History Monster / Supernatural

* "[[Recap/SupernaturalS07E19OfGraveImportance Of Grave Importance]]": [[SerialKiller Whitman Van Ness]] was a murderer operating in the early 1900s, responsible for [[SlashedThroat slitting the throats]] of numerous prostitutes who worked in his manor house. Culminating in murdering his own fiancée, Whitman framed the caretaker Dexter O'Connor. Becoming [[OurGhostsAreDifferent a powerful ghost]] after death, Whitman, to protect himself from the decay all ghosts suffer, took to [[SoulPower feeding off other spirts]], destroying them. To ensure his supply, Whitman spent decades killing countless people who came to his house, preventing their spirits from passing on doomed to [[AndIMustScream eventually decay into rotting mindless abominations]], with him openly enjoying his victims' horrific fate. After killing two teenagers, Whitman murders Annie Hawkins, then murders two of the teenager's friends by crushing their hearts, adding them all to his collection. When Dexter protested that he already had more than enough victims, Whitman drained him on the spot. The evilest spirit the Winchesters ever faced, Whitman's final act was to attempt to drain Bobby.

%% NOTE: Due to the controversial nature of this trope, any changes (additions, removals, edits) should be discussed [[https://tvtropes.org/pmwiki/posts.php?discussion=6vic3f9h1cy5qivsenw8llok here]].

-->--"[[Recap/SupernaturalS14E10Nihilism Nihilism]]"

Entries after God and Lucifer are by first appearance.

* "[[Recap/SupernaturalS07E19OfGraveImportance Of Grave Importance]]": [[SerialKiller Whitman Van Ness]] was a murderer operating in the early 1900s, responsible for [[SlashedThroat slitting the throats]] of numerous prostitutes who worked in his manor house. Culminating in murdering his own fiancée, Whitman framed the caretaker Dexter O'Connor. Becoming [[OurGhostsAreDifferent a powerful ghost]] after death, Whitman, to protect himself from the decay all ghosts suffer, took to [[SoulPower feeding off other spirts]], destroying them. To ensure his supply, Whitman spent decades killing countless people who came to his house, preventing their spirits from passing on doomed to [[AndIMustScream eventually decay into rotting mindless abominations]], with him openly enjoying his victims' horrific fate. After killing two teenagers, Whitman murders Annie Hawkins, then murders two of the teenager's friends by crushing their hearts, adding them all to his collection. When Dexter protested that he already had more than enough victims, Whitman drained him on the spot. The evilest spirit the Winchesters ever faced, Whitman's final act was to attempt to drain Bobby.

* [[Anime/{{Supernatural}} Anime]]: [[SupernaturalGoldEyes The Yellow-Eyed Demon]] is a sinister FallenAngel out to [[HellOnEarth open the gates of Hell itself]]. Conducting numerous [[DealWithTheDevil deals]] for the souls of mortals, the Demon was the murderer of Sam and Dean's mother as well as Sam's girlfriend Jessica, along with the mothers of many of his other "special" children to shape them as he desired. The Demon plays on Maria Masters's love for her sick daughter to have her kill a hunter investigating him, healing the young woman Meg while simply having her [[DemonicPossession possessed]] by a demon servant. The Demon later revives the son of the kind vampire Gayle to use his body to slaughter other Hunters. Later sending John Winchester to hell in exchange for his son's life, the Demon forces his "special" children to fight to the death so he may use the winner to unleash the apocalypse and the deaths of almost all humanity.

** [[{{Satan}} Lucifer]], once a prideful [[Characters/SupernaturalArchangels Archangel]] who tortured Lilith into being the first demon, was locked in Hell for corrupting Lilith and other human souls. Enacting the misery that befell the Winchester family through his child Azazel, Lucifer achieves freedom in the 5th season and causes mass loss of life across the world, seeking to wipe out humanity before he intends to destroy the demons as well. Freed from his cage in the later seasons to assist God and the Winchesters against God's sister, the Darkness--aka Amara--Lucifer later simply begins causing random mayhem and destruction for fun before attempting to become the new God. Failing miserably at the job, Lucifer supposedly begins to connect with his son Jack, but when Jack sees him for the egotistical monster he really is, Lucifer steals Jack's powers and decides to [[OmnicidalManiac annihilate all life in the universe]] and remake it [[InTheirOwnImage in his own image]], even trying to force Sam and Jack to choose [[SadisticChoice which of them will kill himself first]] to give the other a vague chance at stopping Lucifer. While trying to [[NeverMyFault paint himself as a tragic figure]], Lucifer is an [[PsychopathicManchild egotistical brat throwing a temper tantrum]], whose every redeeming quality is steadily stripped away until he is shown to be a selfish sociopath with [[AGodAmI a god complex]] who utterly rejects love and compassion in favor of cruelty and egotism.

