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 The Trickster 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:
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. Common trait for The Gad Fly 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 Frozen Face; if it's cut into the character's face, it's a Glasgow Grin. Shares living space with The Un-Smile. 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.
Although Alice's Adventures in Wonderland is considered the Trope Namer, the term "grin like a Cheshire cat" was actually common in Britain during Lewis Carroll's time. The origin is uncertain; the most likely sources are some Cheshire cheeses that were molded into the shape of smiling cats, and a famous inn in Cheshire that had a painted grinning lion on the door.
- Legendary schemer and thief, Lupin III, has a smile, when not showing teeth, that is more of a Cat Smile, but when he shows teeth and does the raised eyebrow, it's pure Cheshire Cat Grin.
- 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 does Gengar actually frown.
- 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." Here, have a look.
- Washu of Tenchi Muyo!, usually right before she's about to stuff Tenchi into some machine or another.
- Kisuke Urahara, particularly before unleashing one of his training regimes on someone.
- Shinji Hirako has an even more classic version of a cheshire cat grin.
- This is Ichimaru Gin's near-permanent expression.
- Kenpachi actually does this when he gets to fight a strong opponent. According to Yachiru it means he's having a lot of fun.
- Ichihara Yuko from Xxx HO Li C 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 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."
- 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.
- Invoked by Kaede when speaking with "Kunel Sanders", a mysterious, suspicious, and very powerful man who is interested in Negi but refuses to say why. In the end it turns out that he is trustworthy, but he also admits people tend to not believe his smiles.
- Higurashi: When They Cry has a few characters sport these. Most of the time it's either 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.
- 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. She's usually teasing with it, instead of plotting things with bad consequences.
- Hikaru and Kaoru from Ouran High School Host Club when up to mischief, usually at Haruhi's expense.
- 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 Katekyō 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. May actually be more malevolent, as we don't know much about her. The fact that now that she's not The Faceless we see her smile doesn't reach her eyes isn't good.
- Lots of the eponymous Titans of Attack on Titan sport unnerving grins, even when they logically should be in pain. For some these cross the boundary into Glasgow Grin because of the fact they're missing bits of skin.
- Roronoa Zoro from One Piece, whenever he's not sleeping or eating. Also, Urouge.
- This is basically Gold Roger's default expression.
- 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:The Gold-Tooth Alchemist often wore 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.
Shinji: This is really bad! We've got to go back and find Misato!
Asuka: (looks sideways and grins) Wunderbär!
- 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.
- Asuka pulled one off in her debut episode when Gaghiel attacked the UN fleet carrying her Eva.
- 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 artificial origin, Supernatural Gold Eyes and his desire to spark the world to eternal war it's quite creepy. It will occasionally flicker into Slasher Smile territory, especially towards the end of the series.
- Captain Gotoh in the Patlabor manga specializes in these wonderfully awful toothy grins.
- Lain's alter-ego from Serial Experiments Lain does this constantly.
- Drosselmeyer from Princess Tutu is always sporting one.
- Neferpitou from Hunter × Hunter is almost never seen without his (cat) smile. It doesn't help that he has a deadly and terrifying Battle Aura and permanent creepy eyes.
- Kawarino from Yes! Pretty Cure 5, especially in his human form with Eyes Always Shut. And you don't want to see any other of his facial expressions.
- Puella Magi Madoka Magica brings us Charlotte's One Winged Angel form right before ''that'' scene.
- Dragon Ball
- Goku as a kid in often gave these kinds of smiles when he was up to something especially mischievous.
- Krilin also gives Cheshire Cat Grins when he's thinking up a dirty plan or find something funny at someone's else expense; mostly Goku and Vegeta.
- Yano of Shirobako uses these to encourage lazy subordinates to get to work.
Tarou: And Yano's smile multiples fear.Yano: *smiling* Does it?Tarou: I'm sorry! I'll watch what I say!
- Seijirou from 3-gatsu no Lion. A deadbeat father and Consumate Liar, this is practically his default expression to emphasize how unsettling he is, and it's the first clear sign to the audience that he's up to no good when he's first introduced as he's meeting up with his daughters several years after abandoning them for his new wife.
- 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.
- 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).
- X-Men team leader Cyclops wears one◊ right before answering the man's question... he lied about his powers being gone!◊
- Loki has this down, especially in his younger and less evil iterations, older ones more prone to Slasher Smile. The Asgardian Agent even pulled one combined with the disappearing trick... and nothing but the smile remained.
