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[[quoteright:270:[[Franchise/ResidentEvil https://static.tvtropes.org/pmwiki/pub/images/sinister-shades_uc-wesker_6073.png]]]]
->''"Syme's eye always caught the black glasses and the blind grin. [...] They took away the key of the face -- you could not tell what his smile or his gravity meant. Partly from this, and partly because he had a vulgar virility wanting in most of the others, it seemed to Syme that he might be the wickedest of all those wicked men."''
-->-- ''Literature/TheManWhoWasThursday'', '''Creator/GKChesterton'''

Sun never sets on an asshole.

This trope is where ScaryShinyGlasses meets CoolShades. Quite a bit of villains wear shades for some reason. Usually they hide the malice from the eyes of the one wearing them. If you're MakingASpectacleOfYourself, invoking this trope will fail horribly.

Examples are numerous, including TheMenInBlack, members of [[AncientConspiracy secret societies]], [[SinisterSpyAgency CIA agents]], [[TheMafia mafiosi]], {{Yakuza}}, [[TheBadGuysAreCops sinister police officers]], Agent programs in the [[Film/TheMatrix Matrix]]... you get the picture. Not ''always'' associated with villainous characters but usually a deliberate attempt to intimidate, so chances are that if a hero wears these, they're an example of GoodIsNotNice if not a full AntiHero. May overlap with SpecsOfAwesome. Compare FourEyesZeroSoul. GasMaskMooks takes this a few steps further.

----
!!Examples:

[[foldercontrol]]

[[folder:Anime and Manga]]
* Ubik from ''Manga/{{Berserk}}'' has a pair of round shades that he wears when he's scaring the piss out of those intended to be sacrificed.
* The Black Organization members, Vodka and Korn from ''Manga/CaseClosed'' are never seen without them; the only time when Vodka doesn't wear his shades is when he was masked in a costume party. Their colleague, Calvados, wore sunglasses, too, but [[WeHardlyKnewYe We Hardly Knew Him]].
%%* Rubel in ''Manga/{{Claymore}}'' has really big round ones.
* Yamaki of ''Anime/DigimonTamers'', [[spoiler:even after he finishing his HeelFaceTurn. It's kind of telling that they either [[TheGlassesComeOff come off]] or lighten up when he's doing something good.]]
* JerkJock Agon Kongo from ''Manga/Eyeshield21'' sports some nifty sports goggles, helps that they're opaque most of the time.
** The shades in question are also nefariously ''expensive'' (they're Oakley Juliet sports goggles). Shades of evil ''indeed''.
** Subverted with Akaba, who even combines these with red eyes, but is actually a nice, if eccentric person.
* Smith from ''Anime/FutureGPXCyberFormula'' is never seen without them, [[spoiler:even when he dies after his helicopter crashes]].
* Alucard in ''Manga/{{Hellsing}}'' has these as part of his initial look, but, strangely enough, as he becomes more threatening, he loses them.
%%* Char Aznable, originally of ''Anime/MobileSuitGundam'', sports these in ''Anime/MobileSuitZetaGundam''.
* Shino from ''Manga/{{Naruto}}'' is rarely, if ever seen without his shades. The same goes with his dad, or anyone from the Aburame family, for that matter. Given they host insects inside their bodies, this has lead to some unpleasant speculation as to why, exactly, we never see their eyes.
* ''Anime/NeonGenesisEvangelion'': Gendo Ikari practically revels in this. He's only shown without them in flashbacks; their lack doesn't make him any less scary though.
%%* [[LightIsNotGood Admiral Kizaru]] of ''Manga/OnePiece'' has these.
%%** As does Donquixote Doflamingo.
* Jessie, James, and Meowth of ''Anime/PokemonTheSeriesBlackAndWhite'' have been doing this a lot. They've also lately been approaching competent.
%%** Pokemon Hunter J before them also had these.
%%* Yukishiro Enishi from ''Manga/RurouniKenshin''.
* Colonel Franklin and his men wore SunglassesAtNight at the beginning of ''Anime/TransformersCybertron''. He wore them less after he was revealed as a good guy rather than a sinister government agent.
* ''Manga/{{Trigun}}'' gives us the little {{s|caryShinyGlasses}}hiny sunglasses Vash puts on when [[LetsGetDangerous he's about to kick someone's ass]].
** Remarkably the same CoolShades invoke {{Bishonen}}. In fact, because of the starkness of the character change from the goofball, simply shifting to StoicSpectacles reaches the border of this trope. The shades can change in the same situations where, if his shades didn't go Sinister, we'd probably see the {{Glowing Eyes|OfDoom}} {{Red Eyes|TakeWarning}} [[GlowingEyesOfDoom Of Doom]] instead.
* Kemo (a.k.a. [[WebVideo/YuGiOhTheAbridgedSeries the Hair Guy]]) from ''Anime/YuGiOh''. Bandit Keith as well, where they really enhance the sense of both menace and douchebaggery that he gives off.
** Don't forget Croquet, Pegasus's right-hand man.
* ''Manga/YuYuHakusho'': Younger Toguro, the antagonist of the Dark Tournament arc, wears an intimidating pair of triangular shades that enhance his stoic, merciless attitude. It's shown in flashbacks that he didn't wear them before he became a demon and underwent a FaceHeelTurn.
[[/folder]]

