Complete Monster/When They Cry

""I am the cruelest witch in the world. I will make any opponent of mine surrender without fail. Even if that opponent is the Endless Witch Beatrice. So you must do your best as well. You won't bore me, will you?" — Bernkastel describing herself very accurately." The When They Cry franchise has had its fair share of Ax Crazy Serial Killers, evil witches, and rapists galore. Here are the worst of the worst.

Higurashi no Naku Koro ni

 * The orphanage leader from Miyo Takano's past was quite a despicable bastard. He kept children in line by fear, whipping the disobedient ones while others could hear them. There's a scene where one boy accidentally spills his ink, so the leader forces the boy to eat it. It's his treatment that helped turn Miyo Takano into a delusional psycho herself, since she was even forced to clean a filthy outhouse with her mouth and saw one of her friends turned into chicken feed by this guy!
 * The people working for him at the orphanage are just as bad. In the manga (and probably sound novels), which was excluded from the anime, probably due to censorship or not having enough time, they're shown to kill and abuse the children in horrifying ways. Like what they did to Takano's best friend Eriko, using rabid animals to kill her for no real reason.
 * Teppei Houjo is also a Child Hater who commits child abuse in inventive and chilling ways. Not only is there evidence he raped his own niece Satoko, an 11 year old, he 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, and murdered Rika, another child for getting involved. He's also a swindler, embezzler, and Loan Shark who not only displays a Lack of Empathy for lives he could ruin, but he takes pleasure in it. Even Takano considers him to be utter scum. And unlike most other characters, Teppei doesn't have a mental illness for an excuse - he's just a complete and utter asshole.
 * And of course there's Nomura. She could be viewed as the ultimate monster of the franchise as well. Being the Manipulative Bitch she was, she tricked Takano into helping her bio-weapon research and also indirectly influenced events that led to the Great Hinamizawa Disaster that claimed about 2,000 lives, all for no reason at all other than just to close up a company. And what's worse? She's a Karma Houdini.

Umineko no Naku Koro ni

 * Bernkastel. the Witch Of Miracles, is the worst offender. Starting at the end of Arc 4, she ends up with quite a laundry list of horrendous acts. Conspiring with Lambdadelta so that Beatrice is their own personal plaything is the least of these. In Arc 4 alone, she sets Ange up to have her life screwed over by the irreversibly fucked up at that point Eva and finds the result amusing. And for all her trouble, how does Ange get rewarded? By being RIPPED APART and presumably left that way. Bern and Lambda even JOKE about it. To top it off, Bern's only regret is that she lost a big advantage. Bernkastel has no trouble admitting that her only real pleasure in life remains the suffering of others, and it's something she creates with endless amusement. She ramps this up in Arc 5 when she invokes Decoy Protagonist and Hijacked by Ganon when Battler refuses to play along and pulls out an actual Expy of Rika named Erika Furudo to serve as the new Protagonist. And Erika herself is a Bitch in Sheep's Clothing who immediately points the finger at Natsuhi, who currently is not having a good day. Which gets WORSE, now that being implicated for the murders brings her sister-in-law Eva's wrath down on her as the victims include her husband and Morality Chain, Hideyoshi. She also leads Battler to the Gold Room, which makes him the next successor, adding fuel to the fire regarding his family's stake in the murders. And manages to successfully disprove Beatrice, with Battler unable to help since he's too busy being IMPALED. Then Lambda makes Battler the Golden Sorcerer, effectively cementing him in the role of the 'villian'. Naturally, Bern revels in this, until the point where Erika gets her ass kicked. She even has a smug 'Oh, did I piss you off?' look on her face at times.
 * Black Battler from Ougon Musou Kyoku CROSS is a negative palette swap of regular Battler who lacks the good-guy depths that his real counterpart does, not only talking about killing everyone on Rokkenjima but also suggesting 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.

Higanbana no Saku Yoru ni

 * Yoshihito Kanamori from "Mesomeso-san" (the first chapter) started as the homeroom teacher of Marie Moriya, a young girl bullied by her classmates. He used to defend her from the bullies, until the stress of his job got to him and he started to take his stress out on Marie. His supplementary lessons include molesting her and putting it on camera. When Marie gathered up enough courage to stand up to him, he strangles her to death, singing her a song about graduation from life to death while doing so, then dumps her corpse in the old school's septic tank. He also considered murdering other children when he thought that they were eavesdropping. When he encounters Marie's spirit in the restroom, he gives her a long The Reason You Suck Speech about her not going to the police to report on him while she was still alive and called her an imbecile who couldn't fend for herself. He then opens the door to one of the bathroom stalls, and upon finding that Marie has apparently physically manifested, he tries to strangle Marie a second time. When the deed was seemingly done, he proceeds to rape the corpse when he notices it was still there. While he claims that he did all this out of love for Marie, it's ultimately proven hollow.
 * Nafumi Shintani from Renoir of the Art Room was an art room teacher who seemed to be a Cool Teacher, given her popularity among the young male students. In reality, Nafumi was a prolific child molester who got off on the suffering of young boys, deeming it as beautiful. To this end, she invites young boys into the art room, and she would offer them cups of drug-laced tea, after which she would proceed to torture their unconscious bodies with cigarettes and palette knives. In addition to this, she had dozens of sketches of abused boys in her desk. One of her past victims, Yuuki Noda, loved his teacher to the point that he allowed her to abuse him if it meant his feelings for her were returned. Eventually, Yuuki tried to escape her, but she grabbed his shoulder, which caused him to trip and fall underneath a table, resulting in a heavy bust falling on his head. A week later, she drugged and attempted to torture another boy, but she was stopped by the titular Renoir of the Art Room (who was really Higanbana filling in for the real Renoir). She expressed zero remorse for being indirectly responsible for Yuuki's death, stating that he was a "stupid kid" who deserved to die. Depraved and perverted, Shintani repeatedly showed that she cared only for herself and her lusts.