[[quoteright:319:[[Film/AliceInWonderland http://static.tvtropes.org/pmwiki/pub/images/aiw_cheshire_cat.jpg]]]]
[[caption-width-right:319:Eep.]]

->'''Kaede:''' That's a pretty difficult-to-trust smile.\\
'''Ku:Nel Sanders:''' I get told that a lot...
-->-- ''Manga/MahouSenseiNegima''

A smile is supposed to be a reassuring expression, indicating happiness and complete absence of angst and danger. If someone's smiling, it means all is well with the world...

...unless it's a Cheshire Cat Grin, which always denotes that someone's in for it.

The Cheshire Cat Grin is an expression made by a [[{{Tricksters}} Trickster]] who's up to something, and "something" never bodes well for the person they are smiling at. Usually, it involves their total humiliation -- occasionally it involves mortal danger. A typical scenario runs something like this:

->'''Character A:''' Wait, we need someone to dress in a bikini, swim across a river full of piranhas, placate the pride of man-eating lions with the power of dance and steal the sacred ruby out from under Lord Evil's nose? Who's the poor fool who's gotta do all ''that''?\\
'''Character B:''' ''(grins at character A)''\\
''GilliganCut to character A dressed in a bikini swimming across a river full of piranhas to placate the pride of man-eating lions with the power of dance so he can steal the sacred ruby out from under Lord Evil's nose.''

Generally, this is drawn as a smile with far too many teeth on display, where the mouth doesn't match up with the eyes, going practically from ear to ear. For example, the mouth may be a broad grin, but the eyes definitely have a wicked gleam in them. It occasionally has sexual connotations, particularly when there's a predatory quality about the grin.

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. 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.

Although ''Literature/AlicesAdventuresInWonderland'' is considered the TropeNamer, the term "grin like a Cheshire cat" [[OlderThanTheyThink was actually common in Britain]] during Creator/LewisCarroll's time. The origin is uncertain; the most likely sources are some Cheshire cheeses that were molded into the shape of smiling cats, and a famous inn in Cheshire that had a painted grinning lion on the door.

----
!!Examples

[[foldercontrol]]

[[folder:Anime & Manga]]
* 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.]]
* Literature/HaruhiSuzumiya does this quite a bit, particularly when sizing up Mikuru for a new outfit, or dragging Kyon into trouble. [[http://kidrogue42.deviantart.com/art/Cheshire-Cat-Grin-146187042 Here's an example]].
* 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 Gengar actually frowned.
** 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.
* Kisuke Urahara from ''Manga/{{Bleach}}'', particularly before unleashing one of his [[TrainingFromHell training regimes]] on someone.
** Shinji Hirako has an [[http://manga.animea.net/bleach-chapter-184-page-8.html even more classic version of a cheshire cat grin]].
** This is Ichimaru Gin's [[PerpetualSmiler near permanent experession]].
** [[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.
* 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.
* [[TricksterArchetype 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/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.
** 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/HigurashiNoNakuKoroNi'' 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.
* In ''Anime/TheBigO'', [[CardCarryingVillain Jason Beck]] sports one.
* 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.
** Not to mention Ciel. When he fakes a smile, it's adorable. When he gives a real smile... It probably means someone is about to get hurt. Badly.
** And in one of the [=OVA=]s? Grelle literally had the Cheshire's smile while playing the Cheshire Cat!
* Bel from ''Manga/KatekyoHitmanReborn'' 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. [[TechnicallyASmile The fact that now that she's not The Faceless reveals that the smile does NOT reach her eyes is a bad sign]]]].
* [[StepfordSmiler Xer]][[SweetTooth xes]] [[HeroicAlbino 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.
* [[TricksterArchetype 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.
* ''Manga/FullmetalAlchemist'': Truth's grins are the only visible feature on his otherwise blank body and are too wide and large to be physically possible on a human being. The fact that he lacks eyes or eyebrows makes identifying the emotion behind the grin impossible.
** The Gold-Tooth Alchemist echoed this, often wearing 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.
* Milly Ashford of ''Anime/CodeGeass'' pulls these a lot when she's teasing her friends or getting an idea for a SchoolFestival.
* ''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]].]]
[[/folder]]

