History Main / CheshireCatGrin

* Headon from ''WebComic/TowerOfGod'' has a permanent "smiling" groove across his oddly shaped face. This groove usually looks empty, but it can display either his eyes or a set of sharp teeth. Considering the merciless manipulation he gets up to in the first season, showing his teeth there counts for this trope.

* ''VideoGame/{{Persona 5}}'': Invoked by your GuardianEntity, the [[DealWithTheDevil demonic]] Arsene, who has a constant grin made of hellish flames plastered across his face. In fact, the highest level of [[CastingAShadow darkness magic]] he uses to kill foes has the same blood-red smile of flames inscribed into it.

* Ichihara Yuko from ''Manga/XxxHOLiC'' has a grin that can roughly be summed up in words as: "Not only do I know something you don't know, but it's going to bite you in the ass in a ''very'' [[HilarityEnsues amusing fashion]]." Despite this, it's when she appears ''serious'' that should really scare Watanuki. This is because Yuko's Cheshire cat grin simply means she's going to make him do all the laundry, whereas the latter expression is usually a forecast of man-eating crow demons or similar.

* One ''ComicStrip/BeetleBailey'' Sunday strip had Beetle torment Sarge by periodically giving him one of these smiles. Sarge tore his living quarters and office apart trying to find whatever PracticalJoke Beetle had set up (in fact, there wasn't one).
* In one ''ComicStrip/CalvinAndHobbes'' arc, when Calvin notices Susie left her dolls outside while she had lunch, Calvin makes one and says "That gives me a ''brilliant'' idea!"
* ''ComicStrip/TheBoondocks'' has a strip with a truly ''evil'' grin spreading across Riley's face as his inner monologue contemplates an [[NoodleIncident unspecified act of mayhem]]:
--> "Hmm... mischief... danger...trouble... malevolence... discord... pandemonium... TOTAL CHAOS... ''MASS CONFUSION!''"
* ''ComicStrip/{{Dilbert}}'': Catbert gives two of these [[http://www.dilbert.com/strips/comic/2001-03-04/ in one strip]], though his clueless victim doesn't quite get the message.

* When ''ComicStrip/FoxTrot'' parodied ''Literature/HowTheGrinchStoleChristmas'', Andy as "Mrs. Grinch" had a very accurate recreation of the Grinch's "wonderful, awful idea" face mentioned below.

* The allegedly-catatonic Cameron, just pulled up from the bottom of a pool after keeling over into it face first, broke into one of these in ''Film/FerrisBuellersDayOff'' when Ferris and Sloane realize he saw Sloane stark naked while she was changing into her swimsuit, and enjoyed every minute of it. Cameron's ensuing hysterical laughter led to further dunkings by Ferris.

* Legendary schemer and thief, ''Anime/LupinIII'', has a smile, when not showing teeth, that is more of a CatSmile, but when [[http://imgur.com/lUCnB3O he shows teeth and does the raised eyebrow, it's pure Cheshire Cat Grin.]]
* Gengar, from ''Anime/{{Pokemon}}'', tends to have either this or a SlasherSmile depending on how it's drawn. Either way, it is constantly worn and only twice in the anime does Gengar actually frown.
** See the example under Video Games for a time when he ''does'' frown.
* Dee Laytner, from the ''Manga/{{FAKE}}'' manga and anime, is a good example of a grin with sexual overtones, while he's plotting how to seduce Ryo. Occasionally, Dee's expression is downright scary, and it leads Ryo to comment, "You're grinning like the Cheshire Cat." [[http://caramelcatkin.deviantart.com/art/FAKE-Dee-Laytner-204479481 Here, have a look.]]
* Washu of ''Anime/TenchiMuyo'', usually right before she's about to stuff Tenchi into some machine or another.
* ''Manga/{{Bleach}}'':
** Kisuke Urahara, particularly before unleashing one of his [[TrainingFromHell training regimes]] on someone.
** Shinji Hirako has an even more classic version of a Cheshire cat grin.
** This is Ichimaru Gin's [[PerpetualSmiler near-permanent expression.]]
** [[BloodKnight Kenpachi]] actually does this when he gets to fight a [[WorthyOpponent strong opponent]]. According to [[TokenMiniMoe Yachiru]] it means he's having a lot of fun.

* [[TheTrickster Deviant genius]] Hiruma from ''Manga/{{Eyeshield21}}'' has this as one of his default expressions, to the point where those new to the series -- or complete non-fans -- can [[LoadsAndLoadsOfCharacters identify him]] as "the one with the teeth."
* Road Kamelot of ''Manga/DGrayMan'', several times. Along with some of the AKUMA. Hell, the Earl probably counts as well.
* Haruko of ''Anime/{{FLCL}}'', usually when she's about to be entertained, between the CatSmile and SlasherSmile stages. It's very, very much a bad thing for Haruko to be entertained.
* ''Manga/NegimaMagisterNegiMagi'' plays this for comedy; if Haruna starts smiling, something embarrassing and/or unpleasant is about to happen. The other characters are rightfully scared of her.
** Invoked by Kaede when speaking with "Kunel Sanders", a mysterious, suspicious, and very powerful man who is interested in Negi but refuses to say why. In the end, it turns out that he is trustworthy, but he also admits people tend to not believe his smiles.
* ''VisualNovel/HigurashiWhenTheyCry'' has a few characters sport these. Most of the time it's either [[{{TheGadFly}} Mion, Shion]], or Satako, and it usually involves getting Keiichi into a ridiculous outfit, pulling a prank, pushing someone's buttons or out of his clothes entirely.

* Ed from ''Anime/CowboyBebop'' sports one perpetually, even her little avatar. Very appropriate, given her cat-like nature.
* Holo from ''Manga/SpiceAndWolf'' does this whenever she's sweet-talking someone (usually Lawrence) into doing what she wants. She's usually teasing with it, instead of plotting things with bad consequences.
* Hikaru and Kaoru from ''Manga/OuranHighSchoolHostClub'' when up to mischief, usually at Haruhi's expense.
* In ''Manga/BlackButler'', Undertaker has a very nice one.

