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* 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."
* ''[[Discworld]]''
** Angua in ''[[
** From ''[[
** "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."
* Ford Prefect from ''[[The Hitchhiker's Guide to the Galaxy]]'' is said in the first book to smile in this way, "a little too broadly, giving people the unnerving impression he was about to go for their neck."
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* Shadowchild from ''[[Digger]]'' has smiled like this twice. Both times it went badly for the other guy.
* George from ''[[Johnny Wander]]'' 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 ''[[Girl Genius]]'', "wild" Jagers tend to wear this most of the time: there's so much ''funny'' things to
** [[Mad Scientist|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 ''[https://web.archive.org/web/20140218141836/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, [[Magnificent Bastard|which is all the damn time]].
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* The Grinch in [[Chuck Jones]]' screen adaptation of ''[[How the Grinch Stole Christmas! (animation)|How the Grinch Stole Christmas]]'' when he gets the wonderful, awful idea to... well, steal Christmas.
** This could be arguably [[Chuck Jones]]' [[Signature Style]], when he directed ''[[Tom and Jerry]]'', both characters would smile in the exact same manner when they hit upon a new scheme. As well as the poor schmuck in ''[[One Froggy Evening]]''.
* ''[[Courage the Cowardly Dog]]'': "My name is Fred and I've been very... naughty".
* In the penultimate episode of ''[[Teen Titans (animation)|Teen Titans]]'', 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 ''[[Alice in Wonderland]]''.
** She's in [[Teen Titans (Comic Book)|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]]).
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* Snoopy in ''[[The Charlie Brown and Snoopy Show]]'' does this once, complete with the ability to vanish.
** He has this in the original ''[[Peanuts]]'' comic as well; he calls it his "Cheshire Beagle" trick. He does it a handful of times over the course of the strip.
* A favorite expression of [[Enfante Terrible|Heloise]] on ''[[Jimmy Two-
* The animated [[Beetlejuice (animation)|Beetlejuice]] often grins broadly when scheming. Bonus points for the unsettlingness of [[British Teeth|his gross green teeth]], complete with half-chewed bug bits.
* Henry and June (the latter more often) do this in ''[[KaBlam!]]!''
* Twilight Sparkle of ''[[My Little Pony:
* T-Bone from [[Swat Kats]] donned this grin occasionally, almost uniquely amongst the characters of that series.
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* 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''. [[Fluffy the Terrible|Mister Peanutpants]] does not want to be your friend, kids.
* 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.
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