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Top 10 Ugly Duckling Transformations in Movies

VO: Lisa Yang
Script written by Nick Spake Sometimes the most beautiful girl in the room is the one you least suspect! Join as we count down the Top 10 Ugly Duckling Transformations in Movies. For this list, we’re looking specifically at female characters in films who transitioned from ugly ducklings into beautiful swans, which means there won’t be any male characters, because they deserve a list of their own. Special thanks to our user DarrenZach for submitting the idea on our Interactive Suggestion Tool at

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Top 10 Ugly Duckling Transformations in Movies

Sometimes the most beautiful girl in the room is the one you least suspect! Welcome to MsMojo, and today we’ll be counting down our picks for the top 10 ugly duckling transformations in movies.

For this list, we’re looking specifically at female characters in films who transitioned from ugly ducklings into beautiful swans, which means there won’t be any male characters, because they deserve a list of their own.

#10: Zeta Alpha Zeta Girls
“The House Bunny” (2008)

What happens when a former Playboy bunny moves into a sorority house? The girls get a killer lesson in how to look pretty and attract boys, of course. When Shelley becomes the new “house mother” of Zeta Alpha Zeta, she immediately helps transform the sorority sisters from socially awkward shut-ins to gorgeous guy magnets. Naturally, considering Emma Stone and Katharine McPhee star as two of the sisters, she didn’t really have all that much work to do.

#9: Fern Mayo aka Vylette
“Jawbreaker” (1999)

The “Flawless Four” had it all until a practical joke gone wrong resulted in the accidental murder of their clique leader. To protect their secret and ensure their safety, the girls accept Fern Mayo into their clique. Fern undergoes a complete transformation, and quickly goes from admirer of the girls to the most popular girl in school, and even changes her name to Vylette. Her newfound popularity comes with both friends and enemies, however, as Vylette learns the hard way that being the most popular girl in the school isn’t all it’s cracked up to be.

#8: Cinderella
“Cinderella” (1950)

Easily one of the most iconic transformation scenes in movie history, Cinderella trades in her rags for a beautiful gown with the assistance of her Fairy Godmother. Having been mistreated by her stepmother and stepsisters, Cinderella desires to attend the Prince’s Ball, only to have her dress destroyed by her evil stepsisters. Luckily, her Fairy Godmother arrives, and gives her a new gown with glass slippers as well as a horse and carriage, allowing her to attend the ball and earn the love of the prince.

#7: Josie Geller
“Never Been Kissed” (1999)

Whether you loved or hated high school, most of us would likely have no interest in living through it again. Unfortunately for Chicago Sun-Times reporter Josie, her boss assigns her to go undercover at her former high school. At first, Josie, who struggled mightily through high school her first time, reverts to her old geek persona, complete with the patchy make-up and bad perm. Over the course of the film, however, she becomes more confident and is even crowned Prom Queen. More importantly, she learns that in the grand scheme of things, high school is just a blip on the radar and really doesn’t matter.

#6: Loretta Castorini
“Moonstruck” (1987)

We’ll admit it, most movies on this list are cheesy romantic comedies, but this film was actually nominated for Best Picture and saw Cher, who starred as Loretta Castorini, win Best Actress. After having a one-night stand with her fiancé’s brother, Loretta decides it’s time for a new image. Rejecting her widowed-accountant persona, she gets the gray removed from her hair while styling it in the 80s poof we all know so well. Throw in a glamorous evening gown and you have an entirely new woman, albeit one that still faces the tricky situation of having hooked up with her fiancé’s brother.

#5: Fotoula ‘Toula’ Portokalos
“My Big Fat Greek Wedding” (2002)

A lot of us have an overbearing family, but hopefully they aren’t as exhausting as the Portokalos clan. The Portokalos’ want Toula to marry a Greek boy so she can make Greek babies and cook for the rest of her life, but she strives for something more. After enrolling in a computer class at the local community college, Toula decides to completely change her look in an effort to get out of her rut. She ditches her glasses for contact lenses, wears make-up, and gets a new hairdo. This transformation shows that it’s never too late to change, no matter what your age.

#4: Tai Frasier
“Clueless” (1995)

Another classic 90’s film to make our list, “Clueless” stars Alicia Silverstone as Cher, your prototypical valley girl. Cher decides to use her influence to give back to the community by making Tai, the new girl, popular. Naturally, this involves Cher and her best friend Dionne giving Tai a much-needed makeover. Unfortunately, this move ultimately backfires when Tai becomes more popular than Cher, causing her to reflect on her priorities and what is actually important in life.

#3: Gracie Hart
“Miss Congeniality” (2000)

Gracie needed to undergo a significant transformation when she was tasked with the job of going undercover at the 75th annual Miss United States beauty pageant to investigate a bomb threat. Rough and tomboyish, Gracie didn’t just get a makeover, she got an entire overhaul; including lessons on how to dress, walk, and act like a supermodel. Of course, while Gracie’s appearance may have changed, she demonstrates how good of a cop she is by sussing out the real threat and saving the newly crowned Miss United States’ life.

#2: Eliza Doolittle
“My Fair Lady” (1964)

Considering how beautiful Audrey Hepburn is, it’s surprising that she starred in several films that feature ugly duckling transformations. She got her feet wet in 1954 as Sabrina Fairchild, but it was her performance as Eliza Doolittle in “My Fair Lady” that earned a spot on our list. Initially an unrefined street vendor with a thick Cockney accent, she slowly transitions into a well-mannered member of high society and is even mistaken for a princess. While this film suggests that enough effort and time can allow anyone to turn into a lady, we have to admit that looking like Audrey Hepburn certainly helps.

Before we unveil our number one pick, here are a few honorable mentions:

Cady Heron
“Mean Girls” (2004)

Laney Boggs
“She’s All That” (1999)

Valerie Gail
“Earth Girls Are Easy” (1988)

Selina Kyle
“Batman Returns” (1992)

#1: Mia Thermopolis
“The Princess Diaries” (2001)

Similar to our previous entry, Anne Hathaway is no stranger to undergoing transformations. She becomes a fashion expert in the 2006 comedy “The Devil Wears Prada,” but we’re choosing her debut film for the number one spot on our list. As a geeky and frizzy-haired teenager, Mia Thermopolis is stunned to discover that she is actually a Princess and heir to the Throne of Genovia. Mia receives princess lessons and is also given a glamorous makeover. Of course, true to form, when she accepts her role as the Princess, she appears untidy and drenched, proving that character, not appearance, is the most important thing.

Do you agree with our list? What is your favorite ugly duckling transformation? For more awesome Top 10s published daily, be sure to subscribe to MsMojo.


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