* Bel from ''Manga/Reborn2004'' tends to have this as his default face, along with making one when he laughs his creepy "Ushishishishi~" laugh.
** Hmmmm... notice how his default outfit is actually a pink and purple striped shirt? And how in one Omake he's considered a house pet in the Varia family? Looks like the resemblance isn't just the smile...
* Anime/{{Naruto}} Uzumaki smiles like this a few times, usually when thinking of a prank. Some of those times (notably in the 101 episode) his Cheshire Cat Grin overlaps with SlasherSmile.
** The Kyuubi's face is eternally twisted into a Cheshire Cat Grin.
* Sumiko from ''Manga/{{Kekkaishi}}'' seems to have one of these as her defining trait; when she was TheFaceless it's all we saw of her. [[spoiler:May actually be more malevolent, as we don't know much about her. The fact that now that she's not The Faceless we see her [[SlasherSmile smile]] ''doesn't'' reach her eyes isn't good]].
%%* [[StepfordSmiler Xerxes]] [[SweetTooth Break]] from ''Manga/PandoraHearts'' has a very typical one. And his doll has exactly the same smile. And, oddly enough, the character ''called'' the Cheshire Cat does not.
* Lots of the eponymous Titans of ''Manga/AttackOnTitan'' sport unnerving grins, even when they logically should be in pain. For some these cross the boundary into GlasgowGrin because of the fact they're missing bits of skin.
* Roronoa Zoro from ''Manga/OnePiece'', whenever he's not sleeping or eating. Also, Urouge.
** This is basically Gold Roger's default expression.
* [[TheTrickster Irabu]] from ''Literature/{{Trapeze}}'' gets a disconcerting grin on his face whenever he gives some kind of devious advice [[StealthMentor in order to help his patients somehow.]]
* Ham Egg from Creator/OsamuTezuka's works is easily identified for making this grin constantly, which foreshadows his unpleasant and villainous nature.
* ''Manga/FullmetalAlchemist'':The Gold-Tooth Alchemist often wore a bizarrely-wide grin at times when there was no discernible reason for ''anyone'' to be smiling. Add the unfocused eyes and it moves into SlasherSmile territory.
* ''Anime/NeonGenesisEvangelion'':
** Asuka pulled one off in her debut episode when Gaghiel attacked the UN fleet carrying her Eva.
--->'''Shinji:''' This is really bad! We've got to go back and find Misato!\\
'''Asuka:''' ''(looks sideways and grins)'' Wunderbär!
** Kaworu often wears one himself, particularly in the manga or any of the other alternate universes where he pops up. It fits in well with his cryptic nature.

* ''Manga/{{Hellsing}}'': [[EveryoneCallsHimBarkeep The Major]] is noted as having "a detestable grin which would split his cheeks". Combined with his [[spoiler: [[CyberneticsEatYourSoul artificial origin,]]]] SupernaturalGoldEyes and his desire to [[BloodKnight spark the world to eternal war]] it's quite creepy. It will occasionally flicker into SlasherSmile territory, especially towards the end of the series.
* Captain Gotoh in the ''Anime/{{Patlabor}}'' manga specializes in these wonderfully awful toothy grins.
* Lain's alter-ego from ''Anime/SerialExperimentsLain'' does this constantly.
* Drosselmeyer from ''Anime/PrincessTutu'' is always sporting one.
* Neferpitou from ''Manga/HunterXHunter'' is almost never seen without his (cat) smile. It doesn't help that he has a deadly and terrifying BattleAura and permanent creepy eyes.
* Kawarino from ''Anime/YesPrettyCure5'', especially in his human form with EyesAlwaysShut. And you don't want to see any other of his [[NightmareFace facial expressions]].
* ''Anime/PuellaMagiMadokaMagica'' brings us [[spoiler: Charlotte's One Winged Angel form right before [[WhamEpisode ''that'' scene]].]]

* Seijirou from ''Manga/MarchComesInLikeALion''. A deadbeat father and ConsumateLiar, this is practically his default expression to emphasize how unsettling he is, and it's the first clear sign to the audience that he's up to no good when he's first introduced as he's meeting up with his daughters several years after abandoning them for his new wife.

* ''Fanfic/ChildOfTheStorm'' has Doctor Strange wear a habitual slight smile since everything is pretty much AllAccordingToPlan (excepting the ''Forever Red'' arc of the sequel, when it is very much not). It's one of the things people find both annoying and unsettling about him. However, when he's tap-dancing on the edge of sanity and/or about to pull something spectacular (and usually, terrifying), it widens into something downright manic, with far too many teeth for anyone's comfort.

* In ''Fanfic/TheSecondTry'', when [[spoiler:Gendo demands knowledge of the future,]] Shinji grins coldly and maniacally before replying that he’ll die.

* In ''Batman'' fanfiction ''Fanfic/DanceWithTheDemons'':
** In chapter 16, the Outsiders barge into a Kobra's base full of enemies. Batman just grins.
--->Batman looked at him, briefly, and went to the door of the unit. He sprayed some acid from a vial in his utility belt on the lock. After enough of the metal had sizzled away, he kicked it open.\\
Metamorpho filled the gap in the doorway as a calcium shield, receiving blasts of cold and fire on his surface. He thrust forward like a battering ram, bowling over Heatstroke, Coldsnap, and several others of their foes.\\
The others came behind him, and looked upon a sea of enemies.\\
"Looks like we've been expected," said Batman, with a grim smile.\\
The battle was joined.
** In chapter 21, fifteen armed Kobra cultists rush towards Batman and Nightwing. They can't figure out why Batman is smiling.
--->With that, two doors at opposite ends of the hall flew open. No less than fifteen men, with arms, emerged from them. All wore the suit of the Kobra Cult. They were armed.\\
There was no time to tell Nightwing to engage. Both of them were already rushing at their foemen. The ones Batman was facing were puzzled.\\
They couldn't figure out why he was smiling.
* In crossover fanfiction ''Fanfic/HawkmothDefeated'', Robin gives one to Adrien and Marinette while daring them to take their Miraculous back.
* In ''Fanfic/WithThisRingGreenLantern'': As fighting [[Franchise/GreenLantern Hal Jordan]], Hector Hammond gets an "Uh-Oh" reaction when Hal smiles at him. Seconds later, Hal knocks him out.
-->He looked at the Lantern, huddled there in his green cube with the walls pressing in on him. A bit more, and you'd probably be able to see the juice spurting.\\
But the Lantern was looking at him, and smiling.\\
Hammond hadn't fought the man more than a dozen times without learning something about him. A smiling Lantern was a dangerous Lantern.

