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Villains Love Entertainment

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Most people enjoy entertainment; there wouldn't be movies, books, TV, theatre, games, etc. if they didn't. Villains are no exception, but depending on the character, they may have a very different idea of fun.
Many of them are Sadists who find it amusing to watch others struggle and suffer; it's even the driving motivation behind many villains' actions. Others simply love regular entertainment, enabling the Scheherezade Gambit if a hero can successfully distract them by being fun to watch. Another variation is villains who are highly competitive in things such as sports and games, though it's important that they enjoy doing so.
Despite the numerous different ways bad guys can display their love for entertainment, one thing usually holds true - they dislike being bored. For some it's an important trait, they'll often light fires under the asses of those around them just to keep things interesting or kill those who can't hold their attention. These ones are typically tyrants in positions of power and can often be expected to engage in Orcus on His Throne. A Psychopathic Manchild may have trouble focusing on anything for too long and will demonstrate a fondness for games to exemplify their childish traits. In the case of manchildren, also expect them to be very upset if their fun is taken away. Child antagonists also tend to love TV and games.
Many villains either observe or engage in battles as a means of amusing themselves. In this case, the characters usually prefer tough opponents who can give them a challenge and won't be easily defeated. You may get an Arrogant Kung-Fu Guy in this camp, as while some can have Villain Respect, others may be poor sports. In that vein, sports-playing baddies are often cheaters.
Entertainment for sadists will often come in the form of Forced Prize Fights, Involuntary Battles To The Death, Gladiator Games, Blood Sports, and Deadly Games, often involving Condemned Contestants. If they're a ruler of some sort this can serve as a form of Bread and Circuses to keep their people entertained. Involuntary Dancing is also likely, possibly involving Belly Dancing if the villain is of the more lecherous variety.
On the more normal end of things, having villains enjoy entertainment can be a means of humanizing the characters into Anti Villains and making them more relatable to the audience. Works about sports or competitions also usually feature bad guys dedicated to their games.
If a villain enjoys reading as a pastime, one can usually expect them to be very intelligent and often a Badass Bookworm or Awesome by Analysis. However, this is not a rule.
It's important to note that a villain does not have to be good at their pastimes, nor do they have to understand any media they enjoy to qualify for this trope.
Contrast Fun-Hating Villain, which is when a villain loathes entertainment and fun. Often overlaps with Evil Has a Bad Sense of Humor, It Amused Me, and For the Evulz, especially if the villain is a sadist. If the villain specifically prefers high-quality entertainment, they're Wicked Cultured. If the villain's choices of entertainment are innocuous and wholesome, this trope overlaps with Villains Out Shopping.
As humans are too complex to be considered good or evil, No Real Life Examples, Please!
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Aladdin: The Series: In "Bad Moon Rising", Mamoud is a Royal Brat child king who needs to be constantly cheered up, because whenever he sulks, the kingdom's climate worsens. Jasmine is able to entertain him by telling him stories, but it backfires as he decides to force her to stay in the kingdom forever.
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Genshin Impact: Childe is a Fatui Harbinger, and while he's a usually pleasant guy, he is unhealthily obsessed with fighting, which he takes immense pleasure in, and even mocks his fellow Harbingers for avoiding unnecessary battles with their schemes. Childe also states before his boss fight that he would've preferred skipping straight to combat from the start.
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In A Bug's Life, when the grasshoppers take over the ant colony, P.T.'s circus arrives and Hopper orders the grasshoppers to "squish 'em." However when they see the pill bugs get into an argument the grasshoppers allow the circus to entertain them. The grasshoppers do seem to be enjoying the spectacle, which allows Flick the opportunity to activate the fake bird the colony built right before his exile.
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Danganronpa V3: Killing Harmony:
Kokichi Ouma is the only student who seems to enjoy the Killing Game, getting excited about new developments during Trials and loving anything to do with games, with his Free Time Events usually involving him playing with the protagonist. He also calls Kaede "not boring" before her execution, which is high praise from him. Ultimately subverted as he turns out to have been working to end the sick game, hating it from the very beginning.
It's revealed that in the outside world, Killing Games have become a massive success in the entertainment industry for years. Tsumugi Shirogane, the true Mastermind, is a huge fan and wishes to keep Danganronpa going endlessly, not caring whether the final survivors choose Hope or Despair so long as there's another season. However, when Shuichi and the others succeed in destroying audience interest and therefore end the show, Tsumugi decides to let herself die as she does not want to live in a world without Danganronpa.
