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* Since Shadow the Hedgehog is supposed to be a darker version of ''VideoGame/SonicTheHedgehog'' (Stalwart of the Sideways Smile), when he isn't scowling, he will occasionally drop one of these.
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* Since Shadow the Hedgehog is supposed to be a darker version of ''VideoGame/SonicTheHedgehog'' ''Franchise/SonicTheHedgehog'' (Stalwart of the Sideways Smile), when he isn't scowling, he will occasionally drop one of these.
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* ''Franchise/DespicableMe'': Being an ex-villain, Gru tends toward this expression rather than the CheshireCatGrin when he's up to something. It's most noticeable in the first film, when he decides to take out the "Space Killer" game at Super Silly Fun Land. The sidelong smirk he flashes just before he draws his plasma blaster would set any sane human who saw it running for the hills.
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* Lila from ''Series/{{Dexter}}'' does this in a RevealingHug with Dexter, having successfully gotten him to [[ManipulativeBastard come to see her]] after he'd previously ignored her phone calls.
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* ''Series/{{Dexter}}''
** Fantastic things are done with lighting to make [[Characters/DexterDexterMorgan Dexter Morgan]] look as much like Light Yagami as possible when he turns on the evil grin.
** Lilafrom ''Series/{{Dexter}}'' does this in a RevealingHug with Dexter, having successfully gotten him to [[ManipulativeBastard come to see her]] after he'd previously ignored her phone calls.
** Fantastic things are done with lighting to make [[Characters/DexterDexterMorgan Dexter Morgan]] look as much like Light Yagami as possible when he turns on the evil grin.
** Lila
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* ''Film/GodzillaVsKong'': [[Characters/MonsterVerseWalterSimmons Walter Simmons]] has a particularly small yet devious one on his face when he enters the control hub, right before the test run begins and [[spoiler:Mechagodzilla in all its frightening glory]] is revealed to the audience and to Team Godzilla (whom Simmons is unaware are watching).
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* ''Film/GodzillaVsKong'': [[Characters/MonsterVerseWalterSimmons [[Characters/MonsterVerseApexCybernetics Apex Cybernetics CEO Walter Simmons]] has a particularly small yet devious one on his face when he enters the control hub, right before the test run begins and [[spoiler:Mechagodzilla in all its frightening glory]] is revealed to the audience and to Team Godzilla (whom Simmons is unaware are watching).
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* ''Series/InterviewWithTheVampire2022'': In "[[Recap/InterviewWithTheVampire2022S1E2AfterThePhantomsOfYourFormerSelf ...After the Phantoms of Your Former Self]]", Lestat de Lioncourt grins while [[SarcasticClapping sarcastically applauding]] at the end of the ''Don Pasquale'' performance because he knows he'll relish [[DisproportionateRetribution tormenting and devouring the tenor whose lousy singing spoiled his date night]].
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[[caption-width-right:350:''"Just as planned."'']]
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* Light from ''Manga/DeathNote''. Three words: "Exactly as planned." One smirk he busts out is so momentous, it's accompanied by a sudden earthquake in the cinematography.
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* Light from ''Manga/DeathNote''. Three words: "Exactly [[CharacterCatchphrase "Just as planned." "]] One smirk he busts out is so momentous, it's accompanied by a sudden earthquake in the cinematography.
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%%
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* Master Contra from ''Neo {{VideoGame/Contra}}''.
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* Master Contra from ''Neo {{VideoGame/Contra}}''.''VideoGame/NeoContra''.
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* ''Literature/ThomasAndFriends'': In "Dirty Work", Diesel smirks in triumph when he succeeds in his plan to have Duck sent away.
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* ''Fanfic/DungeonKeeperAmi'': Ami, like her canon counterpart, is as about a nice a girl as you can get. But occasionally she'll have a really 'good' science related idea or figure out how to get back at a villain in the perfect way. Then a very disturbing smile appears on her face, and it really doesn't help that her eyes glow [[spoiler: red]]
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* ''Fanfic/DungeonKeeperAmi'': Ami, like her canon counterpart, is as about a nice a girl as you can get. But occasionally she'll have a really 'good' science related idea or figure out how to get back at a villain in the perfect way. Then a very disturbing smile appears on her face, and it really doesn't help that her eyes glow [[spoiler: red]]red.]]
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* In ''Fanfic/ManehattansLoneGuardian'', Leviathan describes a photo of Iron Gates--a thief she'd previously fought against, and someone who's part of the BigBad's inner circle--as him having this smile, coupled with a raised eyebrow in a blatant reference to the DreamworksFace. Just looking at it makes her want to destroy the photo.
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* In ''VideoGame/FireEmblemHeroes'', during Book VII, [[spoiler: King Njörðr sports an unsettlingly evil smirk during TheReveal that he set up a trap for Seiðr by turning her beloved Heiðr into a eight-headed snake monster, then forcing her to kill her. [[EvilAllAlong This was all part of his plans]] so that the Golden Curse would trasnfer from Heiðr to Seiðr and that she would become Gullveig, the Golden Seer that she had fought to prevent from being born.]]
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* Creator/MichaelKeaton's version of Batman was prone to doing this: twice in ''Film/Batman1989'' (first when telling one of the muggers [[{{Catchphrase}} "I'm Batman,"]] then again when [[ComicBook/TheJoker Jack Napier]] says "Nice suit.") and once in ''Film/BatmanReturns'' (when strapping the bomb to the strongman).
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* Creator/MichaelKeaton's version of Batman was prone to doing this: twice in ''Film/Batman1989'' (first when telling one of the muggers [[{{Catchphrase}} "I'm Batman,"]] Batman," then again when [[ComicBook/TheJoker Jack Napier]] says "Nice suit.") and once in ''Film/BatmanReturns'' (when strapping the bomb to the strongman).
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* Zsasz displays a very creepy one on his character trophy in VideoGame/BatmanArkhamCity.
* This is the second of [[VideoGame/BlazBlue Hazama's]] three smiles, squeezed in between his unpleasant CheshireCatGrin and monstrous SlasherSmile.
* This is the second of [[VideoGame/BlazBlue Hazama's]] three smiles, squeezed in between his unpleasant CheshireCatGrin and monstrous SlasherSmile.
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* Zsasz displays a very creepy one on his character trophy in VideoGame/BatmanArkhamCity.
''VideoGame/BatmanArkhamCity''.
* ''Franchise/BlazBlue'': This is the second of[[VideoGame/BlazBlue Hazama's]] Hazama's three smiles, squeezed in between his unpleasant CheshireCatGrin and monstrous SlasherSmile.
* ''Franchise/BlazBlue'': This is the second of
