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"Are you still feeling angry? Feel free to take it out on her. Even if you beat her too hard, she can be fixed easily, and I’ll still be able to go with my plans. Come on, take some pleasure in punishing the genie for not being subservient to your whims. She’s basically nothing more than an object right now."
Vicegerent Zathir, Ask Genie Twilight

Fan Works based on My Little Pony (especially Friendship is Magic) have a surprisingly large amount of loathsome characters.

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Codex Equus

    Examples 
  • First Age: Shrock is the power-hungry leader of a band of Raptorians. Growing envious of his employers, Shrock would attempt to murder and usurp the throne of his home kingdom. He would then find Porcina and manipulate her, intending to eventually kill her once she's no longer useful to him, while also having her unknowingly turn other servants who got too close to the truth to glass so he could shatter them. After putting ponies to hard labor and threatening their lives to get her magic cloak repaired, Shrock would have her turn all of Ponyland to glass so he and his cohorts could take it as their own, and have as much sadistic fun as they want with the population. Finally uncovered, Shrock would attempt to turn the heroes to glass and shatter them one by one in a fit of pique. While just a normal creature, Shrock proves himself one of the vilest beings the Paradise Empire ever faced.
  • Second Age: Queen Dark Crystal, the Grand Matron of All Witches, is one of the most powerful and evil witches to ever exist. After committing many heinous acts as a Hydianite witch, Queen Dark Crystal's first act upon being empowered into the "Ultimate Witch" is to sadistically murder her entire family and devour their souls. She would then unleash a reign of terror, killing countless innocents and causing the Late Bronze Age Collapse before being sealed away. Even sealed away, Queen Dark Crystal would compel the users of her spell book to continue her evil intentions. Upon being released in modern day, Queen Dark Crystal would instantly level a city and attempt to slowly kill all life on Tellus with a permanent eclipse. She would attempt to destroy most life on Equus and corrupt what's left to create a world of sin and evil. Queen Dark Crystal would kill and devour the souls of the Virtuous Seven when they try to stop her after subjecting them to the pain of their predecessors' deaths at her hooves. Even after her demise, the Hydianite covens Queen Dark Crystal resurrected would go on to menace Tellus for tens of thousands of years.
  • Fourth Age:
    • Ragnarok Cycle: Ragnarøkkr is the High King of the Shadowed Ones and the true mastermind of the Ragnarok cycle. Having fed off and orchestrated destructive cycles for millions of years, Ragnarøkkr would lead the Shadowed Ones in trapping Cerividia and the Nine Realms in a cycle where those who live in them destroyed over and over so the Shadowed Ones can feed on the energy their deaths create to empower themselves. Ragnarøkkr would condemn others to horrible fates for minor slights and even give one of his wives and some of his daughters to his psychopathic cohort Surtr to be personal playthings and sex slaves for displeasing him. When High King Kaldr uncovers the cycle, Ragnarøkkr would attempt to brutally kill him and his allies so he could trap them in a reincarnation cycle where each life is worse than the last as punishment for defying his will, and attempts to take Queen Mzazi as breeding stock and rape her. Forced into his true form, Ragnarøkkr would raze several armies and ultimately attempt to destroy the Nine Realms in a final act of spite when cornered.
    • The Giant Wars: Khuligan the Brutal is a Giant raider living in the Moroz Valley region who has terrorized it for years. Extorting the settlers of the region even if it'd condemn them to a slow death by starvation, any village that can't pay Khuligan's toll would be destroyed. While eating some, he would choose victims at random, even smaller Giants, and slowly crush them to paste under his hooves or dismember them with his teeth—or worse; he was previously exiled from his homeland for similar brutality. When the town of Moroz defies Khuligan, he amasses a huge raiding party to raze the entire valley to the ground out of petty spite.
    • Meridia: Devil Dingo is the right hand of Lord Waking Nightmare and Meridia's vilest Raider. From age 14, he would Rape, Pillage, and Burn countless settlements, only growing worse after becoming a warlock and amassing a body count considered horrifying even by the standards of a Death World like Meridia. Among his favorite pastimes is to feed victims to his pit of Ripdingos for his own amusement. Devil Dingo is a mass murdering psychopath so vile, he considers imprisonment a Fate Worse than Death solely because he can no longer indulge his sadistic urges on anyone else.