->'''[[Characters/SupernaturalApocalypseWorld Michael]]''': Now, at first, I thought I'd do it better. Show Him. Be more God than God. But now... I just want to burn every one of His little worlds until I catch up to the old man.\\
'''[[Characters/SupernaturalCastiel Castiel]]''': And then what?\\
'''Michael''': Even God can die.

* Seasons 8 & 9: [[DarkActionGirl Abaddon]] is one of the [[EliteMooks Knights of Hell]], among the first demons created by Lucifer. Disgusted with her mentor Cain falling in love with a human woman, Abaddon [[DemonicPossession possessed]] and brought about the woman's death before possessing a woman named Josie Sands to infiltrate the Men of Letters and [[HeroKiller all but wipe them out]], knowing Josie's form would hurt her partner more. When she discovers that Hell has been brought under the more pragmatic Crowley in her absence, she sets out to become Queen of Hell and promises her followers a new reign of terror, deciding to cause [[HellOnEarth a demonic invasion of Earth]] to slaughter angels and humans in massive numbers until all Creation bowed to her, even reaping souls before their allotted time to outright double the amount of souls in Hell, stealing even more souls to torture to make new demon armies. Upon learning Crowley had regained human emotions, Abaddon tried to torture his own son Gavin [[ForcedToWatch in front of him]] to hurt him more until he caves to her demands. Abaddon [[ILied gleefully goes back on the deal]] to slaughter them all anyways, not planning to rest until [[TakeOverTheWorld everything in existence is brought under her heel in torment and blood]].

** {{God}} himself, once disguised as [[Characters/SupernaturalProphets Chuck Shurley]], proves himself towards the end of the series to be as [[GodIsEvil cruel and capricious]] as he once described himself in jest. Creating and abandoning countless universes while manipulating events and untold ages of suffering [[ItAmusedMe to craft his own perfect story for the Winchesters]], God tears open the gates of the world to unleash countless horrific spirits into the world to kill endless beings while proving fully willing to kill many himself when the Winchesters' defiance makes him decide the "story's over". Manipulating his sister Amara into merging with him to suppress his only weaknesses, God massacres the entire multiverse before reducing every being in the world to nonexistence save the Winchesters to force them to dwell on a barren, lifeless rock forever, even [[OffingTheOffspring murdering his most faithful son Michael]] for so much as having even considered defying him.

* "[[Recap/SupernaturalS07E19OfGraveImportance Of Grave Importance]]": [[SerialKiller Whitman Van Ness]] was a murderer operating in the early 1900s, responsible for [[SlashedThroat slitting the throats]] of numerous prostitutes who worked in his manor house. Culminating in murdering his own fiancée, Whitman framed the caretaker Dexter O'Connor. Becoming [[OurGhostsAreDifferent a powerful ghost]] after death, Whitman, to protect himself from the decay all ghosts suffer, took to [[SoulPower feeding off other spirts]], destroying them. To ensure his supply, Whitman spent decades killing countless people who came to his house, preventing their spirits from passing on doomed to [[AndIMustScream eventually decay into rotting mindless abominations]], with him openly enjoying his victims' horrific fate. After killing two teenagers, Whitman murders Annie Hawkins, then murders two of the teenager's friends by crushing their hearts, adding them all to his collection. When Dexter protested that he already had more than enough victims, Whitman drained him on the spot. The evilest spirit the Winchesters ever faced, Whitman's final act was to attempt to drain Bobby.

Entries after Lucifer are by first appearance.