[[folder:Comic Books]]
* ''ComicBook/TheAvengers:'' The morality of Peter Gyrich, ObstructiveBureaucrat par none of the Marvel U, can be determined by the opacity of his glasses. If they're completely dark, as they are in ''ComicBook/AvengersTheInitiative'', that's a sign he's going to be a complete bastard. (Not that he's Mr. Cuddles the rest of the time, mind. It just means he's going to be worse than ''usual''.)
* In ''ComicBook/{{Chassis}}'', Chassis' main [[TheRival rival]] Covergirl wears a reflective visor that she never takes off. Given her body had to be reconstructed are after a near-fatal crash, it is possible the visor is permanently attached to her face.
* ''[[Franchise/MonsterVerse Godzilla x Kong: The Hunted]]'': [[Characters/MonsterVerseHumans Raymond Martin]] wears black glasses, and he's [[HumansAreTheRealMonsters more of a monster than the literal monsters that he hunts]], being the BigBad of the comic who commits extreme VanHelsingHateCrimes.
* ''ComicBook/PlasticMan'''s, while usually falling into MakingASpectacleOfYourself, turned into this when he, along with the rest of the JLA, gained a LiteralSplitPersonality.
* Evil Sonic a.k.a. Scourge from ''ComicBook/SonicTheHedgehogArchieComics'' wears these.
* ''ComicBook/{{Superman}}'': ComicBook/PostCrisis General Zod's wife, Ursa, sported a pair of shaded goggles to protect her eyes from excess light. She was also one of the most demented of all the Kryptonians.
* ''ComicBook/UltimateMarvel'':
** ''ComicBook/UltimateSpiderMan:'' Doctor Octopus wears a pair of shades, to hide that his eyes were badly scarred by the disaster that made him Doc Ock.
** ''ComicBook/UltimateXMen'': Mastermind always use those, and is rarely (if ever) seen without them.
[[/folder]]

[[folder:Fan Works]]
* ''Fanfic/ManehattansLoneGuardian'' has Glintlock, an EvilPoacher willingly working for someone who plans to take over Equestria, favoring a pair of shield-type sunglasses at all times. This is less out of intimidation than it is to protect his eyes, which have increased sensitivity to sunlight for reasons unknown.
* In the James Bond FanFilm ''[[WebVideo/DiamondsCut Property Of A Lady]]'', an unnamed enforcer sent to spring the trap on Bond wears these alongside the black suit.
[[/folder]]

[[folder:Films -- Animated]]
* Bad Cop of ''WesternAnimation/TheLEGOMovie'' wears a pair of shades while his Good Cop side wears simple glasses.
* In ''WesternAnimation/TurningRed'', when Grandma Wu shows up she wears reflective sunglasses which contribute to her intimidating appearance despite [[MakingASpectacleOfYourself having rhinestone-encrusted frames]].
[[/folder]]

