Cheshire Cat Grin



"Kaede: That's a pretty difficult-to-trust smile. Albireo Ku:Nel Sanders: I get told that a lot..."

- Mahou Sensei Negima

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 Trickster who's up to something, and "something" never bodes well for the person he or she is 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) Gilligan Cut 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 Zany Scheme in mind, rather than by villains, who tend to prefer the Psychotic Smirk or the Slasher Smile. Heroes and heroines who are slightly eccentric -- or slightly deranged—favour the Cheshire Cat Grin. If it's an anime, expect a Cat Smile instead. If this smile is a permanent feature, it's a subtrope of Frozen Face; if it's cut into the character's face, it's a Glasgow Grin. 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.

Anime and Manga
"Shinji: This is really bad! We've got to go back and find Misato! Asuka: (looks sideways and grins) Wunderbär!"
 * Lupin's smile, when not showing teeth, is more of a Cat Smile, but when he shows teeth and does the raised eyebrow, it's pure Cheshire Cat Grin.
 * Haruhi Suzumiya does this quite a bit, particularly when sizing up Mikuru for a new outfit, or dragging Kyon into trouble.
 * Gengar, from Pokémon, tends to have either this or a Slasher Smile 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 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."
 * Washu of Tenchi Muyo!!, usually right before she's about to stuff Tenchi into some machine or another.
 * Kisuke Urahara from Bleach, particularly before unleashing one of his training regimes on someone.
 * Shinji Hirako has an even more classic version of a cheshire cat grin.
 * Ichihara Yuko from ×××HOLiC 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 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.
 * Deviant genius Hiruma from Eyeshield 21 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.'
 * Road Kamelot of D Gray Man, several times. Along with some of the AKUMA. Hell, the Earl probably counts as well.
 * Haruko of FLCL, usually when she's about to be entertained, between the Cat Smile and Slasher Smile stages. It's very, very much a bad thing for Haruko to be entertained.
 * Mahou Sensei Negima! 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.
 * Higurashi no Naku Koro ni has a few characters sport these. Most of the time it's either Mion or Satoko, and it usually involves getting Keiichi into a ridiculous outfit, or out of his clothes entirely.
 * In The Big O, Jason Beck sports one.
 * Ed from Cowboy Bebop sports one perpetually, even her little avatar. Very appropriate, given her cat-like nature.
 * Holo from Spice and Wolf does this whenever she's sweet-talking someone (usually Lawrence) into doing what she wants.
 * It's probably a Cat Smile, despite the fact that she's a canine. She's usually teasing with it, not actually plotting things with bad consequences.
 * Hikaru and Kaoru from Ouran High School Host Club.
 * In Black Butler, 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 OVAs? Grelle literally had the Cheshire's smile while playing the Cheshire Cat!
 * Bel from Katekyo Hitman Reborn 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...
 * 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 Slasher Smile.
 * The Kyuubi's face is eternally twisted into a Cheshire Cat Grin.
 * Sumiko from Kekkaishi seems to have one of these as her defining trait, when she was The Faceless it's all we saw of her..
 * Xerxes Break from Pandora Hearts has a very typical one. And his doll has exactly the same smile. And, oddly enough, the character called the Cheshire Cat does not.
 * Roronoa Zoro from One Piece, whenever he's not sleeping or eating. Also, Urouge.
 * Irabu from Trapeze gets a disconcerting grin on his face whenever he give some kind of devious advice in order to help his patients somehow.
 * Ham Egg from Osamu Tezuka's works is easily indentified for making this grin constantly, which foreshadows his unpleasant and villainous nature.
 * Fullmetal Alchemist: Truth usually has a grin that's wider than seems possible when seen and its the only feature other than his body's outline that's readily discernible. The lack of eyes makes it hard to decide what kind of smile it is, though.
 * 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 Slasher Smile territory.
 * Neon Genesis Evangelion: Asuka pulled one off in her debut episode when Gaghiel attacked the UN fleet carrying her Eva.


 * 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 Code Geass pulls these a lot when she's teasing her friends or getting an idea for a School Festival.
 * Hellsing: The Major is noted as having "a detestable grin which would split his cheeks". Combined with his  Eyes of Gold and his desire to spark the world to eternal war it plants him firmly in Nightmare Fuel territory. It will occasionally flicker into Slasher Smile territory, especially towards the end of the series.
 * This is Ichimaru Gin's near permanent experession.
 * Captain Gotoh in the Patlabor manga specializes in these wonderfully awful toothy grins.

Comic Books

 * Vilmarh Grahrk from the Star Wars: Republic comics seems to have one of these on his face all the time. Considering his nature, it may be considered a Slasher Smile.
 * Agent Graves from 100 Bullets 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.
 * The Joker. King of this trope.
 * 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).
 * From X-Factor, the anti-mutant militant hate group The Right had mooks with Powered Armor with big grins painted on the faces of the helmets, presumably intended as psychological warfare.