* [[{{Satan}} Lucifer]] was [[TheParagonAlwaysRebels once a prideful Archangel]] who tortured Lilith into being the first demon, [[TheCorrupter corrupting human souls]], for which he was locked in Hell. Enacting the misery that befell the Winchester family through his child Azazel, Lucifer achieves freedom in the 5th season and causes mass loss of life across the world, seeking to wipe out humanity before he intends to destroy the demons as well. Later freed from his cage to assist God and the Winchesters against God's sister, the Darkness, Lucifer later simply begins causing random mayhem and destruction for fun before attempting to become the new God. Failing miserably at the job, Lucifer supposedly begins to connect with his son Jack, but when Jack sees him for the egotistical monster he really is, Lucifer steals Jack's powers and decides to [[OmnicidalManiac annihilate all life in the universe]] and remake it in his own image, even trying to force Sam and Jack to choose [[SadisticChoice which of them will kill himself first]] to give the other a vague chance at stopping Lucifer. While trying to [[NeverMyFault paint himself as a tragic figure]], Lucifer is an [[PsychopathicManchild egotistical brat throwing a temper tantrum]], whose every redeeming quality is steadily stripped away until he is shown to be a selfish sociopath with [[AGodAmI a god complex]] who utterly rejects love and compassion in favor of cruelty and egotism.

* "[[Recap/SupernaturalS07E19OfGraveImportance Of Grave Importance]]": [[SerialKiller Whitman Van Ness]] was a murderer operating in the early 1900s, responsible for [[SlashedThroat slitting the throats]] of numerous prostitutes who worked in his manor house. Culminating in murdering his own fiancée, Whitman framed the caretaker Dexter O'Connor. Becoming [[OurGhostsAreDifferent a powerful ghost]] after death, Whitman, to protect himself from the decay all ghosts suffer, took to [[SoulPower feeding off other spirts]], destroying them. To ensure his supply, Whitman spent decades killing countless people who came to his house, preventing their spirits from passing on doomed to [[AndIMustScream eventually decay into rotting mindless abominations]], with him openly enjoying his victims' horrific fate. After killing two teenagers, Whitman murders Annie Hawkins, then murders two of the teenager's friends by crushing their hearts, adding them all to his collection. When Dexter protested that he already had more than enough victims, Whitman drained him on the spot. The evilest spirit the Winchesters ever faced, Whitman's final act was to attempt to drain Bobby.
* Seasons 8 & 9: [[DarkActionGirl Abaddon]] proved herself to be as evil as any of her demonic predecessors. As one of the [[DemonLordsAndArchdevils Knights of Hell]], the first demons created by Lucifer, she was trained by Cain before he became TheAtoner. Abaddon tricked Cain into murdering the human woman he had fallen in love with with the First Blade, earning his undying hatred. After centuries of serving under Hell's banner, [[Recap/SupernaturalS08E22ClipShow in 1958]] she kills a priest who was researching a demon cure. She [[DemonicPossession possesses Josie Sands]] to infiltrate the Men of Letters, noting that Josie is in love with her partner Henry Winchester and therefore can hurt them more. Abaddon [[HeroKiller massacres the Men of Letters]] and follows Henry through a time portal into 2012, disposing of him after [[ILied going back on a deal]] she made with Sam and Dean. When she discovers that Hell has been brought under the more pragmatic Crowley in her absence, she sets out to become Queen of Hell and promises her followers a new reign of terror. After Crowley regains his human emotions, Abaddon [[Recap/SupernaturalS09E21KingOfTheDamned kidnaps his son Gavin]] and proceeds to torture him in front of his father. He caves in to her demands and helps her to defeat the Winchesters, but then she decides to kill them all anyway.

[[Series/{{Supernatural}} Sam and Dean Winchester, and company]], have faced countless demons and other creatures. Here are the [[CompleteMonster very worst]].

* [[{{Satan}} Lucifer]] was [[TheParagonAlwaysRebels once a prideful Archangel]] who tortured Lilith into being the first demon, [[TheCorrupter corrupting human souls]], for which he was locked in hell. Enacting the misery that befell the Winchester family through his child Azazel, Lucifer achieves freedom in the 5th season and causes mass loss of life across the world, seeking to wipe out humanity before he intends to destroy the demons as well. Later freed from his cage to assist God and the Winchesters against God's sister, the Darkness, Lucifer later simply begins causing random mayhem and destruction for fun before attempting to become the new God. Failing miserably at the job, Lucifer supposedly begins to connect with his son Jack, but when Jack sees him for the egotistical monster he really is, Lucifer steals Jack's powers and decides to [[OmnicidalManiac annihilate all life in the universe]] and remake it in his own image, even trying to force Sam and Jack to choose [[SadisticChoice which of them will kill himself first]] to give the other a vague chance at stopping Lucifer. While trying to [[NeverMyFault paint himself as a tragic figure]], Lucifer is an [[PsychopathicManchild egotistical brat throwing a temper tantrum]], whose every redeeming quality is steadily stripped away until he is shown to be a selfish sociopath with [[AGodAmI a god complex]] who utterly rejects love and compassion in favor of cruelty and egotism.

