History Main / PsychoticSmirk

* Utilized as a game mechanic in ''VideoGame/ShinMegamiTenseiIV'':, where any unit can gain the Smirk status if they score a critical hit or nullify an enemy attack. The following attack will be much more powerful as a result, and the icon for it is depicted as a devilish demon face.

* ''LightNovel/HighSchoolDxD'': [[CombatSadomasochist Akeno Himejima]] [[http://www.mangareader.net/highschool-dxd/1/120 just LOVES to play with her prey.]] The LecherousLicking only enhances the effect.

** And now, [[spoiler: Sasuke]] sports one of these in [[http://mangastream.com/read/naruto/476-14/20 476]], after [[spoiler: crushing Danzo (but not really) for [[BerserkButton speaking ill of Itachi]]]].
** Kyuubi!Naruto sports an ''amazing'' one [[spoiler: near the beginning of his fight with God Realm Pain. It's the middle right panel on [[http://www.onemanga.com/Naruto/438/06/ this]] page]]. You don't ''get'' better Psycho Smirks than that.

* Moka Akashiya's SuperpoweredEvilSide from ''Manga/RosarioPlusVampire'' hardly smiles, but sometimes she does it to look frighting.
** Made all the more frightening in the first season due to ArtEvolution just [[http://www.mangareader.net/320-22357-41/rosario-vampire/chapter-8.html starting]]...

** A rare heroic example, perhaps, would be Commander Shepard him/herself. While the [[AntiHero Renegade Shepard]] does this quite often, there are two particular occasions when even the Paragon Shepard cannot help but break out that [[AddedAlliterativeAppeal signature Shepard smirk]] that says "I just saved the galaxy and I'm not even tired. What can ''you'' do, suckers?" These occasions are when [[spoiler:Shepard emerges quite alive from the rubble after the battle with Saren/Sovereign]] and when [[spoiler:Shepard tells [[TheMan the Illusive Man]] to go fuck himself right after blowing up the Collector base]].

* Literature/ArtemisFowl. [[BigBad That]] [[AntiHero is all]].

* ''Manga/{{Berserk}}'': While the SlasherSmile is Guts's forte, Griffith has mastered the PsychoticSmirk. Suits the ManipulativeBastard quite well.

* Dilandau Albetou from ''Anime/TheVisionOfEscaflowne'', frequently switches between his trademark PsychoticSmirk and a disturbing SlasherSmile.

* [[Franchise/MarvelUniverse Marvel's]] ComicBook/{{Thanos}} of Titan combines the PsychoticSmirk with the GlowingEyesOfDoom (which occasionally has a smoking effect for the extra panache).

** In ''[[Anime/FinalFantasyVIIAdventChildren Advent Children]]'', Sephiroth's PsychoticSmirk is clearly in evidence during his big fight with Cloud. That, a bit of DissonantSerenity, and the fact that he never breaks a sweat or breathes heavy during this fight was supposedly done to show his immense strength.

** ''VideoGame/MassEffect3'': When questioned by Admiral Hackett on how s/he got the krogan and salarians to cooperate (answer: [[spoiler:by sabotaging the genophage cure]]), Shepard's response of "careful diplomacy" is accompanied by a KubrickStare and PsychoticSmirk.

** ''Investigations 2'' takes the PsychoticSmirk UpToEleven with [[spoiler:Horace Knightley]], [[spoiler:Sirhan Dogen]], [[spoiler:Dane Gustavia]], [[spoiler:Blaise Debeste]], and [[spoiler:Simon Keyes]], all making frequent use of one.

** Frank Alexander gets in on the action when [[spoiler: he's torturing Alex with Beethoven's Ninth]], hinting that in this moment, they're NotSoDifferent.

* Moka Akashiya's SuperpoweredEvilSide from ''Anime/RosarioToVampire'' hardly smiles, but sometimes she does it to look frighting.

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* Alucard from ''Manga/{{Hellsing}}'' almost always has this, so much so that it's hard to distinguish this from his SlasherSmile.
** The Major also sports one quite a lot. Pretty much everyone in the series has had one.

