History MonsterClown / Literature

* In R.S Belcher's ''King of the Road'', there's hundreds of 'em in the Harlequin SerialKiller {{Cult}}. What makes them more dangerous than the more mundane Zodiac Lodge cult is that the Harlequins are led by a centuries-old alchemist who makes an addictive alchemical face paint for his clown disciples, giving them a HealingFactor, agelessness, increased size and strength -- which increases further the longer they use it. The oldest of these clowns, "the High Harlequins", have the height of NBA players, the width of NFL linebackers, don't need sleep, can lift over 600 pounds above their heads with no effort, withstand multiple gunshots without bleeding and have been murdering since before World War I.

* In ''Life Expectancy'' by Creator/DeanKoontz, we meet a man with the unfortunate name of Konrad Beezo. He is a clown, he has a pistol and apparent mental problems, and he insists on telling everyone he meets that he '''hates''' aerialists.

[[quoteright:350:[[Literature/ANightmareOnClownStreet https://static.tvtropes.org/pmwiki/pub/images/anightmareonclownstreet_fullart.jpg]]]]

* The titular character from the CreepyPasta ''Literature/LaughingJack'' is a [[GrayscaleOfEvil black and white]] ragdoll-like clown with striped baggy clothes, shoulder feathers and a swirly cone nose. As well as CreepilyLongArms and razor sharp teeth. While originally a benevolent clown, being exposed to violence after years of being abandoned corrupted him into a malicious entity who enjoys torturing and slaughtering children.

* Arguably, the jester from [[Creator/FriedrichNietzsche Nietzsche's]] ''Literature/AlsoSprachZarathustra'' can be seen as a {{Trope Maker|s}} (with Rigoletto, or possibly some Creator/VictorHugo work, as an UrExample).
* "Guignol", in ''Literature/AngelsOfMusic'', revolves around the Théâtre des Horreurs, famous for its stage shows featuring murders and mutilations depicted with disconcertingly realistic special effects (and, for the discerning and well-paying customer, the ''special'' stage shows where the murders and mutilations use no special effects at all). The mascot of the Théâtre is the clown Guignol, "the capering mountebank [with] his padded paunch, his camel's hump, his gross red nose, his too-wide grin, his terrible teeth, his rouged cheeks, his white gloves with long sharp nails bursting the fingertip seams, his red-and-white striped tights, his jerkin embroidered with skulls and snakes and bats, his shock of white hair, his curly-toed boots, his quick mind, his cruel quips, his shrill songs..." [[spoiler:It turns out that he's less monstrous than many at the Théâtre who look more normal, and is secretly working to bring down the people who made the Théâtre — and him — what they are.]]
* The Harlequin is the covert enforcement division of the Vampire Council in Creator/LaurellKHamilton's ''Literature/AnitaBlake'' books. Even to say their name brings a death sentence.
* Horrabin from ''Literature/TheAnubisGates'' by Creator/TimPowers. An evil clown who leads a pack of murderous beggars, Horrabin magically maims some of his minions to be more profitable. His "mistakes" become monsters that he locks away in the catacombs beneath his lair. He wears stilts to avoid contact with the ground.

* In Creator/AndrewVachss's ''Literature/{{Burke}}'' book ''Strega'', one of the villains dresses as a clown while conducting his child sex offences.
* ''Literature/{{Coulrophobia}}'' on Amazon's kindle network.
* One of ''Literature/{{Dexter}}'' Morgan's victims is a professional clown [[spoiler: with a sideline in child murder; Dexter comments that he's been complained of by some parents who pointed out that you don't need to take a child into a dark closet to show him balloon animals]].
* Sparky, in ''Literature/TheDireSaga'', notes that there was an entire era of these, and most of the heroes feel they were more terrifying than the world-ending threats. The most evil of them was The Great Clown Pagliacci.
* The Ankh-Morpork Fool's Guild in the ''Literature/{{Discworld}}'' series realizes that clowns scare and disgust some people. Thus, they prepare their charges through exceedingly harsh conditions to endure a lot of abuse. Creator/TerryPratchett, creator of the series, has described the guild as "the stricter sort of medieval monastery without [the monastery's] non-stop boffo laughs." He also introduces the idea that whiteface clowns are scary even to other clowns because their humor often comes from bullying others. Doctor Whiteface is described as having, under his painted grin, features "cold and proud as a prince of Hell".

