Vile Villain, Saccharine Show

"Shan Yu, one of the most badass Disney villains ever. That dude was a monster. In fact I kinda felt like he was out of place in the movie because Mulan is overall is kind of a silly movie. And then you have this big grim beast of a man just fuck'n shit up."

- the1janitor

Okay, so you have a villain, who is legitimately intimidating and frightening. Maybe he tries to destroy all positive emotions, or maybe he turns people into twisted shambling abominations, or maybe he's plotting genocide. Point is, he's actually a fairly creepy villain. The irony is that he's stuck in a Sugar Bowl.

As one could probably tell, this trope is about villains in normally lighthearted fiction that are so disturbing, or even terrifying, on some level that they kind of clash with the tone of the show/game/whatever. Because of this type of villain's ability to ruin the mood of the story he/she/it is in, this trope can overlap with Complete Monster and Knight of Cerebus. If a series has a lot of villains like this, then it's taking a ride on the Cerebus Rollercoaster.

A major cause of Sugar Apocalypse and Surprise Creepy. Compare and contrast the Crap Saccharine World, where it's not just the villain, but the entire world that is rotten to the core.

Anime and Manga

 * Mon Colle Knights is cheerful and wacky and the enemies usually are the Terrible Trio. When they're not, there's Reda, with his bloodstained wings and a fondness for driving people to suicide and subjecting things to splooshy transformations. The english Gag Dub toned him down and edited some scenes.
 * The usually light-hearted Pokémon anime (which normally has a goofy and incompetent Terrible Trio composing of two delinquents and a talking Meowth as the primary antagonists) has:
 * The coldhearted Diabolical Mastermind, Giovanni, and the psychic Gym Leader with a split personality, Sabrina, in the Kanto Saga.
 * The merciless Pokémon Hunter J, the Omnicidal Maniac Cyrus and his organization Team Galactic, and the abusive Jerkass trainer Paul in the Sinnoh Saga.
 * Complete Monsters, the Iron Masked Marauder and Kodai, in the fourth and thirteenth movies respectively.
 * Oh, and Best Wishes? The goofy, incompetent Terrible Trio isn't so goofy and incompetent anymore....
 * The Bigger Bads in Pretty Cure franchise are usually like this. One of them is an entity that existed before everything and wants to plunge everything into nothingness, another is a life-hating Eldritch Abomination that turns every planet he visits into sand dunes, yet another is a monster born out of humanity's collective negative emotions, etc. etc... Mind you, this is a series that is (supposedly) for little girls in elementary school years.
 * Digimon Adventure starts off fairly lighthearted, then we meet Devimon, a cunning, devil-like monster with the power to brainwash friendly and peaceful Digimon into rampaging, savaging berserkers.
 * Myotismon and Machinedramon are even worse. The former is a sinister, vampiric Digimon with a sadistic streak a mile wide. Myotismon treats his underlings awfully, having taking Gatomon in when she was young and abusing her until she was a killing machine. When his henchmen fail him, he eagerly destroys them. When two harmless minions couldn't bring themselves to harm children, Myotismon killed them on the spot. When he invaded Tokyo, he proceeded to destroy much of it and held a number of children captive to identify the final child connected with Gatomon. He made it clear if it took too much time, he'd simply kill them all. Myotismon also proceeded to attack multiple young women and drain their blood, causing an epidemic through Tokyo. Any minions he hadn't already killed were cannibalized to fuel his Mega transformation. When he was thought destroyed, Myotismon's spirit survived to return as the final villain of the next season as MaloMyotismon. Using a man named Oikawa's sadness and despair to make him a pawn, he proceeded to consume him from within and upon manifesting anew, Myotismon repaid his perfectly loyal ally Arukenimon by sadistically torturing her to death and killing Mummymon when he tried to avenge her. The later is a cold-hearted, brutal and gigantic Killer Robot who speaks, though rarely, with a growling, hateful and metallic voice and mostly acts like a lifeless machine, unless when he's on a murder rampage, which's when his true sociopathic nature is shown, ordering a massive bombing over his own territory and telling the hero's 8-year old sister he's going to kill her as painfully as he can. It makes him one of the scariest villains in the show, and if that wasn't bad enough the Wanderswan games reveal he survives his fight with Wargreymon and becomes Milleniummon.
 * Puppetmon has shades of this despite being Laughably Evil. He's a dark version of Pinocchio who thinks he can make friends by killing and enslaving everyone around him, and uses a revolver to "play" a cruel version of hide-and-seek with T.K. and kills his minions, Mushroomon and Blossomon, with it because he thought they lied. Some countries edited the scenes with Puppetmon killing Mushroomon and Blossomon and holding the gun during the TV run of the series. It's a living puppet pointing at an eight year old child!
 * And then there's Piedmon, a Monster Clown who enjoys to toy with his opponents and sadistically inflict pain and fear upon them before finishing them off, which culminates in him transforming the kids and their Digimon into key chains one by one in a series of sequences that seem to come straight out of a horror movie.

Comic Books

 * Parodied in Steph Cherrywell's Widgey Q Butterfluff, with Lord Meanskull and his Hench-Witches.
 * Les Légendaires is a seemingly kid-friendly comic book, involving a world where everyone has been turned into children following a magical accident. The characters are typically comical (though they do have moments of Badass), and the universe even more. But let's have a look at the main villains:
 * Darkhell is a homicidal, megalomaniac, cruel Evil Sorcerer (and formerly Sorcerous Overlord) who made insane experiments, was The Dreaded for years in his world and cause a large amount of death each time he shows up. While he was scary already as an adult, having turned back to childhood only makes him more disturbing.
 * Skroa is a bird-like demoniacal sorcerer that used to be Darkhell's rival and frequently uses the protagonists as pawn for his plans. Is shown slaughtering a group of armed human beings of his own. Not to mention he once cut his own arm off as a part of his plan;
 * Anathos is basically this universe's version of Satan, being a Magnificent Bastard and Omnicidal Maniac God of Evil that actually succeeded in destroying the world long time ago and almost succeeded a second time. The fact he came back by reincarnating in one of the protagonists and literally crushed the remaining heroes in their first fight, leaving them scarred for life, makes it worst;
 * Abyss; O God... the character is introduced as seemingly extremely nice person in his first appearance, only to be revealed later as a Complete Monster Yandere who seems to have a thing for his foster sister, to the point of forcing her to joining his side by brainwashing her through Puppeteer Parasite.