[[folder:Comic Books]]
* Vilmarh Grahrk from the ''StarWars: 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.
** Topped by Lono, whose presence is often defined by his grin. There are many times throughout the comic where all you can see his smile, shining in the darkness.
* Trolls in the Franco-Belgian comic ''ComicBook/{{Lanfeust}}'' often make those, usually when they are about to brutally slaughter people or cause heavy property damage (which is most of the time).
* 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!]]]]
[[/folder]]

[[folder:Fan Fic]]
* Calvin wears one [[SubvertedTrope for a while]] before the introduction of the [[TimeStandsStill Time Pauser]] in ''Fanfic/CalvinAndHobbesTheSeries''.
* In ''FanFic/MegaManDefenderOfTheHumanRace'', Dr. Wily's evil grins are often described in this manner.
[[/folder]]

[[folder:Films -- Animation]]
* Jack Skellington from ''WesternAnimation/TheNightmareBeforeChristmas'' has this mixed with SlasherSmile as his default smile. Sally [[http://static.tvtropes.org/pmwiki/pub/images/Sally_cheshire_cat_grin_6839.jpg gets a good one]] when she tricks the doctor into eating the poisoned soup.
* The [[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.
[[/folder]]

[[folder:Films -- Live-Action]]
* ''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 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=]!!!'': [[http://www.youtube.com/watch?v=_6NL9m_bS2Y At 9:11.]]. Unless we count this as SlasherSmile.
* 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. No real surprise really, as Cheshire Cat is actually a nickname for the actor Creator/TimCurry.
** 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.
*** Rather fittingly, Creator/TimCurry ''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 realise 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.
* ZeroMostel as Pseudolus delivers one of these to JackGilford's Hysterium in ''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/AliceInWonderland'' includes Whoopi Goldberg as the Cheshire Cat, with a suitably wide and manic smile.
* The Creator/TimBurton version of ''Film/AliceInWonderland'' [[http://materialisticboy.files.wordpress.com/2009/08/alice-in-wonderland-trailer.jpg does not disappoint]].
* In ''Film/TheAvengers'':
** [[Comicbook/IncredibleHulk The Hulk]] gives a great one (with a side of SlasherSmile) when CaptainAmerica is giving the heroes their assignments:
--> '''Cap:''' ''*having just told everyone else what to do, in detail, looks to Hulk*'' Hulk?\\
'''Hulk:''' ''*looks down at him*''\\
'''Cap:''' ''*points up at the Chitauri invaders*'' Smash.\\
'''Hulk:''' >:D
** When he first shows up at the SHIELD facility in the beginning, ComicBook/{{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]].
* The movie version of ''Film/HowTheGrinchStoleChristmas'' also has the scene where the Grinch grins at his "wonderful, awful idea", except also the SlasherSmile one is done in an extremely nasty way during the "You're A Mean One Mr Grinch" musical number, the "You have termites in your smile" line and we are treated to a closeup of his mouth and we see his teeth which have bugs crawling around in them.
* 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.]]

[[/folder]]