- When Supergirl -then a Red Lantern due to the events of Red Daughter of Krypton- met her cousin Superman during the events of Superman: Doomed, she had a huge and disturbingly wicked grin◊.
- In this comic strip, Garfield tormented Jon by Cheshire cat grinning in the dark.
- 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..."
- 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?!" (Garfield hasn't done anything.)
Garfield: I love mental games.
- 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:
"Hmm... mischief... danger...trouble... malevolence... discord... pandemonium... TOTAL CHAOS... MASS CONFUSION!"
- Dilbert: Catbert gives two of these in one strip, though his clueless victim doesn't quite get the message.
- TJ from Luann has this as his default expression. The near-permanent grin indicates his shifty High School Hustler nature, and it takes a lot to wipe it off his face.
- 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 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!" He calls it his "Cheshire Beagle" trick.
- There is a week of strips where he does it again, but got Mode Locked into invisibility, visible only by a toothy Cheshire Cat Frown. Lucy solves the problem — by Percussive Maintenance.
- A Crown of Stars: Jinnai grinned in a very disturbing, creepy way, and his eyes glittered feverishly as he told Shinji and Asuka he personally executed a traitor.
- Calvin wears one for a while before the introduction of the Time Pauser in Calvin and Hobbes: The Series.
- Evangelion 303: Before the Unit-04 flight test Asuka and Jessika wore huge predatory grins. They were quite scary.
- HERZ: Misato wears one in chapter 4 when she hints her plan to prevent Unit 01's deployment in the Congo.
- Last Child of Krypton: In chapter 11, Misato grinned widely and wickedly after catching Asuka flat-footed.
"You really did silence me before the blackout, right?"
"Yes," said Misato. "No one heard you swear your undying love, I promise."
"Good, I- hey, wait!"
Misato grinned a cheshire cat grin. "I'm not stupid. I just want to know how the hell Rei figured out how to use the Evas to make a phone call. Don't worry, no one eavesdropped on you."
- In Mega Man: Defender of the Human Race, Dr. Wily's evil grins are often described in this manner.
- In Thousand Shinji, Rei grins wickedly as she explains how she killed Armisael.
Rei says before letting a feral grin escape from her suppressed face.
- In The Second Try, when Gendo demands knowledge of the future, Shinji grins coldly and maniacally before replying that hell die.
- In X-Men: The Early Years Jean Grey smiles very beautifully and scarily before telling her teammates that spying on her again will not be tolerated.
"Pizza would be great," Jean said, while the other three boys tried to look innocent. "I just came to see what you four were up to since you seem to hang out here on Friday nights, and none of you has ever thought to invite me." Jean grinned slyly as she grabbed a piece of pizza out of the box. "So you guys are up here talking guy talk about stalkers and other strange thing that I, as a woman, should not be party to?" The guys just nodded. Her grin grew. "Well, that's nice to know. And if I ever catch the four of you spying on me again, you'll wish tossing your cookies is the only thing I'll do to you, do you understand?" The four of them just nodded again.
- In the Fairy Tail fanfic Wonderland where Natsu and Lucy get teleported to an Alternate Universe called Wonderland where there are counterparts of the canon characters, who better to have the Cheshire Cat Grin then the Wonderland Happy.
- Jack Skellington from The Nightmare Before Christmas has this mixed with Slasher Smile as his default smile. Sally gets a good one◊ when she tricks the doctor into eating the poisoned soup.
- The cat bus◊ from My Neighbor Totoro is a spitting image of the Cheshire Cat.
- Totoro himself smiles like this when he is happy or delighted by something.
- In the second Ace Ventura film, Ace eventually corners the villain while driving what is essentially a monster trunk. And then this happens.
- 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 Bueller's 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.
- Tim Curry: Dr. Frank-N-Furter walks on stage with this expression in the The Rocky Horror Picture Show, and it's his default expression when he's not angry, jealous, megalomanical, or begging for sympathy. 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.
- Rather fittingly, Curry is from Cheshire, and has gotten nicknamed "the Cheshire Cat" in real life.
- Equilibrium: 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 realize 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's Adventures in Wonderland includes Whoopi Goldberg as the Cheshire Cat, with a suitably wide and manic smile.
