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So you have a guy who is cold, emotionless, or brutally practical, a little cruel or even a soulless monster. To quickly tip off the audience to his personality, give him glasses. The eyes are said to be windows of the soul, so hiding them behind glasses makes the character seem more removed. They mask the spitefulness on a villain's face and usually after the facade is taken off it is seen in their eyes (often going with Creepy Shadowed Undereyes of evil). Particularly effective if the glasses have Opaque Lenses and you can have the light reflect off them in scary ways. Double bonus points if seen on the Evil Genius.

Compare Sinister Shades. Contrast Stoic Spectacles, where the glasses make the guy look aloof, intellectual and cute. Since glasses also evoke physical weakness, this often also evokes Sissy Villain. On the other hand, since Smart People Wear Glasses, it can also signal that the character is a Badass Bookworm. It may also be a parallel to Evil Cripple, in which a physical defect (poor eyesight, in this case) reflects a moral one. When this is treated as a fetish, see Bespectacled Bastard Boyfriend.

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Examples:

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    Anime & Manga 
  • For a short time (like 3 episodes short), Aizen from Bleach personified this trope by massacring the ruling force of Soul Society, near murdering his second in command, and what he did to Rukia. He ditched the glasses after, but he's definitely remained super evil.
  • Girge from Break Blade is a special case. While he's definitely a spectacled blood knight, at times, he can be Stoic Spectacles as well, thanks to his complicated personality.
  • Nikaidou Yuu from Shugo Chara! before his Heel–Face Turn. He used his students' issues to his benefit, destroying their hopes and dreams so that he could try for a promotion. Even worse, he feels no regret, even going so far as to say he finds it so much fun he "can't help himself."
  • Neon Genesis Evangelion: Gendo Ikari — a clearly sociopathic NERV commander, who is so fixated on the death of his wife that sees his own son only as a mean to reverse said death, and everyone else as not even that.
  • Quattro of Magical Girl Lyrical Nanoha Strikers plays with it a bit. She is easily the most sadistic and cruel of the Numbers, but we don't really see just how evil she is until after she takes the glasses off. The glasses themselves are part of her being The Fake Cutie.
  • Tamaki Tsunenaga of Deadman Wonderland, Assistant Warden and de facto tyrant of Deadman Wonderland. Under his calm, almost idiotic attitude, he is something of a sadist, caring nothing about the fact that he butchers dozens of prisoners every day for the sole purpose of gathering money or experimenting on them, or simply for his amusement. As son of the dying Chief Warden of Deadman Wonderland, he eagerly hopes for the death of his father to become truly the supreme ruler of the prison, and he devotes much of his time and resources in studying and experimenting on the powers of the Branch of Sin and their origin. He also is in contact with the upper echelons of the Japanese government, his ultimate goal being the synthesis of artificial Deadmen. In sharp contrast with his cruelty, he enjoys playing with children's toys.
  • Claude "Torch" Weaver from Black Lagoon is a fat, plain-looking man who is always smiling and wears thick glasses with basic "aviator" frames (bearing a strong resemblance to Drew Carey). He is also an insane Pyro Maniac who burned his wife to death and now works as a bounty hunter. Surprisingly capable in a fight too, since he was one of the last men standing during the Greenback Jane arc.
    • Roberta earlier in the series gave off this impression, she appeared meek and polite to hide her terminator-like abilities. Granted she does ditch her glasses, and deeply cares for her young master, Garcia. However glasses or not, NEVER mess with Roberta.
  • Claude Faustus in Black Butler, a literal demon - and not the "they just have horns and tails and cool powers" anime kind of demon - a real, soul devouring demon.
    • Subverted with Sebastian, the series' main demonic Battle Butler, who looks warmer and more human in his bespectacled tutor guise than in his regular costume, and with the Grim Reapers, a Psychopomp bureaucracy who are required to wear glasses, but are a lot warmer and more human than the demons.
  • Inverted in Kara no Kyoukai with Touko Aozaki. While she's wearing her glasses, she's a somewhat eccentric magus with a smoking habit. But when the glasses come off, she tends to get ugly. Her facial expressions even match this change.