* Kagato, in ''Anime/TenchiMuyo''.
* AntiHero type: Count D in ''Manga/PetShopOfHorrors'', particularly when he's manipulating a presidential candidate and his aide in ''Dual'' and when he tells a couple to "take good care" of their new pet rabbit/surrogate daughter in ''Daughter''. In the anime, this is made even more creepy when the darkness of the screen emphasises his smirk and his mismatched, glowing eyes.
* Xellos from ''LightNovel/{{Slayers}}'' is also an antihero version. Of course, he smiles all the time, so his smirks are definitely important when they show up, usually complimented by a slight opening of his eyes, another important visual cue.
* Noa, villain of the Virtual Nightmare arc of ''Anime/YuGiOh'', has this expression when watching the misery of the heroes from the comfort of his cyber-throne. He gets it almost perfectly right.
** Yami himself. An AntiHero example of this and he got it perfected.
* Dio Brando from ''Manga/JoJosBizarreAdventure'', although after he drains Joseph of his blood he gets a SlasherSmile.
* Dilandau Albetou from ''Anime/TheVisionOfEscaflowne'', frequently switches between his trademark PsychoticSmirk and a disturbing SlasherSmile.
* Naraku from ''Manga/InuYasha'' typically has this expression when he has the upper hand and isn't trying to trick the heroes into thinking he doesn't (which is pretty much always).
* Legato Bluesummers from ''Manga/{{Trigun}}'' puts off several of these.

** If you see Aizen smiling even a ''bit'', turn heel and run because it generally means you're on the wrong end of his manipulations - the kind of manipulations that threaten life or sanity. Unfortunately for all the characters, he's always smiling.

* ''LightNovel/HighSchoolDxD'': [[CombatSadomasochist Akeno Himejima]] [[http://www.mangareader.net/highschool-dxd/1/120 just LOVES to play with her prey.]] The LecherousLicking only enhances the effect.

* 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.
** Also, Mello in the scene where [[spoiler: his henchman is killing much of his opponent Near's team. In the anime, in the middle of the scene, while the dice are falling and the people are dying, it cuts to Mello, and a satisfied grin. Also chocolate. Always with the chocolate]].
* Lelouch Lamperouge in ''Anime/CodeGeass'' loves doing this behind that CoolMask of his. [[spoiler:For good reason; whenever he does it without the mask it passes from awesome to ''terrifying'']]. We're first introduced to that smile at the end of the first episode, when he grins just a little ''too'' evilly after Geassing the soldiers about to kill him into shooting themselves. It's the blood splashing onto his cheek [[https://www.youtube.com/watch?v=P8g7pQMMniU&t=03m29s that really does it]].
* Kazuma from ''LightNovel/KazeNoStigma''. He really doesn't like the Tsuwabuki family...
* Gendo Ikari from ''Anime/NeonGenesisEvangelion'' smiles like this whenever something goes AllAccordingToPlan, although he usually camouflages it by leaning forward on his desk with his hands folded in front of his face. At most other times, he is a PerpetualFrowner -- when he smiles ''openly'', it's never good news for anyone but him.
* Itachi from ''Manga/{{Naruto}}'' seems to consider this his favorite expression. Of course, he only has three; frowning, blank stare, and smirking. If he smirks...you're in trouble. Direct, immediate, trouble, that is. Most likely he's just reversed your attack and you're about to kill yourself unless you stop.
** Suigetsu does this most of the time, usually one with his mouth closed if he's genuinely indifferent, or with it slightly open (showing off his shark teeth) if he's about to kill someone face an opponent he thinks he can easily beat. He usually only does otherwise if he's in some sort of danger.
** And now, [[spoiler: Sasuke]] sports one of these in [[http://mangastream.com/read/naruto/476-14/20 476]], after [[spoiler: crushing Danzo (but not really) for [[BerserkButton speaking ill of Itachi]]]].
** Kyuubi!Naruto sports an ''amazing'' one [[spoiler: near the beginning of his fight with God Realm Pain. It's the middle right panel on [[http://www.onemanga.com/Naruto/438/06/ this]] page]]. You don't ''get'' better Psycho Smirks than that.
** Now [[spoiler: Obito has jumped in on the action after being unmasked. His response to being asked if he really is Kakashi's old friend is just a long parade of these one after another.]]
** And lest we forget Gaara before his HeelFaceTurn! As shown [[http://www.exelements.net/kayura232/naruto/sandgaara.jpg here,]] [[http://www.animegalleries.net/img/34520 here,]] [[http://www.animegalleries.net/img/34522 here,]] [[http://www.animegalleries.net/img/34547 here]] and [[http://www.animegalleries.net/img/34570 here!]] And pages [[http://www.animegalleries.net/album/787/page/10 10]], [[http://www.animegalleries.net/album/787/page/12 12]] and [[http://www.animegalleries.net/album/787/page/15 15]] of [[http://www.animegalleries.net/album/787/page/1 this]] gallery have a bunch of his smirks from his battle against Naruto!
* If Akito from ''Manga/FruitsBasket'' (the manga, at least) smiles, this is usually the smile he chooses. Of course, if you take in what his ''eyes'' usually say ("I am ''so'' enjoying ripping your little psyche to shreds!"), [[SlasherSmile it's a little more disturbing...]]

