5 Ugly Duckling Movies That Are All Essentially The Same

Friday, July 12 by Mira Caliban

Films featuring sports stories in which the underdog wins are massively appealing to men. Hollywood has designed underdog movies for teenage girls as well,  in the form of ugly duckling flicks. Just as most underdog sports stories involve similar tales of heroes who succeeds against all odds, ugly duckling tales tend to have very formulaic plots.  In each, an ugly girl transforms into a beauty and thereby manages to catch the eye of a guy who was previously out of her league. Consider these 5 ugly duckling movies that are all essentially the same:

“Guys and Dolls”

Jean Simmons

In this musical, Marlon Brando plays gambling hot shot Sky Masterson who bets Frank Sinatra’s character, Nathan Detroit, that he (Masterson) can take any girl to a restaurant in Havana. Sinatra picks straight-laced, anti-gambling, ugly duckling missionary Sarah Brown. At first, Brown resists Masterson’s advances and maintains the demeanor of an army sergeant. Yet, once in Cuba, she lets her guard and her hair down and trades in her military-style garb for a casual dress. She wins over Masterson’s affections in the process.

“She’s All That”

Rachael Leigh Cook

In  this classic chick flick, Freddie Prinze Jr. plays popular sports star and academic wiz Zac Siler, who breaks up with unfaithful girlfriend. In order to show his friends that he doesn’t need her, he bets them that he can take any girl in the school and make her as popular as his ex. His friends pick ugly duckling Laney Boggs (Rachael Leigh Cook), an anti-social drama geek whose mother died before giving her any tips about hair and make-up. With the help of Siler’s sister, Siler transforms Boggs’ appearance and behavior. After several setbacks and confrontations, Boggs becomes so popular that she is voted Prom Queen. She also manages to win over Siler’s affections.

“Pretty Woman”


In this romance, Richard Gere plays lonely businessman Edward Lewis who hires prostitute, Vivian Ward (Julia Roberts) to keep him company – both at his apartment and at social events. When Lewis provides Ward with the funds and stature to buy dresses at high-end clothing stores, she changes out of her trashy, overly-revealing clothing and transforms from an ugly duckling to a swan.  Just as Masterson and Siler fall for their ugly ducklings, Lewis ends up falling for his.


Julia Ormond


Sabrina is the story of the daughter of an upper-crust family’s chauffeur. As a shy, ugly duckling she goes unnoticed by most of the family. Yet she falls in love with family’s youngest son David, who is known for his womanizing and irresponsibility. Her father sends her abroad to get over her feelings for David; however, when she returns, she comes back with a new haircut and a new way of dressing. She manages to win the affections not only of David, but also of his older brother, who has been given the job of splitting them up.

“The Princess Diaries”


In this film, Anne Hathaway plays Mia Thermopolis, a nerdy, anti-social student whose life changes after she discovers she is really the princess of Genovia. When her grandmother, the queen, oversees her makeover, Thermopolis changes from an outcast to a beauty. The popular girls suddenly want to befriend her and the popular boy she has had her eye on suddenly begins showing interest in her. Thermopolis eventually forgoes popularity and sticks to old friendships, but the story of her transformation follows the same formula as that of the heroines in the other ugly duckling films.

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