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Jim Jones' red evil eyes hide behind those lenses.

Where Scary Shiny Glasses meets Cool Shades. If you're Making a Spectacle of Yourself, invoking this trope will fail horribly.

Examples are numerous, including The Men in Black, members of secret societies, CIA workers, sinister police officers, Agents in the Matrix films... you get the picture.

Examples of Sinister Shades include:

Anime and Manga

  • Yamaki of Digimon Tamers, even after he finishing his Heel Face Turn. It's kind of telling that they either come off or lighten up when he's doing something good.
  • Alucard in Hellsing has these as part of his initial look, but, strangely enough, as he becomes more threatening, he loses them.
  • Younger Toguro in Yu Yu Hakusho.
  • Trigun gives us the little shiny sunglasses Vash puts on when he's about to kick someone's ass.
    • Remarkably the same Cool Shades invoke Megane Bishonen. In fact, because of the starkness of the character change from the goofball, simply shifting to Stoic Spectacles reaches the border of this trope. The shades can change in the same situations where, if his shades didn't go Sinister, we'd probably see the Glowing Red Eyes Of Doom instead.
  • Shino from Naruto is rarely, if ever seen without his shades.
    • The same goes with his dad.
    • Or anyone from the Aburame family, for that matter.
  • Rubel in Claymore has really big round ones.
  • Admiral Kizaru of One Piece has these.
  • Gendo Ikari practically revels in this. He's only shown without them in flashbacks; their lack doesn't make him any less scary though.
  • Char Aznable, originally of Mobile Suit Gundam, sports these in Zeta Gundam. He and his Clones tend to alternate between these and Cool Mask.
  • Jerk Jock Agon Kongo from Eyeshield 21 sports some nifty sports goggles, helps that they're opaque most of the time.
    • The shades in question are also nefariously expensive (they're Oakley Juliet sports goggles). Shades of evil indeed.
    • Subverted with Akaba, who even combines these with red eyes, but is actually a nice, if eccentric person.
  • As of BW, Jessie, James, and Meowth of Pokémon have been doing this a lot. They've also lately been approaching competent.
    • Pokemon Hunter J before them also had these.
  • Kemo (a.k.a. the Hair Guy) from Yu-Gi-Oh!. Bandit Keith as well, where they really enhance the sense of both menace and douchebaggery that he gives off.
  • Yukishiro Enishi from Rurouni Kenshin.
  • The godhand Ubrik from Berserk.
  • Smith from Future GPX Cyber Formula is never seen without them.

Comic Books


  • As mentioned above, the Agents in The Matrix. Also Morpheus, when he was still mysterious and vaguely threatening. They're deliberately shed whenever the character's meant to be vulnerable.
  • The assassin in Ghidorah the Three-Headed Monster.
    • This also applies to the Xilians in both Monster Zero and Godzilla Final Wars.
  • Paul Yau, the hitman hired to replace the title character of John Woo's The Killer, had a pair of these.
  • Soultaker stars Martin Sheen's brother as a Cool Shades-wearing Grim Reaper who falls in love with the leading lady/scriptwriter. The SOL Crew insisted upon singing "Sunglasses At Night" to mock this.
    • After rewatching the episode, I couldn't find any instance of Joe Estevez wearing shades, but the bags under his eyes almost count.
  • The prison guard in Cool Hand Luke wears a pair of sinister shades while watching the prisoners in the hot sun.
  • The cop who wakes up Marion Crane from sleeping in her car in Psycho dons a pair of these.
  • Every portrayal of a Highway Patrol officer has him wearing mirrored aviator sunglasses. The T-1000 in Terminator 2 is a prime example.
  • Parodied in Out of Sight where the two protagonists drive around and spot a number of undercover FBI agents watching them... due to the fact they all wear identical sunglasses.
  • Doctor Octopus in Spider-Man 2. This is explained away in the novelized version, as Octavius was left with very light-sensitive eyes after the tritium exploded.
  • Sheriff Cooley from O Brother, Where Art Thou?. He's implied to be the devil, and in close-ups on his face firelight is often reflected in his shades.
  • In 1945's Leave Her to Heaven, the pathologically jealous and evil Ellen Harland (Gene Tierney) dons a pair of these just prior to letting her husband's disabled kid brother drown in a lake.
  • Masai in The Warriors.


  • One of the anarchists in G. K. Chesterton's The Man Who Was Thursday wears a pair of them. Deliberately. With them, he's terrifying to behold. Without them, he's cheerful and ordinary.
  • The Tonton Macoutes wear these in Graham Greene's The Comedians.
  • The Ankh-Morpork banking community wear these in Making Money, as seen on the cover.
  • The sports glasses Daemon operatives use may be this or Cool Shades.

