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Anime & Manga
- Inverted for one story arc of Deadpool: The normally hideous merc is cursed... into looking like Thom Cruz. Otherwise played exactly straight, as it was an effective punishmentnote .
- In Generation X, Monet St. Croix was turned into the freakish Penance by her evil big brother as a punishment for her vanity.
- In the first issue of Seven Soldiers of Victory: Frankenstein, teenage outcast Uglyhead forges an alliance with the Sheeda to get revenge on his classmates. To this end, one of the girls who made fun of him is forced to accept a Sheeda spine-rider, who forces her to eat herself into obesity.
- In the first arc of X-Statix, the team deals with a disfigured teenage Reality Warper who has used his powers to make almost everyone else in his hometown hideous in revenge for a bunch of kids beating him so badly that he had to be hospitalized.
- The Morlock Masque from X-Men comics does this to victims with his (her?) mutant powers; because Masque can't use his/her powers to make his/her own ugly face handsome, he/she takes it out on others by making them ugly.
- In the film Penelope, the title character is "cursed" to have a pig nose. People tend to respond to her looks extremely negatively.
- In Se7en, the Pride kill has John Doe cutting up the face of a beautiful but vain woman and making her choose between suicide and life with an ugly face. She chooses suicide.
- Freaks, where it's also a Karmic Transformation.
- Spaceballs: After kidnapping Princess Vespa, the villains give an ultimatum to her father, threatening to undo her nose job if he doesn't reveal the air dome's combination. Although Vespa herself pleads with him not to, he eventually caves, averting this trope.
- Beauty and the Beast is the most obvious, with the Beast having been transformed into a grotesque monster in punishment for failing the Old Beggar Test.
- The book Beastly matches this, as it is a modern version of "Beauty and the Beast". Protagonist Kyle is a rich jerk who embarrasses Kendra, an unpopular girl who turns out to be a witch. He gets cursed by turning into a hideous beast, until he receives True Love's Kiss.
- In the book, at least. In the movie, he just gets cursed into looking like a member of the Jim Rose Circus.
- In Dying Earth, the witch Javanne cursed her lover by making him hideously ugly; at the end of that story, she's forced to bring him before a god of justice, who decides a little Laser-Guided Karma is in order.
- In Homecoming Braelin Janquay is turned in to a drider by the priestesses of House Melarn. What makes this worse, is, that driders are outcasts of drow society, not only ugly but reviled by the populance. And the process of turning into one is so incredibly painful that all driders start out with memories of their torment and former lives wiped, because they coudln't stand living otherwise.
- In the final book of The Wheel of Time, Graendal, formerly one of the world's greatest beauties, is punished for her counterproductive Chronic Backstabbing Disorder by being killed and reincarnated as a hideous, deformed old crone. As a Psycho Psychiatrist with horrific Mind Control powers, she promptly starts forcing her victims to see her new form as the highest ideal of beauty.
- An episode of Sabrina the Teenage Witch had a variation: During a particularly vain phase, Sabrina meets a kindhearted and charitable (according to Hilda and Zelda) yet ugly relative (her skin is spotted green) whom Sabrina treats with apprehension. Said relative decides to teach her a lesson...by gradually turning Sabrina's boyfriend Harvey into a werewolf-esque creature (so much for kindhearted). She changes Harvey back only when Sabrina accepts him despite his looks.
- In "The Masks", a fifth-season episode of The Twilight Zone (1959), a wealthy dying man summons his family to his New Orleans home for Mardi Gras. Since they're all grasping creeps waiting for him to die so that they'll inherit, he makes it a condition of his will that they wear grotesque masks matching their personalities until midnight. He dies at midnight and they take off their masks to find that their faces have been permanently molded into those shapes.
Mythology & Religion
- The Greek mythical monster Medusa, who was so ugly that anyone who beheld her face was turned to stone, was supposedly afflicted with this. In many versions of the myth, she was originally a beautiful girl, but made the mistake of being raped by Poseidon in Athena's temple. Athena really didn't take it too well.
- In one Peanuts strip, Peppermint Patty supposed that her ugliness was a punishment for something she had done in a previous life.
- In Vampire: The Masquerade, the Nosferatu Clan often Embraces vain, beautiful people, cursing them into looking like them. Depending on the individual vampire's tastes, this is done for two reasons: Some do this to teach "The Beautiful Elite" a lesson in humility, while others like to do this just so they can watch models and actors writhe in agony. Unfortunate victims of this kind of 'lesson' are dubbed "Cleopatras", allegedly after the character in Freaks.
- It's likewise believed that the Clan's founder, Absimiliard, was one of the most beautiful (and vain) of all the antediluvians, conspiring to murder his second-generation sire because she'd slightly marred his perfect looks during the Embrace. When he went through with it, Caine made things much, much worse.
- In Vampire: The Masquerade – Bloodlines, at least two members of the LA brood are (or were) Cleopatras: A supermodel named Imalia (who hasn't gotten over it), and a former silent movie star and their current primogen "Gorgeous" Gary Golden (who has gotten over it, considering he is Imalia's Sire).
- The Tzimisce do it on occasion as well, given that they've got Vicissitude. There's a NPC in the Mexico City book who made the mistake of pissing off Sascha Vykos; Vykos sealed up all his orifices, then Embraced him. The man has to chisel his eyes and mouth out on a nightly basis.
- Part of the Dragonlance backstory has the Irda, a beautiful, powerful race of blue-skinned humanoids who were the first sentients created on Krynn who enslaved first the elves, than men when they proved more useful as laborers. After growing too arrogant, all but one clan (who were friendly to humans) were cursed by the gods and become the hideous green-skinned monsters known as Ogres.
- One very harsh example in Rocket Age. Although this might have been a side effect of the viral and nuclear bombardment of Io by the Europans, the Iotes went from being described as the most beautiful species in the solar system to looking like disease ridden, mutated dog men. Knowing the Europan's track record, they probably didn't even do anything to deserve it.
- In Into the Woods, the ugly old witch was really a beautiful woman who had been victim of this.
- In Metal Gear Solid 4, Snake apparently thinks of his Rapid Aging as this.
- Inverted in Video Game Kings Quest IV where the ugly, but good hearted Igor-like Edgar is turned into a Prince Charming by the fairy Genesta for his part in helping the Heroine. Though a later Retcon made it so that was his original form.
- In Vampire: The Masquerade – Bloodlines, as in the tabletop game, the Nosferatu sometimes inflict their Looks Like Orlok variety of undeath on vain beauties to take them down a notch. One Nosferatu, Imalia, is a former top supermodel... who will pay handsomely to have her Unknown Rival successor's life ruined, suggesting that the lesson in humility didn't stick.
- Kavonn of Charby the Vampirate cursed a female character with a reactive version of this: She switches between beautiful and ugly depending on her actions.
- Taako of The Adventure Zone sacrifices his elven beauty during the Suffering Game arc. Downplayed slightly in that he only becomes average looking, and immediately casts Disguise Self to make himself look like his past self.
- Parodied in The Simpsons, when Homer is taking an oath when he becomes a Stonecutter.
Homer: And by the sacred parchment, I swear that if I reveal the secrets of the Stonecutters, may my stomach become bloated and my head be plucked of all but three hairs —
Moe: Um, I think he should have to take a different oath.
- In The Smurfs episode "The Tear Of A Smurf", Chlorhydris' daughter Priscilla was a young woman punished by her mother by being turned into an old hag, and she seeks the tears of a Smurf for her formula to restore her youth.