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Tear Jerker: X 1999
Where to start?
Karen's backstory is kind of heartwrenching.
Seishirou's death and the aftermath of it. That's all.
Kotori's death made this troper cry so much in the manga.
If anything, it's even wose in the TV series, because Kotori's soul actually manages to say goodbye to Kamui himself and relay her hope-filled Famouslast Words to him before going to Heaven.
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.
Kakyou Kuzuki is a freaking walking tear jerker. If anything, he was already a woobie in the manga but the anime amped this Upto Eleven upon making him an Ascended Extra in the OAV — not only it explains his backstory and reasons, but it shows him trying to save his Only Friend and sort-of girlfriend Hokuto before Seishirou offs her. And not only he fails, but he gets shot for all his trouble.My God...