Film
"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 * Smash. Hulk: >:D"
 * Jack Skellington from The Nightmare Before Christmas has this mixed with Slasher Smile as his default smile. Sally [[media:Sally cheshire cat grin 6839.jpg|gets a good one]] when she tricks the doctor into eating the poisoned soup.
 * The Machinist: Ivan does a particularly disturbing rendition of this trope.
 * Pirates of the Caribbean: 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 Ferris Buellers Day Off 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!!!: At 9:11.. Unless we count this as Slasher Smile.
 * Thank you very much for the Nightmare Fuel...
 * Dr. Frank-N-Furter walks on stage with this expression in the Rocky Horror Picture Show, 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 Tim Curry.
 * Similarly in his role in Home Alone 2: Lost In New York. They even segue quite unnervingly from his grin to a still from the animated version of the Grinch—the resemblance is uncanny.
 * Equilibrium's Cleric Brandt has a smile which first inspires Fridge Logic when you realise that he's not supposed to have any emotion, then Fridge Brilliance 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.
 * Zero Mostel as Pseudolus delivers one of these to Jack Gilford's Hysterium in A Funny Thing Happened on the Way to the Forum. 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.
 * ''A Fistful of Dynamite's John Mallory is fond of this, especially when he's toying with Juan Miranda.
 * A general movie axiom - if James Coburn grins, run away.
 * The most recent live-action version of Alice in Wonderland includes Whoopi Goldberg as the Cheshire Cat, with a suitably wide and manic smile.
 * The Tim Burton version of Alice in Wonderland does not disappoint. GAH.
 * The Hulk gives a great one (with a side of Slasher Smile) in The Avengers, when Captain America is giving the heroes their assignments:


 * The movie version of How the Grinch Stole Christmas also has the scene where the Grinch grins at his "wonderful, awful idea", except also the Slasher Smile 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.

Literature

 * The Trope Namer is the Cheshire Cat, from 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 Trope Maker, because most of its incarnations stem from the Sir John Tenniel's 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."
 * Discworld
 * Angua in Feet of Clay 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 Wyrd Sisters: "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."
 * 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."
 * Some girls have wonderful smiles. Then there's Kouma of The Longing of Shiina Ryo.
 * In How the Grinch Stole Christmas, the Grinch gets one when he thinks up his "wonderful, awful idea" to steal Christmas from the Whos.
 * Marunde in Someone Else's War wears one of these, though the narrator calls it a "crocodile grin."

Live-Action TV
"Television Without Pity 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."
 * Dr. Phlox from the pilot episode of Star Trek: Enterprise. Somehow his head avoids self-decapitation.
 * Not quite a Cheshire Cat Grin, but with the same effect in "Bride of Chaotica!" an episode of Star Trek: Voyager. 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 Kojak pulls out one of these at least every couple of episodes.
 * Doctor Who: The Fourth Doctor. And the Tenth. Well okay, and Nine. And John Simm as The Master. "What this country needs... is a Doctor."
 * River Song is fond of it, too.

"Lister: All we need's a battering ram. Something, say, 6 foot tall, fairly sturdy, with a flat top. (everyone grins at Kryten)"
 * The Sixth Doctor does one in his opening credits.
 * 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 Eighth Doctor Adventures 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 Nice Guy under the somewhat sleazy exterior and it doesn't tend to mean he's really up to anything all that bad.
 * Vala in Stargate SG-1 has a grin that shows a lot of teeth and can be deeply disconcerting.
 * Michael Westen from Burn Notice does this a lot. His smile will eat your soul.
 * Judge Frasier did this all the time on This Is Wonderland.
 * Red Dwarf:


 * The Sarah Connor Chronicles: Because of 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 Sanctuary.
 * Kamen Rider Fourze 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 Butt Monkey JK into piloting a mecha known as the Power Dizer.
 * Justified has Detroit mob lieutenant Robert Quarles, who has a big, unsettling smile.

Newspaper Comics
""Hmm... mischief... danger...trouble... malevolence... discord... pandemonium... TOTAL CHAOS... MASS CONFUSION!""
 * Garfield
 * In one early strip, Garfield tormented Jon by Cheshire cat grinning in the dark. Jon turns on the light and asks if he's been reading Alice in Wonderland again.
 * 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..."
 * One Beetle Bailey 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 Practical Joke Beetle had set up (in fact, there wasn't one).
 * In one Calvin and Hobbes arc, when Calvin notices Susie left her dolls outside while she had lunch, Calvin makes one and says "That gives me a brilliant idea!"
 * The Boondocks has a strip with a truly evil grin spreading across Riley's face as his inner monologue contemplates an unspecified act of mayhem:


 * Dilbert: Catbert gives two of these in one strip, though his clueless victim doesn't quite get the message.
 * TJ from Luann. Other than the permanent grin, he's actually a pretty regular guy.
 * When FoxTrot parodied How the Grinch Stole Christmas, 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 Peanuts strips: Snoopy is listening to Linus read the chapter of Alice's Adventures in Wonderland 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!"

