"You know, I haven't been up here since Poland '43. Truth is, I loathe it. It's chilly. No stink of blood or sizzle of flesh or the wet flap of flayed skin. I don't know how you stand it."
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.
Castiel: And then what?
Michael: Even God can die.
Castiel: And then what?
Michael: Even God can die.
— "Nihilism"
Saving people and hunting things is the family business. Here are the very worst that Sam, Dean, and company have hunted.
All spoilers are unmarked. You Have Been Warned!
Original Series
- God and Lucifer both demonstrate themselves as a particularly vile father-son duo:
- God Himself, once disguised as Chuck Shurley, proves Himself towards the end of the series to be as cruel and capricious as He once described Himself in jest. Creating and abandoning countless universes while manipulating events and untold ages of suffering 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 murdering His most faithful son Michael for so much as having even considered defying Him.
- Lucifer, once a prideful 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 annihilate all life in the universe and remake it in his own image, even trying to force Sam and Jack to choose which of them will kill himself first to give the other a vague chance at stopping Lucifer. While trying to paint himself as a tragic figure, Lucifer is an egotistical brat throwing a temper tantrum, whose every redeeming quality is steadily stripped away until he is shown to be a selfish sociopath with a god complex who utterly rejects love and compassion in favor of cruelty and egotism.
- Seasons 3 & 4: Lilith is the oldest demon in existence, and one of the worst. She 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 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 The End of the World as We Know It. 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 season 4 finale, Lilith goads him into finishing her, knowing that her death will result in the deaths of all humanity.
- Season 4: 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. Hunting for 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. To break another seal, he murders a Reaper and attempts to murder Tessa. 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.
- Season 7: "Dick Roman" is the leader of the 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 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 devour his minions in a fit of rage or "bib" them: forcing them to 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.
- Seasons 8 & 9: Abaddon is one of the Knights of Hell, among the first demons created by Lucifer. Disgusted with her mentor Cain falling in love with a human woman, Abaddon possessed and brought about the woman's death before possessing a woman named Josie Sands to infiltrate the Men of Letters—which included Sam and Dean's grandfather Henry—and 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 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 in front of him to hurt him more until he caves to her demands. Abaddon gleefully goes back on the deal to slaughter them all anyways, not planning to rest until everything in existence is brought under her heel in torment and blood.
- Seasons 13 & 14: Archangel Michael of the Apocalypse World is the utterly egocentric head of a 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 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.
- "Of Grave Importance": Whitman Van Ness was a murderer operating in the early 1900s, responsible for 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 a powerful ghost after death, Whitman, to protect himself from the decay all ghosts suffer, took to 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 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.
- "Breakdown": FBI agent Terrence Clegg is the notorious "Butterfly", and, despite being only 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 a live broadcast before auctioning their body parts and organs off to monsters as 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.
- The Yellow-Eyed Demon is a sinister Fallen Angel out to open the gates of Hell itself. Conducting numerous 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 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.