[[folder:Literature]]
* The TropeNamer is the [[http://www.ebbemunk.dk/alice/23a_cheshire_cat.jpg Cheshire Cat]], from ''[[Literature/AliceInWonderland Alice's Adventures in Wonderland]]''. He's a mischevious creature, but not malicious to Alice or anyone who doesn't seem to deserve it. He even manages to mock the Queen of Hearts and then fade away before she can retaliate. The character is a play on the phrase "grinning like a Cheshire cat," which simply means smiling broadly. No one is exactly sure where the phrase came from.
** There are several possible explanations, but very little info to support any of them. On another note, the novel might be also a TropeMaker, because most of its incarnations stem from the Sir John Tenniel's [[http://upload.wikimedia.org/wikipedia/commons/thumb/0/07/Cheshire_Cat_Tenniel.jpg/250px-Cheshire_Cat_Tenniel.jpg.png iconic illustrations of the Cheshire Cat]].
* 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."
* ''Literature/{{Discworld}}''
** Angua in ''Discworld/FeetOfClay'' gives a rioter "a friendly smile. That was to say, her mouth was turned up at the corners and all her teeth were visible."
** From ''Discworld/WyrdSisters'': "Greebo's grin gradually faded, until there was nothing left but the cat. This was nearly as spooky as the other way round." Keeping in mind that this is a housecat who rapes wolves and terrifies bears.
** "It was a smile like the one you find on black and orange striped creatures prowling through the jungle looking for someone to smile at."
** Similarly, Vimes is once noted to have a grin like the one pointed at swimmers and has a fin on top.
* Ford Prefect from ''Literature/TheHitchhikersGuideToTheGalaxy1'' is said to smile in this way, "a little too broadly, giving people the unnerving impression he was about to go for their neck."
* Some girls have [[WhenSheSmiles wonderful smiles]]. Then there's Kouma of ''TheLongingOfShiinaRyo''.
* In ''Literature/HowTheGrinchStoleChristmas'', the Grinch gets one when he thinks up his "wonderful, awful idea" to steal Christmas from the Whos.
* ''Literature/ArtemisFowl'' has Artemis' signature vampire smile. It's just as creepy as it sounds.
* Marunde in ''Literature/SomeoneElsesWar'' wears one of these, though the narrator calls it a "crocodile grin."
* 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 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.
[[/folder]]

[[folder:Live-Action TV]]
* 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.
* 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.
* ''Series/DoctorWho'':
** 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.
** And [[Creator/DavidTennant the Tenth]].
** And [[Creator/ChristopherEccleston Nine]], who does this whenever faced with [[BloodKnight imminent]] [[InHarmsWay danger]], usually while uttering "[[{{Catchphrase}} Fantastic!]]"
** And John Simm as TheMaster. "[[http://www.themindrobber.co.uk/doctor-who-season-3/mr-saxon-the-sound-of-drums.jpg What this country needs... is a Doctor.]]"
** Speaking of the Fourth Doctor, Romana II is known for her charming, brilliant grin, too. Especially when doing and/or saying [[https://www.youtube.com/watch?v=rYdg6n4hNps something clever]]. [[ImpossibleGenius Which she does a lot]].
** River Song is fond of it, too.
--->'''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.''
** The Sixth Doctor does one in his [[http://www.youtube.com/watch?v=uUKanwT1elM opening credits]].
** The Eleventh Doctor tends to wear one when [[http://37.media.tumblr.com/tumblr_majcg4FvBz1re8ii2o1_500.jpg he's being extremely clever]].
** 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.
** In the Literature/EighthDoctorAdventures novels, Fitz has been known to smile "with a wicked twist to his mouth that showed far too many teeth", although he's really a very NiceGuy under the somewhat sleazy exterior and it doesn't tend to mean he's really up to anything all ''that'' bad.
** Lampshaded by Creator/JonCulshaw in ''Series/DoctorWhoConfidential'' where he flipped between his Fourth and Tenth Doctor impersonations for the amusement of Creator/DavidTennant, explaining how the facial expression differs:
--->'''Jon''': (''in Fourth Doctor voice, pulling goggle-eyed, grinning face'') Now, with Tom Bakerrr you get ''one'' kind of eyes and teeth... and (''in Tenth Doctor voice, pulling a massively different goggle-eyed, grinning face'') with you, ya get ''anather'' kind af eyes and teeth.
** The Twelfth Doctor has a ''really'' scary kind that has very little resemblance to an actual smile, overlapping heavily with TheUnsmile.
* 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/RedDwarf'':
-->'''Lister:''' All we need's a battering ram. Something, say, 6 foot tall, fairly sturdy, with a flat top.\\
''(everyone grins at Kryten)''
* ''Series/TheSarahConnorChronicles'': [[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.
* Nikola Tesla (as played by Jonathon Young) on ''Series/{{Sanctuary}}''.
* ''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/{{Smallville}}'': Tess Mercer's smile is always a sign she's plotting something. Somewhat subverted, in that she does ave a genuine smile she can use when happy, and her intentions are always for the greater good, but when plotting, her smile can be downright scary.
[[/folder]]