Films -- Animation

 * We're Back! A Dinosaur's Story is a cutesy film about dinosaurs being sent to our time to make children happy. Nothing scary about that at all. Well, except for the creepy old scientist Professor Screweyes, who runs a Circus of Fear, believes that the world is an irrational and cruel place, got his eye pecked out by a bird, and was eaten by birds at the end of the film.
 * The Disney Animated Canon has a disturbingly/wonderfully high occurrence of this trope:
 * Maleficent from Sleeping Beauty.
 * The Disney version of Claude Frollo from The Hunchback of Notre Dame is, for all intents and purposes, a medieval stand-in for Hitler. The movie was already more adult than is normally thought of for Disney, but it was still shocking.
 * More disturbingly, Claude Frollo is one of the most realistic Disney villains ever produced, and he doesn't have an iota of comedic qualities. And people like him existed in reality. There's a reason why many see him as the darkest villain the company has ever made.
 * The evil Queen from Snow White and The Seven Dwarfs is pretty damn creepy. A woman so obsessed with her own beauty that she's willing to let a teenage girl die for being pretty? Yikes. The fact that the teenaged girl is also her step-daughter? Double yikes. Going so far as to painfully transform herself into an ugly old witch to trick the teenage girl so she can poison her? Yikes to infinity.
 * The Princess and the Frog gives us Dr. Facilier, a voodoo witch doctor willing to sacrifice all of New Orleans to pay off his debts to dark voodoo entities. Although he gets in on the light, jazzy theme of the movie with a heck of a cool Villain Song, it's still clear that he's selfish, relentless and bad to the bone. The fact that he cements this.
 * Another well known example is the Coachman from Pinocchio, who runs an amusement park that magically turns young boys who use the attractions into donkeys. The ones that lose their voices are then sold to salt mines and circuses, and the ones who can still talk... well, they're put in cages, and we don't know what happens to them after that. It seems that none of them are ever human or see their homes again, though. And he gets away with it, too! Which is unique, considering just about every other villain falls to the hero.
 * This may be because of his choice of targets: Bad boys who should be at school, making him some karmic bogeyman.
 * Though the Coachman is far worse, Stromboli is pretty bad too.
 * Oliver and Company is a very lighthearted movie, featuring talking cats and dogs. Its villain, Sykes, is a Loan Shark who is played utterly straight. There's nothing cool, funny, sympathetic, or even hammy about him. He's just a cold-blooded thug who wants his money now and doesn't care what he has to do to get it.
 * Though not as frightening as Frollo or Maleficent, Jafar in Aladdin has shades of this. While he doesn't really have any plans beyond conquering Agrabah and becoming sultan (though he eventually decides to become an extremely powerful sorceror in addition to that, then an all-powerful genie after Aladdin persuaded him that the Genie was a threat to him (even though he was incapable of betraying him unless someone else grabbed the lamp, which he safeguarded).), he does lie to Jasmine about Aladdin's execution, which of course devastates her. Because the movie was an action-packed zany comedy, animator Andreas Deja decided to keep Jafar very subtle in contrast. (He also contrasts the art style. Nearly everything else in Agrabah has soft, rounded lines, while Jafar has several sharp angles.)
 * Mulan is the story of a girl who goes into the army to save her father's life. While the movie is comedic much of time (and even has a non-threatening dragon voiced by Eddie Murphy and a cute little cricket), the Big Bad Shan-yu is implied to kill vast numbers of people. The aftermath of his handiwork makes a Mood Whiplash from a song about getting a girl to seeing the most straightforward example of War Is Hell in a Disney movie. The scene with the destroyed village also has a subtle implication that the Infant Immortality was averted with the appearance of a doll without its owner.
 * Professor Ratigan of The Great Mouse Detective, who spends most of the film as the epitome of the Faux Affably Evil, Evil Is Hammy villain (helped by being voiced by Vincent Price, who is very obviously really enjoying himself), so it's easy to forget that he kidnaps frightened children, has no qualms about threatening them or getting them killed, and a throwaway line in his Villain Song refers to "those widows and orphans you drowned". Then his temper gets pushed that little bit too far, and... Holy Shit.
 * 101 Dalmatians has Cruella DeVil, who for all her campy vampiness, her basic goal is still to kill and skin a bunch of puppies to make them into fur coats.
 * Scar, from The Lion King. Simply put, he gets the honor of committing the first onscreen murder in a Disney film.
 * Wreck-It Ralph has the Walking Spoiler that is . He becomes even more vile during his Villainous Breakdown in the climax, and more vile still after . The worst part of all this? !
 * In a (semi) Live Action example, Judge Doom from Who Framed Roger Rabbit?. The film initially seems like a classical Family movie until we meet him. We discover that not only is the responsible of all bad things that happen in the movie.
 * Much like its big brother, Pixar is very fond of this:
 * Hopper in A Bug's Life is a ruthless tyrant who delights in the fear he instills in the ants, and was fully prepared to publicly execute their queen to keep them compliant. He even admits to his minions that they don't even need the food the ants provide, implying his actions are motivated purely by sadism.
 * Toy Story is a lighthearted series where the main conflict is usually within the heroes as opposed to external. Villains tend to be either Obliviously Evil or relatively harmless. Until Toy Story 3, that is, where we meet !
 * Coco has, a far darker take on villains like Balthazaar Bratt.
 * Little Nemo: Adventures in Slumberland has the Nightmare King suddenly show up in a world that was just plain Sugar Bowl till then, ruling over a section of Slumberland known as Nightmareland, the place where nightmares come from.
 * Osmosis Jones: For the most part a lighthearted parody of Salt and Pepper cop movies with copious amounts of Toilet Humour for the kids all set inside the human body. Enter Thrax, a Complete Monster who kills cells by making them melt and explode via fire from the inside out, and we learn his goal is to kill his human host, which in this context would be like an alien arriving on Earth and trying to destroy it For the Evulz. He counts his victims on his fingers at one point in the movie, one of them being "A child who didn't wash her hands like she was told."
 * Mrs. Tweedy from Chicken Run is a sadistic chicken farmer who runs her chicken farm like a manner of horrifying prison that contain prisoners that will given penalty anytime, as the chickens' means to survive in there are nothing more than laying eggs or be executed, and while it isn't out of the ordinary for a chicken farmer to do this, she clearly enjoys it. She crosses the Moral Event Horizon by trying to use a pie machine to cook all the chickens alive into pies, just so that the Tweedy farm would have financial success. Another reason to hate her is how she tries to brutally murder all the chickens at the end, even though by this time she's fully aware they're sentient.
 * Kung Fu Panda 2 has Shen, an evil peacock tyrant who is bent on destroying kung fu with heavy artillery, terrorized many innocent pigs and bunnies with his army of wolves, and he even almost pushed the entire panda species (which includes Po) to the point of extinction! All of this is enough to make Tai Lung, the snow leopard villain of the first Kung Fu Panda film look like a scaredy-cat.
 * Some of the villains from the later Don Bluth films, including an evil owl sorcerer who hates daylight, wears an opera cape and a monocle, and for some reason breathes Lucky Charms; an evil, fat troll queen who hates both nature and New York City; a Complete Monster of a penguin voiced by Tim Curry, and an evil, undead Russian necromancer. Even less so with his earlier films, whose villains include an evil rat, a ferocious green Tyrannosaurus Rex with razor-sharp fangs and blood-red eyes, a mean cat with a gold tooth, and a canine crime boss.
 * The Brave Little Toaster is a cute musical film about talking electrical appliances, but then we meet the Junkyard Magnet...
 * Lord Farquadd from Shrek manages to be pretty damn vile despite being largely Played for Laughs in a film that's very much a comedy. As an extreme racist, he has fairy tale creatures treated like criminals and exiled to Shrek's swamp, while also having Gingerbread Man tortured in his own version of waterboarding. He never treats anyone around him with respect, and it's implied that he shamelessly masturbates to, or at least gets turned on by, Fiona's reflection in full view of the Magic Mirror! Additionally towards the end, Farquadd declares he plans to have Shrek drawn and quartered and have Fiona locked back in the tower for the rest of her life. Needless to say,  It's also indicated that Farquadd's henchmen are afraid of him, seeing how the torturer pulls a Heel Face Turn seconds after the above.
 * The Fairy Godmother in the first sequel and Rumpelstiltskin in the third sequel arguably manage to be even viler than Farquaad. The Fairy Godmother is the only Big Bad in the series who's a true Knight Templar, honestly believing that her villainous actions are justified for keeping the natural order of the Fairy Tale world. She plans for her son Charming to commit martial rape on Fiona by pretending to be Shrek and giving her a kiss that would activate the love potion she'd have drank earlier, making her fall in love with him (which thankfully doesn't happen because King Harold refuses to do that to his own daughter) and one of her spells ends up turning King Harold back into his true form, a frog. Rumple, meanwhile, is the most psychopathic of the villains. He deceives Shrek into making a deal that takes the day Shrek was born out of his life, meaning Shrek doesn't exist to the world anymore, and in the alternate reality that's created due to this wish, Rumple tricked Fiona's parents into making a deal that ended up wiping them from existence so that he took over Far Far Away, instilling a tyrannical dictatorship where he enslaved all it's inhabitants while launching a genocidal campaign against ogres purely out of the spite he has for Shrek and his kind. While both of these villains are Laughably Evil characters, their villainy in the plot is actually played dead seriously.
 * Meet the Robinsons is an idealistic movie which encourages people to keep moving forward, since success doesn't happen overnight. The character in question who keeps moving forward is Lewis, who gets progressively better at building inventions even though his early ones have a tendency to backfire, eventually succeeding with the Memory Scanner. While the story has a villain (in this case the Bowler Hat Guy, he tends to have comedic tendencies and has a Freudian Excuse for his behavior...though unfortunately, he chose not to move forward like Lewis did. However, it turns out he's not the REAL villain. That villain happens to be Dor-15, one of Lewis's malfunctioning inventions that he shut down for the safety of humanity. It ultimately turns out that she is plotting the enslavement of humanity...and she throws the Bowler Hat Guy under the bus once she succeeds in her plans. And yes, in one timeline, she DOES succeed in her horrific plans.
 * SpongeBob SquarePants was a lighthearted series with an Ineffectual Sympathetic Villain. Then The Movie comes out, where we're introduced to Dennis, a somewhat comedic but still surprisingly terrifying hitman wanting to KILL Spongebob and Patrick using sharp spiked boots.
 * Also in The SpongeBob SquarePants Movie, there's the cyclops diver, who captures sea creatures and painfully kills them using the heat of a bright lamp, then he sells them as knick-knacks.
 * Despicable Me has Miss Hattie and .  Although Big Bad Wannabe Vector ended up getting some punishment of some sort, these two both manage to get away with everything!
 * from Cloudy with a Chance of Meatballs 2.
 * Zelda from The Swan Princess III: The Mystery of the Enchanted Treasure (also known as The Swan Princess: The Mystery of the Enchanted Kingdom) is easily the most evil villain in the series. She kidnaps a bird called Whizzer and promises to release him if she spies on Odette and Derek's kingdom for her, but breaks her promise on two separate occasions. When she obtains the forbidden arts she states that she loves is the power to destroy, and when when she finds out that Derek tore off the last word she kidnaps Odette and threatens to kill her if Derek doesn't give her the missing piece, and when she gets what she wants she vaporizes Odette out of pure sadism.