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In The Great Mouse Detective, Basil and Dawson visit a Bad Guy Bar to track down Fidget the bat, where the local criminals watch various performers, such as an octopus juggler, a frog double act, and Miss Kitty Mouse. No prizes for guessing which form of entertainment they like most.
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X-Men: Mojo is the ruler of Mojoworld, home to a race of aliens absolutely obsessed with television whom he has dominated by becoming their most successful producer. He is constantly looking for new content for his shows and is prone to wrecking havoc and abducting people to be on his latest program, often going after various heroes.
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Danganronpa 3: The End of Hope's Peak High School: Downplayed. Izuru Kamukura is the Ultimate Hope imbued with every possible talent, making him superhumanly good at everything. This makes him constantly bored and unmotivated, so Junko Enoshima appeals to his boredom in order to convince him to help start the apocalypse, explaining a world of hope would be tedious while a world of despair would be exciting.
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Alhazad from Wild ARMs subjects people to horrible, torturous experiments that eventually turn them into mindless monsters and, in one case, a demon. He does this purely for his own amusement.
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In Umineko: When They Cry, the story is possibly brought about because the Witches wanted to play a game using the characters as their pieces. The one in charge is Featherine, the Witch of Theatregoing, and she has the power to alter reality based on whether or not she's entertained by what's happening, usually to make things miserable.
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Miraculous Ladybug: A good chunk of akumatized villains love entertainment, with several obsessing around games, sports, television and music. Most, if not all, are also known to be Sadists who enjoy causing harm.
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Bungo Stray Dogs:
Chuuya is a Port Mafia executive responsible for murdering numerous people and likely many other crimes. He's known to greatly enjoy fighting tough opponents, getting especially excited when he realizes Kenji can withstand his strikes, and as a teenager is shown playing video games and pool. On top of that, extra materials state he likes music.
Fitzgerald is seen shooting targets for fun, and tells Twain about how he once tried to earn enough money to buy the gun model he's using, but when he couldn't, went on a killing spree and eventually came to own the company that made them.
Fyodor seems to gain a sick form of amusement from watching people struggle against his plots and enjoys battling against Dazai in a game of wits while in jail, happy he can finally talk to someone at his level of intelligence. He also likes playing the cello.
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Fullmetal Alchemist: Envy gains pleasure from watching humans suffer, and revels in watching humans fight and destroy each other over their lies. They excitedly recount to Ed and Ling how they shot an Ishvalan child to start a genocide, talking about the event as though it was the best day of their life.
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Gabriel from Modesty Blaise is a brilliant and sociopathic crime lord who is utterly ruthless, calculating, cold and stoic, rarely showing emotion, yet his favorite activity is having slapstick themed cartoons played for him in a projector. His demeanor changes entirely as he laughs heartily and greatly enjoys the show, then unfailingly returns to his stoic self after the cartoon ends.
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RWBY:
Mercury is the most violent and sadistic of Cinder's henchmen, and enjoys combat, especially when he has the upper hand. During his debut, he's seen reading a comic he shoplifted from the store run by the man he and Emerald just killed.
After being released from his cell and taking over Ironwood's ship, Torchwick excitedly plays with the buttons on the control panel, laughing when he makes things blow up.
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Loonatics Unleashed has The Ringmaster and Otto the Odd operate a traveling circus that showcases Mix-and-Match Critters they call "galactic oddities." The pair manage to capture the Loonatics, all six of them, and tamper with LEGO Genetics to reshape them into more mismatched freaks. The villains take delight in this deviltry.
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In House of Mouse, this overlaps with Go-Karting with Bowser, as classic Disney villains often appear, but are rarely antagonistic—they just enjoy having fun at the club with the rest of the characters. (In Hades' case, it actually goes beyond being non-antagonistic into being actively helpful—he foils a plot by real antagonist Pete to chase the whole audience out.) Even in the Halloween Special, Mickey's House of Villains, they don't really harm anyone and only take over the House to play slightly Darker and Edgier cartoons.
