History Monster / WebAnimation

** [[VisionaryVillain Jürgen Bennecke]] is the scheming Paneuropeanist put in charge of the European Military Administration, and the worst of the leaders to come to power from the Standstill. Leading the invasion of the USSR in a final crusade against communism, Bennecke strikes a deal with the [[CommieNazis Eurasian Liberation Movement]] to let them rule Russia in exchange for assistance, planning to backstab them later. After killing all European leaders but the French one, Bennecke orders his soldiers to [[RapePillageAndBurn burn the French fields alongside torturing, raping, and killing every Frenchman on sight]], beginning a systematic campaign of genocide on the French people that claims ten million lives by its end. When Domenico Corcione rebels against him for [[ThePurge killing multiple generals]] and his horrid rule, Bennecke threatens to kill all Italians for [[DisproportionateRetribution Corcione's coup]].

* ''WebAnimation/HarmonyAndHorror'': [[MonsterClown Martin Greywhinder]] is the depraved co-founder of M&H Harmony Toys. Once a loving husband, he grew hateful, abusive, and cruel when he learned that his wife had children with his brother. Martin [[DealWithTheDevil allied with demonic forces]] and aired a haunted TV program that horribly mangled the children who watched it. He also murdered his young intern, ripping her spine out. Martin kills his wife Gloria and shoots his brother, fusing him with an animatronic and forcing him to help murder Gloria's children, using Satanic rituals to force them into agonizing toy bodies. In his [[ControlFreak obsession with control]], he turns his dog into a monster and tries to force him to kill the infant Ava. [[SerialKiller Martin]] continues to kidnap, mutilate, and kill swaths of children, using their souls to make them into [[AndIMustScream living toys unable to die]].

* ''WebAnimation/EtraChanSawIt'''s "[[https://www.youtube.com/watch?v=wfp6OHgO_r0 My best friend suddenly passed away and his wife asked me to marry her]]": [[BitchInSheepsClothing This version of Hiiragi]] is seen as both a "perfect" guy and Kuroki's [[FalseFriend best friend]], but in reality this is just a mask to hide his true self. A notorious [[TheBully bully]] in middle school, Hiiragi either ordered or personally participated in bullying so severe that several students dropped out and one received a burn so severe it damaged his eye; Hiiragy acted like an angel in front of the teachers to avoid any punishment, but became feared by the rest of the students. Becoming a better actor in high school, Hiiragi still started dating Yuzuriha solely to get a reaction out of Kuroki, and became upset when the boy he was pretending to be friends with acted as if it didn't bother him. Learning that Yuzuriha inherited a large sum of money from her parents, Hiiragi [[GoldDigger proposed to her]] to take her money. When she saw through this and refused, Hiiragi raped her and force her to marry him, [[DomesticAbuse abusing and treating her like a slave]] for five years before his death. A horrible person who was not mourned by those who knew his true self, to the point they saw his death as karma, his actions continue to haunt his "best friend" and widow months after his death.

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* ''WebAnimation/MetaRunner'': [[MadScientist Dr. James Sheridan]], upon being revealed to have survived the lab incident, is the [[GreaterScopeVillain true mastermind]] of the series. Originally a scientist working for [=TASCorp=], he, under the threat of being terminated, initiates Project Blue as a means of revolutionizing the gaming industry. His ego bruised by [[CorruptCorporateExecutive Derek Lucks]] stealing the idea of the Meta Runner arm from him, Sheridan went into hiding, orchestrating events which climaxed in hacking Masa's arm to force him to shoot Lucks. After [[FrameUp incriminating Masa]], Sheridan joins forces with Evelyn Claythorne and tries to kill his creation Tari and revive Lucinia to make her part of his team. Torturing and brainwashing Belle and Masa, Sheridan's madness reaches its peak when he transfers all Meta Runners into his server to [[InvoluntaryBattleToTheDeath force them to kill each other]] over and over while their physical bodies decayed.

* ''WebVideo/CryptTV'''s ''WebAnimation/{{Woman in the Book}}'': [[StrawMisogynist Antonio Navarro]] is a renowned book publicist, known in his community as a [[VillainWithGoodPublicity loving and generous man]], but behind closed doors, is a deranged and misogynistic [[DomesticAbuse abuser]]. [[HeirClubForMen Obsessed with having a male heir]], Antonio kept his wife, Christina, captive in a dungeon, continuously raping her, and beating her when he discovers her writing material. Whenever Christina would give birth to a girl, Antonio would [[OffingTheOffspring murder the infant]] and cover it up with a stillbirth claim, before starting anew. After Antonio murders six of their daughters, he sneeringly tells Christina he'll let the next one live if it's a boy. When a broken Christina ends up drowning their son, Antonio drowns and smothers her to death. He then discovers Christina and his Curandera were working to expose him, and that the Curandera cursed made a curse to that Christina would live on; Antonio locks the Curandera in his dungeon, leaving her to die as he starts his search for a new wife to give him a new son.