  • Saruhiko Fushimi in K, and his boss, the Blue King, Reisi Munakata - in the first season at least, their Clan looks quite heartless. Munakata commends one of his subordinates for her "blatant disregard of [a powerful prisoner]'s human rights", and Fushimi chloroforms a high school student in order to steal her identity and hack her school's computers - not to mention his constantly picking fights with his ex (a member of the Clan Fushimi betrayed). Subverted in the side stories that focus on them - they get quite a few "Aw, Look! They Really Do Love Each Other" moments, and you see their side of the story more. And in season 2, Fushimi gets an excellent Pet the Dog moment when it's revealed that he didn't actually betray the Blue Clan, he joined Jungle as The Mole and helps the alliance save the world. They are both very much geared to the Bespectacled Bastard Boyfriend -loving crowd, though. (See Munakata's scenes with Kuroh).
  • The Doctor in Black Cat. He's a Mad Doctor For Science! loon who acts as The Medic for the Big Bad, and believes that emotion is pointless, and that dissecting young girls and trapping people in Mind Screw Warp Worlds based on their worst fears is fun. Is it possible to have negative soul points?
  • Kyoya from Ouran High School Host Club invokes this and even some of the lighter shades of Bespectacled Bastard Boyfriend (since the Host Club is all about fulfilling romance-novel stereotypes). He pretends to be polite and charming, but doesn't really make too much secret of the fact that he's ruthlessly scheming underneath it, and willing to go to terrifying lengths to protect and/or advance his own interests. This is at least partly an act: Kyouya in fact cares very deeply about his friends in the Host Club, and is even demonstrated to be kind to strangers when it wouldn't put him at a disadvantage to do so. Being scary just makes it less likely that people will mess with his plans...or his friends.
  • Fullmetal Alchemist:
    • Shou Tucker, who shows no remorse whatsoever when he performs alchemy experiments on his own daughter to advance his career. True to form, he has the creepy glasses, but ironically the glasses become clear and reveal his eyes when he admits what he did in a Motive Rant to Edward.
    • The Gold-Toothed Doctor counts as well. Despite his rare appearances, he still manages to be one of the most vile characters in the series, and is complicit in Father's Evil Plan which involves killing everyone in Amestris and keeping their souls in an And I Must Scream situation while trapped inside Father's body.
  • Sgt. Frog's Kururu is the resident Mad Scientist and wears Opaque Nerd Glasses. He's also the Token Evil Teammate in a group that is trying to take over the world, with a disturbingly blase attitude towards testing his inventions on his own teammates.
  • Director Udo Heinemann from Monster. He has glasses and is a corrupt doctor who doesn't care about the patients of his hospital, but for the money. Also, he has plagiarized the research of his subordinates and is a Bad Boss.
  • The original Mobile Suit Gundam has Degwin Zabi, dictator of Zeon, who likely murdered his way into his position, and now prosecutes a war against Earth from behind his green-tinted glasses. In fairness to him, he's got nothing on his 20/20 sighted children when it comes to being truly evil.
  • Sawa Nakamura from The Flowers of Evil is a middle school student who is detached from - and disgusted with - the society around her. The series follows a classmate of hers as she catches him doing something creepy and blackmails him into letting her "corrupt" him into something more "real" than the "s**tbugs" around them. They're really just preteens acting out, but from their point of view (and that of their classmates), she is this trope personified.
  • Shyamalan from Birdy the Mighty: Decode fits this trope to a T, even invoking Scary Shiny Glasses and making his eyes look more evil on occasions where his glasses come off.
  • Subverted in Detective Conan anime episode 799. An old woman's glasses become Scary Shiny Glasses in a flashback just as Conan is realizing she was responsible for the death of that episode. The subversion is that the death was accidental. The criminal was a burglar who used Wall Crawling as a gimmick. They saw and startled one another, shocking the woman and causing the man to lose his grip, which sent him plummeting to his death.
  • Shiroe from Log Horizon is a subversion. He's a master tactician, but tends not to explain his motives to people. This makes him a Hero with Bad Publicity, as a lot of people assume his ultimately beneficial plans are for his own personal gain. Other characters (including some of his allies) even call him "The Villain in Glasses".
  • Sword Art Online: Sugou Nobuyuki, the Arc Villain of the Fairy Dance arc, wears glasses in real life, though not as Oberon in ALO. He's also a slimeball Corrupt Corporate Executive who does such horrible things as perform inhumane Mind Control experiments on 300 SAO survivors, and try to rape Asuna while making Kirito watch.
  • GUNNM's Desty Nova wears weird metallic goggles that makes his face especially sinister, and is totally unfettered in his quest For Science!. He's the man who crippled thousands in his experiments, and even his most resounding success is a Broken Ace at best. He's also the Deuteragonist of the story, and is on of the better side of the character spectrum. It's that king of series.