* The [[https://web.archive.org/web/20141110210122/http://geek-news.mtv.com/wp-content/uploads/2011/04/catbus.jpg cat bus]] from ''Anime/MyNeighborTotoro'' is a spitting image of the Cheshire Cat.
** Totoro himself smiles like this when he is happy or delighted by something.

* ''Film/TheMachinist'': Ivan does a particularly disturbing rendition of this trope.
* ''Franchise/PiratesOfTheCaribbean'': Right before taking vicious or manipulative action, Captain Jack Sparrow often sports an evil, toothy smile. In the screenplay for ''[[Film/PiratesOfTheCaribbeanDeadMansChest Dead Man's Chest]]'', a "Cheshire grin" is mentioned in Jack's direction during a particularly loathsome act of betrayal.
* The allegedly-catatonic Cameron, just pulled up from the bottom of a pool after keeling over into it face first, broke into one of these in ''Film/FerrisBuellersDayOff'' when Ferris and Sloane realize he saw Sloane stark naked while she was changing into her swimsuit, and enjoyed every minute of it. Cameron's ensuing hysterical laughter led to further dunkings by Ferris.
* ''[=RRRrrr=]!!!'': [[https://www.youtube.com/watch?v=_6NL9m_bS2Y At 9:11.]]. Unless we count this as SlasherSmile.
* Creator/TimCurry: Dr. Frank-N-Furter walks on stage with this expression in the ''Film/TheRockyHorrorPictureShow'', and it's his default expression when he's not angry, jealous, megalomaniacal, or begging for sympathy. Similarly in his role in ''Home Alone 2: Lost In New York''. They even segue quite unnervingly from a still from [[WesternAnimation/HowTheGrinchStoleChristmas the animated version of the Grinch]] to his grin -- [[https://gfycat.com/gifs/detail/dazzlingmassivefiddlercrab the resemblance is uncanny]].
** Rather fittingly, Curry ''is'' from Cheshire, and has gotten nicknamed "the Cheshire Cat" in real life.
* ''Film/{{Equilibrium}}'': [[TheDragon Cleric Brandt]] has a smile which first inspires FridgeLogic when you realise that he's not supposed to have any emotion, then FridgeBrilliance when you realize that he ''doesn't'' have any emotion; his huge smile has nothing to do with real happiness or real satisfaction. Knowing this makes it pretty creepy.
* Creator/ZeroMostel as Pseudolus delivers one of these to Creator/JackGilford's Hysterium in ''Theatre/AFunnyThingHappenedOnTheWayToTheForum''. They've determined that the only way to get a visiting Captain to leave is to convince him that his intended bride is deceased. Hysterium intones, "But where are we going to get a body?" whereupon Pseudolus does a slow take at him with a grin that almost breaks his own face.
* ''Film/AFistfulOfDynamite'''s John Mallory is fond of this, especially when he's toying with Juan Miranda.
** A general movie axiom - if Creator/JamesCoburn grins, run away.
* The most recent live-action version of ''Literature/AlicesAdventuresInWonderland'' includes Whoopi Goldberg as the Cheshire Cat, with a suitably wide and manic smile.

* Film/JamesBond in ''Film/{{Goldfinger}}'', [[http://bplusmovieblog.files.wordpress.com/2012/11/goldfinger-509.png?w=590 as he prepares to trick a guard into thinking that he's escaped from his prison cell.]]

* From the nonfiction desktop book ''Murphy's Law for Lawyers'': "A man who can smile in a crisis is a man who has thought of someone to blame it on."

* Some girls have [[WhenSheSmiles wonderful smiles]]. Then there's Kouma of ''LightNovel/TheLongingOfShiinaRyo''.

* ''Literature/ArtemisFowl'' has Artemis' signature vampire smile. It's just as creepy as it sounds.

* Treecats in ''Literature/HonorHarrington'' can apparently pull this off masterfully. Given their propensity for mischief, it's highly appropriate.
-->'''Capt. Jacquelyn Harmon''': I've always figured Carroll must have met a treecat in an opium dream or something when he invented the Cheshire Cat.
* The Weasley twins in ''Literature/HarryPotter'' are noted to do this when they see a new target for mischief, [[SingleMindedTwins even worse since they do it at the same time.]]
* In ''Literature/DragonBlood'', there is [[spoiler: Oreg]], who likes to show his teeth when there is danger someone might underestimate him. He looks relatively harmless if he wants to, but [[spoiler: he's a dragon-shapeshifter and mage]] and sometimes he'd like people to know what will happen to them if they threaten his loved ones.
* Grey from ''Literature/KnightsOfTheBorrowedDark'' has one as his default, which frequently appears at completely inappropriate times. The results range from quirky and memorable to extremely unsettling.
--> You couldn't be in the army with a smile like that. The man smiled like a cat burglar.
* Aech in ''Literature/ReadyPlayerOne'' is described as having a "Cheshire cat grin", the phrase occurring multiple times (to the point that it becomes an [[AuthorCatchphrase authorial tic]]).

