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Four Eyes, Zero Soul

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They say the eyes are the window to the soul, but as we see, he has no soul.
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.
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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 or Wicked Cultured. 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 Kichiku Megane.


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Examples:

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    Anime & Manga 
  • Battle Angel Alita'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 kind of series.
  • 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.
  • Black Butler:
    • Claude Faustus is 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.
  • 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?
  • 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 Pyromaniac 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.
  • 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 Broken 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.
  • Subverted in Case Closed 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.
  • 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.
  • 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.
  • 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.
  • Inverted in The Garden of Sinners 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.
  • Parodied with Anko Isuna/Dark Grasper from Gonna Be the Twin-Tail!!. In a setting where the main villains are trying to steal people's "attributes" for energy source, Isuna joined the Ultimegil because she takes the glasses attribute very seriously and would rather have them drain out all other attributes besides it to preserve it. She is otherwise more of a Hikikomori, albeit a rather big Loony Fan to Twoearle.
  • In Heavenly Delusion there is the “Glasses Man,” a sinister criminal who took advantage of a post-apocalyptic Japan to rape children. One of his former victims, a girl named Helm, enlisted the aid of Maru and Kiruko to help her end the Glasses Man’s perverted crimes towards children once and for all when she found him in a town many years later.
  • Hellsing: Alucard himself is a very literal monster, and often wears a set of orange sunglasses before and sometimes during his rampages. The Major, gleeful warmonger and Nazi, also fulfills this trope nicely.
  • Grace O' Connor from Macross Frontier is almost a textbook example: a megalomaniacal Mad Scientist who stops for nothing in pursuing grand power, and is quite adept in political intrigues as well. Interestingly, while the glasses sometimes work as Scary Shiny Glasses, they are largely for her Meganekko Fake Cutie persona as Sheryl's kindly manager.
  • 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.
  • 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.
  • 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.
  • 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.
  • Kyoya from Ouran High School Host Club invokes this and even some of the lighter shades of Fetishized Abuser (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.
  • 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.
  • 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."

    Comic Books 
  • The Adventures of Aero-Girl: Dr. Chimera wears red glasses that hide his eyes from view, and is a member of Aero-Girl's rogues gallery.
  • 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.
  • Gideon Graves from Scott Pilgrim is the only Evil Ex who has glasses, and is by far the most notorious one, being a manipulator and controller who had put Ramona subject to Domestic Abuse.
  • Kevin from Sin City (pictured above) is a cannibal Serial Killer. 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.
  • 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 — Animated 
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    Films — Live-Action 
  • 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.
  • 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.
  • 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.
  • 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.
  • Bait: Bristol is a ruthless thief and murderer in glasses. Often speaks in a calm, detached voice. A memorable scene has him nearly crash his car into a truck. He gets out, the truck drives asks if he's crazy. Bristol calmly turns, shoots him, and just as calmly replies, "No, I'm fine."
  • 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 Boondock Saints: The "Sick Mob Man", an utterly cold-blooded hitman who killed a whole family, wears glasses. He can be seen carefully adjusting them before coming out of the bathroom to attack Rocco. So much for "no women, no kids".
  • Bent features a bespectacled evil Nazi that is memorable for his interrogation methods on the train.
  • Arnim Zola seems like an aversion in Captain America: The First Avenger, when he's the seemingly reasonable one in HYDRA and is a less-than-intimidating bespectacled Swiss man. Not so much when it turns out that he was just trying a different method of building a worldwide fascist empire. His uploaded form in Captain America: The Winter Soldier has the glasses appear opaque, meaning he looks like he has no eyes.
  • 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).
  • The Death of Stalin: Beria is the only prominent character in the movie who wears glasses most of the time (aside from Malenkov) and he is definitely the most villainous member of the cast.
  • Nathan from Ex Machina. His thick glasses reflect his cold and detached personality and attitude toward others.
  • Emil Leopold Locque in For Your Eyes Only is Kristatos' quiet, cruel, ruthless enforcer who wears a distinctive pair of glasses.
  • The Funhouse Massacre: Walter "The Taxidermist" Harris is a Serial Killer who would make taxidermy models out of people. He wears a pair of glasses.
  • 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.
  • The House That Jack Built: Jack, a remorseless serial killer who often wears glasses.
  • Hudson Hawk: Snickers, the bespectacled CIA agent, has fewer Affably Evil moments than his companions and is happy to try and incapacitate Hawk and let him know a time bomb is about to kill him.
  • In If, the prim, proper and soulless school prefect Denson wears glasses.
  • 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.
  • Christian Szell from Marathon Man, is a cruel Nazi Grandpa who kills Babe's brother, and tortures Babe himself, over some costly diamonds.
  • In Mirage (1965), Willard is a brutal assassin whose distinguishing characteristic is his wire rim glasses.
  • 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.
  • 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.
  • Larry Thornhill from Psychos. He wears glasses, and sexually abuses his daughter when she was young.
  • Major Arnold Ernst Toht, the creepy-as-hell Gestapo torture guy Raiders of the Lost Ark, wears glasses.
  • 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.
  • 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.
  • Clarence Boddicker, the memorable antagonist in RoboCop (1987), was specifically made to wear glasses to resemble Heinrich Himmler. It shows.
  • Rollo and the Spirit of the Woods: Lackey, the utterly rotten and conceited adviser of the rolleys' chieftain, wears spectacles.
  • Room: The kidnapper, rapist villain Old Nick wears glasses.
  • Shaun of the Dead: David, Dianne's boyfriend and Liz's other flatmate. He was an obnoxious dick before the outbreak. The Zombie Apocalypse makes him outright evil. It turns out he always resented Shaun for getting with Liz.
  • 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.