-->''They are tragic, and [[BlackComedy we laugh at their tragedy as we laugh at our own.]] The painted grin leers out at us from the darkness, [[StrawNihilist mocking our insane belief in order, logic, status, the reality of reality.]] The mask knows that we are born on [[BananaPeel the banana skin]] that leads only to [[DoomyDoomsOfDoom the open manhole cover of doom,]] and all we can hope for are the cheers of the crowd.''
** In the Fools' Guild edition of the ''[[AllThereInTheManual Discworld Diary]]'' series, the Guild's clowns, mimes and jesters are revealed to be agents of a widespread and ruthless spy ring operated purely for its own profit and power. Paul Kidby's portrait of the Guild Council shows a couple of them to also have pretty nightmarish make up. (Brother Bellweather in particular has gone for sparse hair, evil grin, unsettling teeth, and narrowed eyes. He is, inevitably, the Guild's Master of Hospitality. In ''The Ankh-Morpork Archives Vol. 2'' Kidby claims that just ''drawing'' Brother Bellweather was enough to induce coulrophobia.)
** Verence, a former jester who became king of Lancre, was raised by his Fool grandfather in the grim traditions of the Guild. Said grandfather once gave his young grandson a vicious beating for daring to ''make up an original joke'' about a duck.
* "The Dreamclown", a short story by Creator/NancyACollins. The titular clown, rather than being a garish and grotesque creature, is portrayed as a graceful mime-acrobat, in the style of the French Pierrot. It spends evenings on the street outside the house of two boys (the narrator and his brother), entertaining them with its enchanting, almost ''seductive'' performance. [[spoiler: The narrator's brother is drawn in by the Clown's act, and loses his soul.]]
* An [[HilariousOuttake outtake]] in the back of ''Literature/FancyApartments'' parodies this, with a 'evil' clown taking the place of the main villain.
* The FantasticNoir MonsterMash ''Literature/FiftyFeetOfTrouble'' includes the Reverend Bobo Gigglesworth. Creepy, check. Clown, check. Also monster of the cloth.
* ''Literature/TheFortyFirstWink'' has its main villain be a monster clown named Peepers. Notably, this trope is Lampshaded as the main character takes time to say clowns are universally scary and fail horribly at the one thing they're supposed to do (entertain children).
* ''Literature/HonorHarrington'' has a semi-''heroic'' example. Jeremy X was genetically engineered to be a jester. He escaped, founded [[LaResistance the Audubon Ballroom]], and now uses the hand-eye-coordination Manpower intended for sleight of hand tricks to be the best pistoleer in the galaxy and kill slavers in job lots.
* Invoked in Sandra Cisneros's ''Literature/TheHouseOnMangoStreet'', in the chapter "Red Clowns." The AuthorAvatar Esperanza and her friend Sally go to a carnival one night, and at one point Sally disappears. (Unbeknownst to Esperanza, Sally has set each of them up with a boy.) Esperanza waits beside a diorama of some "wacky" red-costumed clowns with their tongues hanging out until another young man comes up to her. He tries to kiss her, and Esperanza resists until he physically overpowers her and rapes her, constantly murmuring, [[AffablyEvil "I love you, I love you, Spanish girl."]] As Esperanza is flat on her back, she looks up at the clowns depicted on the diorama and imagines they are laughing at her. All she can murmur is, "Sally, you lied..."
* Pennywise from ''Literature/{{IT}}'' by Creator/StephenKing is arguably the joint TropeCodifier along with The Joker. In the TV miniseries based on the same, Creator/TimCurry's portrayal of the role was so creepy, the other actors avoided him even off-camera. He is responsible for a hell of a lot of people's coulrophobia. And Pennywise isn't confined simply to "IT", you know. He appears in several other Stephen King novels, and plays no direct role. He simply sits in the background, possibly waiting for something. Perhaps the most disturbing is in ''Dreamcatcher,'' where it's mentioned that the monument erected honoring the Losers Club for defeating "It" is defaced by graffiti saying "Pennywise lives." The ironic part is that while It often used its shape-shifting ability to take the form of nightmarish imagery, one of its primary uses for the Pennywise form was to ''attract'' kids.
* Speaking of Ronald [=McDonald=] crossed with monstrousness, ''Literature/JohnDiesAtTheEnd'' features a deliberately inflicted hallucination of said clown prince of lard being helplessly compelled to eat his own entrails.
* In Douglas Coupland's ''[=jPod=]'', a group of video game company employees are forced by their boss to make a really inane kids' game with a skateboarding turtle, so as a way of getting back at him, they put in an EasterEgg which unlocks a gameplay mode where Ronald [=McDonald=] goes on a bloody killing spree.
* In R.S Belcher's ''King of the Road'', there's hundreds of 'em in the Harlequin serial killer cult. What makes them more dangerous than the more mundane Zodiac Lodge cult is that the Harlequins are led by a centuries-old alchemist. He makes an addictive alchemical facepaint for his clown disciples which gives them a HealingFactor, agelessness, increased size and strength - the longer they use it. The oldest of these clowns, "the High Harlequins" have the height of NBA players, the width of an NFL linebacker, don't need sleep, can lift over 600 pounds above their heads with no effort, withstand multiple gunshots without bleeding and have been murdering before World War I.
* In ''Life Expectancy'', by Creator/DeanKoontz, we meet a man with the unfortunate name of Konrad Beezo. He is a clown, he has a pistol and apparent mental problems, and he insists on telling everyone he meets that he '''hates''' aerialists.
* ''Literature/Mask2020'' has Side-Splitter, a villainous clown with the power to create copies of himself. He plans to destroy some battleships in the San Francisco bay by [[spoiler:sending a cable car with a bomb crashing into them]].
* In the Franchise/StarWars ''Literature/NewJediOrder'' novels, Onimi is the disfigured jester of Supreme Overlord Shimmra of the Vong. He's a creepy little guy who always has an annoying comment for the situation on hand. [[spoiler:He's also TheManBehindTheMan, using MindControl on Shimmra. Onimi's the only Force user among the Vong, thanks to the event that crippled him. The FinalBattle of the series is against ''him''; he puts up a hell of a fight, and would have won if Jacen Solo hadn't taken another level of GodModeSue at the last minute. Onimi's Wookiepedia entry actually compares him to Kefka. With good reason.]]
* ''Literature/NightmareHour'' by Creator/RLStine featured a tale called "Afraid of Clowns" that explained that all clowns are actually [[AlwaysChaoticEvil sick people who enjoy tormenting kids]] and always single out the most frightened of them to pick on. Not to mention how they TickleTorture people to death. And worst of all, [[spoiler:the story's victim becomes one of them to save his own skin and personally picks out future victims]].

