History Main / CheshireCatGrin

** Mentioned in "The Mind of Evil" where the Brigadier snaps at Yates for grinning like a Cheshire cat. Later, the Doctor reminds Yates, when the Brigadier is being especially annoying and it looks like it's going to be 'one of those days', "Cheshire cat, Yates, Cheshire cat".

** 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.

--->'''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 [[https://imgur.com/a/96BmfZV very little resemblance to an actual smile]], overlapping heavily with TheUnsmile. This is thrown into sharp relief during his final episode when he smiles quite genuinely as he thanks his companions for all they meant to him -– [[https://imgur.com/a/gxre3d0 and his face looks COMPLETELY different]].

** 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.

* [[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 identify him as "the one with the teeth."

* ''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.

* [[{{ComicBook/SamAndMaxFreelancePolice}} Sam and Max]] have this trope in spades. Especially Max, whose head may as well be a bear trap.

* In the Fairy Tail fanfic ''Fanfic/{{Wonderland}}'' where Natsu and Lucy get teleported to an AlternateUniverse called [[ThePlace Wonderland]] where there are counterparts of the canon characters, who better to have the Cheshire Cat Grin then the Wonderland Happy.

** [[Comicbook/TheIncredibleHulk The Hulk]] gives a great one (with a side of SlasherSmile) when ComicBook/CaptainAmerica is giving the heroes their assignments:

--->'''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 Judge in ''Videogame/{{OFF}}'' sports a permanent one, with some pretty long fangs to boot. Ironically, he's probably the nicest character in the entire game. Even better, he's actually a cat.
* ''VideoGame/{{Persona 5}}'': Invoked by your FightingSpirit, 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.

* 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.

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

* 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''.

---> '''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.)

[[folder:Light Novels]]

[[/folder]]

[[folder:Literature]]

* 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.

** [[Comicbook/IncredibleHulk The Hulk]] gives a great one (with a side of SlasherSmile) when ComicBook/CaptainAmerica is giving the heroes their assignments:

* Most ''Franchise/TouhouProject'' 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 mischievousness on her sleeve and lips, though.

[[folder:Web Comics]]

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

* In ''Literature/HowTheGrinchStoleChristmas'', the Grinch gets one when he thinks up his "wonderful, awful idea" to steal Christmas from the Whos. Chuck Jones turned it UpToEleven (see Western Animation below).

* Pinkie Pie in the Pony Video [[https://www.youtube.com/watch?v=JSUBuVdkskA "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''!

* [[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."

* 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 mischievousness on her sleeve and lips, though.

* ComicBook/{{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.

* Ham Egg from Creator/OsamuTezuka's works is easily identified for making this grin constantly, which foreshadows his unpleasant and villainous nature.
* 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.

* Vilmarh Grahrk from the ''Franchise/StarWarsLegends: 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.

* 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).
* Franchise/XMen 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!]]]]
* ComicBook/{{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''- meets her cousin during the events of ''ComicBook/SupermanDoomed'', [[http://www.comicbookresources.com/imgsrv/preview/0/0/1/AC-33-6-8fb7d.jpg she sports a huge and disturbingly wicked grin]].

* [[{{ComicBook/SamAndMaxFreelancePolice}} Sam and Max]] have this trope in spades. Especially Max, whose head may as well be a bear trap.

** [[https://www.gocomics.com/garfield/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]].)

* Talk show host/Comedian Creator/JayLeno always seems to have one of these on his face.

** The Twelfth Doctor has a ''really'' scary kind that has [[https://imgur.com/a/96BmfZV very little resemblance to an actual smile]], overlapping heavily with TheUnsmile. This is thrown into sharp relief during his final episode when he smiles quite genuinely as he thanks his companions for all they meant to him – [[https://imgur.com/a/gxre3d0 and his face looks COMPLETELY different]].

* ''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/BendyAndTheInkMachine'': Cartoon Bendy wears one [[PerpetualSmiler all the time,]] and it pushes his cheeks up into his eyes. In his cartoons, he's the KarmicTrickster. This trait carries over into the game's main universe with the dolls, posters, cut-outs, etc. - the cut-outs being the most noteworthy because ''they'' actually ''move.'' Bendy's 3D counterpart's smile? [[SlasherSmile Not nearly as nice.]]
** ''VideoGame/BendyInNightmareRun'': This spin-off takes place in the cartoons' universe, so Bendy keeps his original grin through it - no matter what boss he's running away from or what costume he's wearing. His character profile describes him as having a huge appetite for trouble, and [[AllThereInTheManual the promotional art]] reveals that he's the one who messed with the bosses in the first place, so....

* ''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]].

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 villainous 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.

** [[EverythingsBetterWithMonkeys Aipom]] has one that manages to be kind of cute.

* The titular Burakku (or Black) from the Japanese WebOriginal/{{YouTube}} Animation ''[[https://m.youtube.com/channel/UCXWnW9POrqPuDav-K_rWh0g Burakku Channel]]'' has his mouth [[PerpetualSmiler constantly]] affixed in one of these, regardless of how he actually feels.

* The titular Burakku (or Black) from the Japanese YouTube Animation ''[[https://m.youtube.com/channel/UCXWnW9POrqPuDav-K_rWh0g Burakku Channel]]'' has his mouth [[PerpetualSmilier constantly]] affixed in one of these, regardless of how he actually feels.