"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."Digimon has several especially heinous villains.
- 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.
- Machinedramon is a cold, calculating sadist whose every line clearly shows how much he loves killing people, and according to Piedmon, he lives only to destroy. He lent his machine army to Piedmon for his slaughter of the digital guardians in their castle when he went to steal the tags and crests, as well as wiping out the Geckomon kingdom, leaving only three survivors. When the Digi Destined are in his territory, he rigs the city with death traps in attempts to kill them, kills his own henchmen when he deems them no longer useful, and massacres an entire hoard of Numemon when they attempt to protect Kari from him. The most chilling line he has in the entire show is telling Kari, a little girl and one of the youngest Digidestined, that he is going to kill her in the most painful way he possibly can. Despite being apparently destroyed by WarGreymon, the Wanderswan Games reveal that he survives and becomes Milleniummon, going on to rip Digiworld in half, turn Tai and Agumon to stone, and after being destroyed, a portion of his data forms a Dark Spore which infects Ken and leads him to become the Digimon Emperor. After being reborn again he invades an alternate Digiworld, digivolves to Zeed Milleniummon, and destroys nearly everything in the new Digiworld, setting himself up as absolute ruler over the ravaged husk.
- Piedmon is The Leader and the most powerful of the Dark Masters, leading them in their conquest of the Digital World. An Ax-Crazy 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 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.
- Akihiro Kurata is the bespectacled former assistant of Spencer Daimon, whom he secretly hated. During the expedition to the Digital World, after being frightened by several Digimon, he developed an obsessive hatred of them. Claiming that they are a threat to the world to justify his actions, he creates the artificial Digimon Gizumon, which permanently deletes a Digimon. Sending a group with the Gizumon, they murder hundreds of innocent Digimon in an attempt at their extinction. Upon finding the Digi-Egg of Belphemon, Kurata then decides to take control of the beast in order to make himself the ruler of both worlds. Pretending to be an ally to the heroes, he reveals his true colors with murdering Merukimon, mocking the latter's hope for peace between humans and Digimon among his grieving loved ones. Along this, he hires three criminals and turns them into "Bio-Hybrids" to help him with his plan to continue his murder spree, using the deceased's data to resurrect Belphemon. He also kidnap's Thomas's little sister, promising to "cure" her by making her another Bio-Hybrid while having a bomb strapped to her to make Thomas work for him. In the climax of his plans, he merges with Belphemon and begins making dimensional tears that threaten to destroy the world. In his last attempt at vengeance, he sets off detonations meant to destroy the Digital World, only to open a hole big enough for the two worlds to collide. His last moments are screaming for help as his own actions cause him to be vaporized. A cowardly sociopath guilty of attempting genocide and world destruction, Kurata may not have been a Digimon, but made up for it by being a cruel, irredeemable excuse of a human.
- 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.
- 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 spot 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.