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Assassination Classroom: Karma is not the main antagonist but is a Token Evil Teammate who is the main problem during his introduction. He's a sadist who likes stuffing the nostrils of defeated enemies with spices and mustard until they scream in agony, and suggests hunting for delinquents as a summer activity. In a more normal vein, he watches a movie with Nagisa and Korosensei and mentions he likes works done by that particular director.
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Supernatural: In the final season, this is basically revealed to be Chuck a.k.a. God's true colors all-round. He views all of creation as nothing more than a TV series or game show where he as the writer can put the characters and even entire universes through any trauma he wants if he thinks it'll make the story more entertaining.
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Hazbin Hotel: This is Token Evil Teammate Alastor's stated reason for helping Charlie's dream. He thinks redemption is impossible after one is dead, so he's sure he'll enjoy himself watching sinners try and fail to get into Heaven.
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Kipo and the Age of Wonderbeasts: Scarlemagne is fond of playing the piano and literature, and in a more sinister manner, uses his mind-controlling pheromones to enslave humans and force them to dress up in medieval costumes and dance for him.
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Mighty Morphin' Power Rangers: In "Different Drum", the Gnarly Gnome orders the Putties to dance with the girls he brainwashed with his Mind-Control Music.
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The Transformers:
In "The Golden Lagoon," Starscream forces the captured Perceptor and Seaspray to fight to the death for the Seekers' entertainment.
As shown in "Five Faces of Darkness (Part Four)", the Quintessons would often force their robotic creations (the forebears of the Autobots and Decepticons) to fight to the death in gladiatorial combat for their amusement.
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Hellsing Ultimate Abridged: Alucard is the Villain Protagonist of the series with an insatiable apetite for murder and blood. He only serves the Hellsing Organization due to being defeated and enslaved by the organization's founder and namesake, and as shown in episode 3, Alucard has no problem sacrificing innocent humans. In episode 2, Alucard ignores Integra's cry for help to watch an episode of Adventure Time and is quite displeased when Luke Valentine destroys his tv set. When the Convention of Twelve hear Alucard chowing on Luke and realize how scary he is when he isn't being entertained, they completely change their mind on cutting Hellsing's funding.
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In the Higurashi: When They Cry: Gou and Sotsu anime, the events of the story are manipulated by Eua (who looks like or may be Featherine, the Witch of Theatregoing), who steers Satoko into her Face–Heel Turn because she finds the misery that comes about from it ? especially towards Rika, who has a connection to her fellow Witch, Bernkastel ? entertaining.
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Persona 4: When asked for his motive for committing the murders, Adachi's answer is that he doesn't- he was bored in Inaba and wanted to have some fun. He also expresses delight when causing chaos and finds his ability to push people into television screens to kill them hilarious.
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Persona 5: Goro Akechi turns out to be Black Mask, the culprit behind the mental breakdowns who murdered several of the Phantom Thieves' parents. He also enjoys playing chess, darts, riding bikes, rock climbing, and frequents a jazz club. After revealing his deranged true nature, he shows a disturbing love of fighting and killing, with his lines in Royal sounding downright psychotic.
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Steven Universe: The Movie: Spinel is a jester-like Gem who tries to destroy the earth, yet loves games and used to play with Pink until she was left to wait in a garden for six thousand years when Pink got tired of her.
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Pitch Perfect 3: Fat Amy's evil father Fergus, despite intending to kill the Bellas, still allows them to perform for him with what little time they have left. He even casually mentions to one of his henchmen that they're not bad.
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Toilet-Bound Hanako-kun: Tsukasa is the main antagonist of the series, and is a massive and violent sadist who grants wishes to the dead in the most utterly horrific ways imaginable, just because he finds it fun. He turns Mitsuba into a grotesque monster, forcing Kou to kill his friend, for really no reason other than to amuse himself.
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Captain America: The First Avenger: When Steve Rogers first encounters Johann Schmidt, leader of the Nazi Science Division HYDRA, the latter immediately tells the former that he's a huge fan of his propaganda films.
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The Owl House: The Collector's only goal is to play games and have as much fun as possible, being willing to ally with anyone who promises to play with them. However, while they're not intentionally malicious, they are effectively a child capable of warping reality however they want and have little to no understanding of morality.
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Thor: Ragnarok: The Grandmaster is the ruler of Sakarr and loves entertainment above everything else. He's frequently seen partying, enjoys watching his captives battle each other in his arena and gets excited over whether Loki or Valkyrie will recapture the Hulk first.