[[folder:Newspaper Comics]]
* ''{{ComicStrip/Garfield}}'':
** 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.)
-->'''Garfield:''' I love mental games.
* 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.
* TJ from ''{{ComicStrip/Luann}}''. Other than the permanent grin, he's actually a pretty regular guy.
* 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.
* Very literal example in one series of ''ComicStrip/{{Peanuts}}'' strips. Snoopy is listening to Linus read the chapter of ''Literature/AlicesAdventuresInWonderland'' where Alice meets the Cat, and then Snoopy grins widely. Linus is shocked when Snoopy disappears, leaving only his grin. Then he reappears, and says, "I've been able to do that for years!"
[[/folder]]

[[folder:Theater]]
* Done superbly in the Creator/DavidTennant version of ''Theatre/{{Hamlet}}''. "O villain! Smiling, damned villain...", saying this all while sporting a spine-chilling smile. We know his sanity is long, long gone.
[[/folder]]

[[folder:Video Games]]
* In the SuperFamicom title ''VideoGame/{{Monopoly}} 2'', there are four tournament players in each match including the player. Two of these opponents (which include fortune tellers, ventriloquists, and [[{{Salaryman}} salarymen]]) are dupes, and one is a smug snake par excellance. Want to know which? Just keep your eye out for this facial expression.
* In ''VideoGame/TheLegendOfZeldaTwilightPrincess'', Midna makes quite a few of these (in her imp form). Especially whenever she hits a turning point in her quest to overthrow Zant.
* Link's nightmarish Elegy of Emptiness statue in ''VideoGame/TheLegendOfZeldaMajorasMask''.
* Father Vincent of ''VideoGame/SilentHill3'' smiles one of these quite a lot.
* The wolverine mascot of Alcatraz Elementary from ''VideoGame/NightmareNed'' has this.
* Gengar from ''Franchise/{{Pokemon}}'' is almost constantly making a Cheshire Cat Grin. In the handheld games from Red and Blue all the way to Platinum, ''every single one of his sprites'' is doing it.
** Not quite so in the first ''VideoGame/PokemonMysteryDungeon'' [[SpinoffSeries games]]. A [[spoiler:formerly human]] Gengar shows not only a Cheshire Cat Grin and SlasherSmile; he frowns quite a bit as well, and even ''[[TearJerker tears up]]'' [[spoiler:by the time Gardevoir's body is restored.]]
** We also have [[http://archives.bulbagarden.net/wiki/File:Sableye_anime.jpg Sableye]] from Gen III, but it's generally hard to smile pleasantly when you have a mouthful of sharp teeth.
* Tohsaka in ''VisualNovel/FateStayNight'' is described as being scariest when she's smiling, because then you ''know'' she is going to get you. Nobody else is ever happy when she smiles.
** That's nothing. Sakura's can silence a room and ''extinguish candles''. [[spoiler:It makes sense. They are sisters, after all.]]
* ''VideoGame/MarioAndLuigi'': Fawful's face seems to be permanently frozen into this expression. Whether he's dropping a giant rock on our heroes, fighting them off in a mech, selling them badges, [[spoiler: or mutated by the power of a SealedEvilInACan into a freaky bug thing]], he always has a giant toothy grin on his face.
* ''VideoGame/SuperPaperMario'': Good ol' Dimentio's mask/face is always curled up into an unnerving smirk. Although, to be fair, he was never even trying to be on the heroes' side to begin with, so no mystery there. [[spoiler: Beyond that, it was more so when he ended up possessing the final boss, though that arguably made his joyful look even more unsettling.]]
* Taokaka of ''VideoGame/BlazBlue'' typically makes this face whenever she wants to [[UnusualEuphemism "play"]] or she's about to attack some poor fool. This being a game that centers on, y'know, ''fighting'', she keeps the expression some 90% of the time.
** 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.
* Dee Jay from ''StreetFighter'' smiles because [[FunPersonified he's an almost always happy dude]], but the type of smile he has is this one.
* In ''VideoGame/AWitchsTale'', the Cheshire Cat almost always has one of these. [[DepartmentOfRedundancyDepartment Cause he's the Cheshire Cat]].
* The {{Grimmification}} of ''Literature/AliceInWonderLand'', ''VideoGame/AmericanMcGeesAlice'', naturally stars the Cheshire Cat, albeit a ''much'' more insane and macabre version of him. His Cheshire Cat Grin also has bit of SlasherSmile.
* Travis Touchdown of ''VideoGame/NoMoreHeroes'', particularly whenever he enters a fight while in a good mood. The loading screen for [[VideoGame/NoMoreHeroes2DesperateStruggle the second game]] even shows a small picture of him sporting one.
* The Judge in ''Videogame/{{OFF}}'' sports a permanent one. Ironically, he's probably the nicest character in the entire game. Even better, he's actually a cat.
* ''VideoGame/{{Touhou}}'' characters have such a warm and cheerful smile, even when speaking grim or gory things. But have you seen some art made by fans with Flandre? Yuuka? Marisa? Reimu? Yukari?
* This is pretty much Jade Curtiss's default expression throughout ''VideoGame/TalesOfTheAbyss''. He's more often seen as a StepfordSmiler since he's a borderline sociopath with DarkAndTroubledPast, but he's also the game's king {{Troll}}, and when he's trolling "Cheshire Cat Grin" seems a more appropriate term.
[[/folder]]

