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Villains and evil characters tend to wear excessive, dark colored makeup on and around their eyes. The key word here is "excessive", as in "singlehandedly keeps a cosmetics company in the black" (no pun intended). There's a few ways for the character to apply the Evil Eyeshadow: there's always some on the eyelid accompanied with mascara to darken and lengthen the eye lashes, and the "excessive" extra can be applied as upper or lower eyeshadow... or both to go the extra villainous mile. The color isn't restricted to just black, but just about any color as long as it's sufficiently dark.
Considering villains tend to go overboard, this is usually also accompanied with lots of extra creepy makeup, and some pale foundation and a dark wig or hair dye to make the character really look like Cesare. Finishing this fearsome facial are Evil Eyebrows, either natural or (probably) plucked and stenciled on.
By now the villain has so much product on their face (and hair too probably) that they will have a very real aversion to water... not because it's their Weaksauce Weakness but because a good splash means Your Makeup Is Running. Heroes are advised to avoid making them cry or splashing them, as the resulting fury won't be pretty (Pun intended).
Despite the Trix girls being the page pic, guys can wear Excessive Evil Eyeshadow, usually in the form of Guyliner. They also tend to be a lot... quirkier... than other guy villains. It's also worth noting that this Sub-tope of Obviously Evil is so exclusively villainous it's rare to see even Anti Heroes use Excessive Evil Eyeshadow. If the character also wears a lot of makeup in addition to the excessive evil eyeshadow, expect him/her to be a Monster Clown. When the darkness is natural, rather than from cosmetics, it's Creepy Shadowed Undereyes.
Anime and Manga
- Yuda from Fist of the North Star.
- Kodachi Kuno in Ranma ½ wears a lot of eyeshadow and while not being evil per se, is certainly the one of his suitors that is least likely to play fair or be rational (and in that series that is saying something) and is certainly treated as one of the bad guys.
- Orochimaru from Naruto.
- Sesshomaru and Naraku from Inuyasha, also indicating their nobility.
- Drocell Caines from Black Butler (anime only).
- In Bleach, Filler Villain Muramasa has large fields of purple eyeshadow in a fancy shape. He is fairly reserved, but definitely bold, mysterious, and unsettling. Although being the spirit of a zanpakuto weapon, it could just be part of his anatomy.
- Munchkin has a card called Evil Eyeshadow. It gives +1 bonus, too.
- Marvel Comics' villainess The Enchantress.
- Queen Zsu Zsa's consort from Baritarian Boy, that 'verse's equivalent of Vlad the Impaler. Pimped Out Doublet and decidedly Villainous Fashion Sense aside, some would kill to make their own eye makeup look that good.
- Disney examples:
- Madame Medusa in The Rescuers
- Cruella de Vil in 101 Dalmatians
- The evil queen in Snow White and The Seven Dwarfs
- The wicked stepmother in Cinderella
- Maleficent in Sleeping Beauty
- Zira in The Lion King.
- Yzma in The Emperors New Groove
- Ursula and Morgana from Disney's The Little Mermaid and The Little Mermaid II:Return to the Sea were villains who wore heavy eyeshadow.
- Marina del Rey in the prequel.
- Vanessa, Ursula's human disguise, also utilized this in some official still arts of her.
- Queen Narissa from Disney's Enchanted.
- Mother Gothel from Tangled.
- Rare male example: Jafar from Aladdin. .
- Subverted with the witches from The Black Cauldron. Although neither of them are actually evil, they are all still very nasty.
- Rare heroic example: Megara from Hercules. She was manipulated by Hades, but still...
- The Red Queen from Alice in Wonderland.
- Komodo from Warriors of Virtue wore pretty heavy eyeliner.
- If you have trouble keeping Robot!Maria and the real Maria straight in Metropolis, just remember the robot wears too much eyeliner, and the real Maria doesn't wear any (visible) makeup.
- Peter Parker, while under the influence of his new black suit in Spider-Man 3.
- Ludmilla from Bartok the Magnificent.
- Mr. Robbie from The Psychopath.
- Frank-n-Furter from The Rocky Horror Picture Show.
- Poison Ivy at the end of Batman and Robin.
- The Joker in Batman.
- Lola, the Fetish Fuel Station Attendant and The Dragon in Transporter 2.
- Azkadellia from the Sci Fi miniseries Tin Man.
- The Evil Overlord in The Forbidden Kingdom is quite fond of green eyeshadow.
- In Wyrd Sisters:
You're not a witch, are you? He said, fumbling awkwardly with his pike.
Live Action TV
- Angel when he becomes Angelus on Buffy the Vampire Slayer.
- The Darker and Edgier Wishverse Buffy.
- Mimi from The Drew Carey Show. As I recall, Drew considered her evil. So evil, she's the page picture for Uncanny Valley Makeup.
- Robbie Rotten from LazyTown, a kids' show, wears an excess of eyeshadow.
- Dr. Renfro / Madame X from Dark Angel.
- Caroline from The Vampire Diaries gets this upon first becoming a vampire. Dropped after a few weeks when writers realized it was ridiculous, as Caroline isn't evil nor is she trying to look different, and other vampires don't have this effect.
- "Evil" Kirk in the Star Trek the Original Series episode "The Enemy Within".
- This distinguishes the more evil of the two consorts in Overlord.
- Morrigan of Dragon Age wears tons of purple eyeshadow around her Eyes of Gold.
- Prince Jazan subverts in the Neopets Ancient Egypt-themed "Lost Desert" plot. For most of the plot he's played as a villain, with heavy guyliner. (That is, heavier than other characters.) Later on he's revealed to have been controlled by the real Big Bad, and makes a Heel Face Turn. He never stops wearing the guyliner.
- Dark Nella from The Nostalgia Chick reviews. It even gets lampshaded.
- Sara Waite of the Whateley Universe isn't a villain, but she has this as part of her "scary goth girl" character design. Lampshaded in her introduction; the narrative describes her as "wearing enough make-up to deflect low caliber projectiles at close range". It's not actually makeup though — her face just looks that way.
- Mocked in "Marik's Evil Council of Doom nº 2.
- Pictured above, the Trix Girls from Winx Club.
- Master Cyclonis from Storm Hawks wears a ton of eyeshadow and eyeliner. Then again, with the liner, it's hard to tell whether or not that's just the animation style...
- Wuya in her human form from Xiaolin Showdown appears to have eyeliner, as does Jack Spicer.
- Ember from Danny Phantom
- The Joker has this in Filmation's version of Batman, which was produced in 1968.