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Disambiguating from Literature.The Storm
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* ''Literature/TheStorm'': As the wife watches her abusive husband bleed out from her attack, a demented smile begins to crack on her face, followed by mad laughter.
to:
* ''Literature/TheStorm'': ''Literature/TheStormAravDagli'': As the wife watches her abusive husband bleed out from her attack, a demented smile begins to crack on her face, followed by mad laughter.
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Crosswicking The Storm
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* ''Literature/TheStorm'': As the wife watches her abusive husband bleed out from her attack, a demented smile begins to crack on her face, followed by mad laughter.
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Changed line(s) 36 (click to see context) from:
* ''Literature/GodsAndWarriors'': Alekto, [[DarkChick the only female member of the House of Koronos]], is so sadistic that she draws her lips back from her teeth in a way that's half a smile and half a grimace when she thinks about pain or better yet, observes it.
to:
* ''Literature/GodsAndWarriors'': Alekto, [[DarkChick the only female member of the House of Koronos]], Koronos, is so sadistic that she draws her lips back from her teeth in a way that's half a smile and half a grimace when she thinks about pain or better yet, observes it.
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* Being possibly the [[AxeCrazy craziest]] [[PsychoForHire bastard]] in the series, ''LightNovel/{{Baccano}}'s'' Claire Stanfield has a [[http://img.photobucket.com/albums/v44/Dragynstorm/Baccano15/Baccano15_129.jpg warehouse]] [[http://img.photobucket.com/albums/v44/Dragynstorm/Baccano15/Baccano15_122.jpg full]] [[http://img.photobucket.com/albums/v102/Ensuing/Baccano9/Baccano_16.jpg of]] [[http://img.photobucket.com/albums/v102/Ensuing/Baccano9/Baccano_37.jpg psychotic]], [[http://img.photobucket.com/albums/v102/Ensuing/Baccano9/Baccano_28.jpg blood-soaked]] [[http://img.photobucket.com/albums/v102/Ensuing/Baccano_54-1.jpg grins]] [[http://img.photobucket.com/albums/v102/Ensuing/Baccano12/Baccano_50.jpg and]] [[http://img.photobucket.com/albums/v44/Dragynstorm/Baccano16/Baccano16_88.jpg smirks]] to put to use. Not to say that [[http://img.photobucket.com/albums/v102/Ensuing/Baccano_39.jpg Ladd]], [[http://img.photobucket.com/albums/v102/Ensuing/Baccano10/Baccano_4.jpg Czeslaw]], and [[http://img.photobucket.com/albums/v102/Ensuing/Baccano14_26.jpg Graham]] don't get their fair share.
to:
* Being possibly the [[AxeCrazy craziest]] [[PsychoForHire bastard]] in the series, ''LightNovel/{{Baccano}}'s'' ''Literature/{{Baccano}}'s'' Claire Stanfield has a [[http://img.photobucket.com/albums/v44/Dragynstorm/Baccano15/Baccano15_129.jpg warehouse]] [[http://img.photobucket.com/albums/v44/Dragynstorm/Baccano15/Baccano15_122.jpg full]] [[http://img.photobucket.com/albums/v102/Ensuing/Baccano9/Baccano_16.jpg of]] [[http://img.photobucket.com/albums/v102/Ensuing/Baccano9/Baccano_37.jpg psychotic]], [[http://img.photobucket.com/albums/v102/Ensuing/Baccano9/Baccano_28.jpg blood-soaked]] [[http://img.photobucket.com/albums/v102/Ensuing/Baccano_54-1.jpg grins]] [[http://img.photobucket.com/albums/v102/Ensuing/Baccano12/Baccano_50.jpg and]] [[http://img.photobucket.com/albums/v44/Dragynstorm/Baccano16/Baccano16_88.jpg smirks]] to put to use. Not to say that [[http://img.photobucket.com/albums/v102/Ensuing/Baccano_39.jpg Ladd]], [[http://img.photobucket.com/albums/v102/Ensuing/Baccano10/Baccano_4.jpg Czeslaw]], and [[http://img.photobucket.com/albums/v102/Ensuing/Baccano14_26.jpg Graham]] don't get their fair share.
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* [[TheBerserker Shizuo]] [[HairTriggerTemper Heiwajima]] of ''LightNovel/{{Durarara}}'' is fond of sporting these right before he's about to hurt someone.
* Gauron from ''LightNovel/FullMetalPanic'' usually cracks one of these whenever he's not wearing his PsychoticSmirk. [[MemeticMolester HE WANTS TO RAPE YOU!!!]]