[[folder:Web Animation]]
* Whenever The Cheat from ''WebAnimation/HomestarRunner'' smiles, it's this kind of smile. Things often backfire on him, though.
* Pinkie Pie in the Pony Video "We're Going for a Ride" gives off one of these, and turns it UpToEleven by ''turning the entire screen dark and all you can see are her eyes and mouth''!
-->'''Pinkie Pie:''' Lock the doors and close the blinds, we're going for a ride!
[[/folder]]

[[folder:Web Comics]]
* 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: 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.
* The MadScientist in ''Webcomic/BooksDontWorkHere'' tends to smile like this when he is up to something, and whether it will work or not he always tries to be up to something.
* Rocky, from ''Webcomic/LackadaisyCats'' 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.]]
* 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.]]
* 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.
** [[MadScientist Sparks]] tend to wear a huge grin when they've got an idea. Considering the stuff they usually invent, this is seldom good news for anyone in town.
* 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 an squid in a suit...
* ''Webcomic/TheWhiteboard'': Bandit gets one of these when [[http://www.the-whiteboard.com/autowb129.html Doc upgrades Bandit's firepower]] in one [[PaintballEpisode game]].
* [[http://static.tvtropes.org/pmwiki/pub/images/gallowsCalibrator_5783.gif Terezi]] from ''Webcomic/{{Homestuck}}'' has this as her default sprite expression.
* 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.
* In ''Webcomic/{{Pacificators}}'', [[PlayingWithFire Cinna]] [[FieryRedhead Grossul]] get to bust out a couple [[http://www.sailorenergy.net/MangaPacificators/MangaPacisV03CH01n184.html awesome]] [[http://www.sailorenergy.net/MangaPacificators2/MangaPacisV04n110.html ones]].
* The typical expression on the face of {{Webcomic/Dolan}}.
* ''Webcomic/TheFoxSister'': Often seen on the Kumiho in human form.
* ''Webcomic/QuestionableContent'': Penelope [[http://questionablecontent.net/view.php?comic=1437 vomiting a rainbow]] mixed with LosingYourHead.
* ''Webcomic/{{Karin-dou 4koma}}'': Mifi splits her face with a CheshireCatGrin when she catches Elza masturbating, and again when Seren asks her how she knew.
* Several tricksters and fair folk do this in ''{{Webcomic/Roommates}}'' but the grand master is the Scribble Person/Living Words ([[spoiler: aka the vaguely anthropomorphic personification of the Story]]) whose hard-to-trust grins can literally spell things like "Sacrifice" or "Tragedy" especially when (s)he is offering deals.
* ''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.
* Canta from ''{{Webcomic/Sire}}'' [[http://sire.thewebcomic.com/comics/1958049/chapter-5-page-19/ sports a terrifying one]] while creeping on Leif.
* 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.
* Nesariel in ''Webcomic/AutumnBay'' sports this nearly all the time.
[[/folder]]