* ''WebAnimation/AnimatorVsAnimation'': [[KnightOfCerebus The Dark Lord]] was created with the intentions of protecting the Animator's computer from dangers such as TheChosenOne, but instead turned against his creator and teamed up with his target to destroy the Animator's computer, killing every sapient program in it. Upon escaping into the Internet, the Dark Lord would terrorize and slaughter the citizens of various websites, before creating an army of {{Computer Virus}}es with the intentions of destroying as many computers as he could [[ForTheEvulz for no particular reason]], uncaring of how many programs would die because of it. When the newly-redeemed Chosen One and other animations try to stop him, the Dark Lord tries to kill his years-long friend, temporarily [[HeroKiller kills the Fighting Stick Figures]], and brutally injures the Second Coming. Wanting nothing more than to cause as much destruction as possible, the Dark Lord proves himself to be the most ruthless villain of the series.

* ''WebAnimation/HarmonyAndHorror'': [[MonsterClown Martin Greywhinder]] was the co-founder of M&H Harmony Toys alongside his brother. Even before his [[SerialKiller truly horrible crimes]], he was reported to not be the best father and had several allegations of DomesticAbuse and [[AbusiveParents child abuse]]. He eventually became obsessed with creating the "perfect toy"; to this end he made a DealWithTheDevil, to make his toys lifelike, but in order to do so, he had to kill, a deal that would result in the deaths of several children. Martin would begin his quest by killing his entire family. He would eventually switch to murdering random kids using his multiple costumes to lure them, kidnap them, and finally murder them. After all of these killings, he would use Satanic rituals to bind their souls to toys where they would still be conscious but unable to die.

** ''[[WebAnimation/RedVsBlueZero Zero]]'' (season 18): [[MyHeroZero Zero]], the leader of [[Characters/RedVsBlueZerosSyndicate Viper]], desired revenge against the Alliance of Defense for dropping the project GLASS and taking away his chance to be the leader of Shatter Squad. Desiring the Ultimate Power, Zero attacked several bases in order to steal artifacts and coordinates for temples, viciously slaughtering those who got in his way, having Washington tortured, and only sparing those who he wanted to trounce again in the future. Finally achieving his goal, Zero declared his intention to [[OmnicidalManiac "burn the world down" and "destroy everything"]], all to show off his own strength [[PsychopathicManchild out of petty spite]].

* ''WebVideo/{{Crypt TV}}'s'' ''WebAnimation/{{Woman in the Book}}'': [[StrawMisogynist Antonio Navarro]] is a renowned book publicist, known in his community as a [[VillainWithGoodPublicity loving and generous man]], but behind closed doors, is a deranged and misogynistic [[DomesticAbuse abuser]]. [[HeirClubForMen Obsessed with having a male heir]], Antonio kept his wife, Christina, captive in a dungeon, continuously raping her, and beating her when he discovers her writing material. Whenever Christina would give birth to a girl, Antonio would [[OffingTheOffspring murder the infant]] and cover it up with a stillbirth claim, before starting anew. After Antonio murders six of their daughters, he sneeringly tells Christina he'll let the next one live if it's a boy. When a broken Christina ends up drowning their son, Antonio drowns and smothers her to death. He then discovers Christina and his Curandera were working to expose him, and that the Curandera cursed made a curse to that Christina would live on; Antonio locks the Curandera in his dungeon, leaving her to die as he starts his search for a new wife to give him a new son.

* ''WebAnimation/TheLastLamia'': [[EvilutionaryBiologist Dr. Theodore Erswick]] is the sociopathic leader of Avatech's Project Ascension. After forming a [[DealWithTheDevil Faustian deal]] with a tribe of Lamias, he has them kidnapped from their beds at night to [[PlayingWithSyringes conduct excessive experiments]] and ElectricTorture on them, then wipe their memories so that his pact can remain intact. When instructed to commit genocide on the Lamia species, Erswick sadistically agrees and has their homes burned and the Lamias slaughtered with guns and poisoned blades. When he comes across the dying Lamia Sovereign, he tortures her by shooting her repeatedly, then burns her alive for his own amusement. He has his soldiers collect all the Lamia corpses to harvest for their DNA, and transports them back to the city of Brookhaven, where he experiments with his genetic rewriting by performing horrific and torturous experiments on innocent people just trying to survive, killing them or transforming them into [[AndIMustScream mindless monsters in constant agony]]. When Rebel leader Xander makes a deal with Erswick to turn over his allies in exchange for Erswick curing his sister Lani's fatal disease, Erswick betrays him and instead kidnaps all four members of the rebel group, injecting them with his experimental formula. He then mocks them as they succumb to the formula's effects, with Lani burning to death from the inside and technician Brec transforming into another monster. When Xander confronts Erswick, Erswick tortures and kills him with a Tesla coil. He then commands the monster to capture the survivor, Jason, for further experimentation.