    Comic Books 
  • Kevin in Sin City is a cannibal Serial Killer who gives us the Trope Image (with his representation in the film version made even worse by everyone recognizing Frodo). He's first introduced to us after having eaten a woman's arm while she was still alive. This is further emphasized by how the art style frequently gives the lenses a solid, opaque look.
  • Batman:
    • When out of costume, Jonathan Crane (Alias: The Scarecrow) is a bookish, glasses wearing nerd. Who just so happens to love terrifying those around him and being a general sadist.
    • Professor Hugo Strange, who takes upon himself to torment Batman. Taken Up to Eleven in Prey, where we never ever see his eyes, only what's caught in his glasses' reflections.
  • Kemal in Djinn looks like an completely unassuming man with glasses who doesn't appear to be sinister at first. But then he quickly establishes himself as an violent an misogynistic brute who derives pleasure from abusing women. His boss Amin specifically threatens women with handing them over to Kemal to do anything he wants with them.
  • Baxter Stockman has glasses that fit him both as a villain and as a Mad Scientist in Teenage Mutant Ninja Turtles from the comics to the 2003 series, and even the 2012 series.

    Films — Live-Action 
  • Dr. Herbert West, Re-Animator. In the third film's commentary, the director mentioned how just putting the old-style glasses on actor Jeffrey Combs instantly transformed him into West.
  • Major Arnold Ernst Toht, the creepy-as-hell Gestapo torture guy Raiders of the Lost Ark, wears glasses.
  • Dr. Jonathan Crane from Batman Begins is a bookish, glasses wearing nerd who just so happens to be a general sadist who loves terrifying those around him.
  • The bespectacled Cleaner in the French film Nikita, and the American remake Point of No Return (chillingly played by Harvey Keitel), and the TV series Nikita. Though more efficient than cruel, his only concern over the twitching of the still-living victims is the inconvenience. He also doesn't hesitate to apply his methods to the heroine and allies.
  • Bent features a bespectacled evil Nazi that is memorable for his interrogation methods on the train.
  • Brick Top in Snatch. is a brutal, sadistic gangster who wears a pair of thick rimmed glasses. His introductory shot is him bashing a man's teeth out with a hammer. All the characters in the film who know who he is are terrified of him, lest they get cut into pieces and fed to a pack of pigs.
  • Cameron Alexander from American History X is the sinister xenophobic leader of the Californian Neo-Nazis. He is indirectly responsible for all the bad that happens on the course of the movie, since practically every action is made by the brainwashed youngsters as a result of nothing but his hideous manipulation and evil influence.
  • Boss Godfrey, of Cool Hand Luke. You don't talk to him, ever. The movie's rife with symbolism, and his sunglasses are meant to reflect a distorted view of man (most shots of him are close-ups on his Aviators).
  • Clarence Boddicker, the memorable antagonist in RoboCop (1987), was specifically made to wear glasses to resemble Heinrich Himmler. It shows.
  • George Harvey in The Lovely Bones is a twisted serial killer of little girls. Harvey is maybe the worst example of his kind and a horrible person, so depraved and vicious he can't abstain himself from taking young, innocent lives.
  • Humma Kavula, the evil religious leader in the Film of the Book The Hitchhiker's Guide to the Galaxy also wears glasses. To add to the creepiness, it turns out the apparently transparent "lenses" are actually small video screens. Beneath the glasses, he has no eyes.
  • Gary Winston, the perfidious CEO in Antitrust, is another good example. His malicious nature is revealed not long after the protagonist encounters him. He tries to project the fake image of a well-intentioned visionary.