* Gauron from ''LightNovel/FullMetalPanic'' usually cracks one of these whenever he's not wearing his PsychoticSmirk. [[MemeticMolester HE WANTS TO RAPE YOU!!!]]
to:
* [[TheBerserker Shizuo]] [[HairTriggerTemper Heiwajima]] of ''LightNovel/{{Durarara}}'' ''Literature/{{Durarara}}'' is fond of sporting these right before he's about to hurt someone.
* Gauron from''LightNovel/FullMetalPanic'' ''Literature/FullMetalPanic'' usually cracks one of these whenever he's not wearing his PsychoticSmirk. [[MemeticMolester HE WANTS TO RAPE YOU!!!]]
* Gauron from
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* Xellos from ''LightNovel/{{Slayers}}'' has this in spades. It's less common to see him not smiling than to see him with a smile (or a convenient PsychoticSmirk) on his lips, but if he's smiling ''and'' his eyes are open, you're in serious trouble. Especially exemplified as he's sadistically torturing Valgaav in TRY and a highly amused smile never leaves Xellos' face, backed up by a truly psychotic giggle.
* As a NeatFreak, Ryuuji from ''LightNovel/{{Toradora}}'' gets one whenever he ''cleans''. As in, dirt and dust and mold. Combined with his permanent death glare, he looks like he's rejoicing in the thought of committing genocide on entire societies of dust mites and mold colonies. There's a brief shot of one right in the opening theme.
* As a NeatFreak, Ryuuji from ''LightNovel/{{Toradora}}'' gets one whenever he ''cleans''. As in, dirt and dust and mold. Combined with his permanent death glare, he looks like he's rejoicing in the thought of committing genocide on entire societies of dust mites and mold colonies. There's a brief shot of one right in the opening theme.
to:
* Xellos from ''LightNovel/{{Slayers}}'' ''Literature/{{Slayers}}'' has this in spades. It's less common to see him not smiling than to see him with a smile (or a convenient PsychoticSmirk) on his lips, but if he's smiling ''and'' his eyes are open, you're in serious trouble. Especially exemplified as he's sadistically torturing Valgaav in TRY and a highly amused smile never leaves Xellos' face, backed up by a truly psychotic giggle.
* As a NeatFreak, Ryuuji from''LightNovel/{{Toradora}}'' ''Literature/{{Toradora}}'' gets one whenever he ''cleans''. As in, dirt and dust and mold. Combined with [[FaceOfAThug his permanent death glare, glare]], he looks like he's rejoicing in the thought of committing genocide on entire societies of dust mites and mold colonies. There's a brief shot of one right in the opening theme.
* As a NeatFreak, Ryuuji from
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* Being possibly the [[AxeCrazy craziest]] [[PsychoForHire bastard]] in the series, ''LightNovel/{{Baccano}}'s'' Claire Stanfield has a [[http://img.photobucket.com/albums/v44/Dragynstorm/Baccano15/Baccano15_129.jpg warehouse]] [[http://img.photobucket.com/albums/v44/Dragynstorm/Baccano15/Baccano15_122.jpg full]] [[http://img.photobucket.com/albums/v102/Ensuing/Baccano9/Baccano_16.jpg of]] [[http://img.photobucket.com/albums/v102/Ensuing/Baccano9/Baccano_37.jpg psychotic]], [[http://img.photobucket.com/albums/v102/Ensuing/Baccano9/Baccano_28.jpg blood-soaked]] [[http://img.photobucket.com/albums/v102/Ensuing/Baccano_54-1.jpg grins]] [[http://img.photobucket.com/albums/v102/Ensuing/Baccano12/Baccano_50.jpg and]] [[http://img.photobucket.com/albums/v44/Dragynstorm/Baccano16/Baccano16_88.jpg smirks]] to put to use. Not to say that [[http://img.photobucket.com/albums/v102/Ensuing/Baccano_39.jpg Ladd]], [[http://img.photobucket.com/albums/v102/Ensuing/Baccano10/Baccano_4.jpg Czeslaw]], and [[http://img.photobucket.com/albums/v102/Ensuing/Baccano14_26.jpg Graham]] don't get their fair share.
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* [[TheBerserker Shizuo]] [[HairTriggerTemper Heiwajima]] of ''LightNovel/{{Durarara}}'' is fond of sporting these right before he's about to hurt someone.
* Gauron from ''LightNovel/FullMetalPanic'' usually cracks one of these whenever he's not wearing his PsychoticSmirk. [[MemeticMolester HE WANTS TO RAPE YOU!!!]]
* Gauron from ''LightNovel/FullMetalPanic'' usually cracks one of these whenever he's not wearing his PsychoticSmirk. [[MemeticMolester HE WANTS TO RAPE YOU!!!]]