[[folder:Films -- Live-Action]]
* Peter Cook as the Devil in ''Film/Bedazzled1967'' wears sinister looking 'mod' sunglasses along with a tuxedo, cape, and red socks.
* The antagonist of ''Film/TheBookOfEli'' is Carnegie, the tyrannical ruler of a small town in post-apocalyptic America. He has a pair he wears to cover his eyes from the UV light.
* ''Film/CaptainAmericaTheWinterSoldier''
** Seen in the "police" ambush of Nick Fury where the patrol cops are all wearing sunglasses and peaked caps to hide their identities, while the SWAT officers have their helmets and goggles on.
** Also the Winter Soldier himself during daytime operations until Black Widow cracks one of the lenses with a well-placed shot.
* Creator/BryanCranston's kidnapper character wears particularly sinister orange-shaded glasses in ''Film/ColdComesTheNight''.
* The prison guard in ''Film/CoolHandLuke'' wears a pair of sinister shades while watching the prisoners in the hot sun.
* Fender Tremolo in ''Film/Cyborg1989'' is nearly all the time sporting his pair of 80's vintage black, dirty shades. And believe it or not, he's much better on with these however creepy he is. You really don't want to see what lies behind them.
%%* The assassin in ''Film/GhidorahTheThreeHeadedMonster''.
%%** This also applies to the Xilians in both ''Film/InvasionOfAstroMonster'' and ''Film/GodzillaFinalWars''.
%%** The Saradian Agent is this as well in ''Film/GodzillaVsBiollante''.
* Discussed in ''Film/InTheLineOfFire''; [[Creator/ClintEastwood Frank Horrigan]] is asked why he doesn't wear shades, like the rest of the agents, while standing post. He replies that he likes to get a good look at people's eyes. Given that he has the classic ClintSquint in his arsenal, adding shades might actually make him ''less'' intimidating. The other agents in the film all follow right along with this trope, though.
* ''Film/DrNo''. Film/JamesBond is under surveillance from the moment he arrives at the airport in Jamaica. A pretty girl tries to take his photograph while a man in dark glasses observes him from a balcony. Bond later discovers that the girl is working for the BigBad while the man in shades is his future ally, CIA agent Felix Leiter; when Felix reveals this to Bond, he takes off the sunglasses for the first time.
* Paul Yau, the hitman hired to replace the title character of Creator/JohnWoo's ''Film/TheKiller1989'', had a pair of these.
* In 1945's ''Film/LeaveHerToHeaven'', the pathologically jealous and evil Ellen Harland (Creator/GeneTierney) dons a pair of these just prior to [[spoiler:letting her husband's disabled kid brother drown in a lake]].
* The black-clad Bone, the most brutal of the bank robbers in ''Film/TheLookout'', is never seen without without his sunglasses.
* From ''Film/TheMatrix'':
** Agent programs sport these by default
** Morpheus has them, when, to Neo, he's still mysterious and vaguely threatening. They're deliberately shed whenever the character's meant to be vulnerable.
** Neo and Trinity get their own when they go StormingTheCastle in the first movie.
* In ''[[Film/Napoleon1927 Napoléon]]'' (1927), UsefulNotes/MaximilienRobespierre dons a pair from time to time.
* Sheriff Cooley from ''Film/OBrotherWhereArtThou?''. He's implied to be the devil, and in close-ups on his face firelight is often reflected in his shades.
* Parodied in ''Film/OutOfSight'' where the two protagonists drive around and spot a number of undercover FBI agents watching them... due to the fact they all wear identical sunglasses.
* In ''Film/PokemonDetectivePikachu'', Ms. Norman wears these, as does Roger Clifford during the PCL scenes. [[spoiler:This is because Ms. Norman is actually a Ditto, and the same Ditto is impersonating Roger during the aforementioned scenes. Ditto cannot mimic human eyes, so the shades are necessary to hide its true nature.]]
* The cop who wakes up Marion Crane from sleeping in her car in ''Film/{{Psycho}}'' dons a pair of these.
* In ''Film/SixGunSavior'', the Devil wears a pair of black-lensed glasses that completely conceal his eyes.
* ''Film/{{Soultaker}}'' stars Martin Sheen's brother as a CoolShades-wearing [[TheGrimReaper Grim Reaper]] who falls in love with the [[CanonSue leading lady/scriptwriter]]. [[Series/MysteryScienceTheater3000 The SOL Crew]] insisted upon singing "Sunglasses At Night" to mock this.
* ''Film/SpiderMan2'': Doctor Octopus dons a pair of shades after the freak accident that made him turn evil. This is explained away in the novelized version, as Octavius was left with very light-sensitive eyes after the tritium exploded.
* The T-1000, BigBad of ''Film/Terminator2JudgmentDay'' wears mirrored aviator sunglasses, per his disguise as a Highway Patrol officer.
* [[Franchise/TheTerminator Terminators]] are fond of wearing sunglasses, started by the T-800 donning a set of Ray-Bans to hide his missing eye in the first movie. It's used as symbolism in ''[[Film/Terminator2JudgmentDay Judgment Day]]'' where the T-1000 wears sleek shiny chrome shades in contrast to the T-800's black ones to highlight how more technologically advanced it is. Later in the film the T-800 loses his his shades as he becomes more human, while Sarah Connor dons a pair to go assassinate Dyson to symbolize how she's [[HeWhoFightsMonsters losing her humanity and acting like a Terminator]].
* ''Film/TheWarriors'': Masai is the sinister leader of the Gramercy Riffs, the toughest gang in New York City, and he's never seen without his sunglasses on.
[[/folder]]