  • Emil Leopold Locque in For Your Eyes Only is Kristatos' quiet, cruel, ruthless enforcer who wears a distinctive pair of glasses.
  • Angels & Demons has an assassin who single-handedly leads the Vatican police on a chase that ends with dozens slain. He isn't even killed by the good guys but gets double-crossed.
  • Nightbreed: Dr. Decker is a serial killing, genocidal psychopath. He's more of a monster than every being in Midian combined, and he's the only character in the movie with prominent glasses.
  • X-Men Film Series
  • A subversion in Harry Potter and the Half-Blood Prince: Harry certainly isn't this trope. However, after he uses Sectumsempra on Draco Malfoy, the next scene has him looking like he has Scary Shiny Glasses instead of eyes, expressing his realization that he's gone too far in their enmity.
  • In Mirage (1965), Willard is a brutal assassin whose distinguishing characteristic is his wire rim glasses.
  • Nathan from Ex Machina. His thick glasses reflect his cold and detached personality and attitude toward others.
  • Christian Szell from Marathon Man, is a cruel Nazi Grandpa who kills Babe's brother, and tortures Babe himself, over some costly diamonds.
  • "Sick Mob Man" from The Boondock Saints kills an entire family. So much for "no women, no kids".
  • Thorwald from Rear Window wears glasses. He also cheats on and murders his wife, then kills a dog and attempts to kill Lisa to cover it up.
  • Rollo and the Spirit of the Woods: Lackey, the utterly rotten and conceited adviser of the rolleys' chieftain, wears spectacles.
  • In Allied, there's a high-ranking government man in a suit and glasses, cold as ice, who tells Max that Marianne may be a traitor, that he is not to interfere, and that, if she is guilty, he is to shoot her.
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    Literature 
  • Nineteen Eighty-Four uses this trope to enhance its introduction of "duckspeaking" (spouting politically-correct statements without thinking):
    His head was thrown back a little, and because of the angle at which he was sitting, his spectacles caught the light and presented to Winston two blank discs instead of eyes. ... As he watched the eyeless face with the jaw moving rapidly up and down, Winston had a curious feeling that this was not a real human being but some kind of dummy.
  • Algaliarept from The Hollows series, though he could also be considered a Bespectacled Bastard Boyfriend if you support Al/Rachel.
  • Prof. Frost, from the last book of The Space Trilogy of C. S. Lewis. We never see his eyes because, by a nasty little miracle of staging, they are always hidden behind the reflections of his glasses. Technically, he must have a soul (or had one at one point), but we find out that he objects to the very existence of souls.
  • In Interesting Times, Evil Vizier Lord Hong, who is not so much power-mad as power-sane (he doesn't even think of cackling madly, like the traditional type of Grand Vizier), wears little round glasses.
  • In The Man Who Was Thursday, Saturday wears a pair of round, tinted glasses that obscure his eyes entirely, and have a terrifying effect on people around him. Once the glasses are removed, though, his looks turn out to be so wholesome and commonplace that his terrorist disguise is instantly blown.
  • In The Dark Tower book The Drawing of the Three, we're repeatedly told that Serial Killer Jack Mort wears gold-rimmed glasses.
  • Zack, the Sociopathic Hero of The Mental State, wears elliptical lenses, as shown on the book's cover. He usually appears to be friendly, compassionate and obliging. It is only when he looks at you from over the tops of his spectacles and smiles that you know he has completely screwed you over.