[[folder:Web Original]]
* In ''Roleplay/RubyQuest'', Red has one of these for half his appearances. Ruby keeps just managing to miss it when they get particularly freaky.
* The eponymous Trollface (now in [[http://img.chan4chan.com/img/2010-08-31/1283265262586.png glorious HD]]).
* DoctorSteel's robots all have huge creepy grins.
* In ''Literature/{{Worm}}'', Tattletale tends to flash one of her vulpine smiles right before she uses [[TheOmniscient whatever information she just got from her powers]] to screw with people's plans and/or heads.
[[/folder]]

[[folder:Western Animation]]
* 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''.
* ''WesternAnimation/CourageTheCowardlyDog'': "My name is Fred and I've been very...naughty".
* 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/AliceInWonderland''.
** 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 quicky grows in width, as well as tooth size and sharpness, until it's grinning fanged maw ''as wide her head''.
* PlayedForLaughs on the ''WesternAnimation/DextersLaboratory'' sub-series ''Justice Friends''. Major Glory and Valhallen accidentally break the TV while Krunk is watching TV Puppet Pals. They try to unpress his BerserkButton by offering to make up for it. Cue grin.
* Dr. Bender, the DepravedDentist from ''WesternAnimation/TheFairlyOddparents'', and his son Wendell are constantly giving these grins.
** Timmy gets one of these himself, in the episode F.L.A.R.G. Mark sums it up pretty well.
--> '''Mark''': What's with the face? It is happy, yet at the same time, ''disturbing''!
* 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.
** He has this in the original ''ComicStrip/{{Peanuts}}'' comic as well; he calls it his "Cheshire Beagle" trick. He does it a handful of times over the course of the strip. Theres's one plotline where he gets stuck in invisible mode for a while.
* A favorite expression of [[EnfanteTerrible Heloise]] on ''WesternAnimation/JimmyTwoShoes'', whenever she's not using a full on SlasherSmile.
* The animated WesternAnimation/{{Beetlejuice}} often grins broadly when scheming. Bonus points for the unsettlingness of [[BritishTeeth his gross green teeth]], complete with half-chewed bug bits.
* Henry and June (the latter more often) do this in ''WesternAnimation/KaBlam!''
* Twilight Sparkle of ''WesternAnimation/MyLittlePonyFriendshipIsMagic'' pulls one off in "Lesson Zero" when she prepares to create an argument amongst the Cutie Mark Crusaders in a bid to solve the said problem and have a friendship report to write to Princess Celestia.
* T-Bone from ''WesternAnimation/SWATKats'' donned this grin occasionally, almost uniquely amongst the characters of that series.
* 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!]]"
[[/folder]]

[[folder:Real Life]]
* Chimpanzees "smile" by baring their teeth as a way of warning potential challengers that this chimp is not to be messed with. This has led to more than a few people getting mauled, because, hey, the monkey is smiling at 'em! And ain't he just like a little person? Maybe he wants a hug! '''NO.''' When a chimp smiles at you, he's telling you to fuck off. By the way, those teeth? They go for the face. And chimps are ''strong''. [[FluffyTheTerrible Mister Peanutpants]] does not want to be your friend, kids.
** In fact, this is true of many animals, since their teeth are their main weapons. Its meaning is lost for humans because of our greater variety of expressions and because our teeth are puny compared to theirs.
* Former Australian Treasurer Peter Costello was famous for his Parliamentary savaging of his opponents in debate, of which his Cheshire Cat grin would be a prime indicator to get out of the way of his victims.
* Tony Blair was known as the Cheshire cat (then the less favourable "Cheshire twat") since he became leader of the opposition and then prime minister due to his smile.
* The [[http://www.troublemakerstudios.com/ logo]] of Troublemaker Studios.
* The 2012 vice presidential debate became known for Joe Biden giving these repeatedly when Paul Ryan was talking. There was even a [[http://www.businessinsider.com/joe-biden-laughing-through-the-debate-2012-10 mash-up]] done of them.
* When Music/TheDoors arrived in England for their 1968 European tour, a reporter asks Jim Morrison his occupation in the group; Jim just turns to the camera and [[http://www.youtube.com/watch?v=Io85zu9-SSU&feature=relmfu gives a mischievous smile]].
* [[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.
[[/folder]]


-> [[TheStinger ...]]
-> [[{{Beat}} ...]]
-> ''[[Theatre/{{Macbeth}} There's daggers in mens' smiles.]]''

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