* [[TortureTechnician Alastair]] is Hell's Grand Inquisitor, and assists Lilith in her attempts to free Lucifer. Feared by demons beyond even angels, Alastair is responsible for supervising all the torture of Hell's souls, eventually corrupting them into demons. Having spent a hundred years torturing John Winchester, Alastair brutally tortured Dean every day then healed the damage and starting again for thirty years. Broken, Dean agrees to torture other souls to stop his suffering, thus breaking the first of the seals imprisoning Lucifer. [[Recap/SupernaturalS04E09IKnowWhatYouDidLastSummer Hunting]] for [[Recap/SupernaturalS04E10HeavenAndHell Anna Milton]], Alastair slit her parents' throats. When Ruby offers him Anna in exchange for sparing them Alastair captures and brutally vivisects Ruby with her own knife, beats Castiel senseless and scrambles Dean’s organs. [[Recap/SupernaturalS04E15DeathTakesAHoliday To break another seal]], he murders a Reaper and attempts to murder Tessa. [[Recap/SupernaturalS04E16OnTheHeadOfAPin Captured]], Alastair gleefully psychologically tortures Dean, then brutally beats and attempts to banish Castiel, before finally being killed by Sam. Living only to cause suffering and enjoying every single moment of it, Alastair was one of the worst demons in the series.

* "[[Recap/SupernaturalS07E19OfGraveImportance Of Grave Importance]]": [[SerialKiller Whitman Van Ness]] was a murderer operating in the early 1900s, responsible for [[SlashedThroat slitting the throats]] of numerous prostitutes who worked in his manor house. Culminating in murdering his own fiancée, Whitman framed the caretaker Dexter O'Connor. Becoming [[OurGhostsAreDifferent a powerful ghost]] after death, Whitman, to protect himself from the decay all ghosts suffer, took to [[SoulPower feeding off other spirts]], destroying them. To ensure his supply, Whitman spent decades killing countless people who came to his house, preventing their spirits from passing on doomed to [[AndIMustScream eventually decay into rotting mindless abominations]], with him openly enjoying his victims' horrific fate. After killing two teenagers, Whitman murders Annie Hawkins, then murders two of the teenager's friends by crushing their hearts, adding them all to his collection. When Dexter protested that he already had more than enough victims, Whitman drained him on the spot. The evilest spirit the Winchesters ever faced, Whitman's final act was to attempt to drain Bobby.

