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Tear Jerker: PMD-Explorers
PMD-Explorers is about as sad as it is dark, if not more so. From the apocalyptic destruction to death and depression, PMD-Explorers has something for everyone. Grab a tissue, becuase here comes the Tear Jerkers.
The Mission 6 Prologue, aka the Wham Episode of PMD. If you thought PK would get a break after the destruction of Tao, you'd be dead wrong.Shroomsworth finds out that PK stole the Thistle Whistle from Arianna, ultimately leading to the death of the Elder Shroom. He leaves her with bitter words as PK begs him not to leave getting so depressed that she turns black for the first time in years.
The picture on the right is the cover art to the song Expendable. Why is it called that? GK had spare sap from the Tree of Life and also knew that one of his most loyal guards was mortally wounded. He let him die, anyway
Elder Shroom's death. Especially if you read the second doujin.
The sad story of Charles the Rattata. A blind Rattata, he befreinded PK shortly after all of her "friends" left her in a game of Hide and Seek. After spending more time with him, PK realized he was feeling worse and worse until finally PK discovered he had an almost uncurable disease and was on his deathbed. There was only one cure for Charles at that point, the Life Tea, which can only be made from Gracedia Flowers. Unfortunately, he dies before PK could get even a small fraction of the money for a journey there, and picks up his disease soon afterwards. It's made even more sad by his theme, Chances by Changes.
A meta example: The group closing September 2013. Especially sad for those who had been with the group since the beginning, or for people who never got to get out their final stories or comics.