** Season 1: Colonel Laura Taylor is [[TheDragon the right-hand woman]] of General Hawke. [[EstablishingCharacterMoment Introduced]] interviewing Captain Raine about the Codex before ordering his execution on a whim, after discovering the Flood, she intends to weaponize the parasite for Black Water Ops even after being warned by the Monitor Atlas about it wiping out all life. She proceeds to [[UngratefulBitch thank the Atlas]] by uploading a virus to kill him. Attempting to [[BadBoss use her own soldiers as hosts for the Flood]], she futilely [[TakingYouWithMe activates the Codex to release it in her dying moments]].
** Season 2: General Hawke is the [[BigBad leader]] of Black Water Ops, tasked with overseeing the research outposts of Forerunner structures. Realizing the power they hold, he initiates a Gamma Protocol purge of personnel who he deems disloyal, having his Shadowknife soldiers hunt down survivors. When Captain Raine is captured, Hawke threatens to [[ThrownOutTheAirlock eject his comrades into a nearby planet's atmosphere]] if he doesn't talk. Hawke's ultimate plan is to use the Apex to turn stars supernova in order to [[GalacticConqueror take over the universe]], having Black Water Ops fight the Covenant when they try to stop him. When Atlas tries to stop his plan, Hawke kills him.

* ''WebAnimation/BluebeardAnAnimatedShort'' ([[https://www.youtube.com/watch?v=Hj0VT1IYNoE link]]): In this prequel to the [[Literature/{{Bluebeard}} original fairytale]], Bluebeard is seen presenting his newest wife with a necklace with four heart symbols on it. After she moves into his castle, he warns her of a chamber that she must never enter. Months later, as he is about to leave on a business trip, she swipes the key from him and goes to search the room. Inside, she finds a MagicMirror that shows skulls in the reflections of the heart symbols of her necklace, revealing Bluebeard killed his previous four wives [[DisproportionateRetribution for disobeying his order to not enter the room]], and uses the heart symbols on the necklaces to [[KillTally tally his kills]]. Bluebeard returns and kills her before moving on to his sixth wife.

* ''WebVideo/{{Crypt TV}}'s'' ''WebAnimation/WomanInTheBook'': [[StrawMisogynist Antonio Navarro]] is a renowned book publicist, known in his community as a [[VillainWithGoodPublicity loving and generous man]], but behind closed doors, is a deranged and misogynistic [[DomesticAbuse abuser]]. [[HeirClubForMen Obsessed with having a male heir]], Antonio kept his wife, Christina, captive in a dungeon, continuously raping her, and beating her when he discovers her writing material. Whenever Christina would give birth to a girl, Antonio would [[OffingTheOffspring murder the infant]] and cover it up with a stillbirth claim, before starting anew. After Antonio murders six of their daughters, he sneeringly tells Christina he'll let the next one live if it's a boy. When a broken Christina ends up drowning their son, Antonio drowns and smothers her to death. He then discovers Christina and his Curandera were working to expose him, and that the Curandera cursed made a curse to that Christina would live on; Antonio locks the Curandera in his dungeon, leaving her to die as he starts his search for a new wife to give him a new son.

* ''WebAnimation/MetaRunner'': [[BadBoss Derek Lucks]] is the [[CorruptCorporateExecutive corrupt CEO of TASCorp]] who would partake in any unethical method to advance his company. A cruel boss, Lucks abuses his Meta Runners and remorselessly allows his top scientist Dr. Sheridan to experiment on Lucinia Porter, only to then cover up the incident when both supposedly perish. Lucks takes an interest in Tari for her game jumping abilities and forces her to join his company under the threat of killing her friends, demonstrating this by shooting off Masa Shimamoto's Meta Runner arm; destroying Theo's physical form, and [[AndIMustScream trapping him in a painful, corrupted version of his game]], to serve as a bargaining chip. Resorting to torture whether [[ForScience for scientific purposes]] or just to get what he wants, Lucks proves himself to be a self-serving sociopath [[BelievingTheirOwnLies believing his own lies]].