While posing as Odin, Loki watches a play about himself and is later seen at a party with the Grandmaster. He also takes pleasure in tricking people, though Thor points out this makes him predictable.
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Danganronpa: Trigger Happy Havoc: Junko Enoshima is constantly bored, is always seeking amusement and clearly getting off on making everyone, including herself, suffer, and when confronted even switches personalities on a dime in order to keep the survivors on their toes. Monokuma, as an extension of Junko, loves despair as well and enjoys mocking the students to make them suffer. He also performs comedy skits.
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Every Man Hybrid: HABIT is an immortal Body Snatcher with an extreme sadistic streak and a love of entertainment. He creates an entire game known as the "Seven Trials of HABIT" just to watch audience members act like fools for his benefit, occasionally edits episodes of the show to ramp up the Black Comedy, and is known to enjoy pop-culture, such as Frank Sinatra and Pokémon.
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Phineas and Ferb: Dr. Heinz Doofenshmirtz is a Card-Carrying Villain who tries every day to rule the tri-state area. However, while he enjoys anytime he can beat or capture Perry, he's also frequently seen watching TV or movies, even making entire plots just to ensure he can watch his favorite shows uninterrupted. He also seems to like dance numbers, particularly ones about him.
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Epithet Erased: Most villains in the show seem to like entertainment.
Giovanni likes arts and crafts such as knitting and finds evil doing to be very fun. His minion, Flame Thrower is mentioned to do cheerleading, which his fellow Banzai Blasters apparently enjoy watching. The two Vice Principals take amusement in pushing Giovanni around.
Zora loves hunting people down, to the point of breaking Ramsey out of jail and giving him a head start just to make the chase more fun.
Indus appears to like giving a tour to the students, and does what he can to make it more engaging, much to Mera's ire as it was only supposed to be a cover.
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Star Trek: Recurring antagonist Q is an omnipotent alien who loves to make the protagonists look silly or play "games" for his own entertainment. Among the things he did were put Tasha Yar in a "penalty box" and threaten to kill her, put Picard and his crew into a simulation of Robin Hood, and make Data (an android) laugh.
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Danganronpa Another Episode: Ultra Despair Girls: The Warriors of Hope largely enjoy games and the plot partly centres on their demon hunting game, in which they hunt down and kill various adults and teens.
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Teen Titans: Control Freak is practically a Fanboy priest of sorts, taking many TV shows and movies (and the Titans themselves, sort of) quite seriously. He's also a foe to the Titans, trying to warp reality to suit his geekish whims, and in one episode trapping the Titans in TV Land where he felt more at home.
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30 Rock: Devin Banks likes belittling and making fun of Jack every chance he gets, and takes his time gloating whenever he can pull one over on him. At one point, Devin calls Jack's office using the name I. M. Adouche just to trick the other man into saying it and then excitedly asks if it worked.
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Persona:
Persona 4: When asked for his motive for committing the murders, Adachi's answer is that he doesn't- he was bored in Inaba and wanted to have some fun. He also expresses delight when causing chaos and finds his ability to push people into television screens to kill them hilarious.
Persona 5: Goro Akechi turns out to be Black Mask, the culprit behind the mental breakdowns who murdered several of the Phantom Thieves' parents. He also enjoys playing chess, darts, riding bikes, rock climbing, and frequents a jazz club. After revealing his deranged true nature, he shows a disturbing love of fighting and killing, with his lines in Royal sounding downright psychotic.
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Danganronpa
Danganronpa: Trigger Happy Havoc: Junko Enoshima is constantly bored, is always seeking amusement and clearly getting off on making everyone, including herself, suffer, and when confronted even switches personalities on a dime in order to keep the survivors on their toes. Monokuma, as an extension of Junko, loves despair as well and enjoys mocking the students to make them suffer. He also performs comedy skits.
Danganronpa 2: Goodbye Despair: Nagito Komeada is difficult to work with due to a big case of Blue-and-Orange Morality and pushes Teruteru Hanamura to commit the first murder. This makes Nagito a major obstacle, especially when he finds out about his and his class' pasts as Ultimate Despair and sets up his own death so everyone will vote wrong and die. He tells Hajime he likes to read, and at one point uses a book about a murder where the killer turns out to be the protagonist as an analogy to foreshadow The Reveal.