* Australian novel ''Literature/ThePiloFamilyCircus'' is all about this: the extradimensional [[CircusOfFear Pilo Family Circus's]] clown division is populated by some of the most depraved and insane individuals in existence, acting as the management's henchmen in Our World. Worse still, it's very clear that none of them started this way: the magical facepaint they wear creates a [[EnemyWithin split personality]] that takes over every time they "paint up" until [[SplitPersonalityTakeover the original is reduced to nothing]]. Since it also grants superhuman abilities, most recruits have no choice but to wear it just to survive the first few months in the Circus, and by then, it's already too late.
* A rare heroic example is the scary clown, Mr. Jinx from Tim Waggoner's ''Shadow Watch duology''. Mr. Jinx was born from nightmares that Shadow Watch agent Audra Hawthorne had as a child. As such Mr. Jinx is psychically linked and devoted to his "mother" and is CreepyGood, helping her contain threats to reality from out of the dreamworld. He's unusual even in his world, as nightmare clowns are almost all evil and even formed their own monstrous society to better commit terrible acts.
* In John Connolly's short story "Some Children Wander By Mistake", the clowns of the Circus Caliban are revealed to be monstrous creatures that ''remove'' their makeup for a performance. They [[ChildHater despise children, particularly the ones that still find them funny]], and go out of their way to kill and eat them whenever they can do so without being caught- except for the unlucky few that are selected to become Clowns themselves. These are culled from children that were still unborn at the time of the Circus Caliban's last performance in a particular town, but were conscious enough at the time to kick when the Clowns appeared. Once the circus returns, the child is kidnapped and slowly transformed into a Clown. This is the sad fate of the story's protagonist, William:
-->His teeth fell out and were replaced by sharp, white hooks that were kept hidden behind shields of plastic; and his nails decayed to hard yellow stumps at the end of soft, pale fingers. He grew tall and strong, until at last he forgot his name, and became only "Clown", and a great clown he was. His tongue grew like a snake's, and he tasted children with it as they laughed, for clowns are hungry and sad and envious of humanity. They travel from town to town, looking for those that they can steal away, always marking the child that kicks in the womb, and always finding him upon their return.
-->For clowns are not made.\\
Clowns are ''born.''

