"He's nothing but a deadly, blood-sucking fiend. Nothing is as evil as MaloMyotismon!"Digimon has several especially heinous villains.
—Gatomon, referring to MaloMyotismon through the Digimon Analyzer in Digimon Adventure 02
- Myotismon, or Vamdemon in the original Japanese, 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 leader and the most powerful of the Dark Masters, leading them in their conquest of the Digital World. A psychopathic Monster Clown, he enjoys toying with his victims before finishing them, 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 participates in the murder of Pixiemon with the rest of the Dark Masters, kills Chumon himself, nearly kills WarGreymon, and then transforms most of the Digi Destined and their Digimon into keychains, which he toys with as he hunts the two youngest members of the team down, intent on keeping them all trapped as toys, forever. He's eventually revealed to be The Man Behind the Man to every major villain in the show, from Devimon through fellow Complete Monster Myotismon, and their actions and those of the other Dark Masters can all be laid at his pointy-shoed feet.
- 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 the Evulz. 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.
- The cowardly, bespectacled scientist, Akihiro Kurata, is the single most despicable human being 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 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.