** Gohan counts too (Super Saiyan 2 Gohan that is)
* [[BigBad Aion]] from ''Manga/ChronoCrusade'' is ''very'' fond of this trope. So much so that it's when he ''stops'' smirking that you '''really''' have to be worried.
* Moka Akashiya's SuperpoweredEvilSide from ''Anime/RosarioToVampire'' hardly smiles, but sometimes she does it to look frighting.
** Made all the more frightening in the first season due to ArtEvolution just [[http://www.mangareader.net/320-22357-41/rosario-vampire/chapter-8.html starting]]...
* Ukyo from ''Anime/SamuraiSeven'' is fond of this. And it is ''creepy''.

** In episode 62 of ''[[Manga/FullmetalAlchemist Fullmetal Alchemist: Brotherhood]]'', the camera focuses on [[BigBad Father]] doing this just before he unleashes a WaveMotionGun on the heroes.
* MadScientist BigBad Jail Scaglietti of ''Anime/MagicalGirlLyricalNanohaStrikers'' wears one of these on his face most of the time. He uses a particularly nice one when Due [[spoiler: assassinates the founders of the Space-Time Administration Bureau]].
** [[PsychoForHire Cypha]] from ''[[Manga/MagicalRecordLyricalNanohaForce Force]]'' also has about ninety percent of the time. [[SmugSnake It's less endearing]] than [[MagnificentBastard Jail's]].

* PsychoLesbian Tsukuyomi of ''Manga/NegimaMagisterNegiMagi'' often does this in her early appearances. Later on, it turns into a full SlasherSmile.
** Occasionally Eva slips into this when things are going especially well for her. For example, right before having five of her ribs broken... putting the expression under this trope.

* Gauron from ''Lightnovel/FullMetalPanic'', being the SmugSnake he is, has this as his constant default expression. Only broken when he's having one of his [[SlasherSmile Slasher Smiles]].
* While almost everyone in ''Manga/{{Gintama}}'' does this from time to time, Okita and Takasugi probably do it the most.
* Haruko from ''Anime/{{FLCL}}'' usually has one whenever she is fighting.
* [[MagnificentBastard Tomomi Saikyo]] of ''LightNovel/LadiesVersusButlers!'' is commonly seen with this when she is about to/planning to screw over a classmate of hers. It's hinted that she manipulated [[UnluckyEveryDude Akiharu Hino]], a childhood friend, into saying, "I want to become a bride."