* Shagwell from ''Literature/ASongOfIceAndFire'' is a [[HiredGun sellsword]] who dresses like a jester and deliberately plays it up in numerous ways. He's part of a particularly brutal mercenary company called the Bloody Mummers, and makes jokes about their various atrocities. In battle, he wields a three-headed morningstar, which is a lethal version of a jester's flail.

** Patchface is a possible example, a brain-damaged jester who does very little besides sing songs. However, his songs are often sinister, and include references to things that haven't happened yet. The priestess Melisandre, considered by most to be incredibly creepy herself and prone to burning people alive as sacrifices, senses great evil in him and sees him in her visions with blood on his lips.

* ''Literature/TheWanderingInn'': Tom dressed up as clown hoping to bring laughter to the people, when he and several others were summoned to another world, thus preventing them to see their families ever again. When a little boy he often speaks with dies right in front of his eyes, during an attack of demons, he goes insane, changing into a horrifying clown that even scares the demons, and slaughters them one after another, without stopping to smile.
* ''Literature/ZomB: Underground'' features Mr Dowling. He wears the flayed face of a man on one shoulder and that of a woman on the other, has human entrails wrapped around his arms, his clown nose is a human eyeball, he can create spiders out of nothing, and he appears to have some manner of control over zombies.

* Pennywise from ''Literature/{{IT}}'' by Creator/StephenKing. In the TV miniseries based on the same, Creator/TimCurry's portrayal of the role was so creepy, the other actors avoided him even off-camera. He is responsible for a hell of a lot of people's coulrophobia. And Pennywise isn't confined simply to "IT", you know. He appears in several other Stephen King novels, and plays no direct role. He simply sits in the background, possibly waiting for something. Perhaps the most disturbing is in ''Dreamcatcher,'' where it's mentioned that the monument erected honoring the Losers Club for defeating "It" is defaced by graffiti saying "Pennywise lives." The ironic part is that while It often used its shape-shifting ability to take the form of nightmarish imagery, one of its primary uses for the Pennywise form was to ''attract'' kids.

[[quoteright:350:[[Literature/{{Goosebumps}} https://static.tvtropes.org/pmwiki/pub/images/anightmareonclownstreet_fullart.jpg]]]]

* Pennywise from ''Literature/{{IT}}'' by Creator/StephenKing. In the TV miniseries based on the same, Creator/TimCurry's portrayal of the role was so creepy, the other actors avoided him even off-camera. He is responsible for a hell of a lot of people's coulrophobia. And Pennywise isn't confined simply to "IT", you know. He appears in several other Stephen King novels, and plays no direct role. He simply sits in the background, possibly waiting for something. Perhaps the most disturbing is in ''Dreamcatcher,'' where it's mentioned that the monument erected honoring the Losers Club for defeating "It" is defaced by graffiti saying "Pennywise lives." The ironic part is that while It often used its shape-shifting ability to take the form of nightmarish imagery, one of its primary uses for the Pennywise form was to ''attract'' kids.

