Naruto Uzumaki, as the protagonist of the Naruto series, holds a place as one of the most incredible characters in the story. With the goal of becoming the Hokage of his villiage, Naruto embarks upon quite a difficult journey against all odds but by the end, he conquers every obstacle in his way.
However, while Naruto has come a long way, his journey certainly hasn't been easy. In fact, he's failed on several occasions throughout his life as a ninja, learned from his failures, and only gotten better. After all, if he succeeded every time, there would be no tension or excitement whenever he faced a new challenge.
8 At The Academy
Naruto's time at the Academy was certainly not the best, as he failed on more than one occasion before finally graduating. Naruto also failed at the shinobi Kumite exercises that he engaged in, but his worst failure came when he failed to graduate for, presumably, the second time.
Thankfully, after saving Iruka, Naruto was then passed and was able to become a Genin. Had the fight against Mizuki not come up, Naruto would still have remained a Genin and his friends would all have been a step ahead of him.
7 Against Rock Lee
Shortly after returning from the Land of Waves, Team 7 decided to take part in the Chunin Exams to improve and test themselves against the strong Genin from other teams and villages. Rock Lee, being one of them, openly challenged Sasuke Uchiha and Naruto, being hotheaded as he is, challenged him back.
However, Naruto lost to Rock Lee in the most embarrassing fashion. Despite having become quite strong, it was very easy for Lee to overcome him and even Sasuke Uchiha moments later.
6 Failing To Stop Sasuke
One of the failures that Naruto laments the most is when he failed to stop Sasuke Uchiha from leaving Konohagakure. The two met in the Valley of the End and fought each other in what appeared to be a battle of destiny, which was eventually won by Sasuke Uchiha.
Despite Naruto being incredibly powerful at this point thanks to the Nine-Tails chakra, Sasuke edged him out and left the village to seek more power from Orochimaru. Naruto's failure to stop Sasuke drove him to become even stronger. As soon as he recovered from his injuries, he left to train with Jiraiya, and got much stronger during the timeskip.
5 Bringing Sasuke Back From Orochimaru's Hideout
After the two-and-a-half year timeskip, Naruto returned to Konohagakure having become much stronger than he once was. His improvement was staggering, and even Kakashi Hatake was impressed by how far he had come. Yet, none of this was good enough for him to stand up to the likes of Sasuke, who had reached levels of a Kage already by this point.
When the two met after the Tenchi Bridge mission, Sasuke easily outclassed the entire team and left Naruto in the dust once again. Once again, this served as a reminder that Naruto Uzumaki was, in fact, quite weak and needed to get much stronger to catch up to Sasuke.
4 Failing Protect Everyone During Pain's Assault
Pain's Assault arc proved to be the biggest turning point for Naruto Uzumaki. It marked the point when he went from being just a boy who wanted to become Hokage to someone who wanted to bring peace to the entire ninja world.
Before Naruto even traded blows with Pain, however, the leader of the Akatsuki had already blown up the village, killing several people in the process. When Naruto arrived, the damage was already done. Even though Pain later brought all those he killed back to life, Naruto wasn't able to protect them from experiencing pain.
3 Trying To Convince The Raikage
Naruto's love and care for Sasuke Uchiha knew no bounds. When the latter was declared a criminal after the attack on Killer Bee, Naruto wanted to personally ask the Fourth Raikage of Kumogakure for forgiveness and to allow him to deal with Sasuke on his own.
Being the stern man that he was raised to be, the Raikage immediately denied the request. This led Naruto to hyperventilate and eventually pass out.
2 Failing To Save Neji
In the Fourth Great Ninja War, Naruto Uzumaki tried his utmost best to save every single shinobi that fought alongside him from death when they faced Obito and Madara Uchiha. Sadly, his efforts weren't enough as Neji, one his best friends, died before him. This was one of the most painful losses he faced.
Along with Neji, countless others were brutally massacred by the two in an attempt to break Naruto Uzumaki. However, thanks to Hinata, Naruto was able to move forward from their losses.
1 Failing To Keep Obito From Dying
Obito Uchiha was redeemed towards the end of the Fourth Great Ninja War. After being saved by Naruto Uzumaki, he tried his best to put the war that he started to end, and do whatever he could to help Naruto to bring peace to the world and succeed as the next Hokage of the village. Against Kaguya Otsutsuki, however, Obito Uchiha gave his life up to save Naruto from imminent death, sealing his fate in the process.
Naruto, while he had grown quite strong at this point, failed to protect him. Nonetheless, Naruto kept his promise and defeated Kaguya Otsutsuki, following which he restored peace to the world. Eventually, he became the Seventh Hokage of Konohagakure.
