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Mischief Face

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Do people take one look at a character and automatically know that they're up to something? Are they prone to sly smiles, cunning grins, narrowed eyes, often accompanied by shiny gleams of light reflecting suddenly? Do they rub their chin while showing a toothy grin? Is it, in fact, a Grin of Audacity? If so, this character may have a severe case of Mischief Face.
Some character types are prone to this, such as The Gadfly, the Cloud Cuckoolander, and the Insufferable Genius. Book Dumb characters who think they're smarter than they are can also engage in these expressions regularly, particularly if it's their turn to hold the Idiot Ball for the episode.
The Prankster may also sport a mischievous look, though they're much more likely to be successful when they hide their intent rather than have it show in their expression.
If we don't hear what it is they're scheming, then they may well be covered by an Unspoken Plan Guarantee.
But expect others to know that they're up to something, and make the accusation based on their facial expressions.
Of course, for some of the more successful mischief makers, having people aware that they're scheming might not be any sort of hindrance. For some of them, in fact, it might be part of a Batman Gambit, or even a Xanatos Gambit if they're just that good.
The Karmic Trickster is prone to a Mischief Face and is also very likely to succeed in whatever they're scheming, largely because their target has it coming.
They may or may not make any sort of statement about their intended goals.
More malicious or morally ambiguous characters might be noted for having a Cheshire Cat Grin. Commonly seen on many a Smug Snake.
Some characters may not be regular mischief makers but still have their own moments when they don a Mischief Face to indicate that for whatever reason, be it the Idiot Ball or something else plot-specific to a story arc or episode, they're called on to be the one engaged in merry mischief making.
Contrast The Stoic, where someone is capable of hiding their intentions quite well.
See also Troll and Cat Smile, which may overlap. Compare Dreamworks Face.
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In The Far Side, one comic has an anthropomorphic dog asking his students which of them didn't eat their homework on their way to school. The ones who ostensibly did eat their homework are wearing cheeky smiles.
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Looney Tunes: Woe to the villain who provokes Bugs Bunny to his status as Karmic Trickster. He'll give a sly smile, and declare, "Of course you know, this means war." From that point on, a mischievous set of hijinks will ensue to the offender's detriment.
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Campfire Cooking in Another World with My Absurd Skill: When informed that they would be able to obtain high-quality beef from defeating the blood-horned bulls, both Fel and Mukohda share a mischievous look between themselves at the prospect of being able to taste high-quality beef, to the confusion of the guild-master informing them.
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Garfield:
This comic, Jon knows Garfield did something bad when he sees him grin and tries to figure out how big the damage is.
This comic, Garfield plots to steal Jon's lunch, but then Jon ruins it by revealing he lunched early, prompting Garfield to ask Jon what he's supposed to do now with the sneaky expression he already made in anticipation of his mischief.
In this comic Jon again knows Garfield is up to no good because he just keeps smiling. He is proven right when Garfield orders an unseen person to release the anvil.
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BanG Dream!: Moca Aoba often sports a mischievous grin on her face, alerting her band members that she might be up to something. Usually, Moca will settle for playful teasing or Romantic Ribbing, but it is not uncommon for the other members of Afterglow to wonder what she's up to when she starts grinning. A good example is when the band went to the school at night to retrieve Himari's homework and Moca decided it was the perfect time to tell ghost stories.
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Galaxy Quest: The Thermians are being suffocated. The controls that can save them are being guarded by a score of Saris's armed troops. Guy Fleegman tells Fred Kwan and Laliari that he will perform a Heroic Sacrifice, lure the troops away, and allow them to access the controls, saying he's just an expendable extra. Fred stops him, suggesting that he's the Plucky Comic Relief, and then he gets a sly grin on his face and begins chuckling, saying he has a much better idea; teleporting a giant rock monster into the control room to thrash the Mooks.
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M*A*S*H: There was plenty of mischief at the 4077, and plenty of scheming faces to go with it.
Hawkeye and Trapper got away with a great deal, considering they were very bad at hiding their mischievous intent. From the pilot episode:
Frank also had a scheming face, but he was far less successful in his various schemes. Unlike Hawkeye, Trapper, or BJ, Frank was simply too obvious about whatever it was he was up to at any given moment, from trying to have any of them arrested at any given moment to belittling his commanding officers, Frank's scheming and feckless attitude earned him the nickname "Ferret Face."
Interestingly, BJ was very good at hiding his scheming intent. It comes as a shock to Sidney Freedman in "Dear Sigmund" that BJ is the resident prankster who has become a folk hero to everyone in camp. He also skillfully hides his intent when he tricks Hawkeye into taking the blame for a series of pranks involving Maj. Winchester's pants, until Klinger tips Hawkeye off.