* [[{{Satan}} Lucifer]] was [[TheParagonAlwaysRebels once a prideful Archangel]] who tortured the below-mentioned Lilith into being the first demon, [[TheCorrupter corrupting human souls]], for which he was locked in hell. Enacting the misery that befell the Winchester family through his child Azazel, Lucifer achieves freedom in the 5th season and causes mass loss of life across the world, seeking to wipe out humanity before he intends to destroy the demons as well. Later freed from his cage to assist God and the Winchesters against God's sister, the Darkness, Lucifer later simply begins causing random mayhem and destruction for fun before attempting to become the new God. Failing miserably at the job, Lucifer supposedly begins to connect with his son Jack, but when Jack sees him for the egotistical monster he really is, Lucifer steals Jack's powers and decides to [[OmnicidalManiac annihilate all life in the universe]] and remake it in his own image, even trying to force Sam and Jack to choose [[SadisticChoice which of them will kill himself first]] to give the other a vague chance at stopping Lucifer. While trying to [[NeverMyFault paint himself as a tragic figure]], Lucifer is an [[PsychopathicManchild egotistical brat throwing a temper tantrum]], whose every redeeming quality is steadily stripped away until he is shown to be a selfish sociopath with [[AGodAmI a god complex]] who utterly rejects love and compassion in favor of cruelty and egotism.
* Myth/{{Lilith}}, from seasons 3 and 4, is the oldest demon in existence, and one of the worst. She [[Recap/SupernaturalS03E12JusInBello massacres a police station]], killing everyone that Sam and Dean had just finished saving, uses her position as the holder of Bela's contract to try and force her to kill Sam, and keeps a personal chef on hand to prepare human infants for her to eat. Lilith also has a thing for possessing little girls, destroying their families from the inside out for her own personal amusement. In the [[Recap/SupernaturalS03E16NoRestForTheWicked season 3 finale]], she holds a family hostage, killing the grandfather for making her mad, and has Dean dragged off to Hell, laughing the entire time. Reappearing in season 4, Lilith reveals that her current plan is to free Lucifer, bringing about the TheEndOfTheWorldAsWeKnowIt. When she discovers that freeing Lucifer will ensure her death, she tries to back out, offering to put off the apocalypse if Sam and Dean will let her kill them. Defeated by Sam in the [[Recap/SupernaturalS04E22LuciferRising season 4 finale]], Lilith goads him into finishing her, knowing that her death will result in the deaths of all humanity.
* [[TortureTechnician Alastair]], from season 4, is Hell's Grand Inquisitor, and assists the aforementioned Lilith in her attempts to free Lucifer. Feared by demons beyond even angels, Alastair is responsible for supervising all the torture of Hell's souls, eventually corrupting them into demons. Having spent a hundred years torturing John Winchester, Alastair brutally tortured Dean every day then healed the damage and starting again for thirty years. Broken, Dean agrees to torture other souls to stop his suffering, thus breaking the first of the seals imprisoning Lucifer. [[Recap/SupernaturalS04E09IKnowWhatYouDidLastSummer Hunting]] for [[Recap/SupernaturalS04E10HeavenAndHell Anna Milton]], Alastair slit her parents' throats. When Ruby offers him Anna in exchange for sparing them Alastair captures and brutally vivisects Ruby with her own knife, beats Castiel senseless and scrambles Dean’s organs. [[Recap/SupernaturalS04E15DeathTakesAHoliday To break another seal]], he murders a Reaper and attempts to murder Tessa. [[Recap/SupernaturalS04E16OnTheHeadOfAPin Captured]], Alastair gleefully psychologically tortures Dean, then brutally beats and attempts to banish Castiel, before finally being killed by Sam. Living only to cause suffering and enjoying every single moment of it, Alastair was one of the worst demons in the series.
* "[[CorruptCorporateExecutive Dick Roman]]", from season 7, is the leader of the [[Characters/SupernaturalLeviathan Leviathans]]. Not content with simply lurking in the shadows to feed on humanity, he planted his minions in key positions, murdering and devouring every human in the way. Taking control of a major company, Roman began to [[TamperingWithFoodAndDrink place chemicals in corn syrup]] so humanity would be rendered helpless as cattle for the Leviathans to feed on. The Winchesters, who he knew could prove an issue, he framed for a nation-wide killing spree. Other monster species were seen as "competition," with Roman planning to exterminate them as well after manipulating them into helping him. A horrible boss even by the show's standards, Roman was known to [[MonstrousCannibalism devour his minions]] in a fit of rage or "bib" them: forcing them to [[{{Autocannibalism}} devour themselves]]. Few villains on ''Supernatural'' have managed to inspire the same fear or hatred as Roman did, and his killing of Bobby Singer only deepened the hatred the Winchester brothers had for him.
* [[SerialKiller Whitman Van Ness]], from season 7's "[[Recap/SupernaturalS07E19OfGraveImportance Of Grave Importance]]", was a murderer operating in the early 1900's responsible for slitting the throats of numerous prostitutes who worked in his manor house. Climaxing by murdering his own fiancée, Whitman framed the caretaker Dexter O'Connor. Becoming [[OurGhostsAreDifferent a powerful ghost]] after death, Whitman, to protect himself from the decay all ghosts suffer, took to [[SoulPower feeding off other spirts]], destroying them. To ensure his supply, Whitman spent decades killing countless people who came to his house, preventing their spirits from passing on doomed to [[AndIMustScream eventually decay into rotting mindless abominations]], with him openly enjoying his victims' horrific fate. After killing two teenagers, Whitman murders Annie Hawkins, then murders two of the teenager's friends by crushing their hearts, adding them all to his collection. When Dexter protested that he already had more than enough victims, Whitman drained him on the spot. The evilest spirit the Winchesters ever faced, Whitman's final act was to attempt to drain Bobby.
* [[DarkActionGirl Abaddon]], from seasons 8 and 9, proved herself to be as evil as any of her demonic predecessors. As one of the [[DemonLordsAndArchdevils Knights of Hell]], the first demons created by Lucifer, she was trained by Cain before he became TheAtoner. Abaddon tricked Cain into murdering the human woman he had fallen in love with with the First Blade, earning his undying hatred. After centuries of serving under Hell's banner, [[Recap/SupernaturalS08E22ClipShow in 1958]] she kills a priest who was researching a demon cure. She [[DemonicPossession possesses Josie Sands]] to infiltrate the Men of Letters, noting that Josie is in love with her partner Henry Winchester and therefore can hurt them more. Abaddon [[HeroKiller massacres the Men of Letters]] and follows Henry through a time portal into 2012, disposing of him after [[ILied going back on a deal]] she made with Sam and Dean. When she discovers that Hell has been brought under the more pragmatic Crowley in her absence, she sets out to become Queen of Hell and promises her followers a new reign of terror. After Crowley regains his human emotions, Abaddon [[Recap/SupernaturalS09E21KingOfTheDamned kidnaps his son Gavin]] and proceeds to torture him in front of his father. He caves in to her demands and helps her to defeat the Winchesters, but then she decides to kill them all anyway.
* [[StrawNihilist Archangel Michael]] of the [[Characters/SupernaturalApocalypseWorld Apocalypse World]], from seasons 13 and 14, is the [[ItsAllAboutMe utterly egocentric]] head of a genocidal regime that seeks to [[KillAllHumans exterminate humanity]], with few survivors. Seeking to leave the world to annihilate others, Michael tortures Lucifer from the main world to obtain his power and murders the archangel Gabriel when he attempts to defend humanity. Eventually possessing Dean, Michael decides on monsters as a "perfect" race, killing many in experiments to perfect them and unleashing them on hunters and innocent humans, even attempting to have Kansas City itself wiped out. Revealing his intentions and [[RageAgainstTheHeavens his anger at God]], Michael intends on pursuing his creator to exterminate world after world and all life therein until he catches and kills God, remaining one of the most brutal and cruel angels ever encountered.
* [[DirtyCop FBI agent Terrence Clegg]], from season 13's "[[Recap/SupernaturalS13E11Breakdown Breakdown]]", is the notorious "Butterfly", and, despite being only [[HumansAreTheRealMonsters human]], is among the worst the Winchesters have faced. Having discovered that monsters exist, and exploiting their hunger for his own greed, Clegg kidnaps numerous humans before torturing and butchering them on [[MurderDotCom a live broadcast]] before auctioning their body parts and organs off to monsters as [[ToServeMan food]]; he has done this for twelve years, racking up a body count of possibly hundreds. When Dean and Sam Winchester investigate Clegg's crimes, he kidnaps Sam and attempts to cut his heart out before auctioning him off to his monstrous clientele.

