Monster / Digimon
"[VenomMyotismon] is Myotismon's left behind hatred. In exchange for his intelligence, he gained ultimate power. He just is overflowing with the desire to kill, kill, KILL!"

"How dare Merukimon mess up my masterpiece! Some Digimon just don't know when to be deleted, I mean seriously, that guy was a pain until the very end! It's so foolish for any Digimon to think that it can ever defy the whims of a human. A time when humans and Digimon can leave together peacefully. What a silly and pointless idea to waste your life on! I can't stop laughing at the absurdity of it all."
Akihiro Kurata mocking the final wishes of the recently-murdered Merukimon around his loved ones, Digimon Savers, Episode 25

Digimon has several especially heinous villains.

Cmon Digimon
  • Shinichiro Josaki is a vicious bully obsessed with being the strongest Digimon tamer in the world. As the spoiled heir to Josaki Industries, Shinichiro uses his resources to create the powerful Deathmon, and forces children to use their pet-like Digimon to duel him under threat of physical violence. After invariably defeating the children's Digimon, Shinichiro gleefully destroys their Digimon just to torment them before moving on to his next victim. Shinichiro always studies up on his coming opponents so as to learn past traumas or fears and use those to further torture them for his own entertainment, notably trying to burn Kentarou's Digimon alive after learning that Ken once had a pet dog who died in a fire. Shinichiro was the first Digimon villain ever created, and stands out as one of its most petty and cruel.

Digimon V-Tamer 01
  • Lord D(a)emon is the lord and master of all Virus Digimon and the driving force of evil in the story. Daemon kickstarts a war in the Digital World to slowly tear it apart and kill everything in his forces' paths, and regularly send out his homicidal generals and commanders who put countless Digimon in danger. Callously murdering any of his minions who fail or attempt to betray him, Daemon corrupts the young Neo into becoming a ruthless psychopath who kills hundreds of Digimon while training the powerful Arukahdimon in the ways of destruction. Though seemingly betrayed by Neo, Daemon arises in the end to reveal his true machinations, assuming control over Arkadimon and boasting his plans to bring death and destruction to both the human and Digital World, wiping out all life on both he sees fit until only those he deems worthy of his rule are left alive.
  • Myotismon (Also known as Lord Vamde(mon)) is a bloodthirsty sadist with the ability to poison the souls of Digimon. Driving an entire town of Digimon to the brink of annihilation by forcing the residents to kill each other, Myotismon captures Tai and brutally beats the boy before attempting to force his Digimon Zero to butcher the boy, all to Myotismon's utter delight. Returning from his seeming deatho as VenomMyotismon, he takes part in a massacre of the Holy Castle, slaughtering everyone in his path while cackling before attempting to butcher an entire group of Digimon children while forcing their teacher, Leomon, to watch.

Digimon Adventure
  • Myotismon is a sinister, Vampiric Digimon with a sadistic streak a mile wide. Myotismon treats his underlings awfully, having taking Gatomon in when she was young and abusing her until she was a killing machine. When his henchmen fail him, he eagerly destroys them. When two harmless minions couldn't bring themselves to harm children, Myotismon killed them on the spot. When he invaded Tokyo, he proceeded to destroy much of it and held a number of children captive to identify the final child connected with Gatomon. He made it clear if it took too much time, he'd simply kill them all. Myotismon also proceeded to attack multiple young women and drain their blood, causing an epidemic through Tokyo. Any minions he hadn't already killed were cannibalized to fuel his Mega transformation. When he was thought destroyed, Myotismon's spirit survived to return as the final villain of the next season as MaloMyotismon. Using a man named Oikawa's sadness and despair to make him a pawn, he proceeded to consume him from within and upon manifesting anew, Myotismon repaid his perfectly loyal ally Arukenimon by sadistically torturing her to death and killing Mummymon when he tried to avenge her. With a near-unparalleled sadistic streak, Myotismon proved he was one of the vilest monsters in the franchise.
  • Piedmon is the most powerful of the Dark Masters, leading them in their conquest of the Digital World. A psychopath, he enjoys toying with his victims before finishing them off, in contrast to his more straightforward associates. Reducing his territory to a barren wasteland, he monitors the actions of his fellow Dark Masters and the main cast, allowing his allies to die without ever interfering. He causes the death of Sukamon by restructuring Digiworld into Spiral Mountain, kills Chumon himself, nearly kills WarGreymon, and then transforms most of the Digi Destined and their Digimon into keychains, planning to keep them all trapped as toys forever, while he hunts the two youngest members of the team down, intent on brutally murdering them.