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* Xellos from ''LightNovel/{{Slayers}}'' has this in spades. It's less common to see him not smiling than to see him with a smile (or a convenient PsychoticSmirk) on his lips, but if he's smiling ''and'' his eyes are open, you're in serious trouble. Especially exemplified as he's sadistically torturing Valgaav in TRY and a highly amused smile never leaves Xellos' face, backed up by a truly psychotic giggle.
* As a NeatFreak, Ryuuji from ''LightNovel/{{Toradora}}'' gets one whenever he ''cleans''. As in, dirt and dust and mold. Combined with his permanent death glare, he looks like he's rejoicing in the thought of committing genocide on entire societies of dust mites and mold colonies. There's a brief shot of one right in the opening theme.
* As a NeatFreak, Ryuuji from ''LightNovel/{{Toradora}}'' gets one whenever he ''cleans''. As in, dirt and dust and mold. Combined with his permanent death glare, he looks like he's rejoicing in the thought of committing genocide on entire societies of dust mites and mold colonies. There's a brief shot of one right in the opening theme.
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Crosswicking Laughing Jack
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* ''Literature/LaughingJack'': Befitting his reputation as a hysterical killer clown, Laughing Jack's constant smile is a demented sharp-toothed grin. When he first catches sight of bloody violence in his origin story, he develops a small smile before it grows along with his [[LaughingMad escalating laughter]], and he keenly watches the rest of Isaac's murderous activities with eager eyes and a big unfading grin.
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Crosswicking Go To Sleep A Jeff The Killer Rewrite
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* ''Literature/GoToSleepAJeffTheKillerRewrite'':
** Randy gets an increasingly demented smile as he teaches Jeff a painful lesson in return for humiliating the former. What starts as a mischievous smile evolves into a less sane expression, which greatly concerns Keith and Troy, his own crew.
** Jeff's outstretched smile before he kills Liu seems to be more [[StepfordSmiler out of pain than joy]], but he wears the insane smile more naturally in the final chapter as he finds Randy to get his revenge.
** Randy gets an increasingly demented smile as he teaches Jeff a painful lesson in return for humiliating the former. What starts as a mischievous smile evolves into a less sane expression, which greatly concerns Keith and Troy, his own crew.
** Jeff's outstretched smile before he kills Liu seems to be more [[StepfordSmiler out of pain than joy]], but he wears the insane smile more naturally in the final chapter as he finds Randy to get his revenge.
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%%* Mr. Grin from the ''Literature/AlexRider'' book ''Stormbreaker''.
* From ''Literature/AliceInWonderland'':
-->"How cheerfully he seems to grin!\\
How neatly spreads his claws\\
And welcomes little fishes in\\
with gently smiling jaws!"
* ''Literature/TheArchonate'': In ''The Spiral Labyrinth'', which is set in homage to the ''Literature/DyingEarth'' setting, one of the significant villains is a wizard by the name of Smiling Bol. He always maintains a cheerful expression -- sometimes less menacing, sometimes more so.
* In the ''Literature/{{Brotherband}}'' book ''The Hunters'', the author describes Thorn's smile as unpleasant when he's warning a captured pirate not to break for it.
* Skeeter Traps from ''Literature/ChroniclesOfMagic'' is known for sporting these, despite being a ten-year-old girl. Combined with the fact that she can kill grown men three times her size, it makes her pretty scary.
* Jame, the heroine of P.C. Hodgell's ''Literature/ChroniclesOfTheKencyrath'' series, smiles like this, and it is very, very bad news. It signifies the depths of her darkness, and the author said, "In a way, everything about Jame grew out of that chilling smile."
* From S.J Bryant's ''Literature/TheNovaChronicles'', when Alden's attempt at turning himself into a monster fails, instead becoming a cute furry creature. Nova sports a wide grin as she brutally stomps the helpless creature to death beneath her metal boots.
* In Creator/RobertEHoward's ''Franchise/ConanTheBarbarian'' story "Literature/AWitchShallBeBorn", Constantius does this while watching the guard be slaughtered and crucifying Conan.
* ''Literature/{{Coraline}}'': Done by the Other Mother, when she's not busy being a StepfordSmiler.
* ''Literature/TheCosmere'':
** The Steel Inquisitors from ''Literature/{{Mistborn}}'' are exceptionally brutal enforcers of the Empire, and the chilling grins they have when going about their work are frequently remarked on. AntiHero Kelsier, leader of the rebellion, also smiles a lot because it's a way of proving that he's not beaten down, but from the point of view of his enemies (to whom he has little to no mercy) it comes off like this.
** Bleeder in ''Literature/WaxAndWayne'' displays one of these while between forms, described as having "a face of stretched muscle and grinning teeth" and being "all smiles" as she scrambles towards her terrified cabbie.