* In ''Life Expectancy'', by Creator/DeanKoontz, we meet a man with the unfortunate name of Konrad Beezo. He is a clown, he has a pistol and apparent mental problems, and he insists on telling everyone he meets that he '''hates''' aerialists.

** Speaking of Ronald [=McDonald=] crossed with monstrousness, ''Literature/JohnDiesAtTheEnd'' features a deliberately inflicted hallucination of said clown prince of lard being helplessly compelled to eat his own entrails.
* Horrabin from ''Literature/TheAnubisGates'' by Creator/TimPowers.
* In ''Literature/UseOfWeapons'', Cheradenine Zakalwe wears a clown disguise when assassinating Ethnarch Kerian.

* In John Connolly's short story ''Some Children Wander By Mistake,'' the clowns of the Circus Caliban are revealed to be monstrous creatures that ''remove'' their makeup for a performance. They [[ChildHater despise children, particularly the ones that still find them funny]], and go out of their way to kill and eat them whenever they can do so without being caught- except for the unlucky few that are selected to become Clowns themselves. These are culled from children that were still unborn at the time of the Circus Caliban's last performance in a particular town, but were conscious enough at the time to kick when the Clowns appeared. Once the circus returns, the child is kidnapped and slowly transformed into a Clown. This is the sad fate of the story's protagonist, William:
-->His teeth fell out and were replaced by sharp, white hooks that were kept hidden behind shields of plastic; and his nails decayed to hard yellow stumps at the end of soft, pale fingers. He grew tall and strong, until at last he forgot his name, and became only "Clown", and a great clown he was. His tongue grew like a snake's, and he tasted children with it as they laughed, for clowns are hungry and sad and envious of humanity. They travel from town to town, looking for those that they can steal away, always marking the child that kicks in the womb, and always finding him upon their return.
-->For clowns are not made.\\
Clowns are ''born.''
* In the Franchise/StarWars ''Literature/NewJediOrder'' novels, Onimi is the disfigured jester of Supreme Overlord Shimmra of the Vong. He's a creepy little guy who always has an annoying comment for the situation on hand. [[spoiler:He's also TheManBehindTheMan, using MindControl on Shimmra. Onimi's the only Force user among the Vong, thanks to the event that crippled him. The FinalBattle of the series is against ''him''; he puts up a hell of a fight, and would have won if Jacen Solo hadn't taken another level of GodModeSue at the last minute. Onimi's Wookiepedia entry actually compares him to Kefka. With good reason.]]
* "The Dreamclown", a short story by Creator/NancyACollins. The titular clown, rather than being a garish and grotesque creature, is portrayed as a graceful mime-acrobat, in the style of the French Pierrot. It spends evenings on the street outside the house of two boys (the narrator and his brother), entertaining them with its enchanting, almost ''seductive'' performance. [[spoiler: The narrator's brother is drawn in by the Clown's act, and loses his soul.]]
* "Scary Clowns" is the name of the psychological warfare division of the Organization in ''Bad Monkeys'' and indeed all its agents dress as clowns.
* The Harlequin is the covert enforcement division of the Vampire Council in Creator/LaurellKHamilton's Literature/AnitaBlake books. Even to say their name brings a death sentence.
* Arguably, the jester from [[Creator/FriedrichNietzsche Nietzsche's]] ''Also Sprach Zarathustra'' can be seen as a {{Trope Maker|s}} (with Rigoletto, or possibly some Creator/VictorHugo work, as an UrExample).
* In Creator/AndrewVachss's Burke book ''Strega'', one of the villains dresses as a clown while conducting his child sex offences.
* ''Literature/NightmareHour'' by Creator/RLStine featured a tale called "Afraid of Clowns" that explained that all clowns are actually [[AlwaysChaoticEvil sick people who enjoy tormenting kids]] and always single out the most frightened of them to pick on. Not to mention how they TickleTorture people to death. And worst of all, [[spoiler:the story's victim becomes one of them to save his own skin and personally picks out future victims]].
* One of the secretaries at the Peoria REC in ''Literature/ThePaleKing'' resembles one.
* Invoked in Sandra Cisneros's ''Literature/TheHouseOnMangoStreet'', in the chapter "Red Clowns." The AuthorAvatar Esperanza and her friend Sally go to a carnival one night, and at one point Sally disappears. (Unbeknownst to Esperanza, Sally has set each of them up with a boy.) Esperanza waits beside a diorama of some "wacky" red-costumed clowns with their tongues hanging out until another young man comes up to her. He tries to kiss her, and Esperanza resists until he physically overpowers her and rapes her, constantly murmuring, [[AffablyEvil "I love you, I love you, Spanish girl."]] As Esperanza is flat on her back, she looks up at the clowns depicted on the diorama and imagines they are laughing at her. All she can murmur is, "Sally, you lied..."