* Dr. Phlox in ''Series/StarTrekEnterprise'' does this in the pilot. Season 4 reveals that his species are capable of [[BizarreAlienBiology inflating their heads]], which goes some way to explain why Denobulan smiles don't lead to self-decapitation.
* Not quite a Cheshire Cat Grin, but with the same effect in "Bride of Chaotica!" an episode of ''Series/StarTrekVoyager''. The holodeck malfunctions and someone must go into the program to resolve the issue playing the part of Queen Arachnia. When Captain Janeway asks Tom "Who do you have in mind?" Tom and the rest of the crew turn to her with evil smirks.
* In ''Series/StarTrekDeepSpaceNine'', Garak smiling is usually a bad sign for ''someone''.
* Talk show host/Comedian Jay Leno always seems to have one of these on his face.
* Theo Series/{{Kojak}} pulls out one of these at least every couple of episodes.

* Vala in ''Series/StargateSG1'' has a grin that shows a lot of teeth and can be deeply disconcerting.
* Michael Westen from ''Series/BurnNotice'' does this a lot. His smile will ''eat your soul.''
* Judge Frasier did this all the time on ''Series/ThisIsWonderland''.

* ''Series/TerminatorTheSarahConnorChronicles'': [[RobotGirl Because of]] [[EmotionlessGirl her basic nature]], anytime Cameron smiles, you should be on your guard. No matter what, that smile is intended to manipulate you.

* ''Series/KamenRiderFourze'' has stoic "I don't wanna be involved with this Kamen Rider Club" foolishness Kengo Utahoshi have one of these as he drags the poor ButtMonkey JK into piloting a mecha known as the Power Dizer.
* ''Series/{{Justified}}'' has Detroit mob lieutenant Robert Quarles, who has a big, unsettling smile.
* ''Series/BabylonFive'': Mr. Morden will give you a big jovial-looking smile, just as he's about to screw you and your entire species over.
* [[SilkHidingSteel Sister Julienne]] of ''Series/CallTheMidwife'', nun-in-charge of Nonnatus House, has one, which she usually deploys right after she has "[[ThatWasntARequest asked]]" someone to do something. The "or ''else''" is implied.

* ''Series/LawAndOrderUK''. When arresting his friend/colleague Alesha's rapist, DS Matt Devlin displays a particularly scary version of one of these--especially considering that he's usually such a NiceGuy--when the guy whines, "You're hurting me!" as Matt handcuffs him and Matt responds, "Yeah, I ''know''. Didn't that feel good?"

* ''VideoGame/ConkersBadFurDay'': Of all the characters in the game, Conker himself is by far the most expressive, especially when it comes to the classic toothy grin. A smile that makes him stand out in Rare games. He does this several times as follows: Whenever he is exposed to cash. He also does a quick cheeky grin thinking "See ya!" with a wave as the Gargoyle is about to fall off the bridge. Sometimes when he's idle, he will get out three balls to juggle with, complete with a toothy grin. Another idle animation shows him with a dirty magazine where he's shown grinning away and of course, there's the moment where he chugs down so much beer in one go under a keg, he sports what is the best grin of his in the entire game sprawled across his face as he is totally tanked.

* The dark/left half of Monokuma's face in ''Franchise/{{Danganronpa}}'' is seemingly [[FrozenFace frozen in this state permanently]], combined with FangsAreEvil. The light/right half is significantly more restrained, but it can be unsettling when the two sides smile together (which is pretty often).
** Kokichi Oma from ''VisualNovel/DanganronpaV3KillingHarmony'' has a few [[https://vignette.wikia.nocookie.net/danganronpa/images/e/ed/Danganronpa_V3_Bonus_Mode_Kokichi_Oma_Sprite_%2811%29.png/revision/latest?cb=20170929121954 sprites]] that would also fit this description.

* Kitty Cheshire from Mattel's web series ''Toys/EverAfterHigh'' is the daughter of the Cheshire Cat, and inherited the trait of leaving behind her signature grin.
* Alastor from ''WebAnimation/HazbinHotel'' basically has this as his default expression when he's not flashing a SlasherSmile.

* Both Zimmy and Coyote in ''Webcomic/GunnerkriggCourt''. Oddly, the effect of each character's grin is heightened by the fact that they have the wrong sort of teeth for their species: Zimmy has shark-like teeth and Coyote has uniform flat teeth.
** Of course, both of them pale before the awesomeness of [[http://www.gunnerkrigg.com/archive_page.php?comicID=458 Jack's smile.]]
** Jack outdoes himself in [[http://www.gunnerkrigg.com/archive_page.php?comicID=620 this]] strip.
* Tedd from ''Webcomic/ElGoonishShive'' has been seen with one of these from time to time, generally when there's a noteworthy bit of AuthorAppeal.

* Rocky, from ''Webcomic/{{Lackadaisy}}'' seems to have this as his default expression. His cousin wears a combination of this and SlasherSmile. [[http://tracyjb.deviantart.com/gallery/?offset=48#/d154crs Like so.]]
** Following a rather severe conk on the noggin courtesy of a runaway hearse, Rocky's [[http://www.lackadaisycats.com/comic.php?comicid=149 grin]] has pretty much become an equal rival with his cousin's in terms of Slasher Smile-ness.
* [[https://realmofowls.com/comics/annoying-doppelgangers Vayandil and Gheralf's doppelgängers]] in ''Webcomic/RealmOfOwls'' grin all the time, except without teeth, because they are owls.
* Smiling Man from ''Webcomic/UserFriendly'' smiles all the time, but sometimes it gets [[http://ars.userfriendly.org/cartoons/?id=20090415 even worse]].
* Webcomic/{{Paranatural}}'s Ed does this frequently. Sometimes edging into SlasherSmile territory, particularly when accompanied by phrases such as [[http://www.paranatural.net/index.php?id=93 "You're all gonna die!"]] Isabel gets in on the act [[http://www.paranatural.net/index.php?id=100 occasionally]] as well.
* Shadowchild from ''Webcomic/{{Digger}}'' has smiled like this twice. Both times it went badly for the other guy.

