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So you have a guy who is cold, emotionless, or brutally practical, maybe a little cruel. Maybe a lot 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 on the soul, so hiding them behind glass makes the character seem more removed. Particularly effective if the glasses have Opaque Lenses. And you can have the light reflect off them in scary ways. This often signals that the character is a Badass Bookworm.
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. When this is treated as Fetish Fuel, see Bespectacled Bastard Boyfriend.
Anime & Manga
- Highschool of the Dead gives us Shidou, a former teacher who uses the chaos caused by them to create what fans refer to as the orgybus.
- Captain Kuro from One Piece.
- Kabuto in Naruto, as well as his temporary teammates Yoroi and Misume.
- Shino is a slightly more heroic example of this...even his own team is a little freaked by him.
- 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.
- Szayel Aporro Granz fits as well.
- 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."
- A borderline version is Kunimitsu Tezuka from The Prince of Tennis, who is less evil and more aloof/ComicallySerious. Eishirou Kite from Higa plays it straighter, though.
- Neon Genesis Evangelion: Gendo Ikari.
- Keel with his visor-like apparatus might count, even though End of Evangelion reveals them to be his real eyes since he's a cyborg.
- The young model Sara from Kami no Shizuku said about Tomine Issei, "Gosh, he's so cold. But... that part about him is kind of good." This may be a bit odd though, since Issei turns out to be her brother.
- Brad Crawford from Weiss Kreuz. Also Reiji and Hirofumi Takatori, Masato Shimojima, and maybe Mayumi Tsujii.
- Yamaki from Digimon Tamers, especially near the beginning of the season.
- Furoku Tsukumo, mother of Teen Genius Susumu from Wandaba Style, is a rare female version.
- Naohiro Usui in the Majin Tantei Nougami Neuro.
- 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 White-Haired Pretty Boy, rich , smart and a totally evil manipulative bastard.
- Amon Garam of Yu-Gi-Oh! GX -- child prodigy, Gadgeteer Genius, Duel Monsters champion... and cold-blooded killer of his girlfriend to fulfill a Deal with the Devil in an attempt to Take Over the World.
- As well as the D aka Kyle Jables.
- Mikami from Death Note.
- Played with in regards to Tooru Hanagata from Slam Dunk. He's very serious but not a strictly bad guy, but yet he's ruthless in the fields.
- Prof. Kurata from Digimon Savers. Mad Scientist and Complete Monster extraordinnarie.
- Quattro of Magical Girl Lyrical Nanoha.
- Telestina Kihara Lifeline from To Aru Kagaku no Railgun. That un-spoilered name is already a dead give away of what to expect, considering how Grandpa Kihara and his son turned out.
- Female Macross Frontier example: Grace O' Connor. Though sometimes it's a monocle.
- Several characters from Hellsing are well within the bounds of this trope. Walter Dorneaz becomes an absolute monster on the battlefield with his Razor Floss takes it further with his Vampirization. Alucard 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.
- Rip Van Winkle too, but maybe she's not the best example as she is sadistic but cheerful.
- Kakei from Legal Drug has several sadistic tendencies, especially when assigning odd jobs to Rikuou and Kazahaya. And mostly, this is for his own amusement. Fortunately, he does have a nice side to him as well.
- In Overman King Gainer, Gainer Sanga himself fits this when he's possessed by the Overdevil.
- Muraki from Yami no Matsuei has hobbies that include raping, torturing, killing, and scientific experiments to revive the dead for the sake of killing them again. He's just a tiny bit psycho.
- Aion from Chrono Crusade, although, to be fair, he's more like Broken Bird Magnificent Bastard.
- Chikusa Kakimoto from Katekyo Hitman Reborn has this going for him. Plus, the first panel where they're really focused on looks suspiciously like the image on this page...
- Katsuragi of Sakura Gari.
- The Millennium Earl of D.Gray-man. While he may at first seem too cheerful and cartoony to be scary. This impression, however, is very quickly corrected as we learn more about him. It's becoming increasingly obvious that he's basically Satan.
- Oh please. Compared to the Earl, Satan is an underachiever.
- 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.
- Subverted. He's actually a hardcore gamer. As such, he only puts live stock into his games.
- Kaito from Yu Yu Hakusho seems like this, until it turns out that he was working for Genkai the whole time
- An interesting subversion occurs with Dr. Nazo, the Big Bad of 60s anime Ougon Bat: he doesn't wear glasses, but he does indeed have four eyes. And less than zero of a soul.
- Depraved Homosexual Professor Aizawa from Sukisho who was responsible for performing sadistic experiments on Sunao and Sora when they were children.
- Tsukuyomi of Mahou Sensei Negima.
- The Brunette in Gunjo.
- 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.
- Claude Faustus in Black Butler.
- Doji in Metal Fight Beyblade.
- The Doctor, the only flat out Complete Monster in Black Cat embodies this. 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 has this. He is the most self-interested guy in the main cast and will go to extreme lengths to get what he wants. Or so he'd like people to believe.
- While not the most evil of the Elite Four, the Pokémon Special incarnation of Lorelei certainly qualifies.
- Shou Tucker from Fullmetal Alchemist, 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 and gives a Hannibal Lecture to Edward.
- Keroro Gunsou's Kururu is the resident Mad Scientist and wears 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.
- Zera from Litchi Hikari Club is a perfect example of this trope. His glasses even shine and all.
- Mahou Shoujo Ai: Akitoshi's best friend Shinji becomes this after being possessed by the demonic Yuragi.
- Michio Yuki from MW.
- Mulmangcho in A Squirrel and a Hedgehog.
