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Anime And Manga
- L from Death Note, an Eerie Pale-Skinned Brunette, has circles around his eyes so dark, he has the fan nickname "Panda".
- Light in the manga is shown to have dark circles around his eyes as well after he became Kira that magically disappear with his Memory Gambit.
- Lovro from Assassination Classroom.
- Colin from Two Keys who is an Eerie Pale-Skinned Brunette with huge dark circles around his eyes, which sometimes double as Hidden Eyes, reflecting both his dark past and mysteriousness.
- Kuroki from No Matter How I Look at It, It's You Guys' Fault I'm Not Popular! has these. While she's not exactly a bad person, it does reduce her physical appeal and reduces her self-esteem.
- Miranda from D.Gray-Man, though heroic, has these to reflect her gloominess and lack of sleep. They also add to her Eerie Pale-Skinned Brunette appearance.
- Almost every character in Houkago Play has this - partly because many of them are hardcore gamers, and partly because of the art style.
- Itachi Uchiha from Naruto manages this in his more serious ass-kicking moments.
- In the original Japanese, Gaara's darkly circled eyes are expressly stated to be Tanuki-like marks he was born with, signifying the animal his bonded demon looks like, much the way Naruto has whisker-marks. In the English dub, they were explained to be caused by his insomnia, which not only makes sense (rather than just assuming the audience wouldn't know what a Tanuki was or just calling it a "raccoon demon") but significantly ups the creep-factor.
- Trafalgar Law, the "Surgeon of Death" from One Piece.
- Hikaru Gosunkugi from Ranma ˝.
- Many of the antagonists from Yu-Gi-Oh!, including Yami Marik, Yami Bakura, and Bonz.
- Additionally, in Yu-Gi-Oh! GX, there is Johan who gets those when he is possessed by Yubel.
- Madame Hecuba and her son Tulip the giant from Jack to Mame no Ki.
- Dr. Hiyari and daughter Hiyariko from Anpanman. They're both mad scientists. Thanks to the simple artwork of the series, their eyes express this by being a dark ring around their eyes (black for Dr. Hiyari, dark purple for Hiyariko).
- Prandine/Fallow from Deltora Quest has these, though they extend out into bags underneath his eyes as well.
- Flare Corona, previously a member of Raven Tail, has these, from Fairy Tail.
- As does Acnologia in his human form.
- Lord Lucifer from "The Wonderful World of Puss 'n Boots" has purple shadows under his eyes.
- Hitoshi Shinsou in My Hero Academia has these, and combined with his Mind Control powers, they make him look like someone who would end up a villain. Nevertheless, he really wants to be a hero.
- An actual villain character named Dabi actually has those in the form of seemingly having burnt or no skin at all below his eyes.
Films — Animated
- Frollo from Disney's The Hunchback of Notre Dame actually has purple shadows.
- Gaston gets these in the last third of Beauty and the Beast, to show that he's a Not-So-Harmless Villain now.
- Played for laughs in Fiddler on the Roof during Tevye's "dream" sequence; all the dead departed have them.
- General Woundwort and his Efrafa officers from Watership Down.
- Joe the pilotfish from Help! I'm a Fish.
- Count Ruber from Quest for Camelot.
- Scar and his hyenas from The Lion King.
- The evil lionesses in The Lion King II: Simba's Pride. The main difference between a good lion and a bad lion in those movies seems to be tons of eyeliner.
- Sa'luk from Aladdin and the King of Thieves.
- Arrow from Rudolph the Red-Nosed Reindeer. The fur around his eyes are darker than the rest of his body, to show he is a Jerk Ass.
- Pitch from Rise of the Guardians.
- Drago Bloodfist from How to Train Your Dragon 2.
- Rasputin from Anastasia This is a common character design used by Don Bluth for his villains in just about every movie he did.
- In Poet Anderson: The Dream Walker, for Jonas, in the waking world and as Poet, though he's definitely the protagonist.
Films — Live-Action
- Betelgeuse from, well, Beetlejuice has dark rings around his eyes. This is actually due to the fact that Tim Burton originally conceived the character as having no eyes at all but changed his mind after noticing how expressive Michael Keaton's were.
- Mike, by his second trip to the loony bin, in Truth or Dare?: A Critical Madness.
- Palpatine from Star Wars.
- Sister Ruth in Black Narcissus goes mad and has these just before she tries to push Sister Clodagh off a cliff.
- Gríma Wormtongue from The Lord of the Rings film series.
- Count Orlok from Nosferatu.
- The "thralls" in Avengers Grimm sport Excessive Evil Eyeshadow that's intended to be natural coloring from their curse.
- The Penguin sports these from Batman Returns.
- In Street Magic, Jebbun Stoneslicer has eyes like these.
- Harry Potter's Sirius Black and Bellatrix Lestrange, after they got out of Azkaban. Actually, most Azkaban prisoners and Death Eaters probably had this.
- In Twilight, all the vampires are described as having dark 'bruised' shadows under their eyes, implied to be a symptom of never sleeping.
- Shuuen No Shiori Project's A-ya.
