History Monster / Digimon

* [[BigBad Myotismon]], or [[KnightOfCerebus Vamdemon]] in the original Japanese, is a sinister, [[OurVampiresAreDifferent Vampiric Digimon]] with a {{sadist}}ic streak a mile wide. Myotismon [[BadBoss 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 [[OneWingedAngel Mega transformation]]. When he was thought destroyed, Myotismon's spirit survived to return as the final villain of the next season. 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 [[ColdBloodedTorture 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.

* The [[DirtyCoward cowardly]], [[FourEyesZeroSoul bespectacled]] [[MadScientist scientist]], [[BigBad Akihiro Kurata]], is the[[HumansAreTheRealMonsters single most despicable human being]] to appear in the franchise. Planning on [[OmnicidalManiac 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 [[IllGirl 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.

* Piedmon is {{the leader}} and the most powerful of the [[BigBadDuumvirate Dark Masters]], leading them in their conquest of the Digital World. A [[TheSociopath psychopathic]] MonsterClown, he enjoys toying with his victims before finishing them, in contrast to his more straightforward associates. Reducing his territory to a [[{{Mordor}} barren wasteland]], he [[BigBrotherIsWatchingYou 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=], 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 TheManBehindTheMan to every major villain in the show, from [[StarterVillain Devimon]] through fellow CompleteMonster Myotismon, and their actions and those of the other Dark Masters can all be laid at his pointy-shoed feet.
* Myotismon. (Spoilers for the most WhamEpisode filled arcs of the first two seasons ahead.) This guy '''was''' the most psychopathic villain of the series until Kurata came calling. First, he took in Gatomon under his wings in order to [[BreakTheCutie abuse and assault her]] to the point she became his [[TheDragon loyal killing machine]]. He tortured his IneffectualSympatheticVillain minion Demi Devimon for petty reasons, entered the human world and [[TheTokyoFireball destroyed much of Tokyo]], killing several of his hench-mon along the way [[YouHaveFailedMe for the slightest failure]] ([[BadBoss he]] ''[[BadBoss very]]'' [[BadBoss seldom leaves a minion alive, in fact]]), kidnapped almost every family in Odaiba and forced Gatomon to identify the children of said families as her partner in his search for the Eighth Child or he would kill them all, and killed poor Wizardmon (okay, Wizardmon had [[HeelFaceTurn turned on him]], but killing a {{Woobie}} will earn you major {{Jerkass}} points.) Any minions he hadn't already killed were cannibalized to fuel his SuperMode, and he was stopped just in time to prevent the entire population of Odaiba from becoming dessert.

!! ''Anime/DigimonAdventure02''
* Myotismon, revealed to be TheManBehindTheMan. He'd played on Oikawa's sadness and despair to use him as a pawn, [[TheCorruption his corrupting influence destroying Oikawa's body from within]]. [[HumanResources Using kids]] to incubate his ''new'' power source wasn't nice, either, but the ''real'' reason Myo is seen as nigh-Kurata-level evil is what he did once [[YouHaveOutlivedYourUsefulness he didn't need Arukenimon anymore]]: he subjected her to a painful and horrible death, while reading her mind and doing everything she feared he'd do to her in that order. The poor DarkActionGirl ''hadn't'' failed him; this was purely ForTheEvulz, and not only that, he infamously claimed to have been kinder with her because she was a woman. And when her DoggedNiceGuy Mummymon tried to avenge her, Myo gleefully incinerated him. Other Anime/DigimonAdventure villains can be {{Bad Boss}}es and tend to be {{Card Carrying Villain}}s, but Myotismon's sadism is unparalleled - or was. (Yes, ''[[UpToEleven Kurata is worse.]]'')

* Lucemon, a fallen angel Digimon with a Messiah complex, and the series' ultimate BigBad. In his own warped, self righteous mind, Lucemon [[KnightTemplar 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 [[ItsAllAboutMe 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 [[YouHaveOutlivedYourUsefulness 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. Not to mention all the various tortures he inflicts on the good guys purely ForTheEvulz. 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.