[[folder:Literature]]
* The Tonton Macoutes wear these in Creator/{{Graham Greene|Author}}'s ''The Comedians''.
* Depending on the person wearing them and the reader's point of view, the sports glasses ''Literature/{{Daemon}}'' operatives use are this, CoolShades or maybe even both. Not to mention [[GogglesDoSomethingUnusual having a number of functions]] besides looking cool and/or intimidating.
* In the ''Literature/DiogenesClub'' series, TheMenInBlack invariably wear dark glasses in all circumstances. In "Literature/SorcererConjurerWizardWitch", it's stated that there's something unpleasantly strange about their eyes that the glasses conceal (the character who's seen what's under there doesn't wish to dwell on the details). On the other hand, in "Literature/TheGypsiesInTheWood", the leader of the group has a private meeting with the protagonist in which, as a show of good faith, he removes his glasses to reveal apparently normal and "surprisingly humorous" eyes.
* ''Literature/TheJenniferMorgue'' [[PlayedForLaughs plays this for laughs]] with the sunglasses-wearing security agents of the villainous [[UsefulNotes/ElizabethBathory Bathory]] [=PaleGrace=][[superscript:TM]] makeup company. One agent grudgingly admits that they're required to wear enchanted eyeliner that enables the BigBad to see through their eyes -- the sunglasses are optional, but they hide the fact that the big beefy guards all have makeup on.
* ''Literature/JohannesCabal'': The titular {{Necromancer}}'s blue-tinted sunglasses are a constant throughout the series, though their sinister connotations are zig-zagged as he progresses from VillainProtagonist to AntiHero.
* The Ankh-Morpork banking community wear these in ''Literature/MakingMoney'', as seen on [[http://www.paulkidby.net/MakingMoneyFinal1.jpg the cover.]]
* One of the anarchists in Creator/GKChesterton's ''Literature/TheManWhoWasThursday'' wears a pair of them. [[spoiler:Deliberately. With them, he's terrifying to behold. Without them, he's cheerful and ordinary.]]
* [[WarGod Ares]] in ''Literature/PercyJacksonAndTheOlympians'' wears sunglasses which cover his FireballEyeballs, in keeping with his BadassBiker image.
* In Joyce Carol Oates' short story ''Literature/WhereAreYouGoingWhereHaveYouBeen'', Arnold Friend, [[spoiler:a creep who forcefully persuades TheProtagonist to accompany him in his car for unknown-but-probably-nefarious purposes]] wears a pair of mirrored aviator shades that hide his true self, [[spoiler:and true age; he's much older than he appears, and much less innocent than Connie thought...]]
[[/folder]]

