Touhou/Tear Jerker

In addition to its many laughs, horrors and beautiful moments, Gensokyo also has quite a few stories of heartbreak.

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• Mokou's backstory is tragic enough, especially when paired with her theme song.
• Yuyuko's backstory is just as bawl-worthy. Her ability was, at first, to manipulate spirits of the dead. As time went on, it grew stronger and stronger, to the point of being able to will death onto mortals. Terrified of her ability, she committed suicide, and her body was used to seal off a misfortune-bringing tree, which later lead to the events of Perfect Cherry Blossom.
  • The fan manga Touhou Tonari focuses on her and Yukari's back story and as one might expect, it is heartwrenching.
• While this is a fanwork, Cool&Create's S Complex puts a really tragic spin on the less memorable Aki sister, Shizuha. She loves her sister dearly, but feels left out and lonely because Minoriko is constantly being invited to feasts. Harsh words are said, and Shizuha's heart is broken.
• Double Scarlet tells a story about the Scarlet Sisters. At the beginning, Flandre and Remilia are lonely, so, with the help of Patchouli Knowledge, they go conquering lands and make friends with Sakuya Izayoi and Hong Meiling after besting them in battle. Over time, though, Flandre becomes more distant from Remilia, and is locked up in the basement. Patchouli shows Remilia a picture depicting the sisters holding hands that Flandre drew. Overcome with guilt, Remilia runs into the basement and shares a tearful and apologetic hug with the sister she's been ignoring for some time.
• The fancomic Red Sky of Japonesia, where Shikeiki passes judgement on Remilia for her crimes against her sister, has a massive double whammy in its second half: first, Shikeiki defeats Remilia in danmaku combat very thoroughly, completely shattering Remilia's facade of being an arrogant, in-control vampiress and causing her to scream for help in exactly the same way her sister did while locked in the basement, and making her realise the weight of what she did to her own sister; the second whammy comes when Flandre interrupts Shikeiki's judgement to forgive her sister of the crime of locking her away out of fear of her power to destroy, absorbing Shikeiki's danmaku barrage and giving her sister a tearful hug. It's difficult to hold the tears in after that.
• This image provides good clue to how Flandre really feels mixed with a small dose of High Octane Nightmare Fuel. It really makes one start to question her insanity.
• A remix of the ever-popular Cirno's Perfect Math Class song turns something cute, playful, and cheerful into a depressing scenario of a grown-up Cirno being Put on a Bus and sent into the big city, getting a job, and parting from her childhood friends. Fed up with work, she wishes for her old life and her friends to come back to her. Growing up really sucks, doesn't it?
• A yukkuri's story has never been more heart wrenching.
• The final stage of the fangame Concealed The Conclusion, where it is revealed that Reimu is dying, and when she dies, all of Gensokyo will go with her. After battling through countless foes, Marisa, perhaps Reimu's greatest friend, has to face her down in one final danmaku duel.
• Gensokyo being home to many races, there are naturally countless fan works dealing with the inevitable regarding the characters' lifespans.
  • The End of the Maiden's Illusion has this troper crying every time he even thinks about it.
  • The "Tragedy of Long Life" pool is 99% Sakuya, Marisa, and Keine dieing, and Remilia/Meiling, Alice, and Mokou (respectively) grieving.
  • Quite a few doujins and pics exist of Sakuya passing on and Remilia and the rest of the Scarlet Devil Mansion having to move on without her.
    • For those of you how are tired of a Sakuya dieing, and like their tear jerker with a side of nightmare fuel; try this.
  • Yuri couplings get them, too. A video of one with Alice.
    • Patchouli and others do not seem to try very hard to get their stuff back from Marisa. Leave it to fans to make Marisa's own rationalization that she won't live long enough for them to miss anything that much more depressing.
  • Amida Kuzu's long line of Mokou doujins includes one where she inevitably outlives Keine.
  • COOL&CREATE puts a tragic twist on the shy kappa Nitori, when she falls in love with a human.
• And of course the Maze animation.