Films -- Live Action

 * Mr. Potter of It's a Wonderful Life is a smaller scale example of this trope, but he nonetheless fills the criteria for the standards of his setting. Described as being "sick in the mind and sick in the soul", this unpleasant old man is someone who feels he literally has to own everything and thus resents anything he cannot have. He very nearly owns the entire town of Bedford Falls and had George Bailey not been in the way, he might have turned the town into a dark dystopia where crime runs rampant, all the poor folk are forced to live in his slums while the people with money go squander it all on tasteless establishments, with all the profit going back to Potter and his associates who'd control the town. He's also a narcissist of the highest degree, and he feeds his own ego by bringing others down and ruining their lives while simultaneously making himself more powerful. In his office, there is an oil painting of himself on the wall and a bust of Napoleon (presumably his two favorite people.) The chair where visitors sit is deliberately smaller than his desk so that he can lord over them, and on the desk is a paperweight shaped like a skull. What really pushes him into this trope is his actions towards the end of the film: not only does he (unbeknownst to everyone else) confiscate George Bailey's Building and Loans' cash funds in order to make the business go bankrupt and frame George for bank fraud, but when the defeated George comes begging pathetically for a loan, Potter tries to have him arrested. On Christmas Eve! For losing money that Potter himself stole. That really takes something special. This, and Potter's line to George "You're worth more dead than alive!" immortalized him as one of the most hateful villains in cinema history.
 * Even in some of the more comical Marvel Cinematic Universe entries, there still can be quite dark villains featured.
 * Guardians of the Galaxy's Ronan, a genocidal Kree warlord who wants to wipe out the Xandarians off the face of the cosmos.
 * All three 2017 MCU entries were largely comedies, and all but one introduced some of the cruelest and strongest villains in the MCU to date. Guardians of the Galaxy Vol. 2's A jackass would be downright charitable. Thor: Ragnarok'' has Hela, the Goddess of Death and Thor's estranged elder sister, capable of raining down thousands of blades on her enemies and raising the dead.