* [[SerialKiller Whitman Van Ness]], from season 7's "[[Recap/SupernaturalS07E19OfGraveImportance Of Grave Importance]]", was a former rich man turned murderer in the early 1900s. He [[SlashedThroat slit the throats]] of numerous prostitutes who worked in his manor house, climaxing with the murder of his own fiancée and [[FrameUp framing]] the caretaker Dexter O'Connor for everything, leading to Dexter being shot by the authorities. Following his death, Whitman became [[OurGhostsAreDifferent a very powerful spirit]], and, to protect himself from the decay all ghosts suffer, began [[SoulPower feeding off other spirits]], effectively destroying them. Whitman spent decades killing countless people who came into his house, then used his powers to prevent their spirits from passing on; trapping his victims in constant terror of him [[AndIMustScream whilst they all slowly decay into rotting mindless abominations]] so he could stay strong. Whitman also takes amusement from their horrific fate and enjoys lording his power over them. In the present he murders two teenagers who hide in his house, and then murders Sam, Dean and Bobby's old friend [[HunterOfMonsters Annie Hawkins]]. A few nights later he murders two friends of the first pair of teenagers by crushing their hearts, adding all of them to his collection. When Dexter protested that he already had more than enough victims, Whitman drained him on the spot. Whitman's final act was to try and drain Bobby, before Sam and Dean burnt his bones.

