Punished with Ugly

A beautiful character is punished by being turned ugly, which is apparently a Fate Worse Than Death. Usually a punishment for vanity, but not necessarily. See also Beauty to Beast, which is the general trope of a beautiful person turning ugly for whatever reason, including plain old-fashioned aging.

Related to Beauty Equals Goodness.

Anime and Manga

 * In the Yu-Gi-Oh! manga and first series anime, a beautiful, but sadistic teacher is challenged to a shadow game by the main character. Her punishment for losing is having her face shattered, revealing her inner ugliness.

Comic Books

 * 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 punishment.

Film

 * In the recent film Penelope, the title character is "cursed" to have a pig nose. People tend to respond to her looks extremely negatively.
 * In Se7en, the villain cuts up the face of a beatiful but vain woman and makes her choose between suicide and life with an ugly face.

Literature

 * 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.

Live-Action TV

 * 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.

Newspaper Comics

 * In one Peanuts strip, Peppermint Patty supposed that her ugliness was a punishment for something she had done in a previous life.

Oral Tradition, Myths, Legends, and Folklore

 * Beauty and The Beast is the most obvious.
 * 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 her pride got the better of her and she eventually proclaimed that she was more beautiful than Athena. Athena responded to this badly.

Tabletop Games

 * 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.
 * 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).
 * 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.

Theatre

 * In Into the Woods,.

Video Games

 * In Metal Gear Solid 4, Snake apparently thinks of his Rapid Aging as this.

Web Comics

 * 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.

Western Animation
"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."
 * Parodied in The Simpsons, when Homer is taking an oath when he becomes a Stonecutter.