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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."
- November 11 in Darker Than Black alternates between "sociopathic jerk" and The Charmer and habitually wears glasses with Opaque Lenses.
- Suitengu from Speed Grapher. Bespectacled Bishōnen, rich note , smart and a totally evil manipulative bastard.
- 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.
- When Lady Une puts on her glasses in Mobile Suit Gundam Wing, it means that her utterly ruthless "Iron Une" personality is in command, and that anyone who crosses her is going to die.
- 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.
- Tamaki Tsunenaga of Deadman Wonderland. The primary antagonist revealed so far, Tamaki is 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.
- Depraved Homosexual Professor Aizawa from Sukisho who was responsible for performing sadistic experiments on Sunao and Sora when they were children.
- 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.
- 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.
- 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 "Aww, 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".
- Kevin in Sin City is a cannibal Serial Killer who gives us the Trope Image (with his representation in the film version). 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.
- 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.
- 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.
- In X2: X-Men United, William Stryker wears glasses in his older age and looks for the complete genocide of mutants.
- Bolivar Trask in X-Men: Days of Future Past wears glasses and the things he had done to the mutants who were Killed Offscreen between First Class and Days of Future Past seem to indicate that he made them victims of Playing with Syringes.
- 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.
- Principal Abacus Cinch from My Little Pony: Equestria Girls – Friendship Games is a bespectacled school principal blackmailing her star student to do her bidding.
- 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.
- Zabulon, the head of Moscow's Dark Others in Night Watch, 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.
- 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.
Live Action TV
- 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.
- 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.
- A recurring villain on Alias was a Chinese torturer named "Suit-and-Glasses" because, you guessed it, those were his only identifying features.
- 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)
- 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).
- 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.
- 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.
- 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.
- Babylon 5 has the interrogator who tortured Sheridan in the episode "Intersections in Real Time".
- The Supervisor in The Prisoner, although the effect is enhanced by being combined with the character's booming Robo Speak voice and his almost never-changing deadpan facial expression.
- 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.
- 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 had Charles Augustus Magnussen, a bespectacled man whom Sherlock had described as "the Napoleon of blackmail."
- 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.
- 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.
- 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.
- 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.
- James Wesley is the right hand of Wilson Fisk, and a total sociopath - his flat expressions and glasses greatly unnerve many of those around him. It's rare that he's seen without his glasses on.
- Leland Owlsley wears thick glasses that mask the eyes of a well-dressed white-collar crook.
- 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).
- 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.
- 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.
- 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.
- Danganronpa 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.
- 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.
- 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.
- Iggy Koopa in the Super Mario franchise, who's one of Bowser's top underlings, prone to crazy laughter and taunting his opponents when he has an advantage.
- 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.
- Vriska Serket from Homestuck, arguably the nastiest troll in her group - and that's saying something. Bonus points for having her "8" motif extend to her eyes, making her doubly four-eyed.
- Much more appropriate now is Eridan Ampora after his From Nobody to Nightmare transformation. He attempts to kill his romantic rival, succeeds in murdering his Morality Chain, kills the only other person who he ever considered a friend, and dooms his own race to extinction, all in a matter of seconds without a single blink.
- Samurai Princess's Fawdry qualifies after nonchalantly blowing a hole in Itchyknee-san's head and laughing about it
- 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.
- The Story of Anima has Hector, a glasses-wearing Psycho for Hire who has no qualms with murdering children.
- 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.
- 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.
- Edmund pre-Heel–Face Turn in The Lion, the Witch and the Wardrobe (1979).