[[folder:Live-Action TV]]
* ''Series/{{Battlestar Galactica|2003}}''. The Brother Cavil Cylon interrogating Saul Tigh while he's imprisoned on New Caprica wears one of these.
* The [[MonsterOfTheWeek Spider People]] from ''Series/BigWolfOnCampus''.
* ''Series/BreakingBad'': Early on, when Walter White is cultivating his "Heisenberg" alias, he does so with sunglasses and porkpie hat to intimidate and somewhat hide his real identity. In later seasons he just uses transparent glasses, as he's already [[TheDreaded intimidating]].
* ''Series/{{Community}}'': in "Intro to Politics", Secret Service agent Robin Vohlers is always wearing dark glasses, attempting a FourEyesZeroSoul level of intimidation, but Abed sees into her soul anyway.
* Mr. Eldritch in ''Series/DarkSeason''.
* Franchise/MarvelCinematicUniverse:
** ''Series/Daredevil2015'': On occasion, Matt Murdock will invoke this trope when he has to act in his Daredevil persona while out-of-costume.
** ''Series/LukeCage2016'': Hernan "Shades" Alvarez wears his namesake Ray-Bans almost all the time, even at night, and makes it known that he means business when he takes them off, so [[OOCIsSeriousBusiness any scene where he's not wearing them is usually a serious and pivotal one]]. Theo Rossi has commented in interviews about taking a few cues from Charlie Cox's portrayal of Matt Murdock, as the role similarly required him to act without using his eyes to express emotion.
* ''Series/MightyMorphinPowerRangers'': Rita's fake Rangers from "A Bad Reflection On You" wear these in civilian guise.
* ''Series/TwinPeaks'' : Thomas Eckhardt's reappearance in Double Play (Episode 21), especially when the fireplace reflects on his sunglasses.
[[/folder]]

[[folder: Professional Wrestling]]
* Wrestling/{{CHIKARA}}: Wrestling/SidneyBakabella's shades protected him from [[Wrestling/TheOsirianPortal Ophidian]]'s hypnosis, which usually works on whoever is subjected to it.
[[/folder]]

[[folder:Tabletop Games]]
* Being a clan of [[TheCorrupter corrupters]] who are highly sensitive to any form of bright light, Followers of Set in ''TabletopGame/VampireTheMasquerade'', often wear these, to the point that it's become a stock accessory for Setite player characters.
[[/folder]]

[[folder:Theatre]]
* Commander Khashoggi, the head of the SecretPolice in ''Theatre/WeWillRockYou''.
** In the Toronto version of the musical, he is also shown to have two different colored eyes, which might explain why he wears them.
[[/folder]]

[[folder:Toys]]
* ''Toys/SuperThings'' has the third faction of the Spies, who all wear eye-hiding sunglasses. While the faction is made up of heroes and villains, no one can tell which Spy is on which side, due to the fact they hide their eyes, the automatic tell of morality for [=SuperThings=]. As such, the Spies have been labeled untrustworthy by both the heroes and the villains, since no one can tell which side they're on at first glance. The only way to reveal their allegiance is to splash their glasses with water, thus negating the power.
[[/folder]]