** ''Zero'' (season 18): [[MyHeroZero Zero]], the leader of [[Characters/RedVsBlueZerosSyndicate Viper]], desired revenge against the Alliance of Defense for dropping the project GLASS and taking away his chance to be the leader of Shatter Squad. Desiring the Ultimate Power, Zero attacked several bases in order to steal artifacts and coordinates for temples, viciously slaughtering those who got in his way, having Washington tortured, and only sparing those who he wanted to trounce again in the future. Finally achieving his goal, Zero declared his intention to [[OmnicidalManiac "burn the world down" and "destroy everything"]], all to show off his own strength [[PsychopathicManchild out of petty spite]].

* ''WebAnimation/TheWaltenFiles'' ("[[https://www.youtube.com/watch?v=dbsvgZhCM3c&t The Mysterious House]]"): [[SoftSpokenSadist The Pumpkin Rabbit]] is a robotic, masked [[HairRaisingHare rabbit]] who invites two children named Duckie and Tammy to his house to stay over for the night. In reality, however, he's a sadistic SerialKiller who has been [[WouldHurtAChild killing children]] like this for what's implied to be years. Once Tammy enters one of the rooms in the house, she finds the mutilated corpses of Duckie and three other kids who met the same fate before them. Once the Pumpkin Rabbit sees her, he kills and mutilates her corpse too, [[KarmaHoudini escaping without any punishment for his crimes]].

* ''WebAnimation/{{Sherwood}}'': [[CorruptPolitician The Sheriff of Nottingham]] is the ruler of the [[AfterTheEnd now-almost-entirely-sunken]] London. At some point in the past, he gained the trust of "King John" and imprisoned him, leading everyone to believe that the King's will was for him to rule in his absence. He wastes no time creating a totalitarian regime where the wealthy upper class uses [[Creator/HPLovecraft Lovecraftian-like]] robots to steal rations and medicine from the lower classes, leaving them starved and prone to disease. Hating his dependence on the lower classes to survive, the Sheriff spends most of the series hatching a plan to make the Upper City mobile, which damages the ecosystem further in the process. Next, he sends his robots to steal all food and medicine, leaving the citizenry to suffer a particularly violent epidemic that makes the victim cough blood before dying. When the protagonists try to contain the explosion of a power reactor, the Sheriff, now accepting of death. refuses to help them. On top of everything, he is also an [[AbusiveParents abusive father]], a sadist, and he attempts to kill his only ally once [[YouHaveOutlivedYourUsefulness he sees no more use for him]].

* ''Machinima/DeusExMachina2007'': [[StarterVillain Leonard Phillips]] is a [[MadScientist sociopathic scientist]] who seeks to develop a suit of power armor for his boss. To this end, he turns a Covenant elite into a killing machine, and then commits robberies to fund himself, having his assistant kill any witnesses. When he learns about Deus Ex Machina's exploits, he has a civilian killed as a warning and threatens to kill more.

* ''Machinima/Outpost99'' ([[https://www.youtube.com/playlist?list=PLUPr42_BGEIeu-p8baZP1IDqrHaaLj6iP link]]):

-->-- '''[[Characters/RedVsBlueFelix Felix]]''' to [[Characters/RedVsBlueLaverniusTucker Lavernius Tucker]], ''Machinima/RedVsBlue'', "[[Recap/RedVsBlueS12E18FedVsNew Fed vs. New]]"

* ''Machinima/RedVsBlue'': In a universe that runs on ComedicSociopathy, these villains are more sociopathic than comedic.
** ''[[Machinima/RedVsBlueTheRecollection The Recollection]]'' (seasons 6-8) & ''[[Machinima/RedVsBlueTheProjectFreelancerSaga The Project Freelancer Saga]]'' (seasons 9-10): [[AIIsACrapshoot Sigma]], representing the Alpha's [[AmbitionIsEvil ambition]] and [[ManipulativeBastard creativity]], is the evilest [[Characters/RedVsBlueArtificialIntelligences AI]] in the Meta. Interested in becoming human, Sigma gradually took over the mind of Agent Maine and increased his violence. He also manipulated Agent Carolina into getting two AI, leading to a mental breakdown, and helped torture the Alpha. Using Maine, Sigma stole Carolina's AI before nearly killing her. As part of the Meta, Sigma hunted down other Freelancers for their equipment and AI. The AI would be forcibly implanted into the Meta, whether they were willing or not. He also slaughtered multiple simulation teams as well as any recovery agents encountered. In a final bid to steal the Alpha, Sigma and the Meta attacked Freelancer Command, killing everyone stationed there and cornering and almost killing Agent Washington. Even with his destruction by {{EMP}}, Sigma's manipulation ensured that the broken Maine would continue to act as the Meta.
** ''[[Machinima/RedVsBlueTheChorusTrilogy The Chorus Trilogy]]'' (seasons 11-13) has two members of [[Characters/RedVsBlueCharonIndustries Charon Industries]]:

