History Main / CheshireCatGrin

* Dr. Phlox from the pilot episode of ''Series/StarTrekEnterprise''. Somehow his head avoids self-decapitation.

* [[StepfordSmiler Xer]][[SweetTooth xes]] [[WhiteHairedPrettyBoy Break]] from ''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.

* In ''LupinIII'', Lupin's smile, when not showing teeth, 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.]]

* Vala in ''{{Stargate SG-1}}'' has a grin that shows a lot of teeth and can be deeply disconcerting.
* Michael Westen from ''BurnNotice'' does this a lot. His smile will ''eat your soul.''

* Lots of the eponymous Titans of 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.

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* Trolls in the Franco-Belgian comic ''{{Lanfeust}}'' often make those, usually when they are about to brutally slaughter people or cause heavy property damage (which is most of the time).

* Penelope [[http://questionablecontent.net/view.php?comic=1437 vomiting a rainbow]] mixed with LosingYourHead.

* The Judge in ''Videogame/{{OFF}}'' sports a permanent one. Ironically, he's probably the nicest character in the entire game.

** Not quite so in the first ''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.]]

* 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.

** Eh, I'd be inclined to say she goes full-on SlasherSmile at least twice.

* ''{{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 [[Manga/{{Bleach}} Ichimaru Gin's]] [[PerpetualSmiler near permanent experession]].

* SelfDemonstrating/TheJoker. King of this trope.
** The Joker's is arguably a [[SlasherSmile Slasher Smile.]]

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* [[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. This smile is especially notable when compared to her ''genuine'' smile, which lights up her face like a sunbeam and generally makes everyone around her feel like all is right with the world. (She also has her "reassuring smile", which basically means, "I know things suck right now, but don't worry. We'll get through this together.")

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. 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.