"When they're alive, you can enjoy watching them struggle. When they're dead, you can enjoy tearing out their guts. Tales are things you get to enjoy twice."The When They Cry franchise has had its fair share of Ax-Crazy serial killers, evil witches, and other monstrosities. Here are the worst of the worst. Franchise-wide unmarked spoilers ahead
—Spoiler Character, Umineko
- The leader of the Orphanage of Fear in Miyo Takano/Miyoko Tanashi's past was a sadistic disciplinarian who believes in brutalizing the children by whipping any he deemed "disobedient" so that the others could hear. When one boy accidentally spilled the ink in his pen, the orphanage leader forced him to eat the ink. Takano herself was even forced to clean a filthy outhouse with her mouth and saw one of her friends turned into chicken feed.
- Teppei Houjo is a Child Hater who commits child abuse in inventive and chilling ways. Not only is there evidence he raped his own niece Satako, an 11-year-old, he also forces her to strip naked so he can use her for a "table" and humiliate her; he regularly uses psychological torture on her as well. He also murdered Rika, another child, for getting involved.
- Nomura, despite having very little screentime, plays a major role in the plot. She tricks Takano amidst her Despair Event Horizon into helping her, helping to indirectly cause the Great Hinamizawa Disaster note . This is all to achieve her goal of closing up a competing company.
- Bernkastel, the Witch Of Miracles, reveals herself as a cruel sadist over the course of the story. Embracing her role as Big Bad in the fourth arc, Bernkastel set up Ange Ushiriyoma to have a hell of a life in order to manipulate her as a pawn later on before deciding Ange is of no further use and leaving her to turn into shredded meat. In the "game" on Rokkenjima island, Bernkastel introduces a pawn named Erika Fudo to mentally torment the mentally fragile Natsuhi by accusing her of being the murderer. She helps the elimination of the Golden Witch Beatrice to seize control of the game and cement the protagonist, Battler, in a forced role of villain. Bernkastel's only real pleasure in life remains the suffering of others, and it's something she creates with endless amusement.
- Ougon Musoukyoku CROSS: Black Battler, who also appears in "Forgery no.XXX", is a negative palette swap of regular Battler Ushiromiya who lacks the good-guy depths that his real counterpart does. Not only does he talk about killing everyone on Rokkenjima, he also suggests to female characters that he's going to rape them, and he "tastes" male characters. He has a wicked habit of killing anyone he feels like killing, strictly For the Evulz, and laughing about it.