    • Severed Strings is a cannibalistic Serial Killer. Known as the Beast Killer, he was known for mutilating his victims until they looked like an animal had mauled them. Severed Strings would eventually become a Skin Walker by murdering and eating his own sister before slaughtering his hometown during a sandstorm. Over the centuries, Severed Strings would amass a body count in the thousands and every hundred years wipe out another town like he had his own, as well as possess people and make them kill their loved ones and poison towns using powdered infant remains. When Vinyl Scratch discovers his latest string of murders, Severed Strings would try twice to possess Octavia and make her kill Vinyl out of pure sadism.

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Other Examples

    A - G 
  • Ask a Pony:
    • Ask Genie Twilight's "Return to Saddle Arabia" arc: Vicegerent Zathir believes Genies should be bound to their master's will and captures Twilight with a black lamp to leave her aware but unable to defy his commands. Planning to use her to conquer her own homelands, Zathir's tool leaves her in a constant state of feeling electric shock and if she isn't freed from his control in three days, will be tortured by the pain for eternity. Persuading his superior to allow his plans to go uninterrupted by allowing him to rape Twilight, Zathir later tries to have her murder her friends and loved ones.
    • Ask Jappleack: Appelox, the former Titan of Honesty, one of the ancient Titans who created Equestria, later betrayed his siblings and ate all of them, and became a reality-eating monster. In the present, Appelox had been devouring entire planes of existence, all of which were populated, to build up enough power to break a barrier his sister Twilus had placed around Equestria Prime—the version of Equestria seen in the show—and complete his consumption of the Multiverse. While talking to Jappleack, Appelox reveals that he was also the one who had sent his two sons, Discord and Wolflor, to destroy everything and everyone in her version of Equestria, and is the reason that her sister is dead.
  • The Assassination of Twilight Sparkle: Amadeus Blueblood is a powerful Canterlot noble who at first just treated ponies of lesser status, especially the guards and servants, like trash. He's soon revealed to be far worse, involved in, among other deeds, bribery, blackmail and outright assassinations. Manipulating his own son, who he's heavily implied to have corrupted into becoming what he is at the time of the story, he has him assassinate Twilight Sparkle; blackmails Gallant Heart with his beloved brother's life; and has the entire conspiracy, including his son, brutally killed to cover his tracks. After the princess punishes his clan for his association with his son, he poisons his own wife so he can escape to Unicornia with his daughter, Majesty, who he drives down the path of evil, just like he did with her brother.
  • The Captain Goodking Saga: Sanies begins his career by consuming his future master's assistant and practicing the spells he taught him on various unwilling victims, leaving them dead or in various awful states from him absorbing their life and magic. Sanies proceeds to massacre a village in the Dragon Lands to gain Celestia's attention and to take over her mind. Failing at this, Sanies tricks Luna and Discord into resurrecting the Storm King, allowing him to go on a magic-fueled rampage before betraying him and using his power to destroy the world. When Sanies's master returns, Sanies uses Chrysalis's body to disguise himself as a corrupted Star-Swirl and uses corrupted illusions of the other Pillars so he and his master can convince Stygian to become the Pony of Shadows again. Sanies then possesses Luna's body, killing Captain Goodking numerous times within a dream world to burn time while making the moon slowly descend upon Equestria to crush it. In his final outing, Sanies uses the power of the Seals of the Planets that his future self gave him to wipe out all life in the universe.
  • The Dear Sweetie Belle Continuity:
    • Dear Cutie Mark Crusaders: Former Captain Feather Duster was fired for drunkenly flooding rabbit holes during Winter Wrap-Up, taking revenge by causing a catastrophic storm, killing Applejack's parents. Feather Duster would have happily let Rainbow Dash, his replacement, face the wrath of Ponyville, had he not drunkenly passed out at the scene of his crime. Lashing out at Dash again, Feather Duster forces her to choose between saving Scootaloo and stopping him from unleashing another, even more destructive storm. After seemingly being stopped, Feather Duster returns in "Cutie Mark Crusaders Dream Warriors", where his disembodied spirit returns to feed off the nightmares of ponies and tries to possess Scootaloo's body to murder Dash.