Danganronpa V3: Killing Harmony:
Kokichi Ouma is the only student who seems to enjoy the Killing Game, getting excited about new developments during Trials and loving anything to do with games, with his Free Time Events usually involving him playing with the protagonist. He also calls Kaede "not boring" before her execution, which is high praise from him. Ultimately subverted as he turns out to have been working to end the sick game, hating it from the very beginning.
It's revealed that in the outside world, Killing Games have become a massive success in the entertainment industry for years. Tsumugi Shirogane, the true Mastermind, is a huge fan and wishes to keep Danganronpa going endlessly, not caring whether the final survivors choose Hope or Despair so long as there's another season. However, when Shuichi and the others succeed in destroying audience interest and therefore end the show, Tsumugi decides to let herself die as she does not want to live in a world without Danganronpa.
Danganronpa Another Episode: Ultra Despair Girls: The Warriors of Hope largely enjoy games and the plot partly centres on their demon hunting game, in which they hunt down and kill various adults and teens.
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In Wings of Fire, Queen Scarlet loves things to be "thrilling", which usually means lots of Gladiator Games. While Queen Coral has a more "normal" taste in entertainment, liking to read and write books, this leads to her being Wrong Genre Savvy and tending to think real life will play out like the books she read.
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Hogfather: Teatime revels in killing people- he passes his time thinking up hypothetical means of killing things, including gods and deities, and has the time of his life while enacting his plan to kill the Hogfather. This is in stark contrast to the other assassins, who take care to cleanly 'inhume' people for the money and are disturbed by Teatime's gleeful and spectacularly gory kills.
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In The Woman in White, Big Bad Count Fosco is a huge fan of Italian opera. Walter and Pesca track him down when he goes to the theatre to see Lucrezia Borgia.
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Super Solvers: Morty Maxwell, the Big Bad of the series, has displayed a love of games and contests throughout the series. This is best shown in Gizmos & Gadgets and Mission T.H.I.N.K., where he challenges the player to a series of races and board games respectively, promising to relinquish the buildings he has taken control of if the player can beat him in every level of the games. Morty sometimes shows Villain Respect for the Super Solver, implying that he enjoys competing with them, but other times, he turns out to be a Sore Loser. Also, in Spellbound, he participates in a spelling bee. This seems to be Morty's only game where he's not doing anything overtly evil.note Although, aside from the Super Solver, all the other competitors in the spelling bee are Morty's robots. This implies that he entered them into the contest to stack the odds in his favor, which is pretty unscrupulous of him.
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The British comic strip Axa has Axa visit the City of Hope, run by the corrupt villain Mister Nero. The whole place is one big gambling den, where losers that can't pay their debts are shunted into an arena to fight in Gladiator Games for their lives. Nero has an executive box in the arena, there to oversee the carnage that plays out below. He even forbids his henchmen from using bullets, as that'd spoil the fun.
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Young Justice: Klarion the Witch Boy is a Psychopathic Manchild who enjoys using his powers to create chaos. He is frequently seen laughing while deploying magic to inflict harm on those around him, or even the world at large. Fittingly for a lord of chaos, he also has no patience or attention span and always wants to make things entertaining for himself.
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Warhammer 40,000:
The Chaos Gods drive their mortal followers to provide them with entertainment. Each god has something that amuses them more than anything else: Khorne loves war and turns his champions into slasher villains. Slaanesh is a Sense Freak and turns their champions into coked-up perverts. Nurgle loves illness and disease and loads his followers down with Beneficial Diseases. Tzeench is a schemer and makes his champions scheming douchebags. They even refer to their eternal conflict as "The Great Game."
Drukhari literally feed off of the suffering of others to keep themselves alive and virile, indulging in vile tricks, theatrical torture and gladiatorial sports when they are not invading realspace or stabbing each other in the back.
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Danganronpa 2: Goodbye Despair: Nagito Komeada is difficult to work with due to a big case of Blue-and-Orange Morality and pushes Teruteru Hanamura to commit the first murder. This makes Nagito a major obstacle, especially when he finds out about his and his class' pasts as Ultimate Despair and sets up his own death so everyone will vote wrong and die. He tells Hajime he likes to read, and at one point uses a book about a murder where the killer turns out to be the protagonist as an analogy to foreshadow The Reveal.