* Professor Akihiro Kurata is the most despicable human villain to ever appear in the ''Digimon'' franchise. While Ken from ''Adventure 02'' didn't think [[VideoGameCrueltyPotential that he was doing anything wrong]] (and may or may not have been under MoreThanMindControl), Oikawa was under MindControl in a significant way, and Yamaki from ''Tamers'' was a WellIntentionedExtremist who ultimately had a HeelFaceTurn, Kurata's only goal is to TakeOverTheWorld and sadistically destroy all Digimon because of a petty grudge. Creating the Gizumon, mechanical monstrosities that make other Digimon DeaderThanDead by stopping them from reincarnating like usual, and experimenting in creating half-Digimon hybrids were only the start. Creating a weapon of mass destruction to kill thousands of Digimon in one shot, forcing the TeenGenius on the heroes' side to a FaceHeelTurn by threatening to kill his IllGirl little sister, trying to replicate his experiments on said IllGirl, and finally awakening a mighty Demon Lord and merging with it to destroy all of his enemies...well, that should give you an idea of how loathsome this guy is.
** Laughing hysterically as Ikuto/Keenan sobs over the loss of his surrogate father, whom his Gizumon have just [[DeaderThanDead permanently deleted]]. He is not just the most despicable human villain to ever appear in the Digimon franchise. He is the most despicable VILLAIN to ever appear in the franchise. Period. He even beat out Myotismon, the previous holder of the most complete monster in the series - not an easy feat.
** A very good showing of just how horrid this guy is would be the reaction the heroes have to him in the last phase of the final battle. [[spoiler:Marcus finally gets [=ShineGreymon=] to reach [[SuperMode Burst Mode]] and turns the tables on him. Cue [=ShineGreymon=] shooting Kurata one of the most hate-filled {{Death Glare}}s in anime history while everyone else [[AndThereWasMuchRejoicing cheers for Kurata's demise]] before Marcus and [=ShineGreymon=] put Kurata down while he's begging for mercy. Normally, trying to kill someone off who's begging for mercy is the job of the AntiHero or in a BigDamnVillains moment, and if the hero does it, it's normally a sign that they've crossed the line. Kurata is such a horrible, ''evil'', terrible excuse for a human being that finishing him off while he's begging for mercy is a [[KickTheSonOfABitch completely acceptable action]].]] Kurata is the digimon equivalent of [[VideoGame/MegaManZero Doctor Weil]].

* Tactimon is the one leader of Lord Bagra's armies with no positive or redeeming features about him. Not only is he responsible for rounding up several good Digimon into labor camps, including Cutemon's parents, he was prepared to torture [[WouldHurtAChild Mikey, a child, to death instead of the quick, painless execution he could have ordered.]] As if that wasn't bad enough, he's a full follower of the We aveReserves mantra and has no compunctions about sacrificing his own subordinates for the sake of maintaining his supposedly perfect battle record. This practice disgusted his follower Dorulumon enough to make him defect from Tactimon's side. 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 destroying what they valued. Shortly afterwards, he attempts to murder Mikey, Angie, and Jeremy with his bare hands. When it comes time for him to do battle with his enemies, all he can feel is [[BloodKnight pure excitement over the thrill of combat and bloodshed.]]
* Another example from the same series is Neo Myotismon, an {{Expy}} of ''Adventure's'' Myotismon and the second of Lord Bagramon's Death Generals. The ruler of the Vampire Land, he was characterized by only one thing: 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 partner, Metal Greymon, into himself as well, forcing Metal Greymon into an AndIMustScream BodyHorror situation.
* The other particularly heinous Death General is Gravimon, ruler of the Canyon Land. 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 MindRape, 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.

!! Other
* An underrated but important example is Millenniummon of the ''DigimonWonderSwanSeries''. A reborn Machinedramon, he is responsible for the cataclysmic events of the Digimon Adventure/Zero Two by traveling through time and releasing Apocalymon. In ''DigimonWonderSwanSeries'', it is stated that Apocalymon's existence brought Devimon, Myotismon, and Dark Masters into existence. By releasing Apocalymon, Millenniumon is responsible for everything that goes wrongin ''Adventure'' and ''Adventure 02'' and is responsible for the creation for some of complete mosnters in this page. His Zeed incarnation is even worse; by ''Brave Tamer'' he's actually destroyed almost everything in his timeline and turned it into a CrapsackWorld with himself as its king. And this isn't even taking into account the InferredHolocaust that must have happened when he ''broke the Digital World in half.''
** When Milleniummon was destroyed, his data turned into Dark Spores and one buried itself into Ken's neck, exerting its influence on him. Since then, it grew within Ken and was later harvested and implanted into other children by Yukio Oikawa, meaning that Milleniummon is so evil that his data can corrupt anyone and turn them into insane and hateful beings.

* Tactimon bears special mention in that he was prepared to ''torture a child to death'', as opposed to a quick, painless execution (not that that's any better; it just shows how sadistic Tactimon is). As if that wasn't bad enough, he's a full follower of the WeHaveReserves mantra and has no compunctions about sacrificing his own subordinates for the sake of maintaining his supposedly perfect battle record.
* Another example is [=NeoVamdemon=], an {{Expy}} of Adventure's Myotismon, who [[spoiler: absorbs a great number of innocent Lopmon in order to remain immortal, while also absorbing Kiriha's partner, [=MetalGreymon=], into himself. Then he basically forced them to destroy themselves in order to avoid letting him use them as batteries anymore.]]
* Gravimon, considering how mercilessly he [[spoiler: MindRaped Kiriha and set in motion the events that resulted in, among other things, the death of Deckerdramon.]]