    • The Changelings Have A King: Prince Blueblood is the spoiled nephew of Celestia who becomes king of the Changelings. After he and Chrysalis marry, he begins making plans to take over Equestria and gain revenge on Rarity. To that end, he starts isolating her in order to make her dependent on him. After moving to Ponyville, he kidnaps ponies to feed to his monstrous spawn and stirs drama between Spike and Crescendo—Rarity's former lover—to the point that Spike nearly kills him. After being found out, he unleashes his horde of flesh-hungry Changelings on Ponyville, watching with a smile as innocent ponies get violently ripped apart. After his offspring are killed, he brushes off their deaths and simply tries to kill Rarity outright, only for Spike to take the shot. He then attempts to kill his aunts in an attack that ends up killing Trixie and Shining Armor, and then drains a mortally wounded Chrysalis of all the love he gave her before leaving her to die. Even after being defeated, he shows no remorse when asked if he has any regrets; he simply states he regrets not killing everyone sooner.
  • Equestria: Across the Multiverse:
    • "Winter Wedding" arc: Princess Spring Heart/"Chrysalis" is Princess Rosie's Evil Aunt who was banished from the Isle of Pony for attempting to murder her older sister Starburst and intentionally got her infant niece lost at sea in an attempt to usurp the throne and use the stash of magical artifacts the royal family protects to conquer the world. Years later, she kidnaps her sister Winter Song and impersonates her with intent of slaughtering their entire family to continue her plans, including the now-teenager Rosie and Patch. When that plan is foiled, she attempts to slaughter the entire wedding party with her stolen jaunt tech-enhanced army, with a Dead Man's Switch that will nuke the Isle if she dies, eventually turning her homeland into a war zone. As her plans fall apart, she stops carrying about killing her own soldiers in the crossfire, and ultimately orders her sub to nuke as many places as possible out of pure spite, nearly destroying Ponyland's capital in the process. Spring Heart will destroy anyone and anything without a moment's regret to get what she desires.
    • "Monstrous 5" arc: Eustace "Mr. E" DeMonic is the morally bankrupt CEO of Scum Labs. Obsessed with profit above all else, he subjects his workers and the public to unethical and potentially deadly working conditions and products. Taking over Crystal Prep, the student body are made into guinea pigs to be subjected to all manner of potentially deadly and untested products, with any who object disgraced, framed, or even assassinated by DeMonic's underworld connections. Making the Shadowbolts into scapegoats for the loss at the Friendship Games, they are forced to submit to horrific "product tests" under threat of their families being ruined. This ends with them horrifically ill and on death's door, a process Mr. E intended to subject 35 other innocent people to. Despite warnings of the possible consequences, Mr. E has the five subjected to cruel experimentation, resulting in them mutating into Kaiju. The end result is millions dead, all because of Mr. E's bottomless greed. Concerned with his own profit above all else, DeMonic will sink to any low to get it.
  • The Flash Sentry Chronicles: Dark Mist is the brutal leader of the Tricksters and the Arch-Enemy to Sharp Paw and the Jakhowls. Wishing to spread chaos throughout Equestria, he raids villages to either enslave or burn them down to exterminate the population, garnering a body count of 100 ponies. When he mind controls one such village, he orders his servants to attack the guards sent to stop him and raze the village to kill everyone present. He later helps create the Alicorn Amulet to strengthen the Tricksters and all them to wipe out the Jakhowls, even when warned that the rune magic associated with the amulet could kill the Tricksters as well. With his tribe, he formally challenges to the Jakhowls to a final battle, threatening to kill Sharp Paw's wife, Calm Paw, if he refuses. When the battle commences, he orders his Tricksters to slaughter as many Jakhowls as they can and tries to kill Sharp Paw himself. When facing defeat, he activates a rune that results in the extinction of both the Jakhowls and Tricksters, maniacally laughing at satiating his hatred for the Jakhowls. A depraved creature who created destruction for his own amusement, Dark Mist stands out as one of the greatest monsters in Equestrian history.