* UsefulNotes/{{Lilith}}, from seasons 3 and 4, is the oldest demon in existence, and one of the worst. She [[Recap/SupernaturalS03E12JusInBello massacres a police station]], killing everyone that Sam and Dean had just finished saving, uses her position as the holder of Bela's contract to try and force her to kill Sam, and keeps a personal chef on hand to prepare human infants for her to eat. Lilith also has a thing for possessing little girls, destroying their families from the inside out for her own personal amusement. In the [[Recap/SupernaturalS03E16NoRestForTheWicked season 3 finale]], she holds a family hostage, killing the grandfather for making her mad, and has Dean dragged off to Hell, laughing the entire time. Reappearing in season 4, Lilith reveals that her current plan is to free Lucifer, bringing about the TheEndOfTheWorldAsWeKnowIt. When she discovers that freeing Lucifer will ensure her death, she tries to back out, offering to put off the apocalypse if Sam and Dean will let her kill them. Defeated by Sam in the [[Recap/SupernaturalS04E22LuciferRising season 4 finale]], Lilith goads him into finishing her, knowing that her death will result in the deaths of all humanity.

!Note: [[Administrivia/SpoilersOff All spoilers are unmarked.]] Administrivia/YouHaveBeenWarned!

* [[DirtyCop FBI agent Terrence Clegg]], from season 13's "[[Recap/SupernaturalS13E11Breakdown Breakdown]]", is the notorious "Butterfly", and, despite being only [[HumansAreTheRealMonsters human]], is among the worst the Winchesters have faced. Having discovered that monsters exist, and exploiting their hunger for his own {{greed}}, Clegg kidnaps numerous humans before torturing and butchering them on [[MurderDotCom a live broadcast]] before auctioning their body parts and organs off to monsters as [[ToServeMan food]]; he has done this for twelve years, racking up a body count of possibly hundreds. When Dean and Sam Winchester investigate Clegg's crimes, he kidnaps Sam and attempts to cut his heart out before auctioning him off to his monstrous clientele.

* [[DirtyCop FBI agent Terrence Clegg]], from season 13's "[[Recap/SupernaturalS13E11Breakdown Breakdown]]", is the notorious "Butterfly", and, despite being only [[HumansAreTheRealMonsters human]], is among the worst the Winchesters have faced. Having discovered that monsters exist, and exploiting their hunger for his own greed, Clegg kidnaps numerous humans before torturing and butchering them on [[MurderDotCom a live broadcast]] before auctioning their body parts and organs off to monsters as [[ToServeMan food]]; he has done this for twelve years, racking up a body count of possibly hundreds. When Dean and Sam Winchester investigate Clegg's crimes, he kidnaps Sam and attempts to cut his heart out before auctioning him off to his monstrous clientele.

* [[StrawNihilist Archangel Michael]], from seasons 13 and 14, of the [[Characters/SupernaturalApocalypseWorld Apocalypse World]] is the [[ItsAllAboutMe utterly egocentric]] head of a genocidal regime that seeks to [[KillAllHumans exterminate humanity]], with few survivors. Seeking to leave the world to annihilate others, Michael tortures Lucifer from the main world to obtain his power and murders the archangel Gabriel when he attempts to defend humanity. Eventually possessing Dean, Michael decides on monsters as a "perfect" race, killing many in experiments to perfect them and unleashing them on hunters and innocent humans, even attempting to have Kansas City itself wiped out. Revealing his intentions and [[RageAgainstTheHeavens his anger at God]], Michael intends on pursuing his creator to exterminate world after world and all life therein until he catches and kills God, remaining one of the most brutal and cruel angels ever encountered.

* [[StrawNihilist Archangel Michael]] of the [[Characters/SupernaturalApocalypseWorld Apocalypse World]] is the [[ItsAllAboutMe utterly egocentric]] head of a genocidal regime that seeks to [[KillAllHumans exterminate humanity]], with few survivors. Seeking to leave the world to annihilate others, Michael tortures Lucifer from the main world to obtain his power and murders the archangel Gabriel when he attempts to defend humanity. Eventually possessing Dean, Michael decides on monsters as a "perfect" race, killing many in experiments to perfect them and unleashing them on hunters and innocent humans, even attempting to have Kansas City itself wiped out. Revealing his intentions and [[RageAgainstTheHeavens his anger at God]], Michael intends on pursuing his creator to exterminate world after world and all life therein until he catches and kills God, remaining one of the most brutal and cruel angels ever encountered.

!NOTE: ALL SPOILERS ARE UNMARKED

* [[StrawNihilist Archangel Michael]] of the [[Characters/SupernaturalApocalypseWorld Apocalypse World]] is the [[ItsAllAboutMe utterly egocentric]] head of a [[OmnicidalManiac genocidal regime]] that seeks to exterminate humanity, with few survivors. Seeking to leave the world to annihilate others, Michael tortures Lucifer from the main world to obtain his power and murders the archangel Gabriel when he attempts to defend humanity. Eventually possessing Dean, Michael decides on monsters as a "perfect" race, killing many in experiments to perfect them and unleashing them on hunters and innocent humans, even attempting to have Kansas City itself wiped out. Revealing his intentions and [[RageAgainstTheHeavens his anger at God]], Michael intends on pursuing his creator to exterminate world after world and all life therein until he catches and kills God, remaining one of the most brutal and cruel angels ever encountered.