Live Action TV

Real Life

  • In Real Life, the US Secret Service goes for the Sinister Shades look on purpose, to discourage anyone from messing with their "protectees". They also do it so they can stare at someone without being noticed, i.e. no one knows where they are looking.
  • The late Reverend Jim Jones wore them to hide the evilness in his eyes.
  • Serial killer Richard Ramirez wore shades in the courtroom.
  • The image above is of Kim Jong-Il, leader of North Korea. The ruthless dictator wears them to look even more menacing. Well, to try to look the part anyway - it's not all that successful. The shades don't make up for the fact that he's short, fat, and unbelievably goofy looking, though. Unless you're actually under his heel it's pretty hard to find him scary, especially after Team America: World Police.
  • Muammar Gaddafi, the former dictator of Libya, was frequently photographed wearing them in the past few years. It works roughly as well for him as it does for Kim Jong-il.
  • This (in)famous photo of the late Chilean dictator Augusto Pinochet is probably the very definition of this trope.
  • Blogger and self admitted pedophile Jack McClellan claims that he wears the sunglasses because of the studio's lighting. Steve Wilkos makes him take them off.


Video Games

  • In Resident Evil, Albert goddamn Wesker. Eventually, it's to cover up with bizarrely inhuman eyes, but mostly they're just there to be rockin'.
    • The strange eyes thing doesn't explain why he did it before he got them and why he wore them in the lab, so yeah; it's mostly to be Badass.
    • Originally, in the PS 1 game, each character could only have so many 'skins' or textures. Wesker was wearing them in the begining, and they just probably didn't have enough room for a retexture without them. (they'd have to do a whole new face texture.) Could also possibly be a Viewers are Morons as perhaps they thought that without his defining shades, and the low-resolution textures of the time, He'd be unrecognizable as...Wesker. In future versions as well as the R Emake, they kept it because it was just part of his character.
  • Machi Tobaye in Apollo Justice : Ace Attorney may be a deliberate subversion, as his shades make him come off as creepy when he really isn't.
  • The World Ends With You gives us Megumi "Shades" Kitaniji. Sinister indeed.
  • Rude (his name, not his description) in Final Fantasy VII has these, making him as scary as possible for being a member of the Goldfish Poop Gang.
    • Rude also seems to carry around multiple pairs. In Advent Children, his shades get stepped on, so he just pulls another one out of this jacket pocket.
  • The Doctor character from ~Assassin's Creed~: Brotherhood multiplayer has mirrored goggles over a White Mask of Doom. The Engineer has proper sunglasses.
  • Khaled Al-Asad in Call of Duty 4 is never seen without his sunglasses.
  • Dr Ivo "Eggman" Robotnik Sonic the Hedgehog is never without his trademark shades that helps goes with his image

Web Comics

  • Professor Broadshoulders from the webcomic Zebragirl wears these, and when he's in silhouette they become straight-up Scary Shiny Glasses.
  • Agent Ben and Agent Jerry, The Men in Black from The Inexplicable Adventures of Bob. Of course, they're ineffectual enough that it's debatable just how sinister the glasses make them.
  • Tip of Skin Horse attempts to invoke this when dealing with a local sheriff. We emphasize "attempts".
  • Black Monday Blues of dead winter has red-tinted pairs. Yes, multiple, he carries spares.
  • Ricci's manager in Fite
  • Terezi Pyrope of Homestuck wears pointy red ones because she's blind.
    • It's funny how the person who's wearing the shades can affect whether they count as cool shades or sinister shades. Bro's shade's on Bro? Cool. Bro's shades after having been taken from his own bloody corpse by Bec Noir? HOPY SHIT HOLD ME
      • And when Gamzee is seen wearing Terezi's glasses?
    • Also reversed. Nepeta is adorable when wearing Equius' shades. On Equius himself, they come across as more perverted than sinister. Then played straight again when Gamzee gets ahold of those too...

Web Original

  • The Shadow Men, Chessmasters of Broken Saints, both sport these, as does sleaze ball strip club owner Mars, whose shades are red and glowing.
  • Lonelygirl15 loves this trope. Lucy, Virgil, and various Shadows, Deacons and hired thugs all wear these.
  • Michelle Clore of Kate Modern wears these, as does Kate when under her influence.
    • Let's not forget "Dr. Specialist", either.
  • Bridget in Sorority Forever has worn these on occasion.
  • Doctor Steel is never seen without his antique dark welding goggles (which in one of his music videos, reflect flames).
  • Agamemnon Tiberius Vacuum always wears black Willy Wonka-style goggles.

Western Animation

  • Colonel Franklin and his men wore Sunglasses At Night at the beginning of Transformers Cybertron. He wore them less after he was revealed as a good guy rather than a sinister government agent.
  • Protoman had these in the Ruby-Spears Mega Man cartoon; at a few points, we could see Mega reflected in them as he was about to sneak up on him.
  • Heather was introduced with these on Total Drama Island, complete with scary background music.