    Literature 
  • 1984 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.
  • Gold Glasses in The Bourne Identity. He guns down several bystanders (including a fellow assassin) without batting an eye. Later, he breaks Bourne's fingers by slamming them in a car door for no apparent reason.
  • In The Dark Tower book The Drawing of the Three, we're repeatedly told that Serial Killer Jack Mort wears gold-rimmed glasses.
  • 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 James and the Giant Peach, the abusive Aunt Spiker wears steel-rimmed spectacles.
  • 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.
  • 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.
  • Zabulon, the head of Moscow's Dark Others in Night Watch (Series), looks like a sensitive glasses-wearing intellectual. He's also a Magnificent Bastard who not only plays global Xanatos Speed Chess with his ages old nemesis Geser, but also manages to maintain the fearful respect of most of his Dark underlings — quite a feat in a faction of egoists which operates on a Klingon Promotion basis. He's also fond of having rough sex in his "true form" — a huge, monstrously endowed demon. While it's probably hard for him to find long term lovers, he has no reservations against tossing them aside once they're no longer useful to him, or even sacrificing their lives to further his agenda.
  • 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.

    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.
  • Columbo: a very chilling example occurs in an early episode. After the villain offs his victim, his efforts to clean the crime scene are superimposed on each of his spectacles, while his face keeps unnervingly still. Watch the scene in all its Hitchcockian glory here: https://youtu.be/S1rLbO6RcCg
  • 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.
  • Gotham: The Riddler in this canon swaps in his traditional domino mask for a pair of glasses, and is a smug, petty sadist.
  • Grange Hill: the much-hated teacher Mr Bronson wears glasses.
  • 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.
  • Judge John Deed: The somewhat sinister circuit administrator Lawrence James, who wears thick-framed glasses.
  • 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 Führer 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.)
  • In the Mini Series "I Know My First Name Is Steven", based on the kidnapping of Steven Stayner, Steven's abductor Kenneth Parnell wears glasses throughout. His Real Life counterpart didn't, so presumably either the actor or the producers correctly surmised that they would be very effective in conveying how much of a creep he was.
    • This is somewhat referenced in the HBO movie based on the McMartin trial, where an accused pedophile's lawyer orders him to get rid of his glasses — " You look like a child molester!" (The cruel irony is that the man is innocent, but his lawyer is clearly aware of this trope).
  • Sandy Furness, one of the most amoral characters on Succession, wears glasses that often obscure his eyes due to how the light reflects off them, only reinforcing his villainy.
  • Professor Nakagawa from the Ultraman 80 episode, The Devil Doctor's Laborator is a bespectacled scientist who appears to be a friendly and wise man and an old friemd of Emi Jouno's father, but turns out to be an amoral Evilutionary Biologist. He stole the harmless infant monster, Myu, from UGM's research facilities, intending to turn a harmless creature into an experimental bio-weapon to prove to the UGM of his superiority as a scientist. Performing all sorts of experimentations on the harmless Myu, including force-feeding it a serum and putting it through electrical torture, Nakagawa's exploits ultimately causes Myu to enlarge to a kaiju-sized behemoth going on a rampage. This bespectacled asshole is perhaps the only human character in the show without a single redeeming quality.