* [[ItsAllAboutMe Archangel Michael]] of the [[Characters/SupernaturalApocalypseWorld Apocalypse World]] runs a [[OmnicidalManiac genocidal regime]] that seeks to exterminate humanity, with few survivors. Seeking to leave the world to annihilate others, Michael tortures Lucifer from the main world to obtain his power and murders the archangel Gabriel when he attempts to defend humanity. Eventually possessing Dean, Michael decides on monsters as a "perfect" race, killing many in experiments to perfect them and unleashing them on hunters and innocent humans, even attempting to have Kansas City itself wiped out. Revealing his intentions and [[RageAgainstTheHeavens his anger at God]], Michael intends on [[StrawNihilist pursuing his creator to exterminate world after world]] and all life therein until he catches and kills God, remaining one of the most brutal and cruel angels ever encountered.

* [[ItsAllAboutMe Archangel Michael]] of the [[Characters/SupernaturalApocalypseWorld Apocalypse World]] runs a [[OmnicidalManiac genocidal regime]] that seeks to exterminate humanity, with few survivors. Seeking to leave the world to annihilate others, [[StrawNihilist Michael]] tortures Lucifer from the main world to obtain his power and murders the archangel Gabriel when he attempts to defend humanity. Eventually possessing Dean, Michael decides on monsters as a "perfect" race, killing many in experiments to perfect them and unleashing them on hunters and innocent humans, even attempting to have Kansas City itself wiped out. Revealing his intentions and [[RageAgainstTheHeavens his anger at God]], Michael intends on pursuing his creator to exterminate world after world and all life therein until he catches and kills God, remaining one of the most brutal and cruel angels ever encountered.

* [[StrawNihilist Archangel Michael]] of the [[Characters/SupernaturalApocalypseWorld Apocalypse World]] runs a [[OmnicidalManiac genocidal regime]] that seeks to exterminate humanity, with few survivors. Seeking to leave the world to annihilate others, [[ItsAllAboutMe Michael]] tortures Lucifer from the main world to obtain his power and murders the archangel Gabriel when he attempts to defend humanity. Eventually possessing Dean, Michael decides on monsters as a "perfect" race, killing many in experiments to perfect them and unleashing them on hunters and innocent humans, even attempting to have Kansas City itself wiped out. Revealing his intentions and [[RageAgainstTheHeavens his anger at God]], Michael intends on pursuing his creator to exterminate world after world and all life therein until he catches and kills God, remaining one of the most brutal and cruel angels ever encountered.

* The Apocalypse World version of ArchangelMichael, from seasons 13 and 14...

* [[StrawNihilist The Apocalypse World version of Michael]], from seasons 13 and 14...

* [[SoulPower Whitman Van Ness]], from season 7's "[[Recap/SupernaturalS07E19OfGraveImportance Of Grave Importance]]", was a former rich man turned SerialKiller in the early 1900s. He [[SlashedThroat slit the throats]] of numerous prostitutes who worked in his manor house, climaxing with the murder of his own fiancée and [[FrameUp framing]] the caretaker Dexter O'Connor for everything, leading to Dexter being shot by the authorities. Following his death, Whitman became [[OurGhostsAreDifferent a very powerful spirit]], and, to protect himself from the decay all ghosts suffer, began feeding off other spirits, effectively destroying them. Whitman spent decades killing countless people who came into his house, then used his powers to prevent their spirits from passing on; trapping his victims in constant terror of him [[AndIMustScream whilst they all slowly decay into rotting mindless abominations]] so he could stay strong. Whitman also takes amusement from their horrific fate and enjoys lording his power over them. In the present he murders two teenagers who hide in his house, and then murders Sam, Dean and Bobby's old friend [[HunterOfMonsters Annie Hawkins]]. A few nights later he murders two friends of the first pair of teenagers by crushing their hearts, adding all of them to his collection. When Dexter protested that he already had more than enough victims, Whitman drained him on the spot. Whitman's final act was to try and drain Bobby, before Sam and Dean burnt his bones.