  • A Future of Friendship, a History of Hate: Ruinate was the Token Evil Teammate of the Sentiox, and created Equestria as a Crapsack World just to make those living in it suffer. When the other Sentiox healed his world, Ruinate went on a rampage, destroying the planets they created and killing the other Sentiox. Originally imprisoned in another dimension for his crimes, after his escape, Ruinate plans to return Equestria to its former state before destroying all the other planets in the universe. Ruinate kidnaps the Mane Six (sans Twilight) and experiments on them to make himself immune to the Elements Of Harmony, and sends a brainwashed Spike to try and kill Twilight.

    H - Z 
  • Getting Back on Your Hooves: Checkmate "Checker" Monarch is Trixie's sociopathic sister and a surprisingly dark villain for an otherwise lighthearted fanfic. Finding out that Trixie's getting back on her hooves, she dedicates herself to ruining Trixie's life like she did before, starting with using an illegal dream infiltration spell to give Rainbow Dash frightening nightmares about Trixie bullying her, and later invading Trixie's dreams when her plan to turn Trixie and Dash against one another fails. When Checker's attempts at breaking Trixie's confidence fail, she tries to murder Dash with a lightning bolt as a response to her not doing what Checker wanted, and has the Diamond Dogs kidnap Trixie so she can force her to choose between leaving Ponyville forever or watch as she destroys the homes and livelihoods of her friends, dumping her in the desert when she chose to leave, still intending on following through her threat anyway. When her plans were publicly exposed, she traps Trixie, the Mane Six, and herself in their dreams, knowing that others won't be able to do anything because forcefully waking up a pony affected by a dream invasion spell would kill the target. She then exploits the inner doubts of the Mane Six, in the forms of their friends and families turning against them because of said self-doubt. As for Trixie, she drops the manipulation and actively tries to murder her, taking the form of a mutated Ursa Major specifically so Trixie would die terrified.
  • Grogar: A Hearths Warming Horror Story & Screams Upon A Winters Night, by Jade Ring: Grogar is an Evil Sorcerer who sacrificed the rest of his race for immortality. Banished to the land of Tambelon by Celestia and Luna, Grogar returns every Hearth's Warming Eve to kill those who lose their faith in the spirit of Hearth's Warming and transform them into his undead minions, along with everyone else who happens to be in the area. In the original, he kills Applejack, Big Mac, Granny Smith, Silver Spoon, Scootaloo, and Marble Pie, before freezing all of Ponyville and killing the inhabitants. In the sequel, Grogar returns and kills more ponies before freezing Trottingham, and it is revealed that he plans to keep gradually freezing towns across Equestria until he has turned the entire land into a frozen wasteland devoid of life, so he can rule over it and keep everyone's souls enslaved forever.
  • Harbinger, Tealove: Revenant is the father of all harbingers, zombie-like creatures that devour life and possess the bodies of their victims. After his initial attack on the dragons failed ages ago, he launches another attack on the ponies, exterminating nearly every being in Equestria. He also launches attacks on the dragons and griffons, while also planning to invade other nations when he's finished with Equestria. When most of the ponies congregate in Fillydelphia, Revenant wipes out every surrounding settlement he could find and launches a final attack on the city, planning to slaughter everyone there. Although harbingers need to feed on life to survive, Revenant clearly enjoys all of the suffering he inflicts on every being he meets.
  • The Immortal Game: Titan, once known as Order, is the despotic father of Luna, Celestia, and Terra. After temporarily defeating Discord, Titan murders his first wife, Harmony, and forces Terra to be his new wife. In the process, he inflicts the Insanity on her, turning her into a sadistic maniac who was more than willing to torture Celestia. When the creations of his wife rebelled against him, Titan warred with them until his daughters imprisoned him and Terra. Freed by General Esteem, he fought the subjects that were still loyal to his daughters and tried to force Luna to be wed to his second son, Empyrean. When Empyrean is depowered, Titan snaps his neck before mercilessly beating the Element bearers for trying to use the Elements of Harmony against him.