* Rock from ''Manga/BlackLagoon'' has started doing this.
* In ''Kunisaki Izumo no Jijou'', Kumedara gives one to Izumo before [[DraggedIntoDrag dragging him into drag]].
* ''Manga/{{Berserk}}'': While the SlasherSmile is Guts's forte, Griffith has mastered the PsychoticSmirk. Suits the ManipulativeBastard quite well.
* ''Anime/YuGiOh'': Seto Freakin' Kaiba! [[WebVideo/YuGiOhTheAbridgedSeries Everytime he smiles, a puppy dies]].
* Orga Sabnak, Cortho Bauer, and Sting Oakley of ''Anime/MobileSuitGundamSEED'' and ''Anime/MobileSuitGundamSEEDDestiny'' typically sport one of these. Both Cortho and Sting graduate to full on {{Slasher Smile}}s following the deaths of their teammates.
* Mewtwo from ''Anime/PokemonTheFirstMovie'' spends most of the movie [[PerpetualFrowner wearing a cold, stern expression]], but he gives a couple of smirks when amused by Ash and co. defiance towards him.
* [[BigBad Vincent Volaju]]'s default expression in ''Anime/CowboyBebop: TheMovie'' is this.
* [[GuileHero Harusumi]] of ''Manga/BokuraNoKiseki'' is pretty fond of this. He'll occasionally combine it with a DeathGlare for some truly terrifying expressions.
* ''Manga/AkumaNoRiddle'' has a cast of mostly AxeCrazy ProfessionalKillers. There's plenty to go around.
* ''Manga/FairyTail'': [[OurDemonsAreDifferent Mard Geer]] of [[DarkIsEvil Tartaros]], ''constantly''. Whether it's [[SlouchOfVillainy lounging on his throne]], making a speech on how [[PunyHumans humans are pathetic]], facing down [[PhysicalGod the Celestial Spirit King]], or taking on [[PlayingWithFire three]] [[LightEmUp Dragon]][[CastingAShadow slayers]], it seems to be his default expression as TheStoic. When he's NotSoStoic though, it turns to a full-blown SlasherSmile.
* Nagisa Shiota from ''Manga/AssassinationClassroom'' sports an utterly chilling one whenever [[LetsGetDangerous he gets serious]], adding to his DissonantSerenity.
* Everyone in ''Anime/JokerGame'' does this in one point or another, but especially Yuuki, after succefully gaining what they want from the villains.
* Everybody in the chaotic DysfunctionJunction and CastFullOfCrazy that ''Manga/PandoraHearts'' is made of busts out one of these at some point or another, although in this manga it's commonly crossed with a SlasherSmile.

* [[Franchise/MarvelUniverse Marvel's]] ComicBook/{{Thanos}} of Titan combines the PsychoticSmirk with the GlowingEyesOfDoom (which occasionally has a smoking effect for the extra panache).
* Mender of ''ComicBook/{{Elfquest}}'' fame does the same when riled up during a fight. He uses the FacepalmOfDoom for extra benefit.
* The ''Comicbook/{{Daredevil}}'' villain Bullseye does this a lot.

* ''ComicBook/XWingRogueSquadron'': Every now and again BigBad ManipulativeBastard Ysanne Isard [[http://starwars.wikia.com/wiki/File:IsardHead.jpg gets]] [[http://starwars.wikia.com/wiki/File:IsardMR.jpg to]] [[http://starwars.wikia.com/wiki/File:IsardMad_copy.jpg do]] [[http://starwars.wikia.com/wiki/File:Isards_plaything.jpg this]].
* ''ComicBook/{{Watchmen}}'': Who could forget Ozymandias' classic smirk when Dan questions his ability to catch a bullet?

* The ''ComicBook/{{Runaways}}'' villain Kid Twist has one as he guns down the Street Arabs. Given that he is a 1900's expy of the above-mentioned Bullseye, this is probably to be expected.

