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Anime and Manga
- Pixy Misa from Magical Project S.
- Buggy the Clown from One Piece as well as one of his mooks.
- The beautiful Suzuki from YuYu Hakusho.
- Papillon from Busou Renkin fits this due to his campy behavior and dress and being Affably Evil.
- Will in Pokémon Special. In every other continuity he's strictly a good guy though.
- Impmon in Digimon Tamers, until his digivolution and Heel–Face Turn not long after.
- The Juggler in B't X. Dressed like a harlequin/jester, with a funny mask and a B't named 'Vanilla Fudge', you wouldn't expect this character to be one of the most fearsome, powerful and outright sadistic of the Demon Generals that guard the Area.
- Joker from Smile Pretty Cure!. Notable for being much worse than he initially appears.
- Jeager/Lazar from Yu-Gi-Oh! 5D's. He pulls a Heel–Face Turn in Season 3.
- The Joker has wobbled between More Monster / More Clown depending on the decade, with the 50s and 60s leaning most strongly to the latter. Interestingly, the addition of his sidekick Harley Quinn (who takes this to a literal example) ends up balancing the 'more Monster' situations. It's interesting to note that Harley is only Played for Laughs when she's fawning over The Joker. When she goes out on her own, especially when she's out to prove herself to "Mistah J", she takes a serious level in bad ass and becomes a dangerous threat to even Batman himself.
- The Joker's one-time sidekick Gaggy (a dwarf in a jester costume) also fits. The character was recently revived in Gotham City Sirens where he sought vengeance on Harley Quinn whom he viewed as having taken his place.
- The Charlton/DC villains Punch and Jewelee are a married couple who both fit this role, as did the version of Toyman who was a member of the Legion of Doom on the Superfriends.
- The Golden Age Green Lantern foe the Harlequin (aka Molly Mayne), who he later ended up marrying.
- And Molly was just one of four DC villainesses to use the name The Harlequin over the years, not including Harley Quinn (who doesn't count because she spells it different...and it's a shortened version of her real name).
- Pierrot Lunaire is a foe of the Musketeer who dresses as the Commedia dell'Arte character Pierrot. He was a member of the Club of Villains that appeared in the Batman R.I.P. storyline.
- The Flash's enemy, The Trickster. Just imagine The Joker, but with more of a scientific genius and less psychosis. Like the rest of the Rogues, he's generally focused on petty theft instead of thinking bigger with his advanced tech.
Films — Animated
Films — Live-Action
- One of the ten named demons from The Divine Comedy is known as Alichino, a name derived from the Italian for "harlequin." He is the only one whose blood-lust so overcomes his sense that he trusts a damned politician who promises to deliver more souls to kill; naturally, the politician betrays Alichino and leaves him looking like quite the fool.
- Foundation and Empire has Magnifico Giganticus, who plays the Sad Clown part so well at first that nobody even suspects him of being a villain. In fact, he's the Mule himself.
- In Murder Must Advertise, Lord Peter Wimsey takes on the persona of a sinister harlequin in order to infiltrate a murderous drug ring.
- Dorothy of Oz by Roger S. Baum featured a jester who went evil after getting his hands on a Magic Wand.
Live Action TV
- Many, many villains from Power Rangers. Rita Repulsa (even when she was the Big Bad), Jindrax (from Wild Force) and Marah/Kapri (from Ninja Storm) are probably the most straight examples of this trope.
- Maaen from Tomica Hero Rescue Force.
- Evil Jester from The Amazing Extraordinary Friends.
- Five Characters in Search of an Exit had a menacing clown. He wasn't quite evil, but he was all nihilistic and ominous and strange.
- One episode of The Fresh Prince of Bel-Air has Will, Carlton and Uncle Phil dealing with one of these, who demands to be taken to the courthouse (where Phil is to preside over a trial that will be televised) just so he can show his act in front of the cameras. He uses dynamite sticks strapped to his body in order to persuade people into following through with him. However, the bombs later prove to be gag props complete with a "BANG!" flag. He's promptly kicked out of the court for his troubles.
- In Merlin, a king sends a magic-using jester named Trickler to cause Prince Arthur to fall in love with Princess Vivian, causing her Overprotective Dad to challenge him to a duel and disrupt a peace treaty negotiation.
- Googler from Ace Lightning. An insane, maniacal jester, Googler is summoned by Lord Fear after obtaining an Amulet fragment in the first season's seventh episode "Only Human". Imprisoned in a place called White Hot Oblivion by Ace, Googler seeks revenge against Ace. He speaks in third person and creates his own words like "googlerize" (an alternate use of "pulverise"). He wears a spiked shell on his back, which he can curl into, turning him into a dangerous, fast-moving bouncing ball. Googler is accompanied by two talking sock puppets named Zip and Snip, who are able to fly, can chew through any surface, absorb powers, and brainwash Ace in one episode.