* George from ''Webcomic/JohnnyWander'' is always depicted with one of these. Except one time when he grimaced and it was basically the same thing but upside down. [[http://www.johnnywander.com/comics/128 Even his tombstone has that grin.]]

* Joey Von Krause from ''[[http://mortifer.smackjeeves.com Mortifer]]'' is almost always smiling like this, even when [[http://mortifer.smackjeeves.com/comics/318885/chap18page12/ you've succeeded in pushing his Berserk Button]] ([[spoiler:Looking under his eyepatch, in case you were wondering]]). It's later stated that he smiles whenever he's in control of the situation, [[MagnificentBastard which is all the damn time]].
* [[spoiler:Dagre]] from ''Webcomic/TheMeek'' sports one...kind of. It's more of his jowls drooping, giving an absolutely terrifying grin appearance.
* Subverted/defied with Florence Ambrose in ''Webcomic/{{Freefall}}'' -- her natural smile is a face full of teeth since she's an anthropomorphic "Bowman's Wolf." She has to remember to smile with her lips closed to avoid this trope -- though she's not above invoking it...
** Occasionally, Sam [[http://freefall.purrsia.com/ff2500/fc02411.htm gets one of these]]. That's rather a lot of teeth for a squid in a suit...
* ''Webcomic/TheWhiteboard'': Bandit gets one of these when [[https://web.archive.org/web/20160530203646/http://www.the-whiteboard.com/autowb129.html Doc upgrades Bandit's firepower]] in one [[PaintballEpisode game]].

* Claud Southend of ''Webcomic/QuantumVibe'' pulls an epic one [[http://www.quantumvibe.com/strip?page=397 (complete with fade-out)]] in full trickster spirit in his farewell towards the end of the Luna arc.

* The typical expression on the face of {{Webcomic/Dolan}}.
* ''Webcomic/TheFoxSister'': Often seen on the Kumiho in human form.

* ''Webcomic/KarinDou4koma'': Mifi splits her face with a CheshireCatGrin when she catches Elza masturbating, and again when Seren asks her how she knew.

* ''Webcomic/{{Visseria}}'': Done by a couple of characters, but [[http://visseria.net/?comic=00098-highguard-again Jack in particular]] pulls off a nice one when convincing a guard to follow him along.

* In ''Webcomic/OffWhite'', the wolf [[spoiler: Sköll]] does this when [[spoiler: asked to bring his dead father figure back to life]], showing he's gone insane.
* The mysterious being following Stephen, [[spoiler: Nesariel]] in ''Webcomic/AutumnBay'' sports this nearly all the time.
* In ''{{Webcomic/Namesake}}'' Alice Purcell can do this, [[http://namesakecomic.com/comic/overpowered/ literally]] - including vanishing and reappearing somewhere else. It turns out [[spoiler: her first trip to Wonderland almost ended at the beginning, and [[http://namesakecomic.com/comic/pissing-off-the-queens/ a family of Chashire Cats each gave her one of their lives]] to save her.]] They also adopted her.
* The cover page for the first segment of ''Webcomic/DNATheWebcomic'' shows the grinning face of Sirius, with a bloody nose and mouth, a missing tooth, and a huge facial bruise. The original version of the cover had an even more pronounced grin, which the artist changed because it made him look too crazy.

* ''Webcomic/ChampionsOfFaraus'': Hypnolytic spirits have a default expression that looks like this, and it doesn't get any better when they actually ''do'' smile.
* ''Webcomic/Elwood2015'': In the "Slumber Party Manic - Part 4" strip, D.W. makes a very disturbing one that brings to mind [[WesternAnimation/HowTheGrinchStoleChristmas The Grinch]].

* Music/DoctorSteel's robots all have huge creepy grins.

* The Grinch in Creator/ChuckJones' screen adaptation of ''WesternAnimation/HowTheGrinchStoleChristmas'' when he gets the wonderful, awful idea to... well, steal Christmas.
* This could be arguably Creator/ChuckJones' SignatureStyle, when he directed ''WesternAnimation/TomAndJerry'', both characters would smile in the exact same manner when they hit upon a new scheme. As well as the poor schmuck in ''WesternAnimation/OneFroggyEvening''.

* In the penultimate episode of ''WesternAnimation/TeenTitans'', a character named Cheshire appears, wearing a large mask with a permanent Cheshire Cat Grin on it. One of her powers was to turn invisible except for the eyes and the grin, much like the cat in ''Literature/AlicesAdventuresInWonderland''.
** She's in [[ComicBook/TeenTitans the comics]], too, minus that power. For the record, her name is Jade Nguyen, and she has done things justifying that grin (like nuking {{Qurac}}).
** The Amazing Mumbo gives off a rather literal example in "Bunny Raven[[note]] (Or How To Make A Titanimal Disappear)" [[/note]].
---> '''Mumbo''': Tonight, I will make the Titans disappear... [[DramaticPause (Dramatic Pause)]] ...forever.
** In ''WesternAnimation/YoungJustice,'' Jade has the mask (which isn't in the comics. The previous animated Cheshire made just ''that'' much of an impression in her less than a minute of screentime.) but not the invisibility. She's an assassin for the League of Shadows initially but is ''far'' from AxCrazy enough to nuke a small country out of existence ForTheEvulz. She also has more than one mask (since one of them currently resides in Kid Flash's trophy case.)
* On ''WesternAnimation/TheGrimAdventuresOfBillyAndMandy'', [[VoluntaryShapeshifting shapeshifter]] Nergal Junor replaces the teacher in order to get revenge on the class bully Sperg. "Ms. Butterbean" approaches the bully with a smile that starts as a PsychoticSmirk and quickly grows in width, as well as tooth size and sharpness, until it's grinning fanged maw ''as wide her head''.