* In the ''Literature/{{Everworld}}'' series, the witch Senna [[EmotionlessGirl almost never smiles]]. However, when she's using magic to attack or to [[CompellingVoice control]] someone, she occasionally makes small smiles to herself. She never shows teeth, but they're so disturbingly described that they would probably qualify as a SlasherSmile if she was more open with them.
* When [[Literature/TheThrawnTrilogy Grand Admiral Thrawn]] smiles, which happens ''very'' rarely, it tends to be this. He's quite self-possessed.
* This seems to be [[Literature/HarryPotter Draco Malfoy's]] default facial expression.
* Literature/ArtemisFowl. [[BigBad That]] [[AntiHero is all]].
* [[Literature/TheMillenniumTrilogy Lisbeth Salander's]] [[TheUnSmile crooked half-smile]].
* Creator/EdgarAllanPoe, in his humorous essay "Diddling Considered As One Of The Exact Sciences", declares that one of the defining traits of a ConMan is his grin, which he only permits himself in private when no one is there to see it.
* Whenever Zack, the AntiHero of ''Literature/TheMentalState'', has succeeded in one of his devious schemes, he always sports this expression. Sometimes, you only realise just how badly you have been screwed and who is responsible when he gives you one of these looks directly.

** The waif has a small gleeful smirk on her face after she receives her charge to assassinate Arya.

* In ''VideoGame/Kirby64TheCrystalShards'' the ruler of Ripple Star does one of these behind Ribbon's back during the game's false ending.
%%* Clyde from ''VideoGame/ArmyOfTwo''. Just...[[http://uk.youtube.com/watch?v=7G_Pw0Oh_UU Clyde]].
* Albert Wesker of the ''Franchise/ResidentEvil'' games ''loves'' this, especially in ''Resident Evil 0'' and ''Code: Veronica''. In both games, he's controlling a series of deathtraps that the player has to navigate through. He also smirks evilly when he takes on ''Code: Veronica's'' BigBad; after finding himself over his head, he smirks and leaves the two of you alone to work out your differences.
* This is Wong's default expression in ''VideoGame/PsychicForce''. Guy's a very happy [[TheChessmaster Chessmaster]].

* Vidocq from DoctorLautrecAndTheForgottenKnights does these a few times throughout the game; the first time is about [[ObviouslyEvil five seconds after his first appearance.]]
* Jeanette Voerman in ''VideoGame/VampireTheMasqueradeBloodlines'' does a minxy one of these when sending you off on her schemes, Rawr.
* Ishida Mitsunari in the opening video of ''VideoGame/SengokuBasara 3'', after dealing swift death to a couple of mooks. And then he [[PerpetualFrowner glares for the rest of the entire game]].

* VideoGame/TeamFortress2's [[http://www.teamfortress.com/macupdate/ Mac Update]] trailer features a Scout that meets up with his team's Demoman and Heavy (who are enjoying music courtesy earbuds on thin, white wires), trades his clunky 1950s headset for a matching pair of sleek white earbuds, slings his bat over his shoulder, and unleashes the smirk.
* [[BigBad Master Xehanort]] of ''VideoGame/KingdomHeartsBirthBySleep'' is nearly ''always'' wearing one of these.
** [[VideoGame/KingdomHeartsChainOfMemories Larxene]] pulls one of these before kicking Sora to the ground.
* 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.
* This is the second of [[VideoGame/BlazBlue Hazama's]] three smiles, squeezed in between his unpleasant CheshireCatGrin and monstrous SlasherSmile.
* Norman Jayden from ''VideoGame/HeavyRain'' sports one of these in the ending "Uploaded" [[spoiler:right after scaring the shit out of Carter Blake in ARI]].

* In ''[[VideoGame/TheLegendOfZeldaCDIGames Zelda: Wand of Gamelon]]'', Zelda gives a creepy little smirk after she kills [[TheDragon Hectan]]--
-->'''Hectan:''' [[LargeHam YOOOOU'VE KILLED MEEEEEEEE!]]
-->'''Zelda:''' ''Good.''
* Ganondorf's default expression in ''VideoGame/TheLegendOfZeldaOcarinaOfTime''.
* Zsasz displays a very creepy one on his character trophy in VideoGame/BatmanArkhamCity.
* Master Contra from ''Neo {{VideoGame/Contra}}''.
* Volsung from ''VideoGame/WildArms5''.