* Vlad Dracula in ''Literature/CountAndCountess''. Every time he's about to kill someone with his artificially sharpened teeth, he grins at them first, just to give them a preview of what's to come.
* Sometimes it's a matter of perception. In Creator/AlanDeanFoster's ''The Damned'' trilogy, the first encounter between the multiracial alien alliance's and humans highlights the differences between them and us when the human, Will Dulac, first bats the gun out of the hand of the nearest alien scout out of a self-defense reflex, then offering a handshake and smiling when he realized they weren't hostile. The sudden reflexive strike nearly broke the scout's hand, and the smile confuses and alarms them as they wonder why baring one's teeth could ever be considered a friendly gesture. They also didn't get the handshake.
* ''Literature/DeptfordMice'': In ''The Dark Portal'', a rat called Smiler had a Slasher Smile on his face all the time... because he'd been rude to his superior as a child, and said superior had [[FamilyUnfriendlyViolence cut off his lips]].
* Creator/TerryPratchett's ''Literature/{{Discworld}}'':
** Carcer Dun and Mr. Teatime are described as smiling like this ''all the time''. The drawing of Mr. Teatime in ''The Art of Discworld'' perfectly illustrates this. Marc Warren does a good job with this in the TV adaptation, too.
** At one point in ''Literature/{{Jingo}}'' the seriously pissed off "Vimes's grin was as funny as the one that moves very fast towards drowning men. And has a fin on top."
** [[OurWerewolvesAreDifferent Angua]], who at one point must have been smiling because "her mouth was open, and [[OhCrap all of her teeth were showing]]".
* ''Literature/{{Dragaera}}'': Perhaps inspired by the Jack Vance example, ''Literature/FiveHundredYearsAfter'' has the court wizard as a minor character and he is similarly described as always smiling creepily and chuckling in a questionably sane manner.
* In Jack Vance's ''Literature/DyingEarth'' series, the character Iucounu the "Laughing Magician" perpetually supports one of these providing a clue that his sense of humor is not exactly benevolent.
* Creepy caretaker Heimertz from the ''Literature/EdgarAndEllen'' series has a constant slasher smile. During the TV adaptation, it is shown that he has had this smile since he was a child.
* In Abnett's series ''Literature/{{Eisenhorn}}'', the demonhost Cherubael sometimes sports one of these. When he/it does, ''someone'' is going to die, very painfully.
* ''Literature/TheEschatonSeries'': Portia Hoechst, in ''Iron Sunrise'', is described as having this by several other characters, both good and evil, in the novel.
* A few Death Eaters display this, as does Snape on occasion and Voldemort in the ''Literature/HarryPotter'' series.
* Benjamin, the serial killer antagonist of ''Literature/HollowPlaces'' manages to torment one of his surviving victims while in court simply by showing her a disturbing smile.
* ''Literature/GodsAndWarriors'': Alekto, [[DarkChick the only female member of the House of Koronos]], is so sadistic that she draws her lips back from her teeth in a way that's half a smile and half a grimace when she thinks about pain or better yet, observes it.
* ''Literature/TheIcelandicSagas'': OlderThanPrint: Skarphéðinn Njálsson has one in ''Brennu-Njáls Saga''. "And he grinned" is a common phrase in the story that implies that something really bad is about to go down.
* In ''Literature/{{Jam}}'' everybody goes a little crazy during the course of the book but {{Cult}}-Leader Lord Awesomo has a memorable grin when he sees [[EveryMan Travis]] in the crowd and realizes he can spin the election to his favor and get Travis killed.
* ''Literature/TheJenkinsverse'': Since most sapient species are herbivores and herd animals, they get ''very'' uncomfortable with human smiles, which involve far too many sharp teeth for their liking. [[ShownTheirWork Note that this is realistic]]; even on Earth among primates, humans are one of the only species that doesn't consider showing teeth to be a threat. Most humans who interact with aliens learn quickly to smile with closed lips. In ''Salvage'', Adrian Saunders doesn't bother with that, which enhances his already terrifying reputation. When he finally meets more humans, it turns out that they find his smile even scarier than aliens do. At least aliens have little experience with humans and can assume that he's just normal. Humans know he's not.
* In the ''Literature/KateDaniels'' series, Kate is trying to enlist a man's cooperation with her plan to hunt down and kill the people who have hurt her friend.
-->I gave him a smile. I was aiming for sweet, but he turned a shade paler and scooted a bit farther away from me. Note to self: work more on sweet and less on psycho-killer.
* Nathan in ''Literature/KillTimeOrDieTrying'' does this inadvertently; it's just how he naturally smiles.
* Creator/StephenKing:
** Randall Flagg/The Dark Man is described as having a grin of such good cheer and jolliness which comes across however as so unsettling the human mind seems to block it out.