* In the ''WesternAnimation/CodeLyoko'' episode "Killer Music", Odd has one of these planted on his face for all but a few minutes of the episode... ''while comatose and dying''. He does it a few other times too, especially when he's being sneaky.
* In the ''WesternAnimation/ExoSquad'' episode "A Traitor Among Us", J.T. gets one of these when he explains his plan for getting TheSquad to Venus. "We need to become official undesirables. That's one assignment you troopers might enjoy."
* Snoopy in ''WesternAnimation/TheCharlieBrownAndSnoopyShow'' does this once, complete with the ability to vanish.

* The animated WesternAnimation/{{Beetlejuice}} often grins broadly when scheming. Bonus points for the unsettling effect of [[BritishTeeth his gross green teeth]], complete with half-chewed bug bits.
* Henry and June (the latter more often) do this in ''WesternAnimation/KaBlam!''

* More often than not, ''WesternAnimation/{{Mr Bogus}}'' will very often grin like this whether the situation calls for it or not.
* Aang from ''WesternAnimation/AvatarTheLastAirbender'' pulls off [[http://piandao.org/screenshots/water/water3/water3-22.jpg a relatively innocent one]] while planning to wake [[TheComicallySerious Sokka]] up
* Heffer from ''WesternAnimation/RockosModernLife'' does a ridiculously exaggerated grin when he is about to film Rocko naked without permission. "He's COMPLETELY...[[CheshireCatGrin NAAAKEEED!]]"
* ''WesternAnimation/GravityFalls'': [[EldritchAbomination Bill Cipher]]'s [[DemonicPossession possession of Dipper]] (a.k.a. Bipper) has this is his default expression.
* Muttley will usually do this to the camera [[WesternAnimation/WackyRaces on the two shows]] [[WesternAnimation/DastardlyAndMuttleyInTheirFlyingMachines in which he stars]] after he snickers, followed by a Groucho eyebrow waggle.
* ''WesternAnimation/{{Amphibia}}'' has [[AntiVillain Sasha]] give one of these after [[spoiler:she agrees to become Grime's second-in-command]], as this gives her the resources to find Anne and Marcie in addition to creating untold amounts of chaos.

* Creator/TimCurry: Dr. Frank-N-Furter walks on stage with this expression in the ''Film/TheRockyHorrorPictureShow'', and it's his default expression when he's not angry, jealous, megalomaniacal, or begging for sympathy. Similarly in his role in ''Home Alone 2: Lost In New York''. They even segue quite unnervingly from his grin to a still from [[WesternAnimation/HowTheGrinchStoleChristmas the animated version of the Grinch]] -- [[https://gfycat.com/gifs/detail/dazzlingmassivefiddlercrab the resemblance is uncanny]].

Strangely, it's usually done by heroes who have a ZanyScheme in mind, rather than by villains, who tend to prefer the PsychoticSmirk or the SlasherSmile; a rough villanous equivalent would be to [[OminousAdversarialAmusement start laughing ominously]], which is ''not'' a good thing for the hero to hear when cornering them. Heroes and heroines who are slightly eccentric -- [[{{Cloudcuckoolander}} or slightly deranged]] -- favour the Cheshire Cat Grin. If it's an anime, expect a CatSmile instead. Common trait for TheGadFly and serves as a warning that they're going to pull their antics on someone. If this smile is a permanent feature, it's a subtrope of FrozenFace; if it's ''cut into'' the character's face, it's a GlasgowGrin. Shares living space with TheUnSmile. If you ever see someone with the Cheshire Cat Grin in real life, vacate the premises before you can discover what they're smiling about. Or, for that matter, how their face manages to do that.

** Shinji Hirako has an even more classic version of a cheshire cat grin.

** Invoked by Kaede when speaking with "Kunel Sanders", a mysterious, suspicious, and very powerful man who is interested in Negi but refuses to say why. In the end it turns out that he is trustworthy, but he also admits people tend to not believe his smiles.

* [[TheTrickster Irabu]] from ''Literature/{{Trapeze}}'' gets a disconcerting grin on his face whenever he give some kind of devious advice [[StealthMentor in order to help his patients somehow.]]
* Ham Egg from Creator/OsamuTezuka's works is easily indentified for making this grin constantly, which foreshadows his unpleasant and villainous nature.

** Agent Graves rarely displays any sort of emotions but when he does smile its usually means someone is going to be in a world of hurt.

* ''Fanfic/ChildOfTheStorm'' has Doctor Strange wear a habitual slight smile, since everything is pretty much AllAccordingToPlan (excepting the ''Forever Red'' arc of the sequel, when it is very much not). It's one of the things people find both annoying and unsettling about him. However, when he's tap-dancing on the edge of sanity and/or about to pull something spectacular (and usually, terrifying), it widens into something downright manic, with far too much teeth for anyone's comfort.
* ''Fanfic/{{HERZ}}'': Misato wears one in chapter 4 when she hints her plan to prevent Unit 01's deployment in the Congo.

Misato grinned a cheshire cat grin. "I'm not stupid. I just want to know how the hell Rei figured out how to use the Evas to make a phone call. Don't worry, no one eavesdropped on you."

* Creator/TimCurry: Dr. Frank-N-Furter walks on stage with this expression in the ''Film/TheRockyHorrorPictureShow'', and it's his default expression when he's not angry, jealous, megalomanical, or begging for sympathy. Similarly in his role in ''Home Alone 2: Lost In New York''. They even segue quite unnervingly from his grin to a still from [[WesternAnimation/HowTheGrinchStoleChristmas the animated version of the Grinch]] -- the resemblance is uncanny.

** When he first shows up at the SHIELD facility in the beginning, Loki wears a truly ''magnificent'' grin -- one that declares in no uncertain terms that: A) He is not at all sane; and B) Everyone in the vicinity is in [[SlasherSmile terrible trouble]].

* Not quite a Cheshire Cat Grin, but with the same effect in "Bride of Chaotica!" an episode of ''Series/StarTrekVoyager''. The holodeck malfunctions, and someone must go into the program to resolve the issue playing the part of Queen Arachnia. When Captain Janeway asks Tom "Who do you have in mind?" Tom and the rest of the crew turn to her with evil smirks.