Digimon Frontier

Digimon Savers

Digimon Xros Wars
  • Tactimon is the leader of Lord Bagra's armies, and his honor code is based solely on his standards of perfection rather than true honor and decency. Not only is he responsible for rounding up several good Digimon into labor camps, including Cutemon's parents, but he was prepared to torture Mikey, a child, to death, as opposed to the quick, painless execution he could have ordered, and later tries to kill him with a beam cannon blast. As if that wasn't bad enough, he's a full follower of the We Have Reserves mantra and has no compunctions about sacrificing his own subordinates for the sake of maintaining his supposedly perfect battle record, a practice that disgusted Dorulumon enough to defect from his side. Towards the end, he uses the negative energy of many Digimon in order to turn their data into dark spirits that he absorbs into his sword in order to boost his own power and ends up taking the life of Grademon without an iota of remorse. Once he got out into the real world, he proceeded to lay waste to the entire area in hopes of getting his enemies killed and taking away what they value. Shortly afterwards, he attempts to murder Angie and Jeremy with his bare hands. When it comes time for him to do battle with his enemies, all Tactimon can truly feel is pure excitement over the thrill of combat and bloodshed.
  • NeoMyotismon (NeoVamdemon) is an Expy of Adventure's Myotismon and one of Lord Bagra's Seven Death Generals. The ruler of Vampire Land, he was characterized by an undying thirst for power. He possesses familiar spirits known as Evilvils that seek out the life energy of Digimon and give it to him. Not only does he fuse both his minions and his enemies into himself, but he absorbs a great number of innocent Lopmon living in his domain in order to gain immortality from their hidden power. During his battle with the Fusion Fighters, he attempts to absorb Christopher's (Kiriha’s) partner, Metal Greymon, into himself as well, forcing Metal Greymon into an And I Must Scream Body Horror situation.
  • Gravimon, ruler of Canyon Land, is another of the Death Generals. He uses his own core as a way to take Christopher hostage, and then reveals himself as a sadist who uses his cables to torture Christopher and probe his mind. He revels in the following Mind Rape, mercilessly playing off of Christopher's psyche until Christopher becomes broken enough to join him and obey his wishes. This set in motion the events that resulted in, among other things, the tragic death of Deckerdramon, which he ensured by dropping a large gravity attack on top of him. When fighting against the Fusion Fighters, Gravimon tries to physically crush both the kids and their Digimon in his grasp before trying to manipulate Christopher again with a Sadistic Choice- he'd inserted his core into Mikey's body, causing Mikey to endure agonizing pain in the process, and tells Christopher that the only way to destroy both the core and him is to kill Mikey. When Christopher refuses and surrenders instead, Gravimon deems his trust in his friends to be weakness.

Video Games
  • Digimon World & related games: Analogman, along with Kurata easily the most vile human in the entire franchise, is a hacker who turned into an Omnicidal Maniac. He came to the Digital World, and sought to rule it by taking over Digimon and turning them into weapons. He saw them as little more than slaves to be used and abused as he saw fit, and says so more than once. The child protagonist, Mameo, fights against him and his partner Machinedramon, and wins. Analogman tries to kill Mameo with a bomb, but he dies instead. He later returns as a ghost in Digimon Digital Card Battle. The Player Character, heavily implied to be Hiro again, comes back to compete in a card tournament that takes a sinister twist when some of the villains from Adventure return. The last boss is apparently VenomMyotismon, but he is abruptly hijacked when Analogman returns and possesses the vampire. VenomMyotismon's mind is killed, but his body is now used by Analogman as a suit. Analogman challenges Hiro again, and loses, but before he can act on his revenge plan, he is sealed away in the "Deep Net." Analogman returns again in Digimon World -next 0rder-. Possessing Tsuzuki Shoma, Analogman tries one more campaign of terror against the Digital World, poisoning Digimon all over the world and forcibly turning them into Machinedramon clones. The process is painful, and worse, contagious. While it can be fought, it can also be enhanced by torturing the victims, as Analogman demonstrates more than once. His ultimate goal is to take the Executor—Noir the Omnimon Zwart D, and use his power to destroy a Cosmic Keystone that would erase the entire Digimon multiverse from existence, just to see what happens next.
  • Digimon World Data Squad: Lucemon is The Man Behind the Man for both Tsukasa Kagura and Creepymon. The king of the Dark Area and the Chao-Mao Digimon, he's orchestrated everything in the plot by manipulating Kagura's feelings of jealousy to do whatever it took to revive himself. Through him, Lucemon made sure five children throughout the world were merged with one of the Code Keys of the Seven Deadly Sins to create Mao Digimon, The Great Demon Lords. He also has Creepymon attack Kosaburo Katsura and Biyomon to retrieve the Code Keys he's attained. After Creepymon assaults DATS HQ but is defeated, it's revealed Creepymon was made of a former DATS member Masaki Nitta, who was aware of his situation but unable to stop himself, and cannot go back to being human, essentially dying as data before his daughter. When Kagura finally releases the seal on Lucemon, he betrays Kagura and tells him how he deceived the scientist. After absorbing Kagura, Code of Key of Pride himself, Lucemon flees, but not before spreading the influence of the Dark Area. An evil Digimon who deemed himself infinite, immortal, and absolute, Lucemon is a remorseless Omnicidal Maniac who desired to engulf everything in the Dark Area.