- Kevin in Sin City. (The Trope Image)
- Gideon Gordon Graves of Scott Pilgrim.
- Thomas in The Walking Dead turns out to be completely evil and insane. Not actually surprising.
- WARNING: WORLD-CLASS SPOILERS: Alberto Falcone of The Long Halloween and Dark Victory.
- Professor Hugo Strange, Batman villain. Taken Up to Eleven in Prey, where we never ever see his eyes, only what's caught in his glasses' reflections.
- Jim Gordon Jr. fits as well.
- When out of costume, Jonathan Crane is a bookish, glasses wearing nerd. Who just so happens to love terrifying those around him and being a general sadist.
- 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 Toht, the creepy-as-hell Gestapo torture guy Raiders of the Lost Ark.
- Dr. Jonathan Crane from Batman Begins
- The Warden in O Brother, Where Art Thou?, heavily implied to be the Devil himself.
- 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.
- Comes up frequently in the films of Alfred Hitchcock.
- Bent features a bespectacled Nazi that is memorable for his interrogation methods on the train.
- 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.
- 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.
- 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 in RoboCop was specifically made to resemble Heinrich Himmler. It shows.
- The evil cult leader in the Film of the Book The Hitchhikers 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.
- Emil Leopold Locque in For Your Eyes Only is Kristatos' quiet, cruel, ruthless enforcer who wears a distinctive pair of glasses.
- Dr. William Block, played by Josh Brolin in the Grindhouse segment Planet Terror. What do you think?
- Angels and 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.
- Mark Collins, played by Christian Slater, in Twisted.
- Judge Doom in Who Framed Roger Rabbit?.
- Zabulon, the head of Moscow's Dark Others in Night Watch; looks like a sensitive glasses-wearing intellectual, but is also fond of having rough sex in the form of a snake demon.
- Done deliberately in The Man Who Was Thursday.
- In their demonic forms, the Denarians of The Dresden Files make this trope literal -- one set of glowing demon eyes over another set of (glowing a different color) human eyes.
- 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.
- And O'Brien, who plays this trope horrifying straight.
- Arguably Algaliarept from The Hollows series, though he could also be considered a Bespectacled Bastard Boyfriend if you support Al/Rachel.
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.
- HRG in Heroes. Though he turns out to be mostly good if ruthless.
- And Sylar, who began his murderous streak while he was still a bespectacled watchmaker. Taken to extremes with the multi-lens glasses he wears for his job.
- Alias's season-one Big Bad 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)
- Jim Keats of BBC's Ashes to Ashes. He has this sinister 60's government agent look.
- 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.
- Nyder from the Doctor Who story 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.
- On The Muppet Show, Dr. Bunsen Honeydew's For Science! attitude and callousness toward Beaker make him a comedic example. Then again...
- Kasei Araragi the Blaziken gijinka is a mad scientist who experimented on a vampire girl who can regenerate and his sister, Luca Araragi the Lucario gijinka just because he could.
- Cyberswine: The scientist working for Vice-President Bryce Gets. He wears glasses and is willing to transfer human brains into animal bodies and erase people's personalities without a qualm.
- 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.
- Big Bad Kristoph Gavin from Apollo Justice.
- Tsukihime's Tohno Shiki is an inversion - his cold, ruthless side shows itself when The Glasses Come Off.
- Eh... sort of an inversion. He's still a complete dick to Arcueid and Arihiko with his glasses on, he just goes waaaaaaay Up to Eleven with them off.
- With Arihiko its mutual, they did start their relationship by beating each other up. With Arcueid, its just his way of showing his affections; as is stated, he treats everyone with his default kindness except Arc because she's special.
- Actually, the glasses have nothing to do with it. It's his Nanaya blood, that turns him into a killer. It's just, most times when his Nanaya personality shows up, the glasses are already off.
- 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.
- Yaginuma in Kara no Shoujo is even described in the ingame notebook with Still An Asshole.
- DoubleSwitch. 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.
- Mordecai Heller from Lackadaisy Cats.
- "No. Leave her.This one has...potential."
- Misfile has Sheldon.
- 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
- Ask That Guy, in his Memetic Molester Complete Monster glory, and Mechakara play this straight.
- Jon Lajoie's rapist glasses. Because "...ladies love the bad boy look".
- Owen from Gargoyles is a cold version. Stone cold.
- Metalocalypse: Charles Foster Ofdensen, sympathetic version.
- The Venture Brothers: Arguably Dr. Venture himself. Certainly Dr. Henry Killinger.
- 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.
- Dr. Scientist on Jimmy Two-Shoes.
- Agent Bishop from Teenage Mutant Ninja Turtles 2003.
- Dick Hardly from The Powerpuff Girls wearing eyeglasses and he's Complete Monster.
- Lavrenti Beriya (Stalin's second-in-command).
- Heinrich Himmler (Hitler's second-in-command). He famously kept his spectacles on even while fighting a duel as a student.
- One could probably also add Tojo Hideki (Emperor Hirohito's second-in-command).
- For a much more heroic example, Pius XII (the Pope): real name Eugenio Maria Pacelli, member of a very high class Roman family. Elected pope in 1939, he reigned during World War II. A competent, well-read, stoic, and popular pope, but accusations, made by some historians, that he did not not do enough to save the Jews during the Holocaust have made him a controversial figure after his death. However, several sources, including Israeli scholars, estimate that as many as 860,000 European Jews were saved from death through concealment in Church facilities, issuance of fake Baptismal certificates, public appeals and other methods he ordered: this means, he didn't speak up in public a lot but did work like crazy behind the scenes.
- The reflective glass example gets used as a selling point for non-reflective spectacle coatings.
- The BTK killer could also qualify for this.