Literature

 * Charlie and the Great Glass Elevator, by Roald Dahl, has the sudden intrusion of a Horde of Alien Locusts into an outer space sequence that until then is mostly whimsical.
 * Redwall; it seems like a happy fluffy world full of cuddly talking animals. Then you meet the villains, who get their own Complete Monster page.
 * Tove Jansson's The Moomins take place in Moominvalley which is, at least at a very quick glance, somewhat of a saccharine world in the early novels and some of the adaptations. Then we are introduced to the Groke who, especially in her earliest appearances, is truly horrifying.

Live Action TV

 * Even though Seinfeld is not exactly a cheerful show (it's actually quite cynical), Joey "Crazy Joe" Devola still adds a surprising dash of darkness to it. If Elaine continued dating him past the episode "The Opera", he probably would have been a full-fledged Token Evil Teammate.
 * An in-universe example appears on Star Trek: Voyager with the Show Within a Show The Adventures of Flodder, a series of fantasy holonovels for children. One of the titular adventures involves a character called the Ogre of Fire, who shows-up, vaporizes the main character in front of the child's eyes, and then torches the setting to the ground.
 * Yogoshimacritein in Engine Sentai Go-onger. Not only is he more evil than his son, but he's also a very Bad Boss, . He also has access to a device that deletes people from existence. Although, he's nowhere near as dark as his American counterpart Venjix, whom was from an a very non-saccharine show to begin with.
 * Kamen Rider Fourze—a High School version Kamen Rider penned by the same guy who made Tengen Toppa Gurren Lagann—seems cheerful, right? Wrong. The monsters, known as Zodiarts, are actually fellow students—many of them having lots of psychological issues—alongside the teachers who actively are giving them the means to become evil.
 * Mighty Morphin Power Rangers introduced Lord Zedd in season 2 to pull this off, but sadly he was toned down from there. Season 3 also introduced Master Vile. Many of the later villains (often from seasons that were pretty damn dark to begin with) are darker still.

Theatre

 * Arsenic and Old Lace is mostly a lighthearted "comedy of murders", but more or less treats the character Jonathan Brewster as a completely serious and frightening villain. He's indicated to be a prolific murderer with a love of torture, and it's clear that he's been this way since he was a child, since his hobby then was torturing his brother by putting needles under his finger nails.

Video Games
"The Sorceress: What did you think I was going to do with all those eggs? Put them in a zoo?
 * The Kirby series is set in a Sugar Bowl. The main villain, Dark Matter, is an Eldritch Abomination who appears in a multitude of disturbing forms. These include Zero from Kirby's Dream Land 3, the boss of Dark Matter who cuts its own iris and bleeds as an attack, and later it rips its own iris out. It is reincarnated as 02 (pictured) in Kirby 64, a creepy angel thing with a blood-dripping eye.
 * Another is.
 * Kirby Mass Attack has Necrodus, the monster that split Kirby into ten pieces, and the Skull Gang, his minions.
 * It's been pointed out that very disturbing final enemies make a great deal of sense in Kirby: he lives in Dream Land. What would be the villain of Dream Land other than something out of a nightmare? One of them is even called "Nightmare".
 * EarthBound combines this with Mood Whiplash, in the final fight, in what had started as a funny and lighthearted game, with Giygas, a horrifying Eldrich Abomination with more than a few similarities to Azathoth that you cannot defeat in the normal manner and whose attacks are so powerful your mind cannot comprehend them,
 * In Mother 3, there's . While he doesn't look as scary as Giygas does, he's actually worse than he is. He
 * in Disgaea 2: Cursed Memories even has her own ominous leitmotif. She's made even more horrifying in the infamous worst ending,
 * While Amateur Surgeon is not exactly saccharine, is still pretty light, with Black Comedy and friendly criminals. Then we have the Big Bad,, a frighteningly evil madman who had tried to get Aureola and Dr. Bleed killed, and given Alan hell throughout the entire story.
 * NiGHTS Into Dreams has a relatively cutesy and bright-colored aesthetic to it (much like Kirby, but to a lesser extent), but the bosses, in addition to being (arguably) the most difficult parts of the game are Eldritch Abominations. that look like something out of a Tim Burton movie.
 * All the Mario villains appearing in the RPGs. You've got the Omnicidal Maniac of Dimentio in Super Paper Mario, the super-creepy Cackletta in Mario & Luigi: Superstar Saga, the weapons crazed Smithy in Super Mario RPG, the force of evil that's Dark Star in Mario & Luigi: Bowser's Inside Story, the demonic Shadow Queen in Paper Mario: The Thousand-Year Door, the invading Shroobs in Mario & Luigi: Partners In Time... That's a fair amount of disturbing villains in the otherwise quite light-hearted series.
 * Smithy in particular set the standards as the villain of the first Mario RPG. After traversing the Mushroom Kingdom which as to be expected is bright, colorful and full of wacky and strange enemies...you find the portal to Smithy's realm and find it a dark, gloomy, mist-covered factory full of machines and ghosts.
 * Arch Enemy Bowser sometimes counts underneath all the ham. He is Great Demon King Koopa after all, and can cause major damage when he's actually trying. He tries on two separate occasions to remake the universe in his own image, which is exactly what Dimentio wanted to do, but old Bowser did it by stealing from God with nothing but his Airship fleet and his army. Dry Bowser is him resurrected as a huge demonic skeleton. And of course, there's Giga Bowser....
 * Cave Story is a pretty cheery-looking game with Ridiculously Cute Critters, a Quirky Miniboss Squad with a memorable Catch Phrase and a main character who's pretty much Badass Adorable incarnate. And you're facing a Mad Scientist who is irredeemably evil.
 * It gets even creepier when you enter the Brutal Bonus Level.
 * , the main villain of the Pokémon Mystery Dungeon series games. Prior to the second game's events, he steals artifacts responsible for the balance of the universe as an attempt to destroy both space and time and in the process, he makes one of the gods evil and crazy, then he wipes the hero(ine)'s memory clean and turns him/her into a Pokémon. Later, when this doesn't work, he decides that the easiest way to get rid of his aforementioned archnemesis is to make him/her commit suicide!
 * Not to say the main games aren't proofed against this trope, either. On one hand, you have Ridiculously Cute Critters in beautiful grassy fields. On the other, Jerkass rivals, mafia goons, emotionally repressed (and hateful of living spirit in general) Cyrus, extremely misanthropic Purple Eyes, notorious childbreaker Ghetsis, and the mind-rapist Mad Scientist Ein.
 * Pokémon Sun and Moon deserves special elaboration, because it is significantly upbeat and happy, even for this franchise, and yet it also contains who is a Bitch in Sheep's Clothing, and one of the most seriously disturbed and disturbing villains the series has ever had. . Guzma, on the other hand, is more of what you'd typically expect in a Pokemon game.
 * The prior game's as well.
 * Necrozma is, and one of the few Pokemon to be portrayed as truly evil.
 * Hi, Ghetsis. Especially when this child-murdering, abusive, deceitful sack of shit  Even his henchmen are intimidating and not very funny.
 * The Spyro the Dragon series takes place in a dreamlike environment with mostly cute characters...but occasionally has genuinely creepy enemies. The Dark Passage level from the first game is rife with these as is Haunted Towers. The Metropolis level from Spyro 2 is a rather jarring break in an otherwise cutesy game, with its psychotic cows in space suits who stare angrily and shoot you, as well as exploding pigs who come flying at you out of nowhere (and they will always hit you unless you kill them first). The robotic sharks in water levels are horrifying, especially when you try to go in there without a submarine (you are killed instantly). And also there are levels where plants can eat you. There are quite a few bosses who are pretty unnerving as well.
 * While the first two villains weren't terribly scary, the same cannot be said for the Sorceress in 3, who steals all the baby dragon eggs because  Scorch, the 3rd boss, is pretty damn creepy as well, being solely created for the purpose of brutally murdering not just Spyro and Bentley, but everyone who dared to stand in the Sorceress's way. She does receive a comedic moment, but it doesn't detract from her viciousness.
 * Mook in the background giggles quietly*"


