Question: what is the saddest moment in naruto?
Answer: 8 Gaara's Sad Back Story. ... 
7 Sealing The Nine Tails. ... 
6 Minato's Final Farewell. ... 
5 Hinata Confesses Her Love. ... 
4 Neji's Death. ... 
3 Naruto Vs. ... 
2 Itachi's Death(s) ... 
1 Jiraiya's Death. Naruto didn't often kill main characters but when it did, the impact was keenly felt.