying. He was impaled and his throat was crushed. Pain was sure Jiraiya's heart stopped, but he began to rise. He used his last bit of strength to etch a coded message into Pa Toad's back. As he struggled to write, he thought about Naruto and his inability to give up. While he wrote, he reiterated that he couldn't give up and thought, "everyone knows a student inherits his ninja way from his teacher."

1/10 "Now... It's About Time I Put Down My Pen."

Jiraiya falling into ocean

Knowing that he delivered the message that would help Naruto defeat Pain, Jiraiya sunk into the ocean with a smile on his face. He revisited his former negative thoughts about his life and his failure. He now felt at peace and believed his life's story had an ending he could be proud of.

Jiraiya mentioned his sequel at dinner with Tsunade, he felt it was time he wrote it. He didn't believe his sequel would be his own accomplishments, but the accomplishments of his successor. As he sunk further into the ocean he thought about what his sequel's title should be. He decided on "The Tale of Naruto Uzumaki." Naruto would be the sequel to his incredible life's journey.