 * Wario Land 3 has enemies and bosses typical of the series... and then there's Rudy the Clown, who turns this Up to Eleven via Interface Screw and sudden subversion of a core game mechanic. Not only is he a powerful demon (blood-red teeth and Evil Laugh not shown), but he's the only thing in the game that can actually kill Wario, and the game auto-saves if he does.
 * Kane in Pirate 101 might be in a very lighthearted game, but wouldn't be out of place in a M-rated game. He betrays his father and locks him up, uses a mechanical army to control many planets (including Valencia), enslaves the common people on Valencia (and makes the guinea pigs a slave race) in Valencia, GRINDS ISLANDS WITH PEOPLE ON THEM TO DUST FOR RESOURCES FOR HIS ARMY, throws out his own "son" Phule for being a failed creation, shoots his own father and is downright gleeful about it while mocking the protagonist about it, and tries to genocide the ENTIRE SPIRAL out of nothing but a superiority complex and the desire to find El Dorado and make himself a "perfect body". DEAR GOD HE IS DARK.
 * Heck, the whole Armada is this. As a whole, nothing about them is Played for Laughs and their appearance is always a serious problem in the story. Captain Avery calls them "heartless, soulless, ruthless" and the play explaining their backstory shows them BURNING VILLAGES AND CITIES TO THE GROUND. The ones who actually talk have a chilling voice and always give intimidating death threats before they fight you. The way they walk and act without emotion is also rather chilling.
 * Let's not forget about Kane's court of Elites. Deacon is the Big Bad for the first half of the game and is always a Faux Affably Evil and very dark villain due to his narcissism. Rooke (the only one with redeeming qualities) is a terrifying behemoth who is extremely difficult to beat, has a dark voice that makes him the stuff of nightmares, and comes close to killing Admiral Nelson twice. Bishop is the least dark of them, though still counts due to having little care about killing thousands to million of Marleybonians with the Beachhead Station. Phule isn't one and is more of an Affably Evil Woobie.
 * A Hat in Time is the type of game where the enemies wouldn't seem out of place with Mario or Sonic. Then you get to Queen Vanessa's Manor in  Subcon Woods and wonder, "When did I start playing Silent Hill?" A thing like Queen Vanessa does not seem like the type who belongs here, being a dark, evil shadow who relentlessly stalks and hunts Hat Kid, her mere presence when she doesn't know where you are being chilling, let alone when she does. Even worse, there's  no way to fight her, the only true way for Hat Kid to survive being to run for her life.
 * Under the Skin is a cartoonish, comedic game where the protagonist is an alien child who has come to Earth to play jokes on humans. In one level, he stops by Raccoon City in order to do so to Nemesis. Yep, that Nemesis. (Seeing as Under the Skin is a Capcom title, this level is sort of a Self-Parody.) While the game does a pretty good job making Nemesis and the other zombies look much goofier than they do in "their" game, it's still odd.
 * Echo the Dolphin looks at first to be a cute, kid-friendly game with an equally-cute dolphin as the protagonist. But any player who actually gets to the last stage (not easy, because the game as a whole is, in fact, Nintendo Hard) finds that the true antagonist is the Vortex Queen, a monstrous floating head with Gigas-level potential of Nightmare Fuel. In fact, this monstrosity wouldn't seem out of place in a game with xenomorphs, just look at it!

Web Comics

 * The entire point of Hello Cthulhu.
 * Sakana has quite the dark antagonists in its Big Bad Ensemble:
 * On one hand, we have a Yakuza gang composed by the Faux Affably Evil Ryoji Nishimura and his Co-Dragons Endo and Billy. That alone is dark enough, but the fact that puts them firmly into this category.
 * On the other hand, we have, who somehow manages to be even more despicable than the above. Why, you ask? The worst part? He's never Played for Laughs, and his scenes are downright serious and nightmare-inducing. By comparison, the Yakuza do have Laughably Evil moments even now and then.

Web Original

 * Most Neopets villains are Laughably Evil, but plot villains tend to be really, REALLY EVIL.
 * Much of the time, Suburban Knights has the same tone as the rest of the That Guy With The Glasses site; definitely not for children and sometimes resorting to Refuge in Audacity, but still comical and not taking danger very seriously. However, this doesn't hold true when Malachite - an apparent complete sociopath who murders multiple innocent people just for using technology - is on screen. While most of the site's villains are Played For Dark Comedy, Malachite is almost always Played for Drama.
 * Another unusually serious villain for the site is The Entity from Atop the Fourth Wall. This may be because it's an Eldritch Abomination that tries to destroy the universe.
 * Reflets d'Acide, is a fantasy Affectionate Parody with comical characters, but antagonists Belial and Alia-Aenor, while both having comical moments, are actually threatening villains, with Belial possessing a Complete Monster status and Alia-Aenor being a Bitch in Sheep's Clothing.

