Naruto V/s pain fight was one of the overpowered moments in the history of anime.
Naruto fights Pain in episode 163 of the anime. The ‘Pain arc’ introduced Naruto to his father, Minato. Hence, we all got to meet the ‘Yellow Flash of the Leaf‘ in this arc. Also, this arc was the most emotional of all. Naruto’s godfather and his Master, Jiraya- The Legendary Sanin lost to his student Nagato who possessed the Legendary Rinnegan implanted in him by Madara Uchiha. Whereas, our beloved Itachi sacrificed himself yet again to save Sasuke from Orochimaru’s curse and atone his sins for the ‘Uchiha Massacre.’ Itachi, in the end, died with a smile.