!! Anime/DigimonAdventure

!! Anime/DigimonAdventure02

!! Anime/DigimonSavers

!! Anime/DigimonXrosWars

* Splashmon. Seriously - Cyber Land became a ghost town due to his actions. He killed every Digimon in it (he didn't directly kill them, but he set the motion as he absorbs negative energy from the citizens).

* Apollomon Whispered was designed to be everything his other half was not, and Bagramon succeeded beyond his wildest dreams. This thing was a horrifict example of TheStarscream that had a god complex and was planning on massacring an entire kingdom of digimon for no reason other than it was the ''easy route.''

!! Other:

* Then there's Lilithmon, who orchestrated the fall of the Goddess' Warriors in the Sand Zone and then ''laughed'' about it to its sole survivor. And then killed him too. On top of that she almost murdered an innocent child for no reason other than shits and giggles.

!! Anime/DigimonTamers
* ''The motherfucking'' '''''[[EldritchAbomination D-Reaper]]'''''. Imagine a monster that combines the most horrifying aspects of [[CthulhuMythos Lovecraftian horror]], [[Anime/NeonGenesisEvangelion the Angels]], and [[TengenToppaGurrenLagann the Anti-Spirals]]. Now remove any [[WellIntentionedExtremist Well Intentioned Extremism]] or BlueAndOrangeMorality and keep all the [[KickTheDog Labramon kicking]] and [[MoralEventHorizon Mind Raping]] - you have the D-Reaper in a nutshell. Up until [[Anime/DigimonSavers Kurata]] came around, it was tied with [[Anime/DigimonAdventure Myotismon and Piedmon]] for the position of the nastiest Digimon baddie ever.
** More precisely, the D-Reaper from the Digital World was really just [[PunchClockVillain performing its' function]] [[ObliviouslyEvil but in a destructive way.]] The split D-Reaper that emerges in the ''real world'', however, which includes J-Reaper and all the agents that follow it, is cold, calculating and intelligent, using Jeri's feelings to come to the conclusion that all humanity is worthless and must be purged. And it attempts to do so in ''insane'' and ''sadistic'' ways. It cares nothing for all life, not even it's own artificial existance, making it truly [[TheHeartless heartless.]]
** There's also everything it did to Beelzemon; namely, using Jeri's voice to taunt him about being a failure and remind him ([[TheAtoner as if he'd forgotten]]) about all the horrible things he did as a villain, speaking with barely-concealed sadistic glee. After nearly pushing him to a HeroicBSOD, it then let him get '''this''' close to saving Jeri before ''flaying his back open'' with sharp, rusty metal discs. After ''that'' it tried to throw him into the sea of deletion below, and would have succeeded had Grani not caught him at the last second. It's not as bad as what it did to Jeri, but it's still pretty awful.
** It's actually even ''creepier'' than [[Anime/DigimonSavers Kurata]]

!! Anime/DigimonFrontier
* Lucemon should count,between manipulating all the Digimon into following him the first time,corrupting an archangel Digimon into doing his dirty work. Said work was destroy the whole Digital World and Human World in the hopes of "rebuilding" it,but it was really just FortheEvulz. He even [[BadBoss murders both of his loyal servants]] just to get a power up. It gets even worse once Susanoomon scans only the good data and he becomes the appropriately named Satan Mode.

* Analogman from ''VideoGame/DigimonWorld''. To put things in perspective, a lot of people think he ''inspired'' Kurata.

* Piedmon is a psychotic MonsterClown who doesn't give a damn about life at all. He ruthlessly kills a large amount of the team's allies in brutal ways, and when the Digidestined finally face him down, he savagely beats them down before [[AndIMustScream turning them into living keychains]] for him to toy with. The sequence where he hunts down the kids and their digimon one by one before transforming them, all while laughing with sadistic glee and mocking the two youngest team members (who he saves for last) is surprisingly frightening.