* ''VideoGame/HauntingGround'': If [[NinjaMaid Daniella]] isn't [[EmotionlessGirl expressionless]], she's doing this.
* [[spoiler: Bloody Mary]] from ''VideoGame/TheWolfAmongUs'' is almost always wearing one from the moment she's introduced in "A Crooked Mile".
* In ''VideoGame/PokemonSunAndMoon'', [[spoiler:Lusamine sports one after the first encounter with UB01/Nihilego. She sports this smile multiple times after she's revealed as the big bad of the story.]]
* ''VideoGame/Persona5'': As befitting his trickster personality, the protagonist smirks a lot; he has a particularly smug one [[spoiler:after he successfully tricks the traitor]]. [[spoiler:In the bad ending where he makes a deal with the BigBad, he gives a particularly evil one, complete with sinister chuckle.]]
* ''VideoGame/TheLegendOfHeroesTrailsInTheSky'': [[spoiler: "Professor Alba"]] adopts one after Joshua accuses him of orchestrating the memory-loss events at the end of the first game. It's an early reveal that [[TheDogWasTheMastermind he's not exactly what he appears to be.]]
* Part of TheReveal in ''VideoGame/SlyCooperThievesInTime'': [[BitchInSheepsClothing Penelope]] comes out of her Black Knight mecha while sporting one, and keeps it throughout the whole scene as she gloats over how she played with Bentley over a false romance, intends to kill his two best friends, and then use his skills to make ''billions'' in weapon designs, unknowingly exposing herself as TheSociopath to Bentley as he was in the rafters at the time. It turns into a SlasherSmile when the Cooper Gang finally confront her.
* This is the default expression of Shadows in ''VideoGame/Persona4''. The exceptions are Shadow [[spoiler:Teddie]], who has a blank grimace, and Shadow [[spoiler:Naoto]], who switches between crying and looking superior.

* Umbria/Zaedalkaah likes doing these a lot in ''Webcomic/OurLittleAdventure''.
* Jack--poor crazy, creepy Jack--of ''Webcomic/GunnerkriggCourt'' is starting to make a habit of cracking these. One or two of them have bordered on SlasherSmile.

* Han Solo in [[http://darthsanddroids.net/episodes/0786.html this]] ''Webcomic/DarthsAndDroids'' comic, right after Luke questions his sanity.
* Things start getting bad in ''Webcomic/BittersweetCandyBowl'' when ''[[http://www.bittersweetcandybowl.com/c12/p6.html they]]'' start smirking.
--->'''Alejandro''': [[http://www.bittersweetcandybowl.com/c12/p19.html What I'll do to you...]]

* In ''Webcomic/KillSixBillionDemons'', the GodEmperor Mottom cracks a [[http://killsixbilliondemons.com/comic/wielder-of-names-4-66/ wonderful one]] after inflicting a darkly ironic FateWorseThanDeath on a rebellious vassal in front of her court. As an [[ReallySevenHundredYearsOld ancient]] [[AGodAmI Demiurge]] ruling a DecadentCourt of 111 111 worlds, she does enjoy flexing her power.
--> '''AltText:''' This is probably a "twice a day before breakfast" kind of thing for her.
* In ''Webcomic/TheOrderOfTheStick'', Belkar [[http://www.giantitp.com/comics/oots0648.html does this]] when he figures out what Haley did, while [[ActualPacifist Celia]] does not.
* Daniel in ''Webcomic/TheGuideToAHealthyRelationship'' is friendly and generally well-liked, but shots like [[http://tgtahr.spiderforest.com/index.php?comic_id=173 this one]] hint at what a BitchInSheepsClothing he is.

* ''WesternAnimation/TheLegendOfKorra''
** Amon from wears a mask with a built-in evil smirk that's both deceptively inviting and unnerving.
** Criminal waterbender Ming Hua occasionally displays one, usually while delivering a vicious beatdown.
** Kuvira from Book 4 will occasionally wear one of these when something goes her way. And for someone portrayed as a [[TheStoic stoic]] IronLady, they are [[http://img2.wikia.nocookie.net/__cb20141009162729/avatar/images/b/b5/Kuvira_enlists_bandits.png surprisingly]] [[http://img3.wikia.nocookie.net/__cb20141009163139/avatar/images/4/44/Kuvira_smirks.png unsettling]].