[[folder:Video Games]]
* Machi Tobaye in ''VisualNovel/ApolloJusticeAceAttorney'' may be a deliberate subversion, as his shades make him come off as creepy when he really isn't.
* The Doctor character from ''VideoGame/AssassinsCreedBrotherhood'' multiplayer has mirrored goggles over a WhiteMaskOfDoom. The Engineer has proper sunglasses.
* From the ''VideoGame/{{Bayonetta}}'' franchise there's Rodin who wears a pair, he's a ScaryBlackMan FallenAngel who is one of the most powerful demons in the entire Trinity of Realities, not to mention a master weaponsmith who forges his wares by [[YourSoulIsMine sucking out the souls of demons]] to fuel them. Despite this and evil-looking shades, [[DarkIsNotEvil he's not actually a bad guy]]... not that it makes him any less sinister.
* Khaled Al-Asad in ''VideoGame/CallOfDuty4ModernWarfare'' is never seen without his sunglasses.
* In the first edition of ''VideoGame/{{Civilization}}'', when the player was running a modern-age despotism, or their civilization was in "anarchy" between governments, the image of the civ's leaders included a generallisimo-type wearing shades.
* ''VideoGame/CosmicStarHeroine'' has [[BigBad Dominic Steele]], the director of Agency of Peace and Intelligence. He always wears shades, and he is a KnightTemplar believing in TheEvilsOfFreeWill and tries to create a better world by brainwashing everyone in the galaxy with him ruling over all. [[spoiler:As it turns out, he himself was actually mind-controlled by Eternity, the true BigBad of the game]]. On lesser note, Groff Brokston, the StarterVillain turned LoneWolfBoss, also wears shades and he is a leader of a criminal gang known as Chaos Dogs.
* Jacob Arthur "Danik" in ''VideoGame/DeadSpace3'' wears them "Albert Wesker" style. In other words, he never takes them off. Even when he is in snowy conditions and under the freaking ground, where he would have literally no reason to wear them.
* ''VideoGame/DoubleSwitch'': The members of the Society of the Scroll and Key all wear sunglasses and are willing to kill people to get an artifact.
* Rude (his name, not his description) in ''VideoGame/FinalFantasyVII'' has these, making him as scary as possible for being a member of the GoldfishPoopGang.
** Rude also seems to carry around multiple pairs. In ''Anime/FinalFantasyVIIAdventChildren'', his shades get stepped on, so he just pulls another one out of this jacket pocket.
* ''VideoGame/FiveNightsAtFreddysSecurityBreach'' has Monty Gator's shades as the ''reason'' he's sinister. One of the mechanics of the game is stunning the animatronics with a camera flash or laser gun. This is explained in-universe as exploiting a glitch in the optic sensors used in the animatronics. Because Monty is wearing sunglasses, he ''can't'' be stunned, forcing you to outrun him when he attacks. [[spoiler:He loses the sunglasses, and this immunity, when he becomes Shattered Monty.]]
* ''VideoGame/GodHand'' has Azel, the Devil Hand, probably as a ShoutOut to the aforementioned Albert Wesker, since both characters were created by Creator/{{Capcom}} and specifically, Creator/ShinjiMikami.
* ''VideoGame/HogansAlley'': One of the gangsters wears a pair of sunglasses.
* In ''VideoGame/KirbyAndTheRainbowCurse'', [[spoiler:the Dark Crafter has shades that he uses to possess Claycia. They seem to be purely cosmetic otherwise, as its single eye is situated in his ''mouth'']].
* The ''Franchise/{{Pokemon}}'' games have the Black Glasses, a pair of sunglasses that heighten the power of [[DarkIsEvil Dark-type moves.]] Krokoroks and Krookodiles have a dark membrane in front of their eyes that act similar to these, letting them intimidate their prey and foes, and allowing them better vision at longer distances.
* ''VideoGame/PaperMario'': In [[VideoGame/PaperMario64 the first game]] and ''[[VideoGame/PaperMarioTheThousandYearDoor The Thousand-Year Door]]'', enemy Koopas are wear sunglasses and [[SpikesOfVillainy spiked collars and bracelets]] to distinguish them from friendly [=NPCs=]. In ''VideoGame/SuperPaperMario'', the shades and studs instead indicate Koopas brainwashed by Nastasia (Koopa Troopas in the Bitlands who are still loyal to Bowser lack them, but are still hostile).
* Leon Bronev, boss of the criminal organization Targent (which is essentially the archeology mafia) and BigBad of ''VideoGame/ProfessorLaytonAndTheAzranLegacy'', sports a villainous pair of TriangleShades for most of the game.
* In ''Franchise/ResidentEvil'', Albert goddamn Wesker. Eventually, it's to cover up for [[InhumanEyeConcealers bizarrely inhuman eyes]], but mostly [[RuleOfCool they're just there to be rockin']], especially since he did it before he got them and why he wore them in the lab, so yeah; it's mostly to be badass.
** Funnily enough, these bite him in the bum during his [[spoiler:final appearance in ''5'']]. Despite all his mutagenic augmentations by that point in his career, for some reason merely shutting off the lights (in an area that wouldn't even be described as "poorly lit" anyway) can confuse him and leave him vulnerable for no reason other than his choice of eyewear, it seems.
* [[BigBad Dr. Eggman]] from ''Franchise/SonicTheHedgehog'' has always worn these, although early Western material [[AmericanKirbyIsHardcore tried to pass them off as pitch black eyes.]]
* ''VideoGame/StardewValley'': Mr. Qi wears purple sunglasses that cover his eyes completely, adding to his already sinister look and vibe.
* In ''VideoGame/Splatoon2'', the enemy [[EliteMooks Octolings]] have swapped their metal goggles from [[VideoGame/Splatoon1 the first game]] out for a pair of shades with a single glowing red eye, Terminator-style. [[spoiler:During the final boss battle, the BrainwashedAndCrazy Callie wears a pair of "Hypnoshades" that do said brainwashing. She's freed after Marie blows the glasses off her face with a well-placed Charger shot.]]
* ''VideoGame/StreetFighterV'' has newcomer [[LeanAndMean F.A.]][[PoisonousPerson N.G.]] wear a sinister pair of round sunglasses.
* ''VideoGame/TimeCrisis'' has [[StayingAlive Wild Dog]], [[ArrogantKungFuGuy Wild Fang]] and [[spoiler:[[RogueAgent Robert Baxter]]]].
* ''VideoGame/TheWorldEndsWithYou'''s BigBad, Megumi Kitaniji, wears a pair of sunglasses and is even nicknamed "Shades"
* In the ''VideoGame/{{Yakuza}}'' series, Jo Amon and every member of the Amon clan wears one. You can acquire their shades as an item after beating them, which increases weapon damage.
[[/folder]]