  • Loved and Lost: Jewelius is the sociopathic nephew of Princess Celestia. Envious of the power his aunt and older cousin, Princess Cadence, have, Jewelius secretly organizes the Changeling invasion and allows Chrysalis to pose as Cadence at her wedding. Publicly accusing Celestia and the Mane Six—except Twilight—of focusing more on the wedding than on national security, Jewelius rallies up the disillusioned populace and royal guards and takes Celestia's position as ruler of Equestria by force. As king, Jewelius has his enemies exiled, orders the guards who were still loyal to Celestia to be murdered and replaced with criminals from the dungeons, raises the taxes in Ponyville and allowing the population there to starve just to spite the Mane Six, betraying Chrysalis and planning to enslave the Changelings, and ordering Celestia's execution when she returns. When he finds out Celestia and the Mane Six are hiding out in Ponyville, Jewelius orders his army to massacre Ponyville and threw one of his own soldiers out of a window for disagreeing with him.
  • The Night the Magic Died: Gralo, aka Garret, is an evil Krassau who desires to absorb all magic to increase his power, leaving lifelessness in his wake, justifying himself with the belief that his species is superior to all other beings. Having already caused widespread death and destruction, Gralo fled to Equestria to escape punishment and possessed Garret while leaving him conscious, reducing him to an Empty Shell when Gralo had no more use for him. He tries to drain all things magical—-including emotions and liveliness—-from Equestria's population, threatening to obliterate all life in the universe. Gralo also gives breaking lectures to the Princesses and threatens to suck Cadance dry to make them suffer. Gralo was a vile enough being that his kind considers him being banished to the Void Between the Worlds the only fitting punishment, and in his final moments of freedom, he spitefully attempts to turn the Princesses against Nahmat.
  • The Nuptialverse's "Metamorphosis": Discord is far more malicious than his later redeemed canon self. He is first introduced offering the rogue Pegasus that will soon be Chrysalis a deal that, in exchange for her servitude, she will have the power of all three tribes. He then made a hidden fourth tribe of ponies, the Flutterponies, painfully transform into the monstrous Changelings so the Pegasus can have an army. After the Pegasus and her changeling army ambushed the meeting, Discord reveals himself and murders the tribe leaders and everypony in the building in unusually cruel methods. When the Pegasus was growing impatient and wondering when Discord would hold up his end of the bargain, he has the Changelings turn the Pegasus into their queen, explaining that he had promised her "the power of all three tribes". When Chrysalis protested, he tortured her and told her she should be grateful for what he did and that she didn't wind up like Celestia and Luna, who he casually revealed to have Forced to Watch as he murdered everyone blood-related to them before making them immortal.
  • Old Mare Luna: King Sombra starts his conquest of Equestria by tricking Luna into killing her sister and the Mane Six before moving onto the Crystal Empire and brutally murdering all who stand in his way, including Princess Cadence and Shining Armor. Deciding to test out an arena he intends to use to celebrate his conquest of Equestria, he forces Sunburst to fight a mind-controlled Starlight Glimmer and, when Starlight snaps out of his control, he impales Sunburst and painfully forces Starlight back under his control before siccing her and the rest of his mind-controlled forces on Sunburst.
  • Pony POV Series:
    • The Shining Armor Arc: General-Admiral Solomon Azure Raven Makarov is actually a reality bending creature who wants to rewrite all of reality to revolve solely around him. Makarov's actions include trying to kill Shining Armor for not knowing who he is; abducting four ponies and converting them into cyborgs who are fully aware but unable to do anything but obey his orders; trying to slaughter a village; and blowing off Running Gag's wing. Makarov's plan is to launch a superweapon that will disable Pegasus and griffin flight, sending millions falling to their deaths and causing a massive war. After Shining feeds him to the Blank Wolf, Makarov awakens to find the world a much better place, showing just how bad he really was. Makarov planned to paint all his victims as the villains and himself as the hero of the story out of a selfish desire to make everything revolve around him.
