History Main / CheshireCatGrin

The Cheshire Cat Grin is an expression made by TheTrickster 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:

* In the UsefulNotes/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.

** The Amazing Mumbo gives off a rather literal example in "Bunny Raven[[note]] (Or How To Make A Titanimal Disappear)" [[/note]].

** 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 [[Recap/DoctorWho2017CSTwiceUponATime 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]].

* 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.

* Captain Gotoh in the ''Anime/{{Patlabor}}'' manga specializes in these wonderfully awful toothy grins.

* 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).
* ComicBook/{{Loki}} has this down, especially in his [[ComicBook/JourneyIntoMysteryGillen 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.

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

* ''Franchise/{{Superman}}'':
** 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]].

* 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.
* 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!]]]]
* ''Franchise/TheDCU'' rogue [[Characters/TeenTitansCheshire Cheshire]] is famous for her coy and maniac smile, resembling that of a Cheshire Cat. It's how she got her {{Codename}}. She also sometimes wears a [[MalevolentMaskedWoman mask]] that is permanently set into one.

* 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.

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.

* 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.

* 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.]]

** In ''Series/StarTrekDeepSpaceNine'', [[ ManipulativeBastard Garak]] smiling is usually a bad sign for ''someone''.

[[quoteright:350:[[WebAnimation/TheAmazingDigitalCircus https://static.tvtropes.org/pmwiki/pub/images/jax_and_ragatha_3.png]]]]

* ''WebAnimation/TheAmazingDigitalCircus'': [[RascallyRabbit Jax]] (pictured above) is the local trouble maker of the titlar circus, and he almost always has a big satisfied grin on his face.

[[quoteright:319:[[Film/AliceInWonderland2010 https://static.tvtropes.org/pmwiki/pub/images/aiw_cheshire_cat.jpg]]]]
[[caption-width-right:319:Meow.]]

* Alastor from ''WebAnimation/HazbinHotel'' basically has this as his default expression when he's not flashing a SlasherSmile.

* 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''.

* The most recent live-action version of ''Literature/AlicesAdventuresInWonderland'' includes Whoopi Goldberg as the Cheshire Cat, with a suitably wide and manic smile.

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

** In ''Series/StarTrekDeepSpaceNine'', Garak smiling is usually a bad sign for ''someone''.

* ''VideoGame/BlazBlue'':

** 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.

* In ''WesternAnimation/TurningRed'', Abby smiles like this when Mei is on the phone with Ming fooling her into thinking Mei is joining an after school club.

** And [[Creator/ChristopherEccleston Nine]], who does this whenever faced with [[BloodKnight imminent]] [[InHarmsWay danger]], usually while uttering "[[{{Catchphrase}} Fantastic!]]"

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

* 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.

* In the second ''Film/AceVentura'' film, Ace eventually corners the villain while driving what is essentially a monster trunk. And then [[https://www.youtube.com/watch?v=QUajqurXur8 this]] happens.