* ''WesternAnimation/StormHawks'': Add a OneLiner and this is basically how half of [[BigBad Master Cyclonis]]' appearances end.
* [[Franchise/{{Transformers}} Megatron and Starscream]], in whichever series they feature in, often sport this expression when a plan is going well.
** In WesternAnimation/TransformersPrime season one, episode 19 "Rock Bottom" ends with Megatron giving Starscream a [[https://vignette4.wikia.nocookie.net/transformersprime/images/d/de/Megatron_face.jpeg/revision/latest?cb=20140128221901 psychotic smirk worthy of Unicron itself]].
** [[AxCrazy Galvatron]] can be seen doing this before the ad break (complete with sparks coming from his head) of Five Faces of Darkness Part II and sports this expression in Season 3 whenever he's in one of his more [[{{Sadist}} malicious]] moods (either through formulating a devious plan, [[ColdBloodedTorture just plain ol' torture]] or ''both).''

* [[VainSorceress Lydia]] from ''WesternAnimation/BarbieAndTheDiamondCastle''.

* Heloise on ''WesternAnimation/JimmyTwoShoes'', whenever she isn't going for a full on SlasherSmile.
* June on ''WesternAnimation/KaBlam'' does this a lot. Unlike others with this trope, she's one of the protagonists (even if her ideas of fun include putting her friend, Henry, through hell).
* In ''WesternAnimation/EdEddNEddy's'' BigDamnMovie, [[spoiler:Eddy's Brother]] sports one just before he beats up Edd and Eddy.
* Surprisingly, ''WesternAnimation/MyLittlePonyFriendshipIsMagic'' has [[spoiler:Fake!Cadance]] pulling this off from time to time, though one of her more memorable ones is when she has a sinister smirk while in front of green fire when she [[spoiler:sends away Twilight to the crystal caves]].
* ''WesternAnimation/{{Kaijudo}}: Rise of the Duel Masters'' has the usually flegmatic, AffablyEvil [[BigBad Choten]] delivering a quite creepy one when [[spoiler:pulling a YouHaveFailedMe on Fingers.]]
* Black Knight on ''WesternAnimation/GeneratorRex'' displays one whenever she has the upper hand. [[spoiler: It also indicates to perceptive combatants she's dropped her guard.]]

** Jeremy Baines/Son of Mine of [[Recap/DoctorWhoS29E8HumanNature the Family]] [[Recap/DoctorWhoS29E9TheFamilyOfBlood of Blood]] is always wearing one of [[http://www.danielkanolik.co.uk/Images/harrylloyd.jpg these]], even after his defeat.

** The Doctor gets a rather horrifying one when he completely loses it in [[Recap/DoctorWhoS30E16TheWatersOfMars "The Waters of Mars"]]. [[http://media.tumblr.com/45e988d61595c03d812ba7037e931824/tumblr_inline_mmxdgumfHl1qz4rgp.gif Behold.]]

* The Trickster from ''Series/{{Supernatural}}'' wears this a couple of times - there's a particularly good example in the episode [[http://images2.fanpop.com/image/photos/12300000/Changing-Channels-gabriel-the-trickster-loki-12335281-640-480.jpg Changing Channels]].

[[folder:Film — Animation]]

* ''WesternAnimation/ToyStory3'': Lotso does this a lot, most notably as he [[spoiler: abandons Woody and his friends to the incinerator]].

[[folder:Film — Live-Action]]

* In ''Webcomic/KillSixBillionDemons'', the GodEmperor Mottom cracks a [[http://killsixbilliondemons.com/comic/wielder-of-names-4-66/ wonderful one]] after inflicting a darkly ironic FateWorseThanDeath on a rebellious vassal in front of her court. As an [[ReallySevenHundredYearsOld ancient]] [[AGodAmI Demiurge]] ruling a DeadlyDecadentCourt of 111 111 worlds, she does enjoy flexing her power.

* Sylar from ''Series/{{Heroes}}'' does this occasionally. Apparently, Sendhil Ramamurthy who plays [[http://img84.imageshack.us/img84/3416/mohinderla9.jpg Mohinder]] does a pretty good one, too!