* ''Literature/HonorHarrington'' has a semi-''heroic'' example. Jeremy X was genetically engineered to be a jester. He escaped, founded [[LaResistance the Audubon Ballroom]], and now uses the hand-eye-coordination Manpower intended for sleight of hand tricks to be the best pistoleer in the galaxy and kill slavers in job lots.
* One of ''Literature/{{Dexter}}'' Morgan's victims is a professional clown [[spoiler: with a sideline in child murder; Dexter comments that he's been complained of by some parents who pointed out that you don't need to take a child into a dark closet to show him balloon animals]].
* One of Creator/DaveBarry's books on [[FauxToGuide childcare]] mentions that when choosing wallpaper for your child's room, make sure they match up: kids who grow up seeing clown torsos come out of rhinoceros bodies end up becoming axe murderers or members of the state cabinet.
* An [[HilariousOuttake outtake]] in the back of ''Literature/FancyApartments'' parodies this, with a 'evil' clown taking the place of the main villain.
* ''Literature/TheFortyFirstWink'' has its main villain be a monster clown named Peepers. Notably, this trope is Lampshaded as the main character takes time to say clowns are universally scary and fail horribly at the one thing they're supposed to do (entertain children).
* Sparky, in ''Literature/TheDireSaga'', notes that there was an entire era of these, and most of the heroes feel they were more terrifying than the world-ending threats. The most evil of them was The Great Clown Pagliacci.
* The FantasticNoir MonsterMash ''Literature/FiftyFeetOfTrouble'' includes the Reverend Bobo Gigglesworth. Creepy, check. Clown, check. Also monster of the cloth.
* "Guignol", in ''Literature/AngelsOfMusic'', revolves around the Théâtre des Horreurs, famous for its stage shows featuring murders and mutilations depicted with disconcertingly realistic special effects (and, for the discerning and well-paying customer, the ''special'' stage shows where the murders and mutilations use no special effects at all). The mascot of the Théâtre is the clown Guignol, "the capering mountebank [with] his padded paunch, his camel's hump, his gross red nose, his too-wide grin, his terrible teeth, his rouged cheeks, his white gloves with long sharp nails bursting the fingertip seams, his red-and-white striped tights, his jerkin embroidered with skulls and snakes and bats, his shock of white hair, his curly-toed boots, his quick mind, his cruel quips, his shrill songs..." [[spoiler:It turns out that he's less monstrous than many at the Théâtre who look more normal, and is secretly working to bring down the people who made the Théâtre — and him — what they are.]]
* ''Literature/TheWanderingInn'': Tom dressed up as clown hoping to bring laughter to the people, when he and several others were summoned to another world, thus preventing them to see their families ever again. When a little boy he often speaks with dies right in front of his eyes, during an attack of demons, he goes insane, changing into a horrifying clown that even scares the demons, and slaughters them one after another, without stopping to smile.
* A rare heroic example is the scary clown, Mr. Jinx from Tim Waggoner's ''Shadow Watch duology''. Mr. Jinx was born from nightmares that Shadow Watch agent Audra Hawthorne had as a child. As such Mr. Jinx is psychically linked and devoted to his "mother" and is CreepyGood, helping her contain threats to reality from out of the dreamworld. He's unusual even in his world, as nightmare clowns are almost all evil and even formed their own monstrous society to better commit terrible acts.
* In R.S Belcher's ''King of the Road'', there's hundreds of 'em in the Harlequin serial killer cult. What makes them more dangerous than the more mundane Zodiac Lodge cult is that the Harlequins are led by a centuries-old alchemist. He makes an addictive alchemical facepaint for his clown disciples which gives them a HealingFactor, agelessness, increased size and strength - the longer they use it. The oldest of these clowns, "the High Harlequins" have the height of NBA players, the width of an NFL linebacker, don't need sleep, can lift over 600 pounds above their heads with no effort, withstand multiple gunshots without bleeding and have been murdering before World War I.
* ''Literature/Mask2020'' has Side-Splitter, a villainous clown with the power to create copies of himself. He plans to destroy some battleships in the San Francisco bay by [[spoiler:sending a cable car with a bomb crashing into them]].