** Seems the writers are aware of how big of monsters these two are: Piedmon and Myotismon are the only two ''Adventure'' villains who ultimately suffer a FateWorseThanDeath as well. Where Myotismon is ultimately killed DeaderThanDead (having his ''soul'' destroyed), Piedmon is sucked into [=MagnaAngemon's=] Gate of Destiny, a portal to a dimension from which he can never escape, and Digimon are immortal baring being killed outright.
* While not on par with Myotismon or Piedmon in terms of sheer evil, Machinedramon also counts. Most {{Killer Robot}}s are unfeeling killing machines. Machinedramon's CreepyMonotone would imply this applies to him too. But it's the things he actually says that pushes him into this. Practically everything he says shows he's a cold, calculating sadist who loves killing people. 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''. The combination of his sadistic lines and his CreepyMonotone make almost everything he says horrific. While he's not the worst CompleteMonster in Digimon, he certainly makes the list.
** What makes things worse is that he actually gets out of Adventure alive. He comes back as Millenniummon, and, well, see the bottom of the list.
* No mention of Devimon? He is probably the only Complete Monster here who also manages to be a MagnificentBastard at the same time, when he lured the kids into a illusion and seperated them afterwards to weaken them. Still, he crosses the MoralEventHorizon when he orders the brainwashed Leomon to [[WouldHurtAChild kill Taichi]]. And in the final battle he is only barely stopped before he crushes T.K. and Patamon with his bare hands.
* Metalseadramon also counts. Slaughtering poor [[SacrificialLion Whamon]] was a real vile act, especialy because he didn't pose any kind of danger to him. The only Dark Master that avoids the Trope is Puppetmon, who is LaughablyEvil.

* A minor example, but [=IceDevimon=] certainly counts. Not content to merely load their data, he keeps the frozen remains of the Digimon he killed as a kind of trophy gallery. Notably, Ruki, who to this point had been rather ruthless regarding Digimon, [[EvenEvilHasStandards is completely horrified]].

* The [=IceDevimon=] in Anime/DigimonFrontier is just as bad, if worse. Here he's an AxCrazy killer whom even the current BigBad didn't want anywhere near him!

* While not on par with Myotismon or Piedmon in terms of sheer evil, Machinedramon also counts. Most {{Killer Robot}}s are unfeeling killing machines. Machinedramon's CreepyMonotone would imply this applies to him too. But it's the things he actually says that pushes him into this. Practically everything he says shows he's a cold, calculating sadist who loves killing people. 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''. And the combination of his sadistic lines and his CreepyMonotone make almost everything he says NightmareFuel. While he's not the worst CompleteMonster in Digimon, he certainly makes the list.

* Myotismon, revealed to be TheManBehindTheMan. He'd played on Oikawa's sadness and despair to use him as a pawn, [[TheCorruption his corrupting influence destroying Oikawa's body from within]]. [[HumanResources Using kids]] to incubate his ''new'' power source wasn't nice, either, but the ''real'' reason Myo is seen as nigh-Kurata-level evil is what he did once [[YouHaveOutlivedYourUsefulness he didn't need Arukenimon anymore]]: he subjected her to [[NightmareFuel a painful and horrible death, while reading her mind and doing everything she feared he'd do to her in that order]]. The poor DarkActionGirl ''hadn't'' failed him; this was purely ForTheEvulz, and not only that, he infamously claimed to have been kinder with her because she was a woman. And when her DoggedNiceGuy Mummymon tried to avenge her, Myo gleefully incinerated him. Other Anime/DigimonAdventure villains can be {{Bad Boss}}es and tend to be {{Card Carrying Villain}}s, but Myotismon's sadism is unparalleled - or was. (Yes, ''[[UpToEleven Kurata is worse.]]'')

* A minor example, but [=IceDevimon=] certainly counts. Not content to merely load their data, he [[NightmareFuel keeps the frozen remains of the Digimon he killed as a kind of trophy gallery.]] Notably, Ruki, who to this point had been rather ruthless regarding Digimon, [[EvenEvilHasStandards is completely horrified]].

** It's actually even ''[[NightmareFuel creepier]]'' than [[Anime/DigimonSavers Kurata]]

* Lucemon should count,between manipulating all the Digimon into following him the first time,corrupting an archangel Digimon into doing his dirty work. Said work was destroy the whole Digital World and Human World in the hopes of "rebuilding" it,but it was really just FortheEvulz. It gets even worse once Susanoomon scans only the good data and he becomes the appropriately named Satan Mode

* Tactimon bears special mention in that he was prepared to ''torture a child to death'', as opposed to a quick, painless execution (not that that's any better; it just shows how sadistic Tactimon is). As if that wasn't bad enough, he's a full follower of the WeHaveReserves mantra and has no compunctions about sacrificing his own subordinates for the sake of maintaining his supposedly perfect battle record. Another example is [=NeoVamdemon=], an {{Expy}} of Adventure's Myotismon, who [[spoiler: absorbs a great number of innocent Lopmon in order to remain immortal, while also absorbing Kiriha's partner, [=MetalGreymon=], into himself,]] along with Lillithmon, who orchestrated the fall of the Goddess' Warriors in the Sand Zone and then ''laughed'' about it to its sole survivor.