Western Animation

 * Care Bears, of all franchises, tends to have this in spades, what with Professor Coldheart, the Spirit in the Book, Dark Heart, No-Heart and others all dedicated to the removal of any ability to feel emotion.
 * The New Adventures of Winnie the Pooh episode Cleanliness Is Next To Impossible where a creature named Crud (voiced by Jim Cummings using his Robotnik voice from the Sonic the Hedgehog SATAM show) imprisons Pooh, Piglet, and Tigger and then tries to force Christopher Robin to help him make the rest of the world dirty by saying "If you don't, YOU'LL NEVER SEE YOUR FRIENDS AGAIN!". Granted, by normal standards this hammy cartoon blob is not much worse or creepier than most Disney Afternoon villains, but he's much more so then you'd expect from one of Disney's lightest and softest universes.
 * Prior to New Adventures the inclusion of any villains period was completely new to the franchise, which usually didn't have any antagonists (par maybe Rabbit, which still isn't saying much). For example this was the first depiction to show real Heffalumps and Woozles. Granted they were all comical and almost as hapless as Pooh himself, but were still a big change from the usually laid back stories of A A Milne's creation.
 * My Little Pony has such characters as Tirek (a demon centaur who wanted to turn the ponies into an army of demonic dragons with his "Rainbow of Darkness"), Katrina (a catwoman sorceress who plotted to enslave the ponies into gathering ingredients for her Fantastic Drug of choice, "witchweed potion"), Squirk (a tyrannical sea monster who wanted to reclaim part of his undersea kingdom by flooding Dream Valley), and The Smooze (an all-consuming blob monster unleashed by a Card Carrying Villainess and her bumbling daughters). The G1 continuity has a lot of villains who came close to enacting a Sugar Apocalypse.
 * Crunch the Rock Dog, a huge dog made out of stone that hates all things soft, and has the power to turn anything he touches to stone, and turn normal rocks into sharp-toothed monsters to stalk his prey. The way he and his rock minions chased after the Bushwoolies, turning them to stone one by one, seems right out of a horror movie.
 * While most villains in the series turned good or simply fled when defeated, two of them (the aforementioned Tirek and the magma-creature Lavan) were so evil and powerful that the heroes actually had to kill them. This is notable not only because a series based on something as innocent as the My Little Pony toys would probably be the last place anyone would expect to see someone die, but also because characters being killed of was something very rare to see in any TV cartoon in the 1980's.
 * The G4 series, My Little Pony: Friendship Is Magic, has Nightmare Moon, sister of Princess Celestia who, in a fit of envy, plotted to bring about The Night That Never Ends (which according to Word Of Faust would have killed all life in Equestria).
 * The Parasprites. Although not so much villains as an unrelenting all-devouring force of nature, their consuming pretty much the entirety of Ponyville in the span of a couple minutes is pretty chilling.
 * Discord, a trickster spirit with a warped sense of humor. Despite his comical mix-and-match appearance, and his first evil act being generating clouds of cotton candy that rain chocolate milk, he turns out to be a formidable foe. Screwing with the heads of Twilight's friends he effectively destroys their connection to their respective Elements of Harmony, all but completely eliminating their only chance of beating him, and subsequently turns Equestria into a realm of madness and chaos where gravity, time, and even basic causality have all taken an extended holiday.
 * "Hearth's Warming Eve" introduced the Windigos, evil spirits who feed off of hatred and cause deadly blizzards. They drove the original ponies from their homelands, and nearly destroyed Equestria. Moreover, it's implied that they freeze people in a state of hatred but keep them alive so that they can have a continuous food supply.
 * "A Canterlot Wedding" has who, and launches a full scale invasion of Equestria, complete with terrified ponies desperately fleeing from her minions.
 * Some of the oldest Looney Tunes shorts had villains that made even Yosemite Sam look timid:
 * The 1949 Porky Pig cartoon "Bye, Bye Bluebeard" had a Serial Killer (that's right, a serial killer) named Bluebeard who would likely have given most of today's children nightmares. Forget the fact that he was hideous, stood 6' 11" tall, actually had a long, blue beard, and the most nightmarish Evil Laugh in Looney Tunes history, he nearly decapitated poor Porky using a homemade guillotine; Porky was saved when a mouse (who Porky had been chasing earlier) tricks Bluebeard into eating some bombs disguised as popovers, causing the villain to explode. It's little wonder that this was one of the few times a character's death in Looney Tunes had no comedic postscript accompanying it, like say, an angel or ghost leaving the body. He was that vile.
 * Even some of the more recent (relatively speaking) shorts had some darker villains, like the Evil Scientist from "Water Water Every Hare". While his trained monster Rudolph was more Laughably Evil, he himself was true Nightmare Fuel, his attempt to kill Bugs using an axe being a scene that likely startles anyone who sees the cartoon for the first time.
 * The Powerpuff Girls
 * Him, one of the scariest (and daring) villains on a Cartoon Network comedy ever, even turned Townsville into a living hell on earth when the girls accidentally traveled forward in time.
 * A soundalike bear from The Teletubbies must be also vile out of universe.
 * At least Him has comedic traits. Dick Hardley, however? Dear GOD.
 * Father from Codename: Kids Next Door. A shadowy figure with control over fire, who brainwashed five children into thinking they were his/being evil? Add that to the fact that he is always beaten by the skin of everyone else's teeth and you've got a very threatening villain for such a harmless show.
 * And then once Father went through massive Villain Decay, The Movie gave us Grandfather, Father's father, who possesses many of Father's abilities as well as the ability to turn all the people in the world into undead senior citizens.
 * Sideshow Bob from The Simpsons has always been distinctly darker than anybody else in a cast of hundreds. Especially prevalent in the classic "Cape Feare" episode where he forgoes evil plans and just tries to slice Bart to pieces with a machete, crouched and approaching with dark rings under his eyes...
 * Perhaps to balance it out, the Sideshow Bob episodes were also frequently Denser and Wackier, even during the show's earlier more "down to earth" depiction. In the same above stated episode, Sideshow Bob was driven through a cactus patch, walked through a pile of rakes and trampled by circus elephants. He later sings the entire score of H.M.S. Pinafore as a final wish to Bart before attempting to murder him (complete with makeshift props, costumes, an issue of Playbill with his picture on the cover, and a giant Union Flag unfurling behind him during the grand finale).
 * While a few of them do play nice, most of the diesel engines in Thomas the Tank Engine are very vocal about their desire to overtake the steam engines and aren't above trying to hurry that day along. At least twice, they've tried to smelt down other engines and escaped any consequences.