- The Tim Burton version of Alice in Wonderland (2010) does not disappoint◊.
- In The Avengers:
Cap: [having just told everyone else what to do, in detail, looks to Hulk] Hulk?
- The Hulk gives a great one (with a side of Slasher Smile) when Captain America is giving the heroes their assignments:
Hulk: [looks down at him]
Cap: [points up at the Chitauri invaders] Smash.
- When he first shows up at the SHIELD facility in the beginning, Loki wears a truly magnificent grin — one that declares in no uncertain terms that: A) He is not at all sane; and B) Everyone in the vicinity is in terrible trouble.
- 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.
- James Bond in Goldfinger, as he prepares to trick a guard into thinking that he's escaped from his prison cell.
- Little Shop of Horrors: The small Audrey II. In the Focus Group Ending theatrical cut, it's just a Punch Line "The End... Or Is It?". In the Director's Cut, it's a nasty I Shall Taunt You.
- The Trope Namer is the Cheshire Cat◊, from Alice's Adventures in Wonderland. He's a mischievous 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.
- 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."
- 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."
- Similarly, Vimes is once noted to have a grin like the one that's pointed at swimmers and has a fin on top.
- Ford Prefect from The Hitchhiker's Guide to the Galaxy is said 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. Chuck Jones turned it Up to Eleven (see Western Animation below).
- Artemis Fowl has Artemis' signature vampire smile. It's just as creepy as it sounds.
- Marunde in Someone Else's War wears one of these, though the narrator calls it a "crocodile grin."
- Treecats in Honor Harrington can apparently pull this off masterfully. Given their propensity for mischief, it's highly appropriate.
Capt. Jacquelyn Harmon: I've always figured Carroll must have met a treecat in an opium dream or something when he invented the Cheshire Cat.
- The Weasly twins in Harry Potter are noted to do this when they see a new target for mischief, even worse since they do it at the same time.
- In Dragon Blood, there is Oreg, who likes to show his teeth when there is danger someone might underestimate him. He looks relatively harmless if he wants to, but 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.
- Grey from Knights of the Borrowed Dark has one as his default, which frequently appears at completely inappropriate times. The results range from quirky and memorable to extremely unsettling.
You couldn't be in the army with a smile like that. The man smiled like a cat burglar.
- Aech in Ready Player One is described as having a "Cheshire cat grin", the phrase occurring multiple times (to the point that it becomes an authorial tic).
- Dr. Phlox in Star Trek: Enterprise does this in the pilot. Season 4 reveals that his species are capable of 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 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.
- In Star Trek: Deep Space Nine, Garak smiling is usually a bad sign for someone.
- 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:
- 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".
- This is one of the Fourth Doctor's most famous gimmicks. Having wide bulging eyes, a very large and toothy mouth and an egotistical, cheery, terrifyingly sly personality, it is virtually his default expression and forms a big part of his frightening yet oddly charming appearance.
- And the Tenth.
- And Nine, who does this whenever faced with imminent danger, usually while uttering "Fantastic!"
- And John Simm as The Master. "What this country needs... is a Doctor.◊"
- Speaking of the Fourth Doctor, Romana II is known for her charming, brilliant grin, too. Especially when doing and/or saying something clever. Which she does a lot.
- River Song is fond of it, too.
- The Sixth Doctor does one in his opening credits.
- The Eleventh Doctor tends to wear one when he's being extremely clever◊.
- 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.
- Lampshaded by Jon Culshaw in Doctor Who Confidential where he flipped between his Fourth and Tenth Doctor impersonations for the amusement of David Tennant, explaining how the facial expression differs:
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 very little resemblance to an actual smile, overlapping heavily with The Unsmile.
- Surprisingly, considering her generally affable and sweet demeanor, the Thirteenth Doctor has a huge penchant for these kinds of wide, vaguely menacing smiles when confronting and taunting her enemies, especially when she's alone with them.
- 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:
Lister: All we need's a battering ram. Something, say, 6 foot tall, fairly sturdy, with a flat top.
(everyone grins at Kryten)
- Terminator: 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.
- Babylon 5: Mr. Morden will give you a big jovial-looking smile, just as he's about to screw you and your entire species over.
- Sister Julienne of Call the Midwife, nun-in-charge of Nonnatus House, has one, which she usually deploys right after she has "asked" someone to do something. The "or else" is implied.