- Creditor The Clown of Chicago debt-settlement firm Legal Helpers. His main shtick is that he demands money he loaned to people by beating them with his inflatable bat, screaming, "Where's my money?" He is eventually thwarted by spokesman Erik Martin, who proceeds to steal his bat and knock him out.
- Invoked in Black Diamond Wrestling with Keith Haught, who along with several other wrestlers was imbued with "dark powers" meant to turn them evil, Haught in particular being remade into "The Jester". Except Jester continued to not be evil, just goofy. And unlike the other wrestlers, he couldn't be cured either.
- One of these shows up as an antagonist in a Pathfinder Dungeons & Dragons module. She's also cheerfully Ax-Crazy, Too Kinky to Torture, and has a crush on her boss.
- In the Dungeons & Dragons 3.5 Edition Monster Manual IV is a creature called the Taunting Haunt, the vengeful spirit of a clown or preformer that can only be destroyed if beaten in a game of wits.
- Champions has the Black Harlequin, a cheerful, smiley villain who just wants to have fun. His signature wepaons are armies of lethal toys, like teddy bears with metal claws, toy soldiers with real rifles and a rag-doll that causes aneurysms.
- Chance from Universal's Halloween Horror Nights initially started off like this when she made her first appearance in 2007; possessing a very childlike and ditsy kind of personality. However, she was was made into a much more significant threat over time; to the point that she became the event's "icon" in 2016. Now, she has far more darker characteristics and is very capable of killing - though at times she'll still display traces of her original childlike self.
- Harley Quinn from the Batman: Arkham Asylum and Batman: Arkham City Games.
- Harlequin, the psychic gambler pig from Link: The Faces of Evil.
- Cuphead has Beppi the Clown, the boss of "Carnival Kerfuffle". He's a clown, who like the other characters of the game, makes use of Deranged Animation. When the protagonists confront him as part of their gig as the Devil's Debt collectors, Beppi fights them on top of a roller coaster's tracks, and transforms into a creepy-looking balloon man, and later a giant carousel, all with a big grin. The ending shows when not threatened by Debt collectors, Beppi is actually a pleasant enough person.
- Shannon, the succubus-slash-stripper from God Hand.
- Deathjester in Seiken Densetsu 3, who lapsed into Monster Clown at times.
- Tira from SoulCalibur.
- Kefka in Final Fantasy VI is initially presented as a Villainous Harlequin. That perception doesn't last long. Good thing we still have Ultros.
- Zorn and Thorn from Final Fantasy IX.
- The appropriately named Harle from Chrono Cross. However, she's far more of an Enigmatic Minion than an ineffectual villain. And being a villain or not doesn't really seem to be under her control.
- Reala and Jackle from Ni GHTS Into Dreams. Turns out NiGHTS itself was originally planned to be that, but a Heel–Face Turn turned it into the hero.
- Dimentio, from Super Paper Mario, fits this trope perfectly, but while his slightly hammy antics and overall Friendly Enemy demeanor is played for laughs, he definitely proves to be a Not-So-Harmless Villain by the end of the game.
- Also, Bowyer, a Boss from Super Mario RPG, is like this.
- Malcolm the Jester from The Legend of Kyrandia, who goes from being a Chaotic Evil Sorcerer to a depowered Villain Protagonist trying to Clear His Name in the third game.
- Overlord has the Minion Jesters, whose duties are to give their Evil Overlord Masters amusing names (or, in Overlord II, make little limericks) while also serving as their Training Dummies at times.
- Played with in regards of the Royal Jester in Princess Maker 2. Everyone thinks he's a bad guy and going talk to him actually drops your daughter's social reputation each time, but he's actually a rather good-hearted fellow... if a bit of a Trickster Mentor to the heroine. Who can choose being a Jester as her main work in the end, if some requirements are met (specifically, having him give her his Royal Harp after several visits, as well as possessing a strong Constitution and very high Art and Conversation skills).
- "The Harlequin" Cahin from Assassin's Creed: Brotherhood, who uses his acrobatics to dazzle and distract his opponents while he (or his sister Caha) move around to deliver a fatal strike.
- The Dragon Age II DLC Mark of the Assassin has enemy rogues as Harlequins to fit the flamboyant Orlesian setting.
- Shaco the Demon Jester in League of Legends. If the title or his glowing green eyes didn't give it away, his name is an anagram of "chaos".
- Dhoulmagus, the Big Bad Wannabe from Dragon Quest VIII is one of these.