* Gravimon, considering how mercilessly he [[spoiler: played off of Kirihia's psyche and set in motion the events that resulted in, among other things, the death of Deckerdramon.]]

* An underrated but important example is Millenniummon of the ''DigimonWonderSwanSeries''. He is responsible for the cataclysmic events of the Digimon universe, mainly the Adventure/Zero Two verse, such as releasing Apocalymon.
** Also, when Milleniummon was destroyed, his data turned into Dark Spores and one buried itself into Ken's neck, exerting its influence on him. Since then, it grew within Ken and was later harvested and implanted into other children by Yukio Oikawa, meaning that Milleniummon is so evil that his data can corrupt anyone and turn them into insane and hateful beings, and Milleniummon is indirectly responsible for some of events in Anime/DigimonAdventure02. Also, on the subject of releasing Apocalymon: in ''DigimonWonderSwanSeries'', it is stated that Apocalymon's existence brought Devimon, Myotismon, and Dark Masters into existence. This means that, by releasing Apocalymon, Millenniumon is responsible for everything that goes down in ''Adventure'' and ''Adventure 02'' and is responsible for the creation for some of complete mosnters in this page.

** Seems the writers are aware of how big of monsters these two are: Piedmon and Myotismon are the only two ''Adventure'' villains who ultimately suffer a FateWorseThanDeath as well. Where Myotismon is ultimately killed DeaderThanDead (having his ''soul'' destroyed), Piedmon is sucked into [=MagnaAngemon's=] Gate of Destiny, a portal to a dimension from which he can never escape, and Digimon are pretty much immortal baring being killed outright.

* Myotismon, revealed to be TheManBehindTheMan. He'd played on Oikawa's sadness and despair to use him as a pawn, [[TheCorruption his corrupting influence destroying Oikawa's body from within]]. [[HumanResources Using kids]] to incubate his ''new'' power source wasn't nice, either, but the ''real'' reason Myo is seen as nigh-Kurata-level evil is what he did once [[YouHaveOutlivedYourUsefulness he didn't need Arukenimon anymore]]: he subjected her to [[NightmareFuel a painful and horrible death, while reading her mind and doing everything she feared he'd do to her in that order]]. The poor DarkActionGirl ''hadn't'' failed him; this was purely [[ForTheEvulz for the hell of it]], and not only that, he infamously claimed to have been kinder with her because she was a woman. And when her DoggedNiceGuy Mummymon tried to avenge her, Myo gleefully incinerated him. Other Anime/DigimonAdventure villains can be {{Bad Boss}}es and tend to be {{Card Carrying Villain}}s, but Myotismon's sadism is unparalleled - or was. (Yes, ''[[UpToEleven Kurata is worse.]]'')

** There's also everything it did to Beelzemon; namely, using Jeri's voice to taunt him about being a failure and remind him ([[TheAtoner as if he'd forgotten]]) about all the horrible things he did as a villain, speaking with barely-concealed sadistic glee. After nearly pushing him to a HeroicBSOD, it then let him get '''this''' close to saving Jeri before ''flaying his back open'' with sharp, rusty metal discs. After ''that'' it tried to throw him into the sea of deletion below, and would have succeeded had Grani not caught him ''literally'' at the last second. It's not as bad as what it did to Jeri, but it's still pretty damn awful.

** Let's not forget laughing hysterically as Ikuto/Keenan sobs over the loss of his surrogate father, whom his Gizumon have just [[DeaderThanDead permanently deleted]]. He is not just the most despicable human villain to ever appear in the Digimon franchise. He is the most despicable VILLAIN to ever appear in the franchise. Period. He even beat out Myotismon, the previous holder of the most complete monster in the series - not an easy feat.
** A very good showing of just how horrid this guy is would be the reaction the heroes have to him in the last phase of the final battle. [[spoiler:Marcus finally gets [=ShineGreymon=] to reach [[SuperMode Burst Mode]] and turns the tables on him. Cue [=ShineGreymon=] shooting Kurata one of the most hate-filled {{Death Glare}}s in anime history while everyone else [[AndThereWasMuchRejoicing cheers for Kurata's demise]] before Marcus and [=ShineGreymon=] put Kurata down while he's begging for mercy. Normally, trying to kill someone off who's begging for mercy is the job of the AntiHero or in a BigDamnVillains moment, and if the hero does it, it's normally a sign that they've crossed the line. Kurata is such a horrible, ''evil'', terrible excuse for a human being that finishing him off while he's begging for mercy is a [[KickTheSonOfABitch completely acceptable action]].]] Basically, Kurata is the digimon equivalent of [[VideoGame/MegaManZero Doctor Weil]].