[[folder:Webcomics]]
* Black Monday Blues of ''Webcomic/DeadWinter'' has red-tinted pairs. Yes, multiple, he carries ''spares''.
* Coach Gordon of ''Webcomic/DearChildren'' is always seen rocking a pair of shades. Whether or not his intentions are sinister, one thing's for sure, his glasses only add to his creep factor.
%%* Ricci's manager in ''Webcomic/{{Fite}}''
* Terezi [[MeaningfulName Pyrope]] of ''Webcomic/{{Homestuck}}'' wears [[http://www.mspaintadventures.com/?s=6&p=003937 pointy red ones]] because she's {{blind|Seer}}.
** It's funny how the person who's wearing the shades can affect whether they count as cool shades or sinister shades. [[spoiler:Bro's shade's on Bro? {{Cool|Shades}}. Bro's shades after having been taken from his own bloody corpse by [[BigBad Bec Noir]]? [[http://www.mspaintadventures.com/?s=6&p=004830 HOLY SHIT HOLD ME]]]]
*** And when [[spoiler:[[MonsterClown Gamzee]] is seen wearing Terezi's glasses?]]
** Also reversed. Nepeta is adorable when wearing Equius' shades. On Equius himself, they come across as more perverted than sinister. [[spoiler:Then played straight again when Gamzee gets ahold of those too...]]
* Agent Ben and Agent Jerry, TheMenInBlack from ''Webcomic/TheInexplicableAdventuresOfBob.'' Of course, they're [[IneffectualSympatheticVillain ineffectual]] enough that it's debatable just how sinister the glasses make them.
%%* Tip of ''Webcomic/SkinHorse'' [[http://www.webcomicsnation.com/shaenongarrity/skinhorse/series.php?view=archive&chapter=36749 attempts to invoke this]] when dealing with a local sheriff. We emphasize "attempts".
* ''Webcomic/UserFriendly'''s [[FakeRussian Pitr Dubovich]] wears these, as does his {{Eviler|ThanThou}} [[EvilTwin Twin]].
* Professor Broadshoulders from ''Webcomic/ZebraGirl'' wears these, and when he's in silhouette they become straight-up ScaryShinyGlasses.
[[/folder]]

[[folder:Web Originals]]
* ''WebVideo/AgamemnonTiberiusVacuum'' always wears black [[Film/CharlieAndTheChocolateFactory Willy Wonka]]-style goggles.
* The [[TheOmniscientCouncilOfVagueness Shadow Men]], {{Chessmaster}}s of ''WebAnimation/BrokenSaints'', both sport these, as does sleaze ball strip club owner Mars, whose shades are red and glowing.
* ''Music/DoctorSteel'' is never seen without his antique dark welding goggles (which in one of his music videos, reflect flames).
* Made fun of by the ''WebVideo/GameGrumps'' during their playthrough of ''VideoGame/ResidentEvil'', when they get to the ([[ObviouslyEvil not so surprising)]] reveal that Albert Wesker is the BigBad:
-->'''Danny:''' I knew it was Wesker!\\
'''Arin:''' Obviously! He wears sunglasses indoors!\\
'''Danny:''' Yeah! No one not evil would do such a thing!
* Michelle Clore of ''WebVideo/KateModern'' wears these, as does Kate when under her influence.
** Let's not forget "Dr. Specialist", either.
* ''WebVideo/{{lonelygirl15}}'' loves this trope. Lucy, Virgil, and various Shadows, Deacons and hired thugs all wear these.
* ''LetsPlay/MikeBurnFire'': [[EvilCounterpart Legion Mike]] is a die-hard supporter of [[VideoGame/FalloutNewVegas Ceasar's Legion]], the most unambiguously evil faction of the setting, and his standard get-up includes a pair of sunglasses.
* Bridget in ''WebVideo/SororityForever'' has worn these on occasion.
* While in his disguise as a kebab restaurant clerk during the Lovers mini-arc in ''WebVideo/VaguelyRecallingJoJo'', Steely Dan wears a pair of shades.
[[/folder]]