** Also from ''Literature/TheStand'' (where King first writes about Flagg) is Harold. Most of the other survivors in Boulder just see him as a StepfordSmiler... but the slightly damaged child Leo sees things a little differently.
--->It's like there are worms behind his eyes, and they're eating his brain and making him smile like that.
* The huge, catlike Kzinti of Creator/LarryNiven's ''Literature/KnownSpace'' universe instinctively show their teeth when they feel a certain way. That way is ''not'' happy.
* In Creator/DevonMonk's ''Literature/MagicInTheBlood'', the villain does this while making demands on Allie.
* Gwynplaine from ''Literature/TheManWhoLaughs'', as touched upon under the examples of The Joker and Mr. Sardonicus.
* In Asi Hart's ''Literature/TheManyHorrorsOfBeingATokyoWaitress'' main character Jonas has a very creepy forced smile until he is told that he's scaring the customers and instructed to use some other facial expressions.
* Mr. Wonderful from ''Literature/{{Mogworld}}'' has this mixed with a CheshireCatGrin. It is described in the book as: "The widest grin he [Jim] had ever seen and he knew people with no skin on their faces" worth noting Mr. Wonderful's grin never drops even when he's hacking his own arm off.
* ''Literature/TheNameOfTheWind'': Cinder of the Chandrian has a smile that is described as "the expression a nightmare wore."
* A rare heroic version: [[TheBigGuy Ivarian Borenson]], of ''Literature/TheRunelords'' fantasy novels, is known for his chilling laughter and grin as he fights, which makes him feared even amongst warriors who have far more endowments (strength, stamina, speed, and so on taken from other people) than him. Not so much out of a love for killing, but [[GenreSavvy because it works far better at frightening other people than a war cry,]] so he got himself into the habit of laughing instead.
%%* Count Olaf in ''Literature/ASeriesOfUnfortunateEvents''.
* Professor Moriarty, Literature/SherlockHolmes' arch-enemy from the short story "The Final Problem." Holmes describes that, though Moriarty "smiled and blinked", there was something about the Professor's sunken eyes that made Holmes, a man who was used to danger, very glad to have a revolver with him.
* Jaime Lannister of ''Literature/ASongOfIceAndFire'' recalls in his youth facing a particularly brutal and psychotic fighter known as 'The Smiling Knight'. 3 guesses why he is named that. Luckily even a slasher smile is no match for Ser Arthur 'The Sword in the Morning' Dayne and his [[ThunderboltIron greatsword Dawn]].
* In Neil Gaiman's ''Literature/{{Stardust}}'', Lamia displays one of these during her search for the fallen star. Fortunately, we only have the Narrator's [[TakeOurWordForIt word on it.]]
-->Her red, red lips curved upward in a smile of such joy, such pure and perfect happiness, that it would have frozen your blood in your veins to have seen it.
* ''Franchise/StarWarsLegends'':
** In some of the ''Literature/XWingSeries'' and any [[Literature/NewJediOrder other]] appearances written by Creator/AaronAllston, Wedge Antilles has often been known to smile like this -- actually, while it can be assumed that he's got normal smiles, almost any time the narration ''says'' he's smiling it's this trope. Humorless, feral. He gives it to politicians when he sees through what they say to what they mean and most often to enemies he's about to shoot down.
** In the same books, "Runt" Ekwesh (being non-human) has a facial structure such that even a friendly smile is described as looking like a prelude to a biting attack. He's keenly aware of this and takes full advantage of it when he wants to be menacing.
** ''Literature/LegacyOfTheForce'' has Wedge shocked and taken aback by being discharged -- Wedge, who was sixty and had been in service since the age of twenty -- then realizing that people are going to try to kill him. The thought is so familiar that it steadies and reassures him, and he's able to flash someone a smile "suggesting that he was a rancor and they were made of meat".
* Rictus in Creator/CliveBarker's ''The Thief of Always'' at first seems to be a harmless goofball who's always got a big, cheesy grin on his face -- until the dark side of the Holiday House (his employer) makes itself known, and his smile becomes terrifying ([[GeniusBonus if Harvey Swick had read his dictionary]], he'd know that a "rictus" is the grin of a skull).
* In Creator/RandallGarrett's "[[https://www.gutenberg.org/ebooks/30869 Thin Edge]]", Harry Morgan is confronting the man who ordered his friend's murder. While discussing the death of a man who tried to illegally search his hotel room while he was out, "Morgan did a good imitation of a shark trying to look innocent"
* Similarly played in David Brin's ''Literature/{{Uplift}} War'' when an allied alien found it disturbing that humans bared their teeth and bark when amused.