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My Little Pony: Friendship Is Magic: When Discord conquers Equestria, he uses his chaos magic to turn it into a World Gone Mad, so he can amuse himself by watching the constant madness.
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Doctor Who: In "The Greatest Show in the Galaxy", the Gods of Ragnarok are Humanoid Abominations with an insatiable craving for entertainment, setting up an entire Circus of Fear to keep themselves amused and killing off acts once their novelty wears off.
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Hunter × Hunter:
After taking over a castle and murdering numerous humans, Meruem has his royal guards bring in numerous champions of various board games to play against him to kill time. He's deeply displeased by those who can't beat him and quickly kills them, though Komugi piques his interest when he finds himself unable to win, leading to him eventually developing feelings for her.
Hisoka loves battle, especially against tough opponents. He even works hard to return Chrollo's power so he can be rewarded by fighting the Phantom Troupe leader at full strength. He's in general driven by impulse and does whatever he wants to amuse himself, which usually results in people losing their lives.
Neferpitou is a wildly powerful chimera ant, and absolutely loves fighting strong opponents, getting excited at the prospect and frustrated when they have to stand guard and thus can't go out. After killing Kite, they take his dead body and develop their nen ability so they can reanimate him and relive their battle.
Shaiapouf appears sensitive and easily driven to tears, but beneath that is a cunning and callous sociopath. He is often seen reading books and playing the violin to pass the time.
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Yu-Gi-Oh!: Pegasus is the main villain of the Duelist Kingdom arc. He is a ruthless businessman who tries to buy out Kaiba's company through underhanded means and steals the soul of Yugi's grandfather to make him enter the tournament. He is also a huge fan of cartoons and even created a deck themed around toons.
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Tombstone: The Cowboys are a murderous band of criminals, but they are also very appreciative of a performance by a travelling show, and even give the leading man a standing ovation for his rendition of the St. Crispin's Day speech.
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She-Ra and the Princesses of Power:
Double Trouble is a Wild Card who only does anything for money and drama. They have a strong love of theatre and performance and enjoy watching chaos unfold. They are also easily bored, getting annoyed when their tricks fail to incite a reaction from the Best Friend Squad and leaving Horde Prime's ranks when they decide brainwashed people are too dull.
Catra often takes sadistic delight in fighting and mocking Adora, and after learning what parties are, decides she enjoys them. In the first episode, she joyrides a Horde vehicle.
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Nekron, the ice wizard from Fire & Ice receives four emissaries from Firekeep, who've come to Icepeak to negotiate with him. When Nekron refuses their offer, the four draw swords on him. Nekron simply uses his wizard powers to compel these men to slay themselves, leering with delight at the slaughter. Later, Nekron meets Larn, and conducts a sword duel with him. Something about Larn appeals to Nekron, which results in Nekron merely toying with him, then sending him to a dungeon, presumably to keep Larn alive as a plaything.
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Oz: Simon Adebisi has fully embraced hedonism to distract himself from how miserable his life has become. He's constantly indulging in sex, drugs, violence, and anything else he finds fun. However, when he takes control of Em City, allowing him to constantly indulge in whatever he likes, he finds that he can no longer enjoy it now that he has constant access to it.
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Both Xykon and The Inter-Fiend Cooperation Commission from The Order of the Stick enjoy watching The Order and other characters fighting, either on scrying devices or in person.
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Demon Slayer: Kimetsu no Yaiba: Demons typically revel in causing pain and strife.
Susamaru is a sadistic, vicious demon who displays excitement while fighting and before her death, pitifully requests Tanjiro play with her, causing him to realize she was actually just a little girl.
Subverted with Doma, who is the Upper Two Demon Moon and thus an immensely dangerous and powerful Demon who has eaten likely hundreds of women. He appears to get a kick out of messing with people and terrifying them, always smiling and giving off Dissonant Serenity. However, Doma doesn't actually have emotions and can't feel, so it's all just an act on his part.
Akaza loves battle and enjoys fighting Kyojuro, praising his ability and strength. He's so impressed by the Hashira that he offers to make Kyojuro a demon so he can spend hundreds of years getting stronger rather than squander his potential due to his weakness and mortality as a human. Naturally, Kyojuro refuses to become a murderous abomination like Akaza.
