The Caligula / Fan Works

• Ask King Sombra presents Sombra as this instead of his depiction in the show. He's pretty dang nuts. In fact, most of the occurrences in the blog are simply him hallucinating after his defeat at the hooves of the mane six, which reduced him to a horn (Coffee Talk is trapped with him). Except the ghost monster. That was actually Luna. His Enemy Within, however, is pretty much how he was depicted in the show proper.
• In A Brief History of Equestria, it is shown that while most of the founders of Equestria were Flanderized in the Hearth's Warming Eve pageant, Chancellor Puddinghead, on the other hand, was toned down, elected via youth vote and managed to get killed shortly after Hearth's Warming in a stupid dare. Among many, many, other things like appointing her pet parrot to her cabinet, which it retained even after it died.
  • On the other hand Commander Sullamander, Hurricane's predecessor was less the humorous type and more the savage dictator type, who in her last years formed a Cult of Personality around herself. General Wind Whistler was able to lead roughly two-thirds of the pegasus military against her when the coup came since she was that hated.
• While Rupert Chill is stated to be the ruler of Planet Zok (which appears in a few Calvinverse stories), he spends most of his time yelling at his crew and trying to capture Calvin.
• The Conversion Bureau: Many iterations of TCB!Princess Celestia portray her as a deranged tyrant who commits genocide against entire species.
• Earth's Alien History has Matriarch T'Kell, the leader of the Vulcan Lost Colony known as the Last-of-all-Cities, who is an utter psychopath who rules with an iron fist and lashes out violently at anyone who disagrees with her. When a rival faction seems close to overthrowing her, she's perfectly willing to use a weapon that might destroy the whole planetoid her people are on to defeat them, seeing it as preferable to letting them win.
• In An Empire of Ice and Fire, Joffrey actually manages to be even worse than in canon, eventually going so insane that he declares himself a god. Around this point, he starts sentencing thousands of people from across Westeros and Essos to slave labor and forcing them to build a giant pyramid in honor of himself, and at another point he gleefully has Myrcella burned alive to power a spell meant to kill all his enemies.
• Eugenesis has Galvatron, who spends most of his time either just sitting on his throne not doing anything, or having hundreds of troops killed for non-existent plots to poison his drinks. It's mentioned that before he came back from wherever it was he'd been, the Decepticons under Soundwave had almost taken back all of Cybertron. The only reason they don't get rid of Galvatron now is that he's Galvatron.
• Flashman and the Throne of Swords: Flashman is quick to identify Joffrey as a mad despot, and even directly compares him to Caligula several times. Seeing how he's met multiple tyrants in Asia and Africa, he's more qualified than most in making that declaration.
• For the Glory of Irk: After becoming Tallest, Xia is convinced that she's the best there's ever been at her job but is only interested in doing the "fun" parts (like warfare and ordering people around) while finding the concept of doing actual work boring.
• Canon Princess Celestia is a wise and reasonable ruler, with just a few trickster shades. Fanon tends to exaggerate those shades out of proportion. The result is "Princess Trollestia", who falls squarely into this trope. The best-known example is probably the flash Friendship Is Magic Bitch.
• In Hivefled Her Imperious Condescension manages to be even crazier than she is in Homestuck canon due to her habit of kidnapping and raping teenagers for fun with The Grand Highblood and keeping one guy she has a crush on wired into her spaceship so she can continue torturing him and even had a child with him that she later forced into Parental Incest with because they "looked so cute together." What's even more disturbing is that she makes the case that her relationship with The Grand Highblood has actually reined in her Caligula tendencies, meaning she could be even worse.
• Scar in The Lion King Adventures, just as in the film. He even becomes so power-crazed that Hago kills him.
• Loved and Lost: After Prince Jewelius overthrows his aunts Princess Celestia and Luna by using the events of "A Canterlot Wedding" to destroy their reputations as well as those of Shining Armor and Twilight's friends (he tries the same with his cousin Princess Cadance, but isn't very successful), he proclaims himself "Holy King Jewelius I". At first, he's a Villain with Good Publicity thanks to his Mask of Sanity, but he's ultimately proven to be a narcissistic sociopath who delusionally regards his reign to be superior to that of the princesses and can't stand it when ponies think about them favourably. He imposes raised taxes and trading prohibitions on the entire town of Ponyville because he hated some comments made by Twilight's friends, and willfully focuses on hunting down the fugitive heroes at the expense of preparing against a new Changeling invasion, even though the fugitives have become the public's smallest concern at that point and Queen Chrysalis has a personal score to settle with him. He gets engaged to Twilight Sparkle in hopes of getting powerful heirs for his legacy, but he admits that if he discovered an even more powerful unicorn mare, he'd get rid of Twilight through a staged accident. He eventually leads his army (most of which is composed of released convicts he hired to replace the murdered Royal Guards who stayed loyal to the princesses) to wipe out Ponyville's inhabitants along with all the heroes as the ultimate statement of his rulership, even though unlike him, none of his chief minions are okay with this. When one of his guards questions the extremeness of such an act, Jewelius throws him out of the throne room's window. Oh, and he demotes Prince Blueblood to his personal servant and replaces the banners that depict Celestia and Luna's symbol with those that depict a proud-looking illustration of himself.