* ''TabletopGame/{{Warhammer 40000}}'':
** Lijah Cuu from the Literature/GauntsGhosts'' novels has one of these. In ''Straight Silver'', it is explicitly noted that "the most evil servants of Chaos would have killed to have a smile that lethal."
** In the next book, Abnett gives Magister Enok Innokenti (one of the evilest servants of Chaos ) an even better one. His smile is so hideous that it causes physical pain and nausea in humans and ''his daemonic bodyguard, who has murdered millions can't bear to look at it.''
* The Hellebore family from the Creator/TadWilliams' book ''Literature/TheWarOfTheFlowers'' liked these. Anton Hellebore was described as having a smile like someone who'd learned it from a book, Lord Hellebore one with absolutely no good feelings in it, and the Terrible Child had one like someone pulling up the corners of a corpse's mouth.
* In ''Literature/WarriorCats'', Mapleshade. She can make Ivypool feel like Daisy is with her, right before trying to drown her.
* ''Literature/TheWitcher'': Geralt of Rivia is frequently said to be "smiling nastily", usually either to intimidate or show his supreme disdain for an idea or position that he's been put in.
%%* The eponymous creature of Edward Gorey's ''[[http://www.geocities.com/dav485q/wugglies/wuggly1.html The Wuggly Ump]]''.
* From ''Literature/AliceInWonderland'':
-->"How cheerfully he seems to grin!\\
How neatly spreads his claws\\
And welcomes little fishes in\\
with gently smiling jaws!"
* ''Literature/TheArchonate'': In ''The Spiral Labyrinth'', which is set in homage to the ''Literature/DyingEarth'' setting, one of the significant villains is a wizard by the name of Smiling Bol. He always maintains a cheerful expression -- sometimes less menacing, sometimes more so.
* In the ''Literature/{{Brotherband}}'' book ''The Hunters'', the author describes Thorn's smile as unpleasant when he's warning a captured pirate not to break for it.
* Skeeter Traps from ''Literature/ChroniclesOfMagic'' is known for sporting these, despite being a ten-year-old girl. Combined with the fact that she can kill grown men three times her size, it makes her pretty scary.
* Jame, the heroine of P.C. Hodgell's ''Literature/ChroniclesOfTheKencyrath'' series, smiles like this, and it is very, very bad news. It signifies the depths of her darkness, and the author said, "In a way, everything about Jame grew out of that chilling smile."
* From S.J Bryant's ''Literature/TheNovaChronicles'', when Alden's attempt at turning himself into a monster fails, instead becoming a cute furry creature. Nova sports a wide grin as she brutally stomps the helpless creature to death beneath her metal boots.
* In Creator/RobertEHoward's ''Franchise/ConanTheBarbarian'' story "Literature/AWitchShallBeBorn", Constantius does this while watching the guard be slaughtered and crucifying Conan.
* ''Literature/{{Coraline}}'': Done by the Other Mother, when she's not busy being a StepfordSmiler.
* ''Literature/TheCosmere'':
** The Steel Inquisitors from ''Literature/{{Mistborn}}'' are exceptionally brutal enforcers of the Empire, and the chilling grins they have when going about their work are frequently remarked on. AntiHero Kelsier, leader of the rebellion, also smiles a lot because it's a way of proving that he's not beaten down, but from the point of view of his enemies (to whom he has little to no mercy) it comes off like this.
** Bleeder in ''Literature/WaxAndWayne'' displays one of these while between forms, described as having "a face of stretched muscle and grinning teeth" and being "all smiles" as she scrambles towards her terrified cabbie.
* Vlad Dracula in ''Literature/CountAndCountess''. Every time he's about to kill someone with his artificially sharpened teeth, he grins at them first, just to give them a preview of what's to come.
* Sometimes it's a matter of perception. In Creator/AlanDeanFoster's ''The Damned'' trilogy, the first encounter between the multiracial alien alliance's and humans highlights the differences between them and us when the human, Will Dulac, first bats the gun out of the hand of the nearest alien scout out of a self-defense reflex, then offering a handshake and smiling when he realized they weren't hostile. The sudden reflexive strike nearly broke the scout's hand, and the smile confuses and alarms them as they wonder why baring one's teeth could ever be considered a friendly gesture. They also didn't get the handshake.
* ''Literature/DeptfordMice'': In ''The Dark Portal'', a rat called Smiler had a Slasher Smile on his face all the time... because he'd been rude to his superior as a child, and said superior had [[FamilyUnfriendlyViolence cut off his lips]].
* Creator/TerryPratchett's ''Literature/{{Discworld}}'':
** Carcer Dun and Mr. Teatime are described as smiling like this ''all the time''. The drawing of Mr. Teatime in ''The Art of Discworld'' perfectly illustrates this. Marc Warren does a good job with this in the TV adaptation, too.