    Live-Action TV 
  • The second season of Agents of S.H.I.E.L.D. had Dr. Whitehall, who wears Himmler-like glasses, probably because not only he's a high-up HYDRA head, but he actually was a Nazi.
  • A recurring villain on Alias was a Chinese torturer named "Suit-and-Glasses" because, you guessed it, those were his only identifying features.
  • Babylon 5 has the interrogator who tortured Sheridan in the episode "Intersections in Real Time".
  • Robert Daly, the antagonist of the Black Mirror episode "USS Callister" wears thick nerdy glasses in his regular life and takes them off inside his Infinity game, where he plays a cool-as-cucumber alpha male starship captain. However Daly also has a malicious and tyrannical side he keeps hidden from the people he interacts with in reality and unleashes with terrifying coldness in the game.
  • Black Sails: Dufresne, an 18th century pirate ship accountant, initially sports Nerd Glasses that establish him as a wimp. Once he toughens up, he also gets more treacherous, becoming prone to dead-eyed stares through his cracked lenses.
  • Breaking Bad:
    • Gus Fring's glasses are inseparable from his politeness, intelligence, and harmless persona... and also from his cool, menacing stares.
    • Walter White becomes one as he embraces his Heisenberg personality.
  • Giles in Buffy the Vampire Slayer slips into this now and again, mostly because of I Did What I Had to Do. Shown perhaps most clearly at the end of season 5, where he's perfectly prepared to sacrifice Dawn and suffocates Ben in cold blood to stop Glory's return.
  • Daredevil (2015):
    • James Wesley. His flat expressions, especially when combined with his glasses, greatly unnerve almost everyone around him.
    • Leland Owlsley wears thick glasses that mask the eyes of a well-dressed white-collar crook.
    • Subverted by Mitchell Ellison. While he wears glasses and is initially presumed by Ben Urich to be on Wilson Fisk's payroll, he's ultimately a good guy, and mentors Karen in season 2.
  • Doctor Who:
    • The War Lord from "The War Games" sought to use Earth's history's greatest warriors to conquer the universe and totally nailed the Steve Jobs look, right down to the glasses. Which is rather more impressive when you consider that Steve Jobs was a 14-year-old nobody when this serial first aired.
    • Nyder from "Genesis of the Daleks" (a blatant Heinrich Himmler Expy). Even his voice is a cold and steely monotone, except when he displays some actual feeling. But don't believe him when he does it.
    • "Demons of the Punjab": Manish, a Hindu fanatic who hates Muslims so much he arranges his brother Prem's murder when Prem marries one, sports a pair of round glasses.
  • The camera lingers quite a bit on Leland Townsend's designer glasses on the pilot episode of Evil, just before he threatens the death of Kristen's daughters. It's later revealed that he encouraged Orson LeRoux to act on his murder fantasies and coached him in how to fake insanity.
  • The Flash (2014): Much like Giles, as mentioned above, Dr Harrison Wells is much more prone to Shoot the Dog than his idealistic team-mates, and has the Nerd Glasses to match this tendency. Interestingly, he usually takes his glasses off before doing morally questionable things. This is because he doesn't actually need them, only wearing them as part of his 'Harrison Wells' persona. When he drops the act and reveals his true identity, he stops wearing his glasses altogether.
  • Sylar from Heroes began his murderous streak while he was still a bespectacled watchmaker. Taken to extremes with the multi-lens glasses he wears for his job.
  • An episode of Law & Order: Special Victims Unit once dealt with a case involving a man who had abducted a teenage girl and was holding her captive as a sex slave. At one point, the girl (who had managed to acquire a phone) mentions the guy was (for some reason...) at his absolute worst and sadistic when he was wearing his glasses (which was a lot).
  • The Mole who infiltrates the OSP on NCIS: Los Angeles is a bespectacled Fat Bastard who poisons Granger, kills a Red Shirt, and takes Eric hostage before being captured.
  • Nazi leader and Fuhrer Heinrich Himmler himself from The Man in the High Castle.
  • Roan from Nikita is a prime example. From his very first introduction, Roan is seen ruthlessly killing the first man they interrogate, and shows virtually no development of sympathy or a moral conscience throughout the series.
  • In the 6th Prime Suspect miniseries, there's a ruthlessly pragmatic woman from the government with large, very thick-lensed glasses. She also looks quite young—though clearly an adult, she sort of looks like a 12-year-old. This gives her a nerdy-schoolgirl look, for dramatic irony.
  • The Supervisor in The Prisoner (1967), although the effect is enhanced by being combined with the character's booming Robo Speak voice and his almost never-changing deadpan facial expression.
  • Criminal gang leader Charlie Elkin (played by Christopher Ellison) in the BBC children's drama serial Running Scared from 1986. In fact, his glasses are a major plot point, as they are a critical piece of evidence that could put him away for good, which is why he ruthlessly searches for them.
  • Sherlock: Charles Augustus Magnussen, a bespectacled man whom Sherlock describes as "the Napoleon of blackmail".
  • Inverted in Stargate SG-1 with alternate/evil Daniel Jackson, who didn't wear glasses. One WMG suggests that glasses are the inverse of beards in the Stargate-verse. (Both the glasses and the evil were the result of some Applied Phlebotinum.)