** This is one of the Fourth Doctor's [[CharacterTics most famous gimmicks]]. Having wide bulging eyes, a very large and toothy mouth and an egotistical, cheery, terrifyingly sly personality, it is virtually his default expression and forms a big part of his frightening yet oddly charming appearance.

** Hazama/Terumi Yuuki sports several smiles that almost never leave his face, but simply tag each other. His default smile is a Cheshire smile [[EyesAlwaysClosed showing no eyes]], no teeth and no compassion. When his [[PsychoSmirk smile]] ''does'' show his SupernaturalGoldEyes and HellishPupils you better start running, 'cuz it might very well be your last chance at getting away with your life. If his [[SlasherSmile smile shows teeth]], YouAreAlreadyDead.

* ''VideoGame/{{Persona 5}}'': Invoked by your GuardianEntity, the [[DealWithTheDevil demonic]] Arsene, who has a constant grin made of hellish flames plastered across his face. In fact, the highest level of [[CastingAShadow darkness magic]] he uses to kill foes has the same blood red smile of flames inscribed into it.

* Daimon Kiyota of ''VideoGame/TheSecretWorld'' is almost always seen wearing one of these, an impish, all-knowing grin that just screams MagnificentBastard; even the lore entries refer to him as "a Ceshire cat in sharp lapels."

* Most ''VideoGame/{{Touhou}}'' characters have warm and friendly and cheerful smiles, [[DissonantSerenity even when speaking about grim or gory things]]... ''Especially'' when speaking about grim or gory things... [[{{Tanuki}} Mamizou Futatsuiwa]] carries her mischeviousness on her sleeve and lips, though.

* Both Zimmy and Coyote in ''Webcomic/GunnerkriggCourt''. Oddly, the effect of each character's grin is heightened by the fact that they have the wrong sort of teeth for their species: Zimmy has shark-like teeth and Coyote has uniform, flat teeth.

* Gabriel Caine frome ''Webcomic/{{EVIL}}'' has this as [[PerpetualSmiler his default expression]].

* In ''Webcomic/GirlGenius'', "wild" Jagers tend to wear this most of the time: there's so much ''funny'' things to happen -- like plowing through a crowd of monsters -- and they have pointed teeth. Gil grins like that when he is stuffed to the gills with combat stimulants and about to blow up something.

* Subverted/defied with Florence Ambrose in ''Webcomic/{{Freefall}}'' -- her natural smile is a face full of teeth, since she's an anthropomorphic "Bowman's Wolf." She has to remember to smile with her lips closed to avoid this trope -- though she's not above invoking it...
** Occasionally, Sam [[http://freefall.purrsia.com/ff2500/fc02411.htm gets one of these]]. That's rather a lot of teeth for an squid in a suit...

* The infamous {{Troll}}face (now in [[http://img.chan4chan.com/img/2010-08-31/1283265262586.png glorious HD]]). Another {{meme|ticMutation}} that invokes this trope (albeit in a modified {{emoticon}} form, without the toothy grin) is the "[[http://knowyourmeme.com/memes/lenny-face Lenny Face]]," which is often used to [[LampshadedDoubleEntendre lampshade double entendres]] or simply to spam Internet communites for trolling purposes.

** In ''WesternAnimation/YoungJustice,'' Jade has the mask (which isn't in the comics. The previous animated Cheshire made just ''that'' much of an impression in her less than a minute of screentime.) but not the invisibility. She's an assassin for the League of Shadows initially, but is ''far'' from AxCrazy enough to nuke a small country out of existence ForTheEvulz. She also has more than one mask (since one of them currently resides in Kid Flash's trophy case.)

* A favorite expression of [[EnfanteTerrible Heloise]] on ''WesternAnimation/JimmyTwoShoes'', whenever she's not using a full on SlasherSmile.

* [[http://cps-static.rovicorp.com/3/JPG_400/MI0001/461/MI0001461662.jpg?partner=allrovi.com This pic of Love frontman Arthur Lee]], who seems to be preparing to flip the camera man off.

* ''Manga/MahouSenseiNegima'' plays this for comedy; if Haruna starts smiling, something embarrassing and/or unpleasant is about to happen. The other characters are rightfully scared of her.

* Bel from ''Manga/KatekyoHitmanReborn'' tends to have this as his default face, along with making one when he laughs his creepy "Ushishishishi~" laugh.

%%* [[StepfordSmiler Xerxes [[SweetTooth Break]] from ''Manga/PandoraHearts'' has a very typical one. And his doll has exactly the same smile. And, oddly enough, the character ''called'' the Cheshire Cat does not.

--> '''[[TheLoad Tarou]]''': And Yano's smile multiples fear.\\
'''Yano''': *smiling* Does it?\\
'''Tarou''': I'm sorry! I'll watch what I say!
* Seijirou from ''Manga/SangatsuNoLion''. A deadbeat father and ConsumateLiar, this is practically his default expression to emphasize how unsettling he is, and it's the first clear sign to the audience that he's up to no good when he's first introduced as he's meeting up with his daughters several years after abandoning them for his new wife.

* [[{{WebOriginal/Creepypasta}} Smile.jpg]] is easily the most [[NightmareFace terrifying]] example of this trope.

* Yano of ''Anime/{{Shirobako}}'' uses these to encourage lazy subordinates to get to work.
--> '''[[TheLoad Tarou]]''': And Yano's smile multiples fear.
--> '''Yano''': *smiling* Does it?
--> '''Tarou''': I'm sorry! I'll watch what I say!

* Vilmarh Grahrk from the ''Franchise/{{Star Wars|Legends}}: Republic'' comics seems to have one of these on his face [[http://images2.wikia.nocookie.net/starwars/images/b/b4/Vilmarh.jpg all the time]]. Considering his nature, it may be considered a SlasherSmile.
* Agent Graves from ''ComicBook/OneHundredBullets'' rarely displays any sort of emotions but when he does smile its usually means someone is going to be in a world of hurt.