* Splashmon. Seriously - Cyber Land became a ghost town due to his actions. He pretty much killed every Digimon in it (he didn't directly kill them, but he pretty much set the motion as he absorbs negative energy from the citizens).

** There's also everything it did to Beelzemon; namely, using Jeri's voice to taunt him about being a failure and remind him ([[TheAtoner as if he'd forgotten]]) about all the horrible things he did as a villain, speaking with barely-concealed sadistic glee. After nearly pushing him to a HeroicBSOD, it then let him get '''this''' close to saving Jeri before ''flaying his back open'' with rusty metal discs and trying to throw him out of the sky into the sea of deletion below, and had Grani not caught him, it ''would'' have succeeded. It's not as bad as what it did to Jeri, but it's still pretty damn awful.

** There's also everything it did to Beelzemon; namely, using Jeri's voice to taunt him about being a failure and remind him ([[TheAtoner as if he'd forgotten]]) about all the horrible things he did as a villain, speaking with barely-concealed sadistic glee. After nearly pushing him to a HeroicBSOD, it then let him get '''this''' close to saving Jeri before [[spoiler:''flaying his back open'' and throwing him out of the sky into the sea of deletion below, something he ''barely'' survives]]. It's not as bad as what it did to Jeri, but it's still pretty damn awful.

* Lucemon should count,between manipulating all the Digimon into following him the first time,corrupting an archangel Digimon into doing his dirty work. Said work was destroy the whole Digital World and Human World in the hopes of "rebuilding" it,but it was really just FortheEvulz

*** More precisely, the D-Reaper from the Digital World was really just [[PunchClockVillain performing its' function]] [[ObliviouslyEvil but in a destructive way.]] The split D-Reaper that emerges in the ''real world'', however, which includes J-Reaper and all the agents that follow it, is cold, calculating and intelligent, using Jeri's feelings to come to the conclusion that all humanity is worthless and must be purged. And it attempts to do so in ''insane'' and ''sadistic'' ways. It cares nothing for all life, not even it's own artificial existance, making it truly [[TheHeartless heartless.]]
*** There's also everything it did to Beelzemon; namely, using Jeri's voice to taunt him about being a failure and remind him ([[TheAtoner as if he'd forgotten]]) about all the horrible things he did as a villain, speaking with barely-concealed sadistic glee. After nearly pushing him to a HeroicBSOD, it then let him get '''this''' close to saving Jeri before [[spoiler:''flaying his back open'' and throwing him out of the sky into the sea of deletion below, something he ''barely'' survives]]. It's not as bad as what it did to Jeri, but it's still pretty damn awful.

*** There's also everything it did to Beelzemon; namely, using Jeri's voice to taunt him about being a failure and remind him ([[TheAtoner as if he'd forgotten]]) about all the horrible things he did as a villain. After nearly pushing him to a HeroicBSOD, it then let him get '''this''' close to saving Jeri before [[spoiler:''flaying his back open'' and throwing him out of the sky into the sea of deletion below, something he ''barely'' survives]]. The whole time, it was speaking with barely-concealed sadistic glee.

* The motherfucking [[EldritchAbomination D-Reaper]]. Imagine a monster that combines the most horrifying aspects of [[CthulhuMythos Lovecraftian horror]], [[Anime/NeonGenesisEvangelion the Angels]], and [[TengenToppaGurrenLagann the Anti-Spirals]]. Now remove any [[WellIntentionedExtremist Well Intentioned Extremism]] or BlueAndOrangeMorality and keep all the [[KickTheDog Labramon kicking]] and [[MoralEventHorizon Mind Raping]] - you have the D-Reaper in a nutshell. Up until [[Anime/DigimonSavers Kurata]] came around, it was tied with [[Anime/DigimonAdventure Myotismon and Piedmon]] for the position of the nastiest Digimon baddie ever.

** Also, when Milleniummon was destroyed, his data turned into Dark Spores and one buried itself into Ken's neck, exerting its influence on him. Since then, it grew within Ken and was later harvested and implanted into other children by Yukio Oikawa, meaning that Milleniummon is so evil that his data can corrupt anyone and turn them into insane and hateful beings, and Milleniummon is indirectly responsible for some of events in Anime/DigimonAdventure02. Also, on the subject of releasing Apocalymon: in ''DigimonWonderSwanSeries'', it is stated that Apocalymon's existence brought Devimon, Myotismon, and Dark Masters into existence. This means that, by releasing Apocalymon, Millenniumon is responsible for everything that goes down in ''Adventure'' and ''Adventure 02'' and is responsible for the creation for some of complete mosnters in this page.