- Nico de Angelo, from Percy Jackson and the Olympians, has these after he Took a Level in Badass
Live Action TV
- The Addams Family: this is one of Wednesday's most pronounced features, as she's an Eerie Pale-Skinned Brunette.
- Uncle Fester also has these.
- Crazy Harry from The Muppet Show.
- In the Supernatural episode "All Hell Breaks Loose, Part One" (S02, Ep21), the Acheri demon has dark circles around her eyes.
- The Medic in Team Fortress 2 has these. They're fairly subtle, but compared to the other characters it's a reasonably noticeable feature. It's probably to make his eyes stand out behind his glasses, show that he's no spring chicken, and suggest that he's the kind of person who likely stays up late doing horrible medical experiments. And maybe the stress of his thankless job is getting to him.
- The Thwomps from the Super Mario Bros. series games. The Boos have them in Luigi's Mansion, and in the sequel they're used to help distinguish King Boo from his servants.
- Knight of the Seal Hanch in Drakengard 2 has these, as a result of the magical pact that cost her her beauty and attractiveness in general.
- Loghain in Dragon Age: Origins has extremely dark circles under his eyes. Though his high stress life makes it totally reasonable for him to have them, the cartoonish appearance of his dark circles has been the subject of much mockery, and even lead many players to correctly predict his treachery and resultant villain status. Some of them were apparently so irritated by the raccoon rings around his eyes that they created mods to tone them down.
- Looking closely in Metroid Prime, you can see that Ridley has these combined with Fireball Eyeballs.
- Colonel Radec removes his goggles at one point in Killzone 2, showing that he is quite pale and unhealthy looking with pronounced bags and redness under his eyes.
- Members of the Parasite Unit in Metal Gear Solid V: The Phantom Pain have faded inkblot-like markings around their eyes, caused by the parasites living under their skin. This, combined with their paleness and erratic movements, reinforces their "undead" appearance.
- Gunnerkrigg Court has Jack while he was going crazy from the influence of a spider-like entity from Zimmy's Mental World. Averted by Winsbury, who's a jerkass initially, but otherwise completely normal. Zimmy (whose eyes are completely covered in black gunk) has these even when her eyes are washed out. Gamma has them as well, presumably because she hardly ever sleeps.
- Azuu of Elijah And Azuu has visible bags under his eyes constantly, but he doesn't have it nearly as bad as his son, who has very obvious Creepy Shadowed Undereyes (and both also have a case of Red Eyes, Take Warning to boot)
- In Homestuck, all of the Trolls have these, but it's especially noticeable on insomniac Karkat, Nepeta, whose quality of sleep is presumably lessened because she doesn't have a proper "bed", Vriska and Eridan, for whom it's largely inexplicable, and Sollux, on the rare occasion he's pictured without his glasses. Equius seems to have this too, but since his are the same colour as his blood it's likely that they're petechiae, possibly incurred in fights with his robots, although autoerotic asphyxiation is a potential cause as well.
- Deadpan Snarker Colin from Two Keys has this, as seen in the picture above.
- Which is actually a milder version. Sometimes he has this to the point where it looks like he's got the Black Eyes of Evil. It's unclear whether he has this due to insomnia, If his magic has a physically draining effect on him or if it has something to do with his Mysterious Past. Not to be confused with when he has his occasional moments of Black Eyes of Crazy.
- Shazam in Something*Positive, after his face is finally revealed.
- Dongtae from Dice The Cube That Changes Everything had noticeable permanent bags under his eyes that he thinks could beat a panda. They don't help his already poor self esteem.
- Persephone from Destroyer of Light has those. It's a subtle hint that she's a bit darker than her mother, Demeter.
- Several Danny Phantom villains have dark circles under their eyes for the look of evil, starting with Vlad.
- Brain's arch enemy Snowball the hamster from Pinky and the Brain.
- Anthony "Fat Tony" D'Amico from The Simpsons.
- Evil Flippy from Happy Tree Friends.
- Mr. Hitcher from Tiny Toon Adventures.
- In the Ben 10 franchise, both Kevin Levin (Pre-Heel–Face Turn) and Aggregor have these.
- This actually a genetic trait, seeing as they are both Osmosians, who get this way after absorbing energy.
- Many animated versions of actor Peter Lorre depicted him with these kind of eyes.
- The Proto-Clown and Pineapple Pokopo from The Tick.
- Jon the meth addict from the American Dad! episode "Adventures in Hayleysitting".
- Mike's evil personality Mal from Total Drama All Stars.
- Leonardo Leonardo from Clerks: The Animated Series.
- The Joker and Ra's al Ghul in Batman: The Animated Series.
- Aladdin's evil twin created by the godlike being Chaos in the Aladdin: The Series episode ''When Chaos Comes Calling" has these.
- The citizens of Bikini Bottom get these while under the influence of jerktonium in the stop motion Spongebob Squarepants special "It's A Spongebob Christmas".
- Svengoolie. The actor uses makeup, but the it's the characters natural look.
- In Real Life the skin around the eyes is much thinner, so some people do have darker areas around their eyes (it's also the reason bruises around the eye are so prominent). Of course, this has nothing to do with a person's morality, so in Real Life, this trope is mostly subverted.