- Smallville: Tess Mercer's smile is always a sign she's plotting something. Somewhat subverted, in that she does have a genuine smile she can use when happy, and her intentions are always for the greater good, but when plotting, her smile can be downright scary.
- Law & Order: UK. 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 Nice Guy—when the guy whines, "You're hurting me!" as Matt handcuffs him and Matt responds, "Yeah, I know. Didn't that feel good?"
- The Grimmification of Alice's Adventures 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.
- Video Game/Conker's Bad Fur Day: Of all the characters in the game, Conker himself is by far the most expressive, especially when it comes to the classic toothy grin. A smile that makes him stand out in Rare games. He does this several times as follows: Whenever he is exposed to cash. He also does a quick cheeky grin thinking "See ya!" with a wave as the Gargoyle is about to fall off the bridge. Sometimes when he's idle, he will get out three balls to juggle with, complete with a toothy grin. Another idle animation shows him with a dirty magazine where he's shown grinning away and of course, there's the moment where he chugs down so much beer in one go under a keg, he sports what is the best grin of his in the entire game sprawled across his face as he is totally tanked.
- Bendy and the Ink Machine: Cartoon Bendy wears one all the time, and it pushes his cheeks up into his eyes. In his cartoons, he's the Karmic Trickster. 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? Not nearly as nice.
- Bendy in Nightmare Run: 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 the promotional art reveals that he's the one who messed with the bosses in the first place, so....
- Taokaka 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 showing no eyes, no teeth and no compassion. When his smile does show his Supernatural Gold Eyes and Hellish Pupils 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 Are Already Dead.
- The dark/left half of Monokuma's face in Danganronpa is seemingly frozen in this state permanently, combined with Fangs Are Evil. The light/right half is significantly more restrained, but it can be unsettling when the two sides smile together (which is pretty often).
- Donkey Kong gives one in the opening sequence of Donkey Kong Country Returns after Kalimba fails to brainwash him. A No-Holds-Barred Beatdown quickly follows.
- The Legend of Zelda:
- Link's nightmarish Elegy of Emptiness statue in The Legend of Zelda: Majora's Mask. Also the default expression of the Happy Mask Salesman.
- 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.
- The Skull Kid has one plastered on his face almost throughout his entire encounter with Link.
- Billy from Lost smile and strange circus has a gigantic grin on his cat head.
- In the Super Famicom title Monopoly 2, there are four tournament players in each match including the player. Two of these opponents (which include fortune tellers, ventriloquists, and 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 wolverine mascot of Alcatraz Elementary from Nightmare Ned has this.
- 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.
- The Judge in 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.
- Persona 5: Invoked by your Guardian Entity, the demonic Arsene, who has a constant grin made of hellish flames plastered across his face. In fact, the highest level of darkness magic he uses to kill foes has the same blood red smile of flames inscribed into it.
- His master, Joker, has one to match in his All-Out Attack win-pose: tugging on his blood-red gloves while his crimson eyes and Cheshire Cat grin tell the tale of his enemies' defeat.
- Electrode along with Gengar and its relatives, Haunter and Gastly, too.
- Gengar's smile isn't quite so permanent in the Pokémon Mystery Dungeon games. A formerly human Gengar shows not only a Cheshire Cat Grin and Slasher Smile; he frowns quite a bit as well, and even tears up by the time Gardevoir's body is restored.
- Aipom has one that manages to be kind of cute.
- Sableye from Gen III, but it's generally hard to smile pleasantly when you have a mouthful of sharp teeth.
- In Pokémon Colosseum, Wes sports one of these when he's blowing up Team Snagem's base at the start of the game and whenever he's riding his Cool Bike.
- Daimon Kiyota of The Secret World is almost always seen wearing one of these, an impish, all-knowing grin that just screams Magnificent Bastard; even the lore entries refer to him as "a Ceshire cat in sharp lapels."
- Father Vincent of Silent Hill 3 smiles one of these quite a lot.
- Street Fighter:
- Dee Jay smiles because he's an almost always happy dude, but the type of smile he has is this one.
- Adon has a permanent Cheshire Cat grin.
- Super Mario Bros.:
- 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, or mutated by the power of a Sealed Evil in a Can into a freaky bug thing, 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. Beyond that, it was more so when he ended up possessing the final boss, though that arguably made his joyful look even more unsettling.