** At one point in ''Literature/{{Jingo}}'' the seriously pissed off "Vimes's grin was as funny as the one that moves very fast towards drowning men. And has a fin on top."
** [[OurWerewolvesAreDifferent Angua]], who at one point must have been smiling because "her mouth was open, and [[OhCrap all of her teeth were showing]]".
* ''Literature/{{Dragaera}}'': Perhaps inspired by the Jack Vance example, ''Literature/FiveHundredYearsAfter'' has the court wizard as a minor character and he is similarly described as always smiling creepily and chuckling in a questionably sane manner.
* In Jack Vance's ''Literature/DyingEarth'' series, the character Iucounu the "Laughing Magician" perpetually supports one of these providing a clue that his sense of humor is not exactly benevolent.
* Creepy caretaker Heimertz from the ''Literature/EdgarAndEllen'' series has a constant slasher smile. During the TV adaptation, it is shown that he has had this smile since he was a child.
* In Abnett's series ''Literature/{{Eisenhorn}}'', the demonhost Cherubael sometimes sports one of these. When he/it does, ''someone'' is going to die, very painfully.
* ''Literature/TheEschatonSeries'': Portia Hoechst, in ''Iron Sunrise'', is described as having this by several other characters, both good and evil, in the novel.
* A few Death Eaters display this, as does Snape on occasion and Voldemort in the ''Literature/HarryPotter'' series.
* Benjamin, the serial killer antagonist of ''Literature/HollowPlaces'' manages to torment one of his surviving victims while in court simply by showing her a disturbing smile.
* ''Literature/GodsAndWarriors'': Alekto, [[DarkChick the only female member of the House of Koronos]], is so sadistic that she draws her lips back from her teeth in a way that's half a smile and half a grimace when she thinks about pain or better yet, observes it.
* ''Literature/TheIcelandicSagas'': OlderThanPrint: Skarphéðinn Njálsson has one in ''Brennu-Njáls Saga''. "And he grinned" is a common phrase in the story that implies that something really bad is about to go down.
* In ''Literature/{{Jam}}'' everybody goes a little crazy during the course of the book but {{Cult}}-Leader Lord Awesomo has a memorable grin when he sees [[EveryMan Travis]] in the crowd and realizes he can spin the election to his favor and get Travis killed.
* ''Literature/TheJenkinsverse'': Since most sapient species are herbivores and herd animals, they get ''very'' uncomfortable with human smiles, which involve far too many sharp teeth for their liking. [[ShownTheirWork Note that this is realistic]]; even on Earth among primates, humans are one of the only species that doesn't consider showing teeth to be a threat. Most humans who interact with aliens learn quickly to smile with closed lips. In ''Salvage'', Adrian Saunders doesn't bother with that, which enhances his already terrifying reputation. When he finally meets more humans, it turns out that they find his smile even scarier than aliens do. At least aliens have little experience with humans and can assume that he's just normal. Humans know he's not.
* In the ''Literature/KateDaniels'' series, Kate is trying to enlist a man's cooperation with her plan to hunt down and kill the people who have hurt her friend.
-->I gave him a smile. I was aiming for sweet, but he turned a shade paler and scooted a bit farther away from me. Note to self: work more on sweet and less on psycho-killer.
* Nathan in ''Literature/KillTimeOrDieTrying'' does this inadvertently; it's just how he naturally smiles.
* Creator/StephenKing:
** Randall Flagg/The Dark Man is described as having a grin of such good cheer and jolliness which comes across however as so unsettling the human mind seems to block it out.
** Also from ''Literature/TheStand'' (where King first writes about Flagg) is Harold. Most of the other survivors in Boulder just see him as a StepfordSmiler... but the slightly damaged child Leo sees things a little differently.
--->It's like there are worms behind his eyes, and they're eating his brain and making him smile like that.
* The huge, catlike Kzinti of Creator/LarryNiven's ''Literature/KnownSpace'' universe instinctively show their teeth when they feel a certain way. That way is ''not'' happy.
* In Creator/DevonMonk's ''Literature/MagicInTheBlood'', the villain does this while making demands on Allie.
* Gwynplaine from ''Literature/TheManWhoLaughs'', as touched upon under the examples of The Joker and Mr. Sardonicus.
* In Asi Hart's ''Literature/TheManyHorrorsOfBeingATokyoWaitress'' main character Jonas has a very creepy forced smile until he is told that he's scaring the customers and instructed to use some other facial expressions.
* Mr. Wonderful from ''Literature/{{Mogworld}}'' has this mixed with a CheshireCatGrin. It is described in the book as: "The widest grin he [Jim] had ever seen and he knew people with no skin on their faces" worth noting Mr. Wonderful's grin never drops even when he's hacking his own arm off.