* X-Men team leader ComicBook/{{Cyclops}} [[http://1.bp.blogspot.com/_Gd8NBIma-zo/RzSgt3KLuhI/AAAAAAAABm8/hjnXT6PbLlA/s1600-h/scottLies1.jpg wears one]] right before answering the man's question...[[spoiler: he lied about [[http://2.bp.blogspot.com/_Gd8NBIma-zo/RzSguHKLuiI/AAAAAAAABnE/VsI5SKYySOM/s1600-h/scottLies2.jpg his powers being gone!]]]]
* Loki has this down, especially in his [[Comicbook/JourneyIntoMystery younger]] [[Comicbook/YoungAvengers and]] [[Comicbook/LokiAgentOfAsgard less evil]] iterations, older ones more prone to SlasherSmile. The Asgardian Agent even pulled one combined with the disappearing trick... and nothing but the smile remained.
* When ''Comicbook/{{Supergirl}}'' -then a [[Franchise/GreenLantern Red Lantern]] due to the events of ''ComicBook/RedDaughterOfKrypton''- met her cousin Franchise/{{Superman}} during the events of ''Comicbook/SupermanDoomed'', [[http://www.comicbookresources.com/imgsrv/preview/0/0/1/AC-33-6-8fb7d.jpg she had a huge and disturbingly wicked grin]].
* Franchise/{{Superman}}:
** ''Comicbook/KryptoniteNevermore'': The Devil's Harp displays a wicked, wide grin when its master uses it. It's very eerie.
** In ''Comicbook/WarWorld'', alien overlord Mongul displays a huge, smug, supercilious grin when he implies he is leading Franchise/{{Superman}} to a battle against Comicbook/MartianManhunter.

** In [[https://garfield.com/comic/1983/08/03 this]] comic strip, Garfield tormented Jon by Cheshire cat grinning in the dark.

** In [[https://garfield.com/comic/1979/08/29 another]] early strip, Jon wakes up to see Garfield grinning widely at him. "Oh, great," he says to himself. "Garfield ate my toothpaste again..."
** [[https://garfield.com/comic/1980/04/11 Another strip]] had him entering a room where Jon was with a huge, toothy smile and shifty eyes for no apparent reason. Jon, annoyed, asked: "All right, Garfield - what have you done?" Garfield of course remained silent, prompting Jon to keep demanding what he had done until he finally snaps and starts screaming: "WHAT HAVE YOU DONE?! WHAT HAVE YOU DONE?!" ([[ParanoiaGambit Garfield hasn't done anything]].)

* ''{{ComicStrip/Dilbert}}'': Catbert gives two of these [[http://www.dilbert.com/strips/comic/2001-03-04/ in one strip]], though his clueless victim doesn't quite get the message.

* In the ''Literature/{{Brotherband}}'' book ''The Hunters'', the author describes Thorn's smile as unpleasant when the ''Heron'' puts ashore early and he prepares [[DrillSergeantNasty to whip the crew into shape]].

** Strangely enough, the gentle, unassuming, {{adorkable}} Fifth Doctor often wore one of these, especially when talking to people taking him prisoner. He smiled most of the time, in fact, but it very rarely reached his eyes.

-->-- ''FanFic/TheVictorsProject''

-->'''Jon:''' You've been reading "Alice In Wonderland" again, haven't you?\\

** Kokichi Oma from ''VisualNovel/NewDanganRonpaV3'' has a few [[https://vignette.wikia.nocookie.net/danganronpa/images/e/ed/Danganronpa_V3_Bonus_Mode_Kokichi_Oma_Sprite_%2811%29.png/revision/latest?cb=20170929121954 sprites]] that would also fit this description.

* The Weasley twins in ''Literature/HarryPotter'' are noted to do this when they see a new target for mischief, even worse since they do it at the same time.

* The Weasly twins in ''Literature/HarryPotter'' are noted to do this when they see a new target for mischief, even worse since they do it at the same time.

--->'''Website/TelevisionWithoutPity [[http://www.televisionwithoutpity.com/show/doctor_who/the_pandorica_opens_a.php?page=2 recap]]:''' I think part of the actual -- not the endlessly explicit and told-not-shown, but the actual, the perceivable -- charm of River is her lovely smile when she's doing something ''really awful.''

* Theo ''Series/{{Kojak}}'' pulls out one of these at least every couple of episodes.

** In [[http://www.garfield.com/comics/vault.html?yr=1983&addr=830803 this]] comic strip, Garfield tormented Jon by Cheshire cat grinning in the dark.
** In another early strip, Jon wakes up to see Garfield grinning widely at him. "Oh, great," he says to himself. "Garfield ate my toothpaste again..."
** Another strip had him entering a room where Jon was with a huge, toothy smile and shifty eyes for no apparent reason. Jon, annoyed, asked: "All right, Garfield - what have you done?" Garfield of course remained silent, prompting Jon to keep demanding what he had done until he finally snaps and starts screaming: "WHAT HAVE YOU DONE?! WHAT HAVE YOU DONE?!" (Garfield hasn't done anything.)

* In ''FanFic/MegaManDefenderOfTheHumanRace'', Dr. Wily's evil grins are often described in this manner.

* ''VideoGame/Conker's Bad Fur Day'': Of all the characters in the game, Conker himself is by far the most expressive, especially when it comes to the classic toothy grin. A smile that makes him stand out in Rare games. He does this several times as follows: Whenever he is exposed to cash. He also does a quick cheeky grin thinking "See ya!" with a wave as the Gargoyle is about to fall off the bridge. Sometimes when he's idle, he will get out three balls to juggle with, complete with a toothy grin. Another idle animation shows him with a dirty magazine where he's shown grinning away and of course, there's the moment where he chugs down so much beer in one go under a keg, he sports what is the best grin of his in the entire game sprawled across his face as he is totally tanked.