"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."
- 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.
- 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.
- Myotismon is a sinister 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.
- Lucemon is a Fallen Angel Digimon with a messiah complex. In his own warped, self righteous mind, Lucemon thinks that the Digital World has gone rotten and wants to tear it apart bit by bit, bringing about the loss of much data and the deaths of countless Digimon, all so he can rebuild it in his image. He describes as a utopia where every Digimon that lives is stripped of their free will and free thought with Lucemon as their shepherd. In reality, what he intends to create is a Hell in Digi-world, where all Digimon are slaves and the only one who will be happy is him. To do this, he corrupted Cherubimon and made him the villain for most of the series. He then used his two Royal Knight followers to erase data from the Digital World, and once he was free, he disposed of said followers just to power himself up. He gets even worse when the Digi-egg containing his darker side turns into Satan Mode, a being filled with nothing but darkness and malice. In this form, he attempts to claim the human world as well. He also uses various methods to torture the good guys purely for fun. Lucemon was, in the end, completely insane and never thoughtful of the lives of others: only himself, his pride, and his hatred towards the Digital World's existence that was not up to his standards.
- Akihiro Kurata is a Mad Scientist and one of the single most despicable human beings to appear in the franchise. Planning on committing genocide on Digimon—due to nothing more than a petty grudge—while conquering the world, Kurata created the Gizumon that would kill Digimon and stop their natural reincarnation cycle, which he first unleashed upon a noble Digimon who had been a surrogate father to the boy Ikuto. Kurata's reaction to Ikuto sobbing over his father's loss was cruel, hysterical laughter. Kurata then created a weapon to kill thousands of Digimon in a single blast and blackmailed one of the humans into working for him by threatening to murder his sick sister, before experimenting on said sister. Kurata's hatred extended to awakening a monstrous demon and attempting to merge with it to obliterate everything he saw as an enemy.
- 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 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.
- WonderSwan series: Millenniumon, born from a Fusion Dance between a dying Machinedramon and a Chimeramon seeks out total domination of everything, and starts by defeating DigiDestined and warping the Digital World through his presence alone. After his first loss against Ryo Akiyama, Millenniumon—as Moon=Millenniummon—is consumed by a lust for revenge, spawning a loose Diaboromon to drag Ryo and Ken to the Digital World that he then tears asunder. Upon losing again, he curses the Digital World with Dark Spores, one of which would ultimately corrupt Ken into the Digimon Kaiser. Finally, as ZeedMillenniumon, he planned on destroying the ENIAC and thus conquering the remnants of the Digimon multiverse. A horrid god who expected everyone and everything to bend to his will, ZeedMillenniumon was bent on conquering every timeline and dimension.
- Digimon World & related games: Analogman is a hacker who arrived in the Digital World and attempted to conquer it. He enslaved multiple Digimon to make living weapons that serve him unwillingly, viewing them as things to use and abuse. After being defeated by Mameo, Analogman tries to blow up the child. Returning as a ghost in Digital Card Battle, he hijacks and kills VenomMyotismon's mind and uses his body as a suit in an attempt to enact vengeance on the protagonist for defeating him before. Analogman's final appearance is in -next 0rder-, where he possesses Tsuzuki Shoma and unleashes a worldwide virus that painfully turns Digimon into violent Machinedramon clones. The process can also be enhanced by torturing the victims. His ultimate goal is to 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.