  Jewelius: If I can't control this nation through propaganda, then I'll just have to control it through fear.
• Ryuko Kiryuin in Natural Selection definitely qualifies. She's moody, violent, and utterly detached from the value of human life. She's also in charge of what should have been a bastion against the Life Fibers and turned it into a den of madness. Every month she throws city-wide slaughter-fests for her own amusement and burned down the Honnouji slums twice over; the first as an act of spite towards her sister, and the second in a fit of rage from being rejected by Mako.
• Rosario Vampire: Brightest Darkness: While she was never officially declared the queen of the chronofly kingdom, Falla Cii fits the bill in several ways. She's an absolute sociopath who only cares about herself and her own power, and sought to become queen so she could go on to become a warmonger and take over the entire world. In fact, her parents passed her over as queen in favor of Luna for this very reason: because she was too focused on the power to actually use it properly. Luna even tells her as such point-blank in Act IV, remarking that if Falla had become queen, her rule would have run their kingdom into the ground and wiped out their race. Ironically, Falla did exactly that when she found out that she was being passed over; she was so outraged at being passed over that she destroyed the entire kingdom and their entire species, declaring that if she can't be queen, then no one will be.
  Falla: Fine… so be it… if I can't be queen… NOBODY WILL BE!
• The backstory of The Smeet Series has Tallest Laven. After his wife died in childbirth, their smeet dying with her, he went mad with grief and eventually decided that if he couldn't have a happy family, no Irken could. To this end, he outlawed natural reproduction in the Irken Empire and led a purge of all pregnant Irkenettes and naturally-born smeets.
• The rewrite of Sonic X: Dark Chaos depicts The Prophet Muhammad (yeah, that one) as a sadistic demagogue with a penchant for slaughtering infidels and pedophilia. The background material expands on him; he tried to irrigate fields with vats of human blood, ordered every dog in the universe to be strangled because one barked at him, and invaded a galaxy based on the commands of a palm tree. It's rather telling that many characters — including his own Muslim followers — fear him more than they fear Maledict and the Demons. Even Jesus and the Angels consider him The Friend Nobody Likes and are planning on quietly assassinating him the first chance they get.
  • Beelzebub is a more straight example; though he isn't a monarch, his Psychopathic Manchild personality and disturbing sexual fetishes make him this trope. He's despised by pretty much all the other Demon leadership — even Maledict thinks his cruelty goes too far but keeps him around for his sheer intelligence.
• In Star Wars Paranormalities Trilogy, we are given Masochus, easily the most unhinged of the Valkoran leaders. For starters, he skinned himself down to the bone (only retaining some connective, vital, and sensory organs; and he's still alive), and he's done similar things (such as for experiments) to other Valkoran soldiers just because he could. He also compulsively hates everything and everyone just to stay alive. This is deconstructed in his backstory as a former Sith Lord, as this behavior got him exiled from the Sith Empire after killing too many civilians and soldiers alike for his own amusement. In the present day of the main story, Emperor Valkor doesn't mind his insanity as long as it isn't too counterproductive to his long-term goals (and Masochus is actually one of his closest supporters), but even then, the majority of the Valkoran Empire still hates his guts.
• Summer Crowns has the Tattered Prince after he conquers Pentos, at which point he runs a Kangaroo Court day and night, slaughtering the magisters for laughs and distributing their holdings amongst his followers.
• Wish Carefully: After the light side gives him control of Wizarding Britain, Voldemort makes the country into a dystopian state; as a massive Control Freak, he passes a bunch of draconian laws including requiring wizards to receive the Dark Mark once they come of age, frequently tortures his Death Eaters at random through their Dark Marks, and at one point tortured everyone on the street wearing glasses. None of this helps his side in any way because nobody wants to move to a country with him in charge, so the Dark Siders wind up suffering population decline and Generational Magic Decline thanks to their inbreeding practices.
• The Pharaoh comes off this way in Yu-Gi-Oh! The Abridged Series. His biggest moment is when he recalls "Slavemas", which is described as like Christmas, but he's the only one who gets presents, and all the presents are slaves. When Thief King Bakura tries to subvert this, the Pharaoh ends up declaring that Slavemas will now be celebrated every day.

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