* The [=IceDevimon=] in DigimonFrontier is just as bad, if worse. Here he's an AxCrazy killer whom even the current BigBad didn't want anywhere near him!

** Also, when Milleniummon was destroyed, his data turned into Dark Spores and one buried itself into Ken's neck, exerting its influence on him. Since then, it grew within Ken and was later harvested and implanted into other children by Yukio Oikawa, meaning that Milleniummon is so evil that his data can corrupt anyone and turn them into insane and hateful beings, and Milleniummon is indirectly responsible for some of events in DigimonAdventure02. Also, on the subject of releasing Apocalymon: in ''DigimonWonderSwanSeries'', it is stated that Apocalymon's existence brought Devimon, Myotismon, and Dark Masters into existence. This means that, by releasing Apocalymon, Millenniumon is responsible for everything that goes down in ''Adventure'' and ''Adventure 02'' and is responsible for the creation for some of complete mosnters in this page.

** Also, when Milleniummon was destroyed, his data turned into Dark Spores and one buried itself into Ken's neck, exerting its influence on him. Since then, it grew within Ken and was later harvested and implanted into other children by Yukio Oikawa, meaning that Milleniummon is so evil that his data can corrupt anyone and turn them into insane and hateful beings, and Milleniummon is indirectly responsible for some of events in DigimonAdventure02. Also, on the subject of releasing Apocalymon: in ''DigimonWonderSwanSeries'', it is stated that Apocalymon's existence brought Devimon, Myotismon, and Dark Masters into existence. This means that, by releasing Apocalymon, Millenniumon is responsible for everything that goes down in DigimonAdventure and DigimonAdventure02 and is responsible for the creation for some of complete mosnters in this page.