- This is pretty much Jade Curtiss's default expression throughout Tales of the Abyss. He's more often seen as a Stepford Smiler since he's a borderline sociopath with Dark and Troubled Past, but he's also the game's king Troll, and when he's trolling "Cheshire Cat Grin" seems a more appropriate term.
- Most Touhou characters have warm and friendly and cheerful smiles, even when speaking about grim or gory things... Especially when speaking about grim or gory things... Mamizou Futatsuiwa carries her mischeviousness on her sleeve and lips, though.
- Sans from Undertale literally never stops smiling (he is a skeleton, after all), but it's usually a smile you can trust... usually◊.
- In A Witch's Tale, the Cheshire Cat almost always has one of these. Cause he's the Cheshire Cat.
- 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. Then there's Sakura's, which can silence a room and extinguish candles. It makes sense, being sisters.
- Whenever The Cheat from Homestar Runner smiles, it's this kind of smile. Things often backfire on him, though.
- Pinkie Pie in the Pony Video "We're Going for a Ride" gives off one of these, and turns it Up to Eleven by turning the entire screen dark and all you can see are her eyes and mouth!
Pinkie Pie: Lock the doors and close the blinds, we're going for a ride!
- Kitty Cheshire from Mattel's web series Ever After High is the daughter of the Cheshire Cat, and inherited the trait of leaving behind her signature grin.
- 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 for their species: Zimmy has shark-like teeth and Coyote has uniform, flat teeth.
- 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 seems to have this as his default expression. His cousin wears a combination of this and Slasher Smile. Like so.
- Following a rather severe conk on the noggin courtesy of a runaway hearse, Rocky's grin has pretty much become an equal rival with his cousin's in terms of Slasher Smile-ness.
- Vayandil and Gheralf's doppelgängers in Realm Of Owls grin all the time, except without teeth, because they are owls.
- Smiling Man from User Friendly smiles all the time, but sometimes it gets even worse.
- Paranatural's Ed does this frequently. Sometimes edging into Slasher Smile territory, particularly when accompanied by phrases such as "You're all gonna die!" Isabel gets in on the act occasionally as well.
- Shadowchild from Digger has smiled like this twice. Both times it went badly for the other guy.
- Niko from Coga Nito is prone to wearing one of these while in her fighting form, Smooth Criminal. It's further enhanced by Smooth Criminal's unnaturally wide mouth and Niko's eccentricity.
- Gabriel Caine frome EVIL has this as his default expression.
- 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.
- Airman Higgs briefly shows a Jager smile when Travek (correctly, it would seem) calls him "General".
- Joey Von Krause from Mortifer is almost always smiling like this, even when you've succeeded in pushing his Berserk Button (Looking under his eyepatch, in case you were wondering). It's later stated that he smiles whenever he's in control of the situation, which is all the damn time.
- Dagre 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...
- Occasionally, Sam gets one of these. That's rather a lot of teeth for an squid in a suit...
- The Whiteboard: Bandit gets one of these when Doc upgrades Bandit's firepower in one game.
- Terezi◊ from Homestuck has this as her default sprite expression.
- Later also pulled by Jasprosesprite^2, as part of her general Cheshire Cat motif. She even does the "everything fades out but the alarming smile" bit.
- Claud Southend of Quantum Vibe pulls an epic one (complete with fade-out) in full trickster spirit in his farewell towards the end of the Luna arc.
- In Pacificators, Cinna Grossul get to bust out a couple awesome ones.
- The typical expression on the face of Dolan.
- The Fox Sister: Often seen on the Kumiho in human form.
- Questionable Content: Penelope vomiting a rainbow mixed with Losing Your Head.
- Karin-dou 4koma: Mifi splits her face with a Cheshire Cat Grin when she catches Elza masturbating, and again when Seren asks her how she knew.
- Several tricksters and fair folk do this in Roommates but the grand master is the Scribble Person/Living Words ( aka the vaguely anthropomorphic personification of the Story) whose hard-to-trust grins can literally spell things like "Sacrifice" or "Tragedy" especially when (s)he is offering deals.
- Visseria: Done by a couple of characters, but Jack in particular pulls off a nice one when convincing a guard to follow him along.
- Canta from Sire sports a terrifying one while creeping on Leif.