    • The Dark World Arc: Nightmare Eclipse, the true villain of the arc, is the one responsible for every previous villain in the arc and every evil act that occurred in the arc. Nightmare Eclipse is a version of Twilight from an alternate future ruled by Discord, who had somehow managed to defeat Discord and trap him in his own world. Eclipse decided to punish Discord by placing him and everyone else in a "Groundhog Day" Loop. Every thousand years, Discord would be defeated and killed, after which, time would reset itself and after another thousand years, he would be killed again. With each cycle, Discord's evil actions would get progressively worse. Likewise, Discord's death would become more and more painful. Trapping everyone else with Discord, Eclipse had them tortured along with Discord. This continued on for several hundred million years, during which Eclipse mind raped alternate versions of her friends into acting as her Co-Dragons. When Twilight and her friends defeat Discord, Eclipse tries to reset time again, and tries to kill Twilight and her friends when they try to stop her. During the battle, Eclipse sets Apple Pie on fire. Determined to torture Discord for all eternity even if it meant having millions of innocents tortured along with him, Eclipse proved herself to be no better than Discord himself.
    • Royal Wedding Arc: Kabuto is the Evil Genius of the Changelings, and the most evil of them, surpassing even Chrysalis in villainy. Kabuto is considered a monster even by the other Changelings, with one half of the hive hating him, and the other half fearing him. Kabuto is introduced by asking Chrysalis for permission to experiment on the Mane 6 after the Changelings take over. Later, Kabuto is revealed to have a long history of killing and experimenting on other beings, including other Changelings, often neglecting to use anesthetic just to make the victim suffer. Kabuto even wants to experiment on Neatly Spell, who is a foal. Kabuto is also the only Changeling aware of Chrysalis's plan to build a giant rune to suck all the love out of every living being in Equestria and give it to her, leaving all living beings in Equestria other than Changelings as lifeless husks. Despite this, Kabuto still aids Chrysalis in her plans. When Misfit Actual and his team try to arrest Kabuto, he tries to vivisect them. Finally, he is the only Changeling who is not redeemed, instead being banished to the sun.
    • The Day Love Cried: This side story has a one-shot villain in the form of the nameless Pegasus filly. Due to her inability to build a relationship, she developed a hatred for the very concept of love itself, and decided to take her anger out on Cupid and his mother Venus. Being a Child Prodigy with an unnatural level of intelligence and an understanding of magic, she crafted the Concept Killing Spear, and set about trying to use it to wipe Cupid and Venus from existence, not caring that she would erase countless lives from existence in the process. After being killed by Venus, her spirit is shown the results of her actions of killing Cupid. Even after seeing all the harm her actions caused, she feels no regret for her actions, not even trying to fake remorse in an attempt to avoid being Dragged Off to Hell just so that she can spite Venus by refusing to apologize. For her limited resources and single appearance, this filly manages to cause more evil than almost every other villain in this story.
  • Recall the Time of No Return: Brotonia, the queen of the Crimson Changelings, took Empress Twilight Sparkle's identity after defeating her 1000 years from the present day. As "Twilight", she quickly became a tyrannical ruler who pretended to have become paranoid about the Crimson Changelings invading Equestria in disguise. She had tens of thousands of ponies executed under "suspicion" of being Changelings, along with several thousand more who dared oppose her, and still more were killed by her monstrous Iron Wolves. At the same time, she herself had been replacing ponies for years with her Changelings, keeping the real ones underground in hundreds of cocoons. She had kept the real Twilight, along with Sterling, the young Alicorn meant to take the place of Princess Luna, in cocoons to act as sort of magic battery chargers, and attempted to doom Sterling's sister Gold Lily to the same fate. When Twilight's friends arrive in the future, she attempts to have them imprisoned in cocoons as well, and when Fluttershy attacks her, she has the guard who let go of her brutally killed by an Iron Wolf. She later mounts a deadly attack against Spike's rebel group, and during a fight with the real Twilight, sends a massive energy blast at Ponyville.
  • The Two Sides of Daring Do: Ahuizotl tries to combine the power of the Belt of Atlas and its temple with the Rings of Scorchero to steal the Princesses' power and use it to turn all of Equestria into a scorching wasteland devoid of life, just because he can. He gives Daring Do's clone a savage beating and nearly kills her and the original Daring Do. It's also revealed that he places Daring Do in death traps specifically because he wants her to die a slow death.

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