* In R.S Belcher's ''King of the Road'', there's hundreds of 'em in the Harlequin serial killer cult. What makes them more dangerous than the more mundane Zodiac Lodge cult is that the Harlequins are led by a centuries-old alchemist. He makes an addictive alchemical facepaint for his clown disciples which gives them a HealingFactor, agelessness, increased size and strength - the longer they use it. The oldest of these clowns, "the High Harlequins" have the height of NBA players, the width of an NFL linebacker, the strength to crumple cheap steel and have been murdering before World War I.

** In the Fools' Guild edition of the ''[[AllThereInTheManual Discworld Diary]]'' series, the Guild's clowns, mimes and jesters are revealed to be agents of a widespread and ruthless spy ring operated purely for its own profit and power. Paul Kidby's portrait of the Guild Council shows a couple of them to also have pretty nightmarish make up. (Brother Bellweather in particular has gone for sparse hair, evil grin, unsettling teeth, and narrowed eyes. He is, inevitably, the Guild's Master of Hospitality.)

* Shagwell from ''Literature/ASongOfIceAndFire'' is a [[HiredGun sellsword]] who dresses like a jester and deliberately plays it up in numerous ways. He's part of a particularly brutal mercenary company called the Bloody Mummers, and makes jokes about their various atrocities. In battle he wields a three-headed morningstar, which is a lethal version of a jester's flail.

** Patchface is a possible example, a brain damaged jester who does very little besides sing songs. However, his songs are often sinister, and include references to things that haven't happened yet. The priestess Melisandre, considered by most to be incredibly creepy herself and prone to burning people alive as sacrifices, senses great evil in him and sees him in her visions with blood on his lips.

* ''Literature/TheWanderingInn'':Tom dressed up as clown hoping to bring laughter to the people, when he and several others were summoned to another world, thus preventing them to see their families ever again. When a little boy he often speaks with dies right in front of his eyes, during an attack of demons, he goes insane, changing into a horrifying clown that even scares the demons, and slaughters them one after another, without stopping to smile.

** In ''Discworld/MakingMoney'', Lord Vetinari proposes that some people hate clowns because clowns aren't really funny, but instead tragic:

** In the Fools' Guild edition of the ''[[AllThereInTheManual Discworld Diary]]'' series, the Guild's clowns, mimes and jesters are revealed to be agents of a widespread and ruthless spy ring operated purely for its own profit and power. Paul Kidby's portrait of the Guild Council show a couple of them to also have pretty nightmarish make up. (Brother Bellweather in particular has gone for sparse hair, evil grin, unsettling teeth, and narrowed eyes. He is, inevitably, the Guild's Master of Hospitality.)

** In the Fools' Guild edition of the ''[[AllThereInTheManual Discworld Diary]]'' series, the Guild's clowns, mimes and jesters are revealed to be agents of a widespread and ruthless spy ring operated purely for its own profit and power.