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Tear Jerker: The Binding of Isaac
The whole premise of the game is pretty bad what with Isaac's mother wanting to kill her son. It doesn't help that Isaac is crying throughout the game.
Ending 13, It depicts Isaac, his pre-insanity mother, and a skinny man who's presumably Isaac's dad, the first few pictures are of all of them living happily, then it gets dark, it shows Isaac crying by a chest, a demonic him in the mirror, and the very last photo? Isaac, with his mother setting her hand on his back to comfort him, looking out to the hill where an earlier picture showed the family picnicking at, that now houses a lonely grave, The End.