- The redesign of Thanatos in Kid Icarus: Uprising goes for this. While he's a rare example who's The Dragon and can prove to be powerful and threatening, more often then not he's the butt of many jokes thanks to his childishness and laziness.
- Clown Man, one of the Robot Masters from Mega Man 8.
- The Dark Wings from Tales of the Abyss subvert this troupe. Initially they seem to be a trio of annoying (if relatively harmless) thieves disguised as circus clowns, but they're actually in league with Asch, putting them at least slightly on the side of good.
- Motley Bossblob from Super Mario 3D World is a Koopa jester who summons sentient blobs to create a larger clown form around him.
- Cicero from The Elder Scrolls V: Skyrim is one of these. You first find him on a road with a broken wagon and he asks you to fetch him some tools to fix the wagon, all while laughing and dancing. Turns out he is actually a member of the Dark Brotherhood, a league of very dangerous assassins. After you find that out he becomes considerably more malicious.
- Junkrat from Overwatch has two Legendary skins that make him this.
- Loki from Smite has two skins that makes him one of these, named "Last Laugh," and "Joki."
- Jester from Devil May Cry 3, who reveals his true evil when he reveals he's actually Arkham, who wanted to maneuver Dante and Vergil into fighting each other so that he could use their blood to undo their father's spell and get his hands on Sparda's power.
- Jokerella from The Non-Adventures of Wonderella would probably fit in here, but she's kinda bad on the 'villainous' part. Her mother Pirouette was a much straighter example when she was alive.
- The Riddler's Gammon comics by MS Paint Adventures' Andrew Hussie feature a harlequin who menaces people with nonsensical puzzles and complicated rhyming schemes. He tends to get arrested, or shoved into garbage.
- In Homestuck every enemy gets decorated in harlequin garb near the beginning of the story. And of course there's Gamzee Makara, who when first introduced is a fairly mellow, perpetually stoned, Faygo-swilling Juggalo who's trying to troll Dave but is laughably bad at it. When he sobers up he goes directly into Monster Clown territory and things get ugly fast.
- In the KITTEN II storyline of Sluggy Freelance, the commander of a paramilitary group devoted to battling the forces of evil is inexplicably dressed as a clown, which terrifies the normally-stoic Riff. It turns out he isn't really a clown, it's just a disguise to divert attention away from them. Somehow. But then it turns out that he's gone insane and believes himself to be chosen by God to control The Evil, which involves killing a lot of the other characters. And then it turns out that he was a clown all along.
- The Adventures of Dr. McNinja: One of the Doctor's lesser opponents is Donald McBonald, the unscrupulous clown (and mime) who owns the McBonald's burger chain.
- Harley Quinn from Batman: The Animated Series. Though it's worth pointing out that her Nightmare Face and insane cackling as she lowers Batman into a vat of piranhas thinking she can finally have the relationship she dreams of with the Joker pushes her this close to Monster Clown levels.
- The Joker goes back to his Silver Age Harlequin feel in Batman: The Brave and the Bold. Even so, he is hilariously no less Made of Awesome than in the comic books or The Dark Knight.
- I'm Dr. Rockso, the rock-and-roll clown! I do cocaine!
- Quackerjack from Darkwing Duck.
- Hexadecimal from ReBoot.
- Jimmy Two-Shoes has a bike gang called The Rodeo Clowns.
- In a Squidbillies episode, Rusty and Early become Clowny Freaks (a parody of Juggalos). To advance up the Ziggurat of the Clownies towards full ninjahood, aspiring clowny freaks must smash stuff while playing "that evil-ass calliope". Clowny Daggers, baby!
- Jack-In-The-Box from Cool McCool.
- The Jester in the "Court Musician" segment in Garfield: His 9 Lives. He keeps taunting "Freddie," the titular court musician, that if he doesn't please the king with his concerto, he faces the guillotine.
- An actual royal court jester was a villain in one Woody Woodpecker cartoon; he wasn't really evil, but he was a pretty bad jester, and when the king threatened to fire him after thinking Woody was much funnier, the guy went after Woody in an attempt to keep his job. (The cartoon ended with Woody getting the job with the guy being punished by being part of Woody's act - getting pies thrown in his face.)
- Jester-themed villain Madkat in SWAT Kats is like this, though he can be scary at times.
- Super Mansion Groaner, who is a villainous prop comic who doesn't seem to be out to actually (intentionally) hurt anyone and has actually accompanied the heroes on a number of missions, but still does things like set a house on fire with a brush so he can make a joke about "brushfires" and actually came closest to beating the league by stealing one of their expense cards and using it to cause them to go overbudget.