From Episode 1 (Enter: Naruto Uzumaki!), we realize Naruto is a natural prankster, as he sprayed graffiti over the Hokage rock, but he does not only act alone. On Episode 101 (Gotta See! Gotta Know! Kakashi-Sensei's True Face!), Naruto involves Sasuke and Sakura in a plan to find out what’s behind their teacher, Kakashi’s, mask. So, the guy is impulsive, right? Naruto is constantly jumping into trouble! Even as the Konoha villagers usually mistreat him, Naruto enjoys the attention he receives as a result of his pranks without measuring the consequences, nor taking into account that the attention is negative.

Sadly but comically, Naruto is also tricked back. In the same Episode 1, Professor Mizuki told him that if he stole the Scroll of Seals, he would keep his spot at the ninja academy. Also, in Episode 177 (Iruka’s ordeal), the kids Naruto pranked in a cemetery tricked him back into believing he was going to be accepted in their gang. So we can see how his desire to be accepted made him jump ahead into trouble.

Naruto’s impulsiveness sometimes comes out for the sake of others, for example on how he defended Hinata on their first day of school, or how he decided to compete against Sasuke as soon as he noticed that Sasuke was popular. But all in all, Naruto did not measure the consequences of his acts, so he was a constant headache for his teachers at the academy.

Then Jiraiya came, and Naruto finally found the ninja master he needed, as we will see in the next reasons…

Enter Jiraiya, one of the Sannin. The legend says there were three ninjas from Konoha village with notable power and abilities, and Jiraiya was one of these warriors. At the Second Shinobi World War, the Sannin were the only surviving ninjas from Konoha at one point. Jiraiya entered into the anime much later because he was living in retirement, tracking Orochimaru’s movements.
So, in short words, Jiraiya is a relaxed sage, as he does not like responsibilities. He has been offered the post of Hokage but always refuses it, preferring a more aisled life. Jiraiya’s light heart and way of making people uncomfortable to only make them laugh later, have won him a curious reputation and several nicknames. Above them, of course, we can find “The village madness”. Jiraiya would rather spend his time making jokes and causing trouble than be responsible.

It is natural that such personality did not appall when Jiraiya first met Naruto in episode 52 (Ebisu Returns: Naruto's Toughest Training Yet!). Our protagonist was under Ebisu’s tutelage at that time, who was easily defeated by Jiraiya at the end of the episode. Impressed by him, Naruto demanded that he became his teacher and comically pursued him around the village when he refused, which takes us to our following reason…

No way to deny it. Naruto has his mischievous side which complements with his curiosity the female figure, so he has been seen attempting to peep into women’s baths. Naruto has also perfected the Sexy technique, which he used to convince Jiraiya to become his teacher. And… it worked! Naruto transformed into a cute, naked girl and thus began his apprenticeship under his new teacher, Jiraiya, who surrounded himself with a bunch of ladies while Naruto trained.

It is also known later that Jiraiya invented the Transparent escape technique, which is shown for the first time in episode 307 of Naruto Shippuden (Fade into the Moonlight) in the context of the Shinobi war. Jiraiya normally uses his technique to peep on unsuspecting women, though.

And how about the Icha Icha perverted novels, which also happen to be written by Jiraiya? We also see Naruto completing a volume of them in episode 177, in order to pursue his ninja training with his teacher.

These pair are just… so much like the other ^^U

As Jiraiya is seen as a perverted sage for most of Naruto’s story, it is often forgotten that he once was a ninja in training. On episodes 127 and 128 from the Naruto Shippuden arc, we can see how he ended up in Mount Myokobu due to a failed ninjutsu technique he was practicing. He had all sorts of weird adventures there but succeeded in the end. Jiraiya wrote his first novel, The Tales of the Gutsy Ninja, based on his adventures.

Sadly, Jiraiya’s first book was not successful, but guess who loved it? None other than his student Minato Namikaze, who happens to be Naruto’s father! Minato and his wife Kushina decided to name their future son as the main character of the book, hoping that he would be as determined as the protagonist. This made into Jiraiya a sort of Godfather for Naruto, who ended up resembling the novel’s protagonist… and Jiraiya himself, of course!

Master and student share a love for eccentricity. Naruto usually talks in a loud, excited voice and uses nicknames for people. Jiraiya loves to make dramatic introductions of himself. Then, Jiraiya and Naruto both pose and like to have fun. Yet, their unorthodoxy has been helpful to accomplish their ninja missions.

For example, in episode 81 (Return of the morning mist) Jiraiya offers to find his former Sannin companion, Tsunade, to occupy the post of village’s Hokage. And guess who was appointed to help him with this mission? None other than Naruto, who was uninterested until Jiraiya offered to teach him a jutsu stronger than Sasuke Uchiha’s Chidori. Here we can see that Jiraiya knows how to persuade him, which was fortunate, as Naruto’s exuberant personality helped convince Tsunade that her deceased comrades’ dreams of a peaceful Konoha were worthy of being pursued once more. So yup, mission accomplished.