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%% Please do not replace or remove without starting a new thread.

* Xellos from ''{{LightNovel/Slayers}}'' is also an antihero version. Of course, he smiles all the time, so his smirks are definitely important when they show up, usually complimented by a slight opening of his eyes, another important visual cue.

* [[Manga/DragonBallZ Vegeta's]] psychotic smirk was one of his trademarks as a villain, given just before blasting someone to Hell (or the [[NeverSayDie Next Dimension]], for those of you who go by the earlier dub).

* [[BigBad A]][[TheAntiChrist i]][[DarkMessiah o]][[CardCarryingVillain n]] from ''Manga/ChronoCrusade'' is ''very'' fond of this trope. So much so that it's when he ''stops'' smirking that you '''really''' have to be worried.

* The TriggerHappy Joichiro Nishi from ''{{Manga/Gantz}}'' wears one of these at all times, [[spoiler:right up until his incredibly painful death. Though of course, he was DeadToBeginWith...]]
* Kiku Honda (Japan) of ''Webcomic/AxisPowersHetalia'' does this very subtly in the anime while being very enigmatic. Coupled with his MonochromaticEyes...
** Russia is the [[http://i171.photobucket.com/albums/u290/Verging/Hetaliatrope.png king of this]] in the series. Almost ''anytime'' he smiles, his smile is like that of a [[SlasherSmile serial killer]]. Or [[Film/TheSilenceOfTheLambs Hannibal Lector]]. ''Especially'' when he wants you to [[MemeticMutation become one with him]]
*** He is only seen smiling one time without the underlying crazy. ''One time''.
* PsychoLesbian Tsukuyomi of ''Manga/MahouSenseiNegima'' often does this in her early appearances. Later on, it turns into a full SlasherSmile.

* [[http://www.mangafox.com/manga/kunisaki_izumo_no_jijou/v02/c015/8.html Here]] in ''Kunisaki Izumo no Jijou'', Kumedara gives one to Izumo before [[DraggedIntoDrag dragging him into drag]].
* ''{{Manga/Berserk}}'': While the SlasherSmile is Guts's forte, Griffith has mastered the PsychoticSmirk, [[http://www.mangareader.net/96-1126-135/berserk/chapter-6.html as seen here]]. Suits the ManipulativeBastard quite well.
* [[Anime/YuGiOh Seto Freakin' Kaiba]]! [[WebVideo/YuGiOhTheAbridgedSeries Everytime he smiles, a puppy dies]].

* ''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]]

* ''WesternAnimation/ToyStory3'': Lotso does this as he [[spoiler: abandons Woody and his friends to the incinerator]].

* In ''Disney/TheHunchbackOfNotreDame'', Frollo does this after he explains to Quasimodo that he plans to find the gypsies' secret hideout and arrest the gypsies, Esmeralda included.

* ''WesternAnimation/TheSimpsons'': In "Monty Can't Buy Me Love," Kent Brockman provides a [[PracticalVoiceOver practical news voice-over]] describing the typical billionaire: "a joyless miser brooding in his cavernous mansion, grasping a glass of brandy with his thin, claw-like fingers and a superior smirk on his greedy, soulless face." Cut to Mr. Burns in this exact position, chilling smirk and all.

* ''WesternAnimation/TheSimpsons'': In "Monty Can't Buy Me Love," Kent Brockman provides a [[PracticalVoiceOver practical news voice-over]] describing the typical billionaire: "a joyless miser brooding in his cavernous mansion, grasping a glass of brandy with his thin, claw-like fingers and a superior smirk on his greedy, soulless face." Cut to Mr. Burns alone in his mansion, pulling a chilling smirk.

* [[CardCarryingVillain Aion]] from ''Manga/ChronoCrusade'' is ''very'' fond of this trope. So much so that it's when he ''stops'' smirking that you '''really''' have to be worried.

* Aion from ''Manga/ChronoCrusade'' is ''very'' fond of this trope. So much so that it's when he ''stops'' smirking that you '''really''' have to be worried.