    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.

    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 
  • 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.
  • 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.

    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.
    • The true mastermind of Danganronpa V3: Killing Harmony, Tsumugi Shirogane is so openly in love with the killing game that she wants it to keep going, even at the expense of hundreds of innocent teens. She also was the reason that Kaede was executed as Tsumugi framed her so well that even Kaede herself believed she was guilty of murder.
  • 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.
  • World End Syndrome has Mibu Kamashiro, heir to his family's business empire — and also an abusive, power-hungry, murderous Jerkass.

    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.
  • Inanimate Insanity gives us Steve Cobs, the creator of the MePhones, who is abusive to his creations if they fail to do the job he assigned them to do.

    Webcomics 
  • Doctor Hayter of Charby the Vampirate is a mad scientist willing to perform a vivisection on a live unwilling patient.
  • Downplayed a tad with Arlen Watson from Dead Winter, he's a very nasty and unpleasant guy towards other people especially to strangers. Treating the Webcomic's main crew with disdain and being more than happy to put a bullet in all of their heads (the most ironic thing is that he's devoutly religious). Despite all that however, his children are the reason why he's so nasty, because he's overprotective of them and isn't the least bit abusive towards his twins.
  • Homestuck:
  • Kaiten Mutenmaru: Pain Solitude was the spectacled tyrant of Throne who used the money of the town only for aristocrats.
  • 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.
  • morphE begins with 8 normal humans taken from their lives and pit against one another in 1-on-1 combat. The one with glasses does not bother with the emotional weight of the predicament. He sees that it is kill or be killed and tries to choke a college girl to death with little need for coercing.
  • 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.
  • Samurai Princess's Fawdry qualifies after nonchalantly blowing a hole in Itchyknee-san's head and laughing about it
  • The Story of Anima has Hector, a glasses-wearing Psycho for Hire who has no qualms with murdering children.
  • In Weak Hero, it's no coincidence that the brutal and cruel Wolf Keum has a pair of aviator shades that frame his keen eyes.

    Western Animation 
  • 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.
  • Batman: The Animated Series:
    • Mr. Freeze is a shades-wearing villain who is cold in every possible meaning of the word.
    • 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.
  • 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.
  • 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.
  • Inverted in Geri's Game; White!Geri wears glasses while Black!Geri does not.
  • Miraculous Ladybug:
    • Gabriel Agreste. With his cold, unfriendly personality. Even more as the true identity of Hawk Moth.
    • Zig-zagged with his assistant, Nathalie Sancoeur. She's aloof and cold, but she has her nice moments. Then she knows Gabriel is Hawk Moth, and is outright helping him.
  • Principal Abacus Cinch from My Little Pony: Equestria Girls – Friendship Games is a bespectacled school principal blackmailing her star student to do her bidding.
  • 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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The key to making your sculpture of a mass murderer is finding the right pair of glasses

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