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Buffy the Vampire Slayer: Spike is quickly introduced as a massive threat to the Scoobies in season two, having murdered two slayers in the past and looking to kill a third. He also stands apart from The Master from season one for being a younger vampire who frequently references pop culture and thoroughly enjoys punk rock, hence his getup. In later seasons he's revealed to enjoy soap operas to the point of getting upset at the thought of missing an episode, and as a human he strived to be a poet.
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Sherlock Holmes: A Game of Shadows: Moriarty listens to Schubert on a grammophone, and at one points attends a performance of "Don Giovanni". Moran expresses disappointment that his duties make him miss the opera.
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Stay Tuned has John and Helen Knable drawn into the underworld through a fiendish TV set. There, the couple find themselves put in mortal peril, by guesting on bizarre television shows, which are produced solely for Satan's amusement. If the Big Bad isn't kept glued to the boob tube, he tends to torment his underlings For the Evulz.
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Durarara!!:
Izaya loves all humans and plays a confusing mixture of boardgames to represent the events going on, treating everyone like pawns and playthings he can break. He explains he loves watching all the different ways people react to things, and sees nothing wrong with causing strife to make things interesting. Outside of that, he's also seen watching TV occasionally and gets bored out of his mind without constant stimulation.
Earthworm has Izaya kidnapped and spends her time happily torturing and belittling him in front of her subordinates, getting a kick out of making him squirm. Unfortunately for her, as seen above, Izaya also fulfills this trope and reveals he got himself caught on purpose to both destroy her operation and have fun watching people.
Izumi loves causing suffering. He's occasionally known to call people up on the phone when they're completely helpless and offering a 'pop quiz' as he explains just how exactly they're screwed and laughs while they have a breakdown. He also takes pleasure in beating Masaomi to a pulp.
Mikado isn't intentionally villainous, but started the Dollars over the internet because he was bored and constantly seeks to remove himself from an ordinary existence. After the Yellow Scarves arc, he starts taking drastic actions to violently cleanse the Dollars, and reveals he isn't nearly as sane as he originally appeared.
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In The Big Sister and Little Sister, the Ice Person ruling family of the Ice Kingdom are constantly sleepy and are afraid of one day falling asleep forever, so they lure living people and animals to the kingdom to amuse them and liven up the palace. Unfortunately, even the victims who genuinely try with all their might to do so quickly become slow and lethargic from all the freezing, and risk getting turned into ice statues for disobedience by the Mad Wind.
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The Batman: Justified with Arthur Brown/Cluemaster. Arthur's Start of Darkness happened when he lost his winning streak on a trivia game show as a kid (after getting several facts in his answer right, he gave the wrong date by just one year.) Arthur never moved on from this moment and plotted to get revenge on three of the people present at the game show who he blamed for his failure. As Cluemaster, Arthur uses a game show motif, forcing his captives to participate in his own game show where he threatens to drop them in an Acid Pool if they lose. Cluemaster's game show motif makes sense because he is motivated entirely by his loss on the game show all those years ago.
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Pathfinder: Wrath of the Righteous: After disappearing for all of chapter 2, the Storyteller reappears in Chapter 3 having been taken prisoner by an Always Chaotic Evil red dragon that took up residence in what turns out to have been the Storyteller's own wizard's tower long ago. He managed to placate the dragon into not killing him on the spot by using his psychometry powers to entertain it with tales about the artifacts in its hoard.
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The Nightmare Before Christmas: Oogie Boogie, the most villainous of the monsters, has a love of gambling. His lair is decorated like a casino where everything glows bright colors under a blacklight. He also likes to make decisions by rolling dice. When preparing to drop Santa Claus and Sally into his stew, Oogie deliberately draws out the moment to relish in his sadistic game.
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Gravity Falls: Bill Cipher is a sadist who likes causing pain and chaos For the Evulz, getting a kick out of putting people in tough spots. During Weirdmageddon, he throws a giant party for him and his Henchmaniacs and later, forces Gideon to dance nonstop for him as a punishment.
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Star Trek: The Next Generation: The episode "Skin of Evil" features an evil, tar-like alien who is bored and lonely and wants everyone to "entertain" him. Among the things he does for entertainment are removing Geordi's visor (which he needs to see with due to being blind) and toying with killing the crew.
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