- In Off-White, the wolf Sköll does this when asked to bring his dead father figure back to life, showing he's gone insane.
- The mysterious being following Stephen, Nesariel in Autumn Bay sports this nearly all the time.
- In Namesake Alice Purcell can do this, literally - including vanishing and reappearing somewhere else. It turns out her first trip to Wonderland almost ended at the beginning, and a family of Chashire Cats each gave her one of their lives to save her. They also adopted her.
- The cover page for the first segment of DNA shows the grinning face of Sirius, with a bloody nose and mouth, a missing tooth, and a huge facial bruise. The original version of the cover had an even more pronounced grin, which the artist changed because it made him look too crazy.
- Zebra Girl: The rabbit lady from the Subfusc, Black Betty, has a very unsettling one.
- Champions of Faraus: Hypnolytic spirits have a default expression that looks like this, and it doesn't get any better when they actually do smile.
- 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 infamous Trollface (now in glorious HD◊). Another meme that invokes this trope (albeit in a modified emoticon form, without the toothy grin) is the "Lenny Face," which is often used to lampshade double entendres or simply to spam Internet communites for trolling purposes.
- Doctor Steel's robots all have huge creepy grins.
- In Worm, Tattletale tends to flash one of her vulpine smiles right before she uses whatever information she just got from her powers to screw with people's plans and/or heads.
- 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's Adventures 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).
- The Amazing Mumbo gives off a rather literal example in "Bunny Ravennote .
Mumbo: Tonight, I will make the Titans disappear... (Dramatic Pause) ...forever.
- In Young Justice, 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 Ax-Crazy enough to nuke a small country out of existence For the Evulz. She also has more than one mask (since one of them currently resides in Kid Flash's trophy case.)
- 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 quickly grows in width, as well as tooth size and sharpness, until it's grinning fanged maw as wide her head.
- Played for Laughs on the Dexter's 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.
- The Fairly OddParents!:
- Dr. Bender, the Depraved Dentist, 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.
Mark: What's with the face? It is happy, yet at the same time, disturbing!
- 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. He does it a few other times too, especially when he's being sneaky.
- 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.
- 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 unsettling effect of his gross green teeth, complete with half-chewed bug bits.
- Henry and June (the latter more often) do this in KaBlam!!
- My Little Pony: Friendship Is Magic:
- Twilight Sparkle 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.
- In the two-part episode "The Cutie Map", the Mane Six characters meet a town of monumentally creepy ponies who all have the same Cutie Mark: an equal sign. These ponies sport a manic grin all the time. During a song, two ponies even disappear, leaving the grins to "dance" around the screen for a moment.
- T-Bone from SWAT Kats donned this grin occasionally, almost uniquely amongst the characters of that series.
- More often than not, Mr. Bogus will very often grin like this whether the situation calls for it or not.
- Aang from Avatar: The Last Airbender pulls off a relatively innocent one◊ while planning to wake Sokka up
- Heffer from Rocko's Modern Life does a ridiculously exaggerated grin when he is about to film Rocko naked without permission. "He's COMPLETELY...NAAAKEEED!"
- Gravity Falls: Bill Cipher's possession of Dipper (a.k.a. Bipper) has this is his default expression.
- Muttley will usually do this to the camera on the two shows in which he stars after he snickers, followed by a Groucho eyebrow waggle.
- Amphibia has Sasha give one of these after she agrees to become Grime's second-in-command, as this gives her the resources to find Anne and Marcie in addition to creating untold amounts of chaos.
- Despite the name, this expression more common in canines than felines. When looking at a fox, wolf, dog, etc, any "smile", no matter how toothy, is a sign they do not intend to seriously hurt you. It may even mean they are happy to see you. That does not mean they are planning something you're about to enjoy, however.
- 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.
- The 2012 vice presidential debate became known for Joe Biden giving these repeatedly when Paul Ryan was talking. There was even a mash-up done of them.
- When The Doors arrived in England for their 1968 European tour, a reporter asks Jim Morrison his occupation in the group; Jim just turns to the camera and gives a mischievous smile.
- This pic of Love frontman Arthur Lee, who seems to be preparing to flip the camera man off.
- In the bloopers reel of The Cat in the Hat, there is an outtake at 4:37 in which Sean Hayes gives an endorsement for purple cupcakes. Sadly, his grin gives the appearance of an evil Pee-Wee Herman.