 * Phineas and Ferb is a show that invokes Rousseau Was Right and usually has a Ineffectual Sympathetic Villain, which makes the presence of the unnamed Drill Sergeant Nasty in "Phineas and Ferb Get Busted" all the more surprising. He spends the entire episode coldly and sadistically pounding out any creativity and happiness from the duo. He even He's also, so the show can get away with this.
 * Cracked.com presents: 7 Badass Cartoon Villains Who Lost to Retarded Heroes.
 * Teen Titans sometimes has this trope. The show itself is usually lighthearted, and most of the one-shot villains are comical (with a couple of notable exceptions)- but lets take a look at some of the Big Bads. Slade is a creepily emotionless diabolical mastermind who pretty much runs on blackmail, Mind Rape, Hannibal Lectures and Foe Yay, and delivers No-Holds-Barred Beatdowns to several characters in surprisingly vivid fashion. Then there's Trigon, who's basically Satan and wants to use the show's main Woobie, who's also his daughter, to bring about The End of the World as We Know It- and he actually succeeds in causing Hell on Earth for two episodes. Fun times.
 * Both villains (as well as Brother Blood) were toned down a lot for the cartoon. For much of the '80s, the Teen Titans was one of DC's darkest books. The fact that they were able to make it a kids' show is a feat for the ages.
 * Adventure Time is more of a Crap Saccharine World than a saccharine one (though the characters inside don't seem to care), but most monsters encountered are easily defeated and the common recurring enemy is an Ineffectually Sympathetic Jerkass Woobie, making Marceline's dad and The Lich still terrifying regardless of all the other nasty things lurking about.
 * The Transformers Animated version of Megatron, given the show's colorful and cartoonish nature.
 * Shockwave, who murdered in an incredibly horrifying manner, Wasp, being in a continuity where his insanity isn't played for laughs and is completely terrifying for it, and Lockdown, a freelance assassin Transformer who's caused Ratchet to have war flashbacks.
 * Lockdown's whole body is a Swiss Army Weapon whose left arm and leg don't match his right. Why? He butchers other Transformers for their parts to increase his power.
 * Prometheus Black/Meltdown is a rare human example in the series. While the other human villains in Animated are deliberately used as filler and to exemplify the Decepticons as a greater threat, Meltdown manages to be genuinely depraved and terrifying. Case in point - in his second appearance, he was experimenting on humans to try and create human transformers (he'd already done at least two adult humans, one of them his former lawyer, and was planning to use 8-year-old Sari Sumdac as his next test subject).
 * The Classic Disney Shorts have The Mad Doctor, who is an evil doctor bent on cutting up Mickey's dog Pluto as part of a lab experiment. Later, he actually threatens to cut open Mickey Mouse himself! Fortunately, he only exists in one of Mickey's nightmares.
 * Zordrak of The Dreamstone. A gargantuan bellowing Eldritch Abomination with a serious Hair-Trigger Temper that frequently abuses or even exterminates his Slave Mooks the Urpneys for the slightest irritatation. While also managing to be rather funny, he's a pretty creepy guy, even when not compared to the cutesy residents of the Land Of Dreams.
 * Gargamel of The Smurfs qualifies for this designation, though not always.
 * Dr. Blowhole in The Penguins of Madagascar. In his debut episode he planned on flooding the world, just because of all the embarrassment humans put him through when he was a circus dolphin. And in his second appearance, he intentionally meant to drown Skipper when he gave him amnesia. And that, after his first appearance, some of the other episodes went through Darker and Edgier territories.
 * A Finnish Children's show called The Moomins stars a family of cute Claymation hippos—occasionally visited by some void/plague/death incarnation that can apparently kill things just by standing near them. It also moves like some kind of demon ghost.
 * Ed, Edd 'n' Eddy has Eddy's brother. Sure, the show itself was a Sadist Show, but everything that happens to the Eds up until his appearance is played for laughs and could be considered lighthearted enough. Come the end of the movie, this guy manages to genuinely harm both his own brother and Edd, and he's been abusing the former for years. What all the typical bullies in the show witness him doing is horrific enough for them to redeem themselves and accept the Eds as their friends once and for all.
 * XANA from Code Lyoko: the show takes place in a college that appears to be a rather lighthearted, comical setting, with a ridiculous gym teacher, a Lovable Alpha Bitch and characters making jokes, but as soon as XANA starts acting, we suddenly get stuff such as Killer Wasps/Rats/Birds invasions, Giant Destructive Teddy Bears, place where Everything Is Trying To Kill You, Zombie Apocalypse, cataclysms, Demonic Possession, and the list goes on.
 * Ben 10, especially the original series, is goofy with a Silver Age feeling to it, yet even some of its recurring villains are outright disturbing. (With the exception of Ben 10: Alien Force and Ultimate Alien, which both have creepy sinister villains such as Aggregor and Diagon but are already dark to begin with.)
 * Vilgax is a Galactic Conqueror stated to be the most feared being in the Universe, who wants get the Omnitrix so he can use it to create an army of invincible shapeshifting drones. He is explicitly stated to have blown up at least one inhabited planet according to flashbacks almost exterminating the species in the process, and Word of God implied it wasn't the only one. When first meeting with Ben, he delivers him a very brutal No-Holds-Barred Beatdown, kidnaps him by taking his relatives hostage, and tries to cut his arm off just so he can take the Omnitrix from it.
 * Zombozo is a Monster Clown Humanoid Abomination with a really creepy design, prone for Slasher Smiles, who fuels his power by harvesting happiness (Fear in Omniverse) from people. Prolonged drain can result in people being reduced to weak, barely alive husks, and he apparently enjoys abducting children to drain them more later. When Ben confronts him, he proceeds to disturb and psychologically torture the kid thanks to weird illusions involving a huge deal of Alien Geometry. And that guy is a minor villain.
 * Ghostfreak/Z'Skayr initially is introduced as one of Ben's ten original form in the Omnitrix, and one that disturbs him so much he is reluctant to use it. Then it turns out his memory is still contained inside the Omnitrix along with his DNA, allowing him to resurrect from Ben's transformation, and he just happens to be a maniac who wants to take Ben's body and use it to his own ends. His schemes involves, amongst other things, covering the world with Darkness while mutating the entire population into hideous monsters. And as long as the Omnitrix contains his DNA, he can always come back from the grave.