** ''[[Machinima/RedVsBlueTheShisnoTrilogy The Shisno Trilogy]]'' (seasons 15-17): [[JerkassGods Genkins]], aka a TricksterGod, was part of a false pantheon of gods, the "[[Characters/RedVsBlueCosmicPowers Cosmic Powers]]", meant to trick other species into subservience. Desiring true godhood, he joined forces with Chrovos to remake the universe InTheirOwnImage. He proceeded to help manipulate the Reds and Blues into causing a TimeCrash, going as far as to exploit Wash's [=PTSD=] he gained from his neck injury and generating a mini black hole to sadistically murder Huggins when she tried to interfere. After the time crash, Genkins traveled around the time stream to cause further paradoxes to further weaken Chrovos's prison. Eventually, Genkins stole Chrovos's power to devour them alive, before trapping the Reds and Blues in the Labyrinth so they could be psychologically tortured to the point of committing suicide.

-->-- '''Felix''', ''Machinima/RedVsBlue'', Season 12, episode 18, "Fed vs. New"

Much like its [[Monster/WesternAnimation western]] and [[Monster/AnimatedFilms film]] counterparts WebAnimation is not lacking in [[CompleteMonster vile villains]].

* WebVideo/{{Crypt TV}}'s ''WebAnimation/WomanInTheBook'': [[StrawMisogynist Antonio Navarro]] is a renowned book publicist, known in his community as a [[VillainWithGoodPublicity loving and generous man]], but behind closed doors, is a deranged and misogynistic [[DomesticAbuse abuser]]. [[HeirClubForMen Obsessed with having a male heir]], Antonio kept his wife, Christina, captive in a dungeon, continuously raping her, and beating her when he discovers her writing material. Whenever Christina would give birth to a girl, Antonio would [[OffingTheOffspring murder the infant]] and cover it up with a stillbirth claim, before starting anew. After Antonio murders six of their daughters, he sneeringly tells Christina he'll let the next one live if it's a boy. When a broken Christina ends up drowning their son, Antonio drowns and smothers her to death. He then discovers Christina and his Curandera were working to expose him, and that the Curandera cursed made a curse to that Christina would live on; Antonio locks the Curandera in his dungeon, leaving her to die as he starts his search for a new wife to give him a new son.

* Crypt TV's ''WebAnimation/WomanInTheBook'': [[StrawMisogynist Antonio Navarro]] is a renowned book publicist, known in his community as a [[VillainWithGoodPublicity loving and generous man]], but behind closed doors, is a deranged and misogynistic [[DomesticAbuse abuser]]. [[HeirClubForMen Obsessed with having a male heir]], Antonio kept his wife, Christina, captive in a dungeon, continuously raping her, and beating her when he discovers her writing material. Whenever Christina would give birth to a girl, Antonio would [[OffingTheOffspring murder the infant]] and cover it up with a stillbirth claim, before starting anew. After Antonio murders six of their daughters, he sneeringly tells Christina he'll let the next one live if it's a boy. When a broken Christina ends up drowning their son, Antonio drowns and smothers her to death. He then discovers Christina and his Curandera were working to expose him, and that the Curandera cursed made a curse to that Christina would live on; Antonio locks the Curandera in his dungeon, leaving her to die as he starts his search for a new wife to give him a new son.

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* ''WebAnimation/TheWaltenFiles'' ("[[https://www.youtube.com/watch?v=dbsvgZhCM3c&t The Mysterious House]]"): [[SoftSpokenSadist The Pumpkin Rabbit]] is a robotic, masked [[HairRaisingHare rabbit]] who invites two children named Duckie and Tammy to his house to stay over for the night. In reality, however, he's a sadistic SerialKiller who has been [[WouldHurtAChild killing children]] like this for what's implied to be years. Once Tammy enters one of the rooms in the house, she finds the mutilated corpses of Duckie and three other kids who met the same fate before them. Once the Pumpkin Rabbit sees her, he kills and mutilates her corpse too, [[KarmaHoudini escaping without any punishment for his crimes]].