The success rate of Klinger's various schemes was inversely proportional to how scheming his face looked at any given moment. For example, he looked downright conniving when he threatened to immolate himself, but Potter was wise to the fact that there was only water in the gas can...until he had Radar swap it out for actual gas, causing Max to run in a panic for the showers. However, he nearly succeeds in getting sent home when he keeps his face neutral and pretends he thinks he's back in Toledo, and only slips up when Potter is about to fill out the Section 8 paperwork and asks him his rank, which Klinger answers out of habit before realizing the trap.
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Arsenic and Old Lace: Shortly after Mortimer and Lorraine are married and return to his family home, Lorraine playfully comments that she doesn't like the look in his eye, and that her father had preached a sermon against it just the Sunday before. Mortimer counters with a grin that that was just on Sundays.
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My-Otome Zwei: Natsuki and Shizuru are spending the day together, ostensibly investigating the remains of a meteorite that was brought down, but mostly relaxing. Shizuru, with a sly smile on her face, comes up behind Natsuki and puts a cold beer bottle against her neck, causing Natsuki to jump at the sudden cold.
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Leverage: Parker is the world's greatest thief. She also has a bit of arrested development and can be something of a Womanchild from time to time. This includes a mischievous grin whenever she gets a notion in her head. One of the earliest examples is in "The Bank Shot Job" when Nate asks her if she's ever robbed a bank while it was already being robbed. You can see the twinkle in her eye as she says, "First time for everything."
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My-HiME has Smug Snake Nagi Homura, who serves as The Dragon. Nagi has the power to control Orphans, often has a sly, smug expression on his face, and has been known to do things either For the Lulz or For the Evulz. In episode 4, for example, an Orphan decides to go Panty Thief and ends up stealing Natsuki's panties, forcing her into a Going Commando situation. When she confronts Nagi about it, having long suspected that he controls the Orphans, he grins mischievously and asks her if she caught a draft on her "cute little bum". She snaps him out of his mischief-making by shooting him point blank and leaving him dangling over the rail. In another episode, he'd send an Orphan out to steal the cake Mai was baking as part of a make-up lesson, expressly for the purpose of stirring up mischief.
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Doctor Who: Several versions of The Doctor, as well as a fair share of companions, have engaged in a bit of telling mischief from time to time.
The Fourth Doctor had a mad grin that made it look like he was perpetually up to something. Of course, he usually was, so there's that. However, if he drops the grin, then he's probably in Tranquil Fury mode.
"The Beast Below", The Doctor seems all too thrilled to find himself in the mouth of the monster, then tells Amy with a grin that he's hitting the "eject button", i.e. he's using the sonic screwdriver to make the monster ill so he'll vomit them out. "Say 'WEEEEEEEE!"
"The Return of Doctor Mysterio": When Doctor Sim tells the Doctor that they'll engage their plan when the time is right, the Doctor gets one of his most mischievous faces ever for this incarnation.
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Hunter × Hunter has resident troll and trickster Killua who alternates between a cat smile and a mischievous expression to highlight his playful nature.
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Pokémon: The Series: In a subplot involving a romantic triangle between Piplup, Oshawott and Meloetta (read: Piplup and Oshawott both want Meloetta's affection), Piplup ends up dancing with Meloetta and gives an impossibly smug face to Oshawott, much to his frustration.
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Teasing Master Takagi-san:
Nishikata always thinks Takagi looks like she's up to something, and she usually is when it comes to teasing him. But while she can and does make mischievous faces from time to time, she's also quite skilled at hiding her intent and putting on a very good poker face (though hers isn't the face of The Stoic, just a neutral smile).
Nishikata, when planning his own efforts to retaliate against Takagi's teasing, will have a scheming or sly expression on his face. Unfortunately for him, Takagi can always spot it and has learned quite handily how to follow his train of thought and plot to use his schemes to her teasing advantage. Unlike Takagi, Nishikata doesn't have a poker face. He shows everything he's thinking very thoroughly.
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How the Grinch Stole Christmas!: When he devises his plan to stop Christmas disguised as Santa, the Grinch breaks into his iconic Cheshire Cat Grin that goes on and on.
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Wander over Yonder: "The Big Day" has Hater preparing to destroy Wander and Sylvia until Wander stops him and asks him if he's going to let it end in such a cheap, unfulfilling fashion. Sylvia asks him what he's doing, until he gives her a smile and a knowing wink, at which point Sylvia realizes that they're doing "a thing". By the end of the episode, Wander and Sylvia have tricked Hater into blowing up his own ship as they, well, wander off.
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