    Music 
  • The music video for Maroon 5's Animals stars Adam Levine as a creepy stalker/serial killer, wearing a pair of stereotypical psychopath glasses all the way through.

    Pro Wrestling 

    Roleplay 

    Theater 
  • Juror #4 in 12 Angry Men is the only one who wears glasses and represents the detached, analytical approach to deliberating the case. He's the second-to-last to switch his vote from guilty to innocent (and the argument that convinces him there's a reasonable doubt is in fact related to eyeglasses).

    Video Games 
  • Jade Curtiss from Tales of the Abyss. Okay, he's a good guy... but that doesn't stop him from being rather cruel to just about everyone.
  • The World Ends with You has Megumi Kitaniji and Mitsuki Konishi.
  • Team Fortress 2: The Medic. And, to some extent, the Engineer, if you're not on his team; one of of his taunts can even be a bone-chilling Evil Laugh. Although it depends on whether you count goggles as glasses, really.
  • Mr Burke, Fallout 3. They're sunglasses, not corrective lenses... but it hardly matters.
  • Jihl Nabaat from Final Fantasy XIII, with an element of titillation. Large breasts, chillingly prim and proper diction, and gracious, the woman walks around with a riding crop.
  • Subverted with Shuji Ikutsuki from Persona 3 - wears glasses, is actually evil, and... is a Pungeon Master (it's not even a facade - you can see practicing his puns while alone in one scene).
  • The Doctor from Cave Story, complete with Scary Shiny Glasses.
  • Double Switch. Early on, Eddie seems to subvert this trope and Lyle seems to play it straight. However, Eddie ends up playing the trope straight, and Lyle ends up subverting it.
  • Director Raymond McMullen, the Director of Research at Gentek, in [PROTOTYPE]. Mad Scientist, Evilutionary Biologist, nice little designer specs. A more spoilery example: Doctor Alexander Mercer himself wore glasses too, before he died. The virus animating his corpse obviously doesn't need them.
  • Dimitri Rascalov in Grand Theft Auto IV.
  • Played with by Klug in Puyo Puyo Fever; he's a jerk, he's impaitent, and he fits the bill for Good Is Not Nice. ...Then he get's possessed by a demon, is practically humiliated as the three people he offends the most save him, and he eventually Pets The Dog... then he has Aesop Amnesia and continues to carry the demon in his book for more games and becomes even more of an asshole.
  • Duke Greene, the Big Bad from Three the Hard Way
  • In the 3DS remake of Pokémon Ruby and Sapphire, Maxie is given a pair of glasses that makes him look more like a Mad Scientist. It also serves the purpose of holding his Mega Stone.
  • Yandere Simulator gives us Info-chan, the game's Knowledge Broker. She actively encourages the Villain Protagonist to murder her rivals, and will provide favors for her should she give her Panty Shot photos for her to sell. Aside from selling said photos to boys, she has a history of blackmailing female students. Naturally, she wears red-framed glasses that gleam brightly.
  • Iggy Koopa in the Super Mario Bros. franchise, who's one of Bowser's top underlings, prone to crazy laughter and taunting his opponents when he has an advantage.
  • The main villain of Ciel nosurge, Revelt, sees his children as expendable, hates the other intelligent race on the planet and only believes an "elite 1%" of humanity is fit to survive the coming apocalypse. He has a pair of glasses in true Mad Scientist fashion.
    • Zill, another antagonist (and one of the main antagonists in the sequel), is also bespectacled, but she is a Well-Intentioned Extremist with a sympathetic cause rather than an all-out villain like Revelt.
  • Asav, the Big Bad of Uncharted: The Lost Legacy, wears a pair of glasses that make him look more like a wise, frail college professor than an immoral, genocidal warlord leading a militant insurrection in a brutal civil war against the Indian government for the sole purpose of assuming personal power by any means necessary. Nadine states that the glasses are an affectation; he doesn't need them, but wears them to cultivate an appearance of intellect and physical weakness so his enemies will underestimate him.
  • Ace Combat
    • Simon Orestes Cohen in Ace Combat 3: Electrosphere, particularly in the Omega Ending. He created Nemo, an Artificial Intelligence, and ran it through a simulation to see if it would be able to kill a Brain Upload version of Abyssal Dison, because he blamed him for the death of Yoko Martha Inoue. The simulation showed that Nemo will indeed kill Dision, and since this was the result that he was hoping for, Simon then created a fresh copy of Nemo that he intended to release upon the world, and would go on to manipulate events to ensure that the corporate war that the simulation had predicted would occur so that Dision would die.
    • Dr. Schroeder at the beginning of Ace Combat 7: Skies Unknown is rather amoral and apathetic towards the strain that Mihaly puts on his body when flying increasingly risky sorties in order to collect data to improve Erusea’s drone army. However, while he discarded it when the Lighthouse War began, Dr. Schroeder’s soul started coming back to him as the war dragged on, and as Mihaly’s granddaughters came to resent him for putting their grandfather through such risky procedures, but he kept pushing away because he believed that it was too late to turn back. In the end, its Subverted once the truth behind his motivations come out, and Ionela calls him out on it, which convinces him to welcome his soul back.
  • Goda from Sentinel Descendants In Time. Subverted at the end when we learn that Beni is really Ramirez.
  • Penelope in Sly Cooper: Thieves in Time starts off as a sweet Meganekko, but is eventually revealed to be a sociopathic Gold Digger who never loved Bentley in the first place; she was only using him as a pawn to Take Over the World. This retcon is one of the factors behind the game's Fanon Discontinuity.