 * Khyber the Huntsman, who was The Heavy in season 1 of Ben 10: Omniverse, is a Predator-esque Egomaniac Hunter who likes to hunt various species in the Galaxy and collect their bodyparts as trophies. He doesn't care if the species he hunts are sentient, and judging by what we see in his ship's Trophy Room, he did slay several sentient aliens before coming for Ben, making him a Serial Killer as well. Oh, and he owns the Nemetrix, an Omnitrix Evil Knockoff allowing his hound to shapeshift into all kind of feral alien predators.
 * Malware, the true Big Bad of season 1 and Khyber's boss, is a psychotic Galvanic Mechamorph born with a malfunction forcing him to sustain himself by cannibalizing people of his own species in exchange of the ability to copy technology by consuming it. His onscreen actions include trying to crash a school bus just to distract Ben, . He especially stands out as this trope among Ben 10 villains, because, despite being in the most goofy and light-hearted entry in the franchise, his viciousness and cruelty rivals some of Alien Force's and Ultimate Alien's Big Bads.
 * While Courage the Cowardly Dog is pretty creepy and no stranger to Nightmare Fuel, most of the villains have some sympathetic motive or backstory or are otherwise Laughably Evil. But there are some who can take villain level much, much further. In order of appearance:
 * Katz, Courage's arch-enemy, is simply put one of the most disturbing examples of a sadistic Serial Killer played straight on a kid's show. Never Played for Laughs, his MO is to set up false businesses to lure victims, then murder them in brutal ways when he's done (feeding them to spiders, turning them into appliances or candy, etc). And it's heavily implied that the family is the latest in a long line of victims and possibly the only ones to escape.
 * Benton Tarentella, one of the lesser known villains, is a zombie director who was a Serial Killer when he was alive, murdering people with his partner while pretending to film them. When he died, he still continued his murderous work. His debut episode had him attempt to revive his partner so they could devour Muriel. His second appearance, however, downplayed his vileness.
 * Mad Dog is a vicious gangster who regularly abused his girlfriend Bunny and implied to put her in prostitution. When Bunny's friend Kitty tried to get her away from him, he threatened to kill her. The event traumatized Kitty to the point where she assumed all dogs were evil and took her rage out on poor Courage. Much like Katz, Mad Dog is played completely seriously and is basically a Domestic Abuser played horrifically straight on a kid's show.
 * King Ramses trumps them all, with his nightmarishly hollow, skeletal appearance coupled with a soft, heavenly-toned voice begging for his slab. Just give him the slab already, Eustace, for the love of the viewers at least!
 * Dora the Explorer normally only has Swiper, but some of the movie Big Bads qualify. Especially the Witch from "Dora's Fairy Tale Adventure", who put Boots in a never ending sleep For the Evulz and was genuinely evil.
 * Bill Cipher from Gravity Falls is a one eyed, pyramid shaped Eldritch Abomination who rules over the realm of nightmares and serves as the primary Big Bad of the story. Originally from the flat 2nd dimension, Bill detested the dull normalcy of his world so much that the first thing he did when he received his Reality Warping powers was lay waste to it and plunge it into total disorder. Viewing Earth as being in similar need of "liberation", Bill sought a way to enter Earth's reality in psychic form so that he could unleash "Weirdmageddon" upon the entire planet. He began his plan years before the start of the show by linking his world of anomalies to the town of Gravity Falls, Oregon. He then entered the mind of the inquisitive Stanford Pines, befriending him as his "muse" and research partner, and deceiving him into constructing a machine that would create a dimensional portal for Bill and his demon underlings to enter through while also generating enough power to tear the entire universe apart. Ford's associate Fiddleford McGucket was left traumatized after accidentally looking through the portal into the nightmare world, and after Ford saw what Bill was truly planning and abandoned construction of the machine, Bill relentlessly hounded him via invading his thoughts and dreams, or sometimes even resorting to Demonic Possession. When we meet Bill in the present day plot, his antics include invading Stanley Pines' mind through the dreamscape as part of a deal with Gideon Gleeful and later attempting to destroy Dipper, Mabel, and Soos purely out of frustration, tricking Dipper into letting him take over his body so that he could smash Ford's old computer (which he succeeds at) and destroy his secret journals (which he fails at), and finally breaking the Dimensional Rift that he coaxes an emotionally distraught Mabel into giving him while in the form of Blendin Blandin, which allows him and his demons to enter the physical world at last. He kicks off his apocalyptic "party" with nearly killing a man by rearranging his face, turning Ford into a golden miniature statue, burning the three journals and ordering his minions to eat Dipper, unleashing distortion and destruction upon the entire town, turning many residents to stone and using them to build himself a "throne of human agony", and wiping out Time Baby and the Time Police when they attempt to crash his party. He also had Mabel trapped in a Lotus Eater Machine trap that would gradually Mind Rape her and anyone else who entered. Bill ultimately intended to spread chaos across the globe so that the world could become his playground, using the rationale that he was making things the way they ought to be. In the Grand Finale, he tortures Ford with around 500 volts of electricity in order to make him tell him how to break the anti-weirdness barrier around Gravity Falls, then deciding that torturing Ford's young niece and nephew, Dipper and Mabel, might get better results given how much Ford cared about them. He takes out the souls of the Pines Family's friends and seals them within banners, and then attempts to murder Dipper and Mabel, stating he was going to "make some children into corpses." Despite being certifiably insane and having a serious case of Evil Cannot Comprehend Good, Bill seemed perfectly aware of basic human morality and sanity, being all too willing to exploit it for his own ends and never caring to follow it himself. He put his own self interest above all else, treated even his own demon "buddies" as slaves to do his bidding, and his quirky, Crazy Awesome, Laughably Evil persona could not detract from his menace. Petty, psychotically childish, sadistic to the extreme, and possessing a sick sense of humor, Bill ended up one of the darkest and most horrifying villains to come out of a Disney animated series.
 * The Flintstones had a few of these. One James Bond-inspired episode had Fred and Barney the victims of Mistaken Identity and wind up kidnapped by a Mad Scientist named Dr. Sinister. One example of how evil the villain was: in one scene, he ordered a henchman to throw another guy in "the bottomless pit", Fred and Barney being able to do nothing but watch, terrified, as the guy was dragged away, begging for his life. When Fred got the nerve to ask who the guy was, Dr. Sinister replied, "Oh, just a former assistant."