Villainous Harlequin

A step down from the Monster Clown, a Villainous Harlequin is a villain that taps into the same vein as a Monster Clown but is usually Played for Laughs and rarely attempts to be outright scary.

A Villainous Harlequin (if female) will often be the Perky Female Minion of the Quirky Miniboss Squad, rarely going any higher on the Sorting Algorithm of Evil. Compared to the Monster Clown- which is genuinely threatening- she is closer to an Ineffectual Sympathetic Villain. She has shades of the Trickster Archetype in her impulsive and anarchic ways, but lacks the intelligence necessary for this trait to provide any real danger. Whether male or female, a Villainous Harlequin may fancy him or herself as a Smug Snake, but his or her childish demeanor and outlandish appearance (which can range from traditional jester costumes to impossibly cool outfits and incredibly impractical poofy dresses if female) ruins any chance of anyone taking him or her seriously. Expect temper tantrums when his/her plans inevitably fail, and for him or her to either be a Chew Toy of The Dragon or a member of the Goldfish Poop Gang.

But be careful: if the Villainous Harlequin gets promoted to The Dragon or Big Bad levels, you're going to have a serious case of Who's Laughing Now? on your hands.

The Villainous Harlequin is the product of the popular view of The Jester, which is that of an idiotic buffoon. (This is despite the fact that The Jester was one of the most insightful members of a king's court, due to his position outside the usual social ranks). Interestingly, in some Renaissance art Death itself is often portrayed dressed in motley, or "pied" clothing, which is often conflated with the true Harlequin outfit. The more danger a Villainous Harlequin poses to the protagonists, the closer he or she gets to Monster Clown.

Examples of Villainous Harlequin include:

Anime and Manga

Pixy Misa from Magical Project S.
Buggy the Clown from One Piece as well as one of his mooks.
~~Suzuki~~ The beautiful Suzuki from Yu Yu Hakusho, anyone?
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.

Comic Books

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 ~~addiction~~ addition of his sidekick Harley Quinn (Who takes this to a literal example, overlapping with Sexy Jester) ends up balancing the 'more Monster' situations.
- 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.
- Far more recently (in 2020, the "Joker War" arc) Punchline was introduced as an Evil (well, eviler) Counterpart to Harley, and was far deadlier than Gaggy. Punchline was an insane sociopath and Monster Fangirl towards the Joker even before she met him. If anything, the first meeting between Harley and Punchline resulted in each reacting towards the other with raw hatred.
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).
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.
Averted in Astro City—Jack-in-the-Box may have the Joker's fashion sense, but he's definitely a hero.

Film

Stitches, Royal Pain's sidekick from Sky High.
In Disney's The Hunchback of Notre Dame Clopin has shades of this. He's mostly Chaotic Neutral but turns downright malicious during "Court of Miracles".

Literature

Magnifico Giganticus in Foundation and Empire.
- His horrifying, horrifying aversion of the sillier, less threatening aspects of this trope should be mentioned, but even having a reference to him tagged as a spoiler could be a dead giveaway if you're sufficiently paranoid about the identity of the Mule.
In Murder Must Advertise, Lord Peter Wimsey takes on the persona of a sinister harlequin in order to infiltrate a murderous drug ring.

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.
- On the Super Sentai side of things, this role usually falls to the solitary human female of the Quirky Miniboss Squad. Recent examples have been Furabiijo from Ninpuu Sentai Hurricaneger and Kaze no Shizuka from Go Go Sentai Boukenger.
Maaen from Tomica Hero Rescue Force.
Evil Jester from 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 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.

Tabletop Games

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.
Interestingly subverted by the Eldar Harlequins, which are technically good (i.e. they fight Chaos), are best described as psychedelic space elf killer clown ninjas, and are so competent even the Dark Eldar, who have an almost psychopathic urge to horrifically maim, torture, and kill every living being they can get a hold of, are afraid to keep them from the otherwise impenetrable Hell dimension they reside in. Oh, and they use some of the setting's most horrific weapons when they're not doing psychically enhanced cautionary interpretive dance, not that they much care for the difference, though.

Video Games

Harley Quinn from the Batman: Arkham Asylum and Arkham City Games.
Harlequin, the psychic gambler pig from Link: The Faces of Evil.
Shannon, the succubus-slash-stripper from God Hand.
Deathjester in Seiken Densetsu 3, who lapsed into Monster Clown at times.
Tira from Soul Calibur.
Kefka in Final Fantasy VI is initially presented as a Villainous Harlequin. Of course, 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 NiGHTS Into Dreams. Turns out Ni GHTS 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 Not So Harmless by the end of the game.
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 make little limericks in the sequel) while also serving as their Training Dummies at times. Still, the first game indicates that he may be Not So Harmless.
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.
Cicero from The Elder Scrolls V: Skyrim, who's a Cloudcuckoolander member of the Dark Brotherhood prone to dancing a jig at the spot.
The latest Dragon Age 2 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"

Web Comics

Jokerella from The Non-Adventures of Wonderella would probably fit in here.
- Though she tends to skimp on the 'villainous' part.
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.
- Let's not forget the fact that just about every enemy is decorated with Harlequin garb in Homestuck!
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. And then it turns out that he was a clown all along.

Western Animation

Harley Quinn from Batman: The Animated Series.
The Joker goes back to his Silver Age Harlequin feel in Batman the Brave And The Bold.
- And 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 an entire bike gang called The Rodeo Clowns.
In a recent 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.