"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 Orphanage of Fear that Miyo Takano is sent to following the deaths of her parents is led by the seemingly kind Staff Leader, who reveals himself as a sadistic disciplinarian by pretending to console Takano, only to immediately slap her in the face. Reveling in the brutalization of children, the Staff Leader rules the Orphanage with an iron fist, dishing out punishments to those he deems "disobedient." His crimes range from being extremely petty—such as forcing a boy to eat ink after he accidentally spilled some—to downright cruel. When Takano and three other kids attempted to escape the Orphanage, he sentences them to grotesque punishments with Eriko—the ringleader of the operation as well as Takano's only friend— receiving the worst one. She is sent to the chicken coop wherein she is pecked to death by the ravenous chickens. Takano herself is then made to clean an outhouse with her tongue. Despite being relatively minor in the series, the Staff Leader left a lasting impact on Takano's life, ultimately warping her mind, and making her the psychopathic, Godhood-obsessed mastermind she is now.
- Teppei Ho(u)jo(u), while not on the same scale as other antagonists, more than makes up for it by being as despicable as possible. Teppei is made to care for his niece and nephew—Satoko and Satoshi respectively—after the deaths of their parents. A Child Hater to repulsive levels, Teppei subjects Satoko to a chilling series of abuse designed to humiliate and demean her. From forcing her to strip naked and using her as a table, to psychologically tormenting her, it's all but stated that he would indulge in sexually abusing her if she were older. Teppei commits embezzlement and fraud through badger games; uses his lover as a means of swindling men out of their money; and he takes sadistic delight from the ruination of their lives. Not above threatening people, Teppei murders Rika in one of the alternate worlds when she attempted to intrude. Selfish, cruel, and deplorable beyond belief, Teppei even manages to earn Miyo Takano's seething hatred.
- Nomura is, despite her limited screentime, the overarching villain of the series. A representative of the secret organization Tokyo, Nomura sought to topple the Old Koizumi faction. A skilled manipulator, Nomura tricks a despondent Miyo Takano into aiding her with her goals, claiming that she'd back her research in return. Working behind the scenes, Nomura masterminds the Great Hinamizawa Disaster, a catastrophic event in which a special forces unit is deceived into massacring over 2,000 people via improvised gas chambers. She then creates a cover up story, citing that sulfide gas spread throughout the town, killing everyone. Viewing Takano as only a tool, she attempts to dispose of her as to severe any loose ends, and ultimately leaves her to take all of the blame.
- 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.