Tear Jerker: Echoes

  • Jinchuuriki!Sakura's life in general: her own mother viewed her as a monster, and her teammates were killed in front of her by Kimimaro, leading to her totally breaking.
  • N's life: When the poor guy finally found a place where people were nice to him, his departure from Konoha triggered a global war.
  • Kazama's rampage through his Konoha, and his reaction after he snaps out of it.
  • Jiraiya's death in Chapter 46. Made especially tragic with the memory of Naruto he sees at the end of his life. It also draws several parallels with the Sandaime's death in canon, which just makes it all the worse.