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Tearjerker: X 1999
Where to start?
Karen's backstory is kind of heartwrenching.
Seishirou's death and the aftermath of it.
Kotori's death made this troper cry so much in the manga.
This troper, who saw the movie first, still cried at every death and Face Heel Turn, but absolutely wailed at the end of the TV series when she saw the different finale.
Kamui: So... I'll die... and entrust my wishes to you...
Saiki's, Nataku's, and Inuki's deaths were all very upsetting (but the last one comes back, so it's okay).
Sorata's death was saddening in the anime, and it was made even worse when Arashi paid a visit to the shrine where he came from and saw what he wrote, placing her head against it.