* ''Literature/TheNameOfTheWind'': Cinder of the Chandrian has a smile that is described as "the expression a nightmare wore."
* A rare heroic version: [[TheBigGuy Ivarian Borenson]], of ''Literature/TheRunelords'' fantasy novels, is known for his chilling laughter and grin as he fights, which makes him feared even amongst warriors who have far more endowments (strength, stamina, speed, and so on taken from other people) than him. Not so much out of a love for killing, but [[GenreSavvy because it works far better at frightening other people than a war cry,]] so he got himself into the habit of laughing instead.
%%* Count Olaf in ''Literature/ASeriesOfUnfortunateEvents''.
* Professor Moriarty, Literature/SherlockHolmes' arch-enemy from the short story "The Final Problem." Holmes describes that, though Moriarty "smiled and blinked", there was something about the Professor's sunken eyes that made Holmes, a man who was used to danger, very glad to have a revolver with him.
* Jaime Lannister of ''Literature/ASongOfIceAndFire'' recalls in his youth facing a particularly brutal and psychotic fighter known as 'The Smiling Knight'. 3 guesses why he is named that. Luckily even a slasher smile is no match for Ser Arthur 'The Sword in the Morning' Dayne and his [[ThunderboltIron greatsword Dawn]].
* In Neil Gaiman's ''Literature/{{Stardust}}'', Lamia displays one of these during her search for the fallen star. Fortunately, we only have the Narrator's [[TakeOurWordForIt word on it.]]
-->Her red, red lips curved upward in a smile of such joy, such pure and perfect happiness, that it would have frozen your blood in your veins to have seen it.
* ''Franchise/StarWarsLegends'':
** In some of the ''Literature/XWingSeries'' and any [[Literature/NewJediOrder other]] appearances written by Creator/AaronAllston, Wedge Antilles has often been known to smile like this -- actually, while it can be assumed that he's got normal smiles, almost any time the narration ''says'' he's smiling it's this trope. Humorless, feral. He gives it to politicians when he sees through what they say to what they mean and most often to enemies he's about to shoot down.
** In the same books, "Runt" Ekwesh (being non-human) has a facial structure such that even a friendly smile is described as looking like a prelude to a biting attack. He's keenly aware of this and takes full advantage of it when he wants to be menacing.
** ''Literature/LegacyOfTheForce'' has Wedge shocked and taken aback by being discharged -- Wedge, who was sixty and had been in service since the age of twenty -- then realizing that people are going to try to kill him. The thought is so familiar that it steadies and reassures him, and he's able to flash someone a smile "suggesting that he was a rancor and they were made of meat".
* Rictus in Creator/CliveBarker's ''The Thief of Always'' at first seems to be a harmless goofball who's always got a big, cheesy grin on his face -- until the dark side of the Holiday House (his employer) makes itself known, and his smile becomes terrifying ([[GeniusBonus if Harvey Swick had read his dictionary]], he'd know that a "rictus" is the grin of a skull).
* In Creator/RandallGarrett's "[[https://www.gutenberg.org/ebooks/30869 Thin Edge]]", Harry Morgan is confronting the man who ordered his friend's murder. While discussing the death of a man who tried to illegally search his hotel room while he was out, "Morgan did a good imitation of a shark trying to look innocent"
* Similarly played in David Brin's ''Literature/{{Uplift}} War'' when an allied alien found it disturbing that humans bared their teeth and bark when amused.
* ''TabletopGame/{{Warhammer 40000}}'':
** Lijah Cuu from the Literature/GauntsGhosts'' novels has one of these. In ''Straight Silver'', it is explicitly noted that "the most evil servants of Chaos would have killed to have a smile that lethal."
** In the next book, Abnett gives Magister Enok Innokenti (one of the evilest servants of Chaos ) an even better one. His smile is so hideous that it causes physical pain and nausea in humans and ''his daemonic bodyguard, who has murdered millions can't bear to look at it.''
* The Hellebore family from the Creator/TadWilliams' book ''Literature/TheWarOfTheFlowers'' liked these. Anton Hellebore was described as having a smile like someone who'd learned it from a book, Lord Hellebore one with absolutely no good feelings in it, and the Terrible Child had one like someone pulling up the corners of a corpse's mouth.
* In ''Literature/WarriorCats'', Mapleshade. She can make Ivypool feel like Daisy is with her, right before trying to drown her.
* ''Literature/TheWitcher'': Geralt of Rivia is frequently said to be "smiling nastily", usually either to intimidate or show his supreme disdain for an idea or position that he's been put in.
%%* The eponymous creature of Edward Gorey's ''[[http://www.geocities.com/dav485q/wugglies/wuggly1.html The Wuggly Ump]]''.