    Visual Novels 
  • Apollo Justice: Ace Attorney has Kristoph Gavin, the Big Bad of the game. Not only does he have a Scary Shiny Glasses animation, using Perceive on said animation and concentrating on his hand will reveal a scar that looks like a demon.
  • Danganronpa: Trigger Happy Havoc has Byakuya Togami, a character so arrogant and antisocial that he openly declares his intention to murder someone, asserts his own invulnerability, and isolates himself because he can't imagine anyone else might have anything to say worth hearing. This being Dangan Ronpa, not only doesn't he ever actually kill anyone, he also survives the entire story.
  • Yaginuma in Kara no Shoujo is even described in the ingame notebook with Still An Asshole.
  • Yakumo from Spirit Hunter: NG is shown to be wearing round, reflective spectacles while dissecting his victims, which make him seem all the more detached and cold.
  • Tsukihime's Tohno Shiki is an inversion. He is somewhat of a Jerkass to Arceuid and Arihiko with his glasses, but his cold, ruthless side really shows itself when The Glasses Come Off.

    Web Animation 
  • In Damaged, one of the two people who seem to be stalking Emily is wearing a pair of glasses, behind which you don't see his eyes.

    Web Comics 
  • Mordecai Heller from Lackadaisy. He's a sociopathic hitman who is extremely bad at expressing genuinely positive emotions, and shows no remorse for the people he hurts and kills. Doubles as a Badass Bookworm.
  • Questionable Content: "No. Leave her. This one has… potential." Justified due to the glasses being augmented reality glasses. When Dale switches them off during an argument with then-holographic May (thereby switching her off as well, since her image was projected onto the glasses), the lenses resemble those of ordinary glasses.

    Western Animation 
  • Given his excessive number of doomsday devices, casual disregard for the life of his employees (and everyone else), willingness to disregard the welfare of the environment for profit or convenience, penchant for creating atomic monsters, and habit of needlessly killing lab animals; Professor Farnsworth of Futurama definitely qualifies.
  • Eustace Bagge from Courage the Cowardly Dog. He ALWAYS mistreats Courage even in life and death situations in which the dog saves his life. He has a low-down and greedy personality, so his glasses do well even as Sinister Shades since his eyes are rarely seen.
  • In Batman: The Animated Series, Mr. Freeze is a shades-wearing villain who is cold in every possible meaning of the word.
    • Interestingly, the trope is inverted with Jonathan Crane, who, while he wears glasses in the comics (see above), never wears them in the show. This might have something to do with his more sympathetic portrayal in the show.
  • Janus Lee, the maniacal inventor from Alpha Teens on Machines. He created a gang of super-assassins with the sole purpose of killing the heroes because they served and accomplished what he wanted, in the first season's finale.
  • Scarlett of Total Drama wears glasses that make her look innocent, but she quickly allies herself with the season's Card-Carrying Villain, Max. Oh, and later she tries to kill the remaining five contestants by hijacking the computer that controls the entire island.

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