* Professor Akihiro Kurata in ''DigimonSavers'' is the most despicable human villain to ever appear in the ''Digimon'' franchise. While Ken from DigimonAdventure02 didn't think [[VideoGameCrueltyPotential that he was doing anything wrong]] (and may or may not have been under MoreThanMindControl), Oikawa was under MindControl in a significant way, and Yamaki from ''DigimonTamers'' was a WellIntentionedExtremist who ultimately had a HeelFaceTurn, Kurata's only goal is to TakeOverTheWorld and sadistically destroy all Digimon because of a petty grudge. Creating the Gizumon, mechanical monstrosities that make other Digimon DeaderThanDead by stopping them from reincarnating like usual, and experimenting in creating half-Digimon hybrids were only the start. Creating a weapon of mass destruction to kill thousands of Digimon in one shot, forcing the TeenGenius on the heroes' side to a FaceHeelTurn by threatening to kill his IllGirl little sister, trying to replicate his experiments on said IllGirl, and finally awakening a mighty Demon Lord and merging with it to destroy all of his enemies...well, that should give you an idea of how loathsome this guy is.
** Let's not forget laughing hysterically as Ikuto/Keenan sobs over the loss of his surrogate father, whom his Gizumon have just [[DeaderThanDead permanently deleted]]. He is not just the most despicable human villain to ever appear in the Digimon franchise. He is the most despicable VILLAIN to ever appear in the franchise. Period. He even beat out Myotismon, the previous holder of the most complete monster in the series - not an easy feat.
** A very good showing of just how horrid this guy is would be the reaction the heroes have to him in the last phase of the final battle. [[spoiler:Marcus finally gets [=ShineGreymon=] to reach [[SuperMode Burst Mode]] and turns the tables on him. Cue [=ShineGreymon=] shooting Kurata one of the most hate-filled {{Death Glare}}s in anime history while everyone else [[AndThereWasMuchRejoicing cheers for Kurata's demise]] before Marcus and [=ShineGreymon=] put Kurata down while he's begging for mercy. Normally, trying to kill someone off who's begging for mercy is the job of the AntiHero or in a BigDamnVillains moment, and if the hero does it, it's normally a sign that they've crossed the line. Kurata is such a horrible, ''evil'', terrible excuse for a human being that finishing him off while he's begging for mercy is a [[KickTheSonOfABitch completely acceptable action]].]] Basically, Kurata is the digimon equivalent of [[MegamanZero Doctor Weil]].
* Speaking of Myotismon. (Spoilers for the most WhamEpisode filled arcs of the first two seasons ahead.) This guy '''was''' the most psychopathic villain of the series until Kurata came calling. First, he took in Gatomon under his wings in order to [[BreakTheCutie abuse and assault her]] to the point she became his [[TheDragon loyal killing machine]]. He tortured his IneffectualSympatheticVillain minion Demi Devimon for petty reasons, entered the human world and [[TheTokyoFireball destroyed much of Tokyo]], killing several of his hench-mon along the way [[YouHaveFailedMe for the slightest failure]] ([[BadBoss he]] ''[[BadBoss very]]'' [[BadBoss seldom leaves a minion alive, in fact]]), kidnapped almost every family in Odaiba and forced Gatomon to identify the children of said families as her partner in his search for the Eighth Child or he would kill them all, and killed poor Wizardmon (okay, Wizardmon had [[HeelFaceTurn turned on him]], but killing a {{Woobie}} will earn you major {{Jerkass}} points.) Any minions he hadn't already killed were cannibalized to fuel his SuperMode, and he was stopped just in time to prevent the entire population of Odaiba from becoming dessert.
** ''[[BackFromTheDead Then he comes back]]'' and proves to be [[TheManBehindTheMan the mastermind of everything in the second season]]. He'd played on Oikawa's sadness and despair to use him as a pawn, [[TheCorruption his corrupting influence destroying Oikawa's body from within]]. [[HumanResources Using kids]] to incubate his ''new'' power source wasn't nice, either, but the ''real'' reason Myo is seen as nigh-Kurata-level evil is what he did once [[YouHaveOutlivedYourUsefulness he didn't need Arukenimon anymore]]: he subjected her to [[NightmareFuel a painful and horrible death, while reading her mind and doing everything she feared he'd do to her in that order]]. The poor DarkActionGirl ''hadn't'' failed him; this was purely [[ForTheEvulz for the hell of it]], and not only that, he infamously claimed to have been kinder with her because she was a woman. And when her DoggedNiceGuy Mummymon tried to avenge her, Myo gleefully incinerated him. Other DigimonAdventure villains can be {{Bad Boss}}es and tend to be {{Card Carrying Villain}}s, but Myotismon's sadism is unparalleled - or was. (Yes, ''[[UpToEleven Kurata is worse.]]'')
* [[DigimonAdventure Piedmon]] is a psychotic MonsterClown who doesn't give a damn about life at all. He ruthlessly kills a large amount of the team's allies in brutal ways, and when the Digidestined finally face him down, he savagely beats them down before [[AndIMustScream turning them into living keychains]] for him to toy with. The sequence where he hunts down the kids and their digimon one by one before transforming them, all while laughing with sadistic glee and mocking the two youngest team members (who he saves for last) is surprisingly frightening.
** Seems the writers are aware of how big of monsters these two are: Piedmon and Myotismon are the only two ''DigimonAdventure'' villains who ultimately suffer a FateWorseThanDeath as well. Where Myotismon is ultimately killed DeaderThanDead (having his ''soul'' destroyed), Piedmon is sucked into [=MagnaAngemon's=] Gate of Destiny, a portal to a dimension from which he can never escape, and Digimon are pretty much immortal baring being killed outright.

* Tactimon of ''DigimonXrosWars'' bears special mention in that he was prepared to ''torture a child to death'', as opposed to a quick, painless execution (not that that's any better; it just shows how sadistic Tactimon is). As if that wasn't bad enough, he's a full follower of the WeHaveReserves mantra and has no compunctions about sacrificing his own subordinates for the sake of maintaining his supposedly perfect battle record. Another example is [=NeoVamdemon=], an {{Expy}} of Adventure's Myotismon, who [[spoiler: absorbs a great number of innocent Lopmon in order to remain immortal, while also absorbing Kiriha's partner, [=MetalGreymon=], into himself,]] along with Lillithmon, who orchestrated the fall of the Goddess' Warriors in the Sand Zone and then ''laughed'' about it to its sole survivor.
** Splashmon. Seriously - Cyber Land became a ghost town due to his actions. He pretty much killed every Digimon in it (he didn't directly kill them, but he pretty much set the motion as he absorbs negative energy from the citizens).
** Gravimon, considering how mercilessly he [[spoiler: played off of Kirihia's psyche and set in motion the events that resulted in, among other things, the death of Deckerdramon.]]
* A minor example, but [=IceDevimon=] of ''DigimonTamers'' certainly counts. Not content to merely load their data, he [[NightmareFuel keeps the frozen remains of the Digimon he killed as a kind of trophy gallery.]] Notably, Ruki, who to this point had been rather ruthless regarding Digimon, [[EvenEvilHasStandards is completely horrified]].
** If anything, [=IceDevimon=] in DigimonFrontier is just as bad, if worse. Here he's an AxCrazy killer whom even the current BigBad didn't want anywhere near him!