Theater

 * Done superbly in the David Tennant version of Hamlet. "O villain! Smiling, damned villain...", saying this all while sporting a spine-chilling smile. We know his sanity is long, long gone.

Video Games

 * In The Legend of Zelda: Twilight Princess, Midna makes quite a few of these(in her imp form). Especially whenever she hits a turning point in her quest to overthrow Zant.
 * Eh, I'd be inclined to say she goes full-on Slasher Smile at least twice.
 * Link's nightmarish Elegy of Emptiness statue in Majora's Mask.
 * Father Vincent of Silent Hill 3 smiles one of these quite a lot.
 * Gengar from Pokémon 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 Pokémon Mystery Dungeon games. A Gengar shows not only a Cheshire Cat Grin and Slasher Smile; he frowns quite a bit as well, and even tears up
 * We also have Sableye from Gen III, but it's generally hard to smile pleasantly when you have a mouthful of sharp teeth.
 * Tohsaka in Fate Stay Night 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.
 * Mario & Luigi: 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,, he always has a giant toothy grin on his face.
 * Super Paper Mario: 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.
 * Taokaka of BlazBlue typically makes this face whenever she wants to "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 with closed eyes, yet with no reassuring kindness in the expression. When his smile shows his Eyes of Gold you better start running, 'cuz it might very well be your last chance at getting away with your life. If his smile shows teeth, you're already dead.
 * Dee Jay from Street Fighter smiles because he's an almost always happy dude, but the type of smile he has is this one.
 * In A Witch's Tale, the Cheshire Cat almost always has one of these. Cause he's the Cheshire Cat.
 * The Grimmification of Alice in Wonderland, American McGee's Alice, naturally stars the Cheshire Cat, albeit a much more insane and macabre version of him. His Cheshire Cat Grin also has bit of Slasher Smile.
 * Travis Touchdown of No More Heroes, particularly whenever he enters a fight while in a good mood. The loading screen for the second game even shows a small picture of him sporting one.

Web Animation

 * Whenever The Cheat from Homestar Runner smiles, it's this kind of smile. Things often backfire on him, though.

Web Comics

 * Both Zimmy and Coyote in Gunnerkrigg Court. 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 Jack's smile.
 * Jack outdoes himself in this strip.
 * Tedd from El Goonish Shive has been seen with one of these from time to time, generally when there's a noteworthy bit of Author Appeal.
 * The Mad Scientist in Books Don't Work Here 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 Lackadaisy Cats seems to have this as his default expression. His cousin wears a combination of this and Slasher Smile. Like so.
 * Smiling Man from User Friendly smiles all the time, but sometimes it gets even worse.
 * 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. 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 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.
 * 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 Mortifer is almost always smiling like this, even when you've succeeded in pushing his Berserk Button . It's later stated that he smiles whenever he's in control of the situation, which is all the damn time.
 * from The Meek sports one...kind of. It's more of his jowls drooping, giving an absolutely terrifying grin appearance.
 * Subverted/defied with Florence Ambrose in 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...
 * The Whiteboard: Bandit gets one of these when Doc upgrades Bandit's firepower in one game.
 * [[media:gallowsCalibrator 5783.gif|Terezi]] from Homestuck has this as her default sprite expression.
 * Pandora from Dangerously Chloe - a succubus from Chloe's class who isn't malicious at all, but loves mischief and messing with people and happily and unceremoniously throws herself into everything she does. As a result, she wears gleeful grins about half of the time.

Web Original

 * In Ruby Quest, 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 glorious HD).
 * Doctor Steel's robots all have huge creepy grins.

Western Animation
"Mark: What's with the face? It is happy, yet at the same time, disturbing!"
 * The Grinch in Chuck Jones' screen adaptation of 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, 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 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).
 * On The Grim Adventures of Billy & Mandy, 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 Psychotic Smirk and quicky grows in width, as well as tooth size and sharpness, until it's grinning fanged maw as wide her head. Cue Nightmare Fuel. And a change of underwear.
 * Played for Laughs on the Dexters Laboratory sub-series Justice Friends. Major Glory and Valhallen accidentally break the TV while Krunk is watching TV Puppet Pals. They try to unpress his Berserk Button by offering to make up for it. Cue grin.
 * Dr. Bender, the Depraved Dentist from The Fairly OddParents, 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.


 * In the Code Lyoko 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.
 * In the Exo Squad episode "A Traitor Among Us", J.T. gets one of these when he explains his plan for getting The Squad to Venus. "We need to become official undesirables. That's one assignment you troopers might enjoy."
 * 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 Heloise on Jimmy Two Shoes, whenever she's not using a full on Slasher Smile.
 * The animated Beetlejuice often grins broadly when scheming. Bonus points for the unsettlingness of 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 Friendship Is Magic 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 Swat Kats donned this grin occasionally, almost uniquely amongst the characters of that series.

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. 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 logo of Troublemaker Studios.