[[folder:Western Animation]]
* In the first ''WesternAnimation/GIJoeARealAmericanHero'' miniseries, the Baroness wears sunglasses before switching to regular ones in the next one.
* Protoman had these in the Ruby-Spears ''WesternAnimation/{{Mega Man|RubySpears}}'' cartoon; at a few points, we could see Mega reflected in them as he was about to sneak up on him.
* ''WesternAnimation/ThePowerpuffGirls'': Ace, leader of the villainous Gangreen Gang, wears an angular pair of shades that work both for the {{cool|shades}}ness factor and the sinister factor. He certainly doesn't look as intimidating without them.
* ''WesternAnimation/SouthPark'': Cartman wears a pair of mirrored ones when he's deputized by Officer Barbrady and starts abusing his [[InsistentTerminology authoritah]] to the extreme.
* [[AlphaBitch Heather]] was introduced with these on ''[[WesternAnimation/TotalDrama Total Drama Island]]'', complete with scary background music.
[[/folder]]

[[folder:Real Life]]
* In RealLife, the US Secret Service goes for the Sinister Shades look on purpose, to discourage anyone from messing with their "protectees". They also do it so they can stare at someone without being noticed, i.e. no one knows where they are looking.
** One additional reason they wear sunglasses is so that their eyes are adjusted to the light when they go indoors. Inside agents almost never wear sunglasses, it’s just that most of the time they are seen they are outdoors and therefore this trope exists.
* The late Reverend UsefulNotes/JimJones wore them to hide the [[RedEyesTakeWarning redness in his eyes]] that his amphetamines and quaaludes gave him. It became a trademark of his along with his white suit.
* "Satanic" serial killer Richard Ramirez wore shades in the courtroom.
* The late Kim Jong-Il, the previous leader of UsefulNotes/NorthKorea, wore them to look even more menacing. Well, to try to look the part, anyway -- it wasn't all that successful. The shades didn't make up for the fact that he was short, fat, and unbelievably goofy-looking, though. Unless you were actually under his heel, it's pretty hard to find him scary, especially after ''Film/TeamAmericaWorldPolice''.
* UsefulNotes/MuammarGaddafi, the former dictator of Libya, was frequently photographed wearing them. It worked roughly as well for him as it did for Kim Jong-il.
* [[http://tinyurl.com/nlwydkr This (in)famous photo]] of the late Chilean dictator UsefulNotes/AugustoPinochet is probably the very definition of this trope.
* Creator/JimmySavile was rarely seen without his signature pink sunglasses, which became this in hindsight after he was exposed as a child rapist.
* Blogger and self-admitted pedophile [[https://www.youtube.com/watch?v=4U6N7AMHzIU Jack McClellan]] claims that he wears the sunglasses because of the studio's lighting. Steve Wilkos makes him take them off.
* U.S. soldiers in the UsefulNotes/TheWarOnTerror. Though probably worn primarily for practical reasons (against the desert sun and as ballistic protective eyewear), they were certainly intimidating enough to inspire [[http://www.nytimes.com/2003/08/07/international/worldspecial/07LEGE.html urban legends]], which say that they give their wearers XRayVision.
* This was one of Music/LouReed's visual trademarks, as well as of most of the rest of his bandmates in the Music/VelvetUnderground.
* Creator/GenUrobuchi ''always'' wears shades whenever he makes appearances at fan conventions and panels.
[[/folder]]

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