Top 20 Ugly Duckling Transformations in Movies
#20: Marisa Ventura
“Maid in Manhattan” (2002)
Jennifer Lopez stars in this modern day Cinderella story that is an amazing early aughts guilty pleasure. In “Maid in Manhattan”, Marisa Ventura works as a member of staff at The Beresford Hotel and a case of mistaken identity causes her to strike up a romance with a wealthy man. We finally get to see her ditch the dowdy maids’ outfit at the end of the film when she gets all dolled up to attend a party. The fact that this scene is set to Diana Ross’ hit “I’m Coming Out” only makes it all the more fun.
#19: Anya
“Anastasia” (1997)
When we first meet Anya, she’s in fact Anastasia, the Grand Duchess of Russia, but through political unrest and the diabolical Rasputin’s deeds, she’s taken away from her family and heritage. Ten years later, she’s forgotten who she is, etiquette and all, until Dimitri and Vlad rope her into a scheme to pass her off as the long-lost Grand Duchess - simple, right? With their help, she gets a crash course in pretending to be someone of a higher station, and along the way becomes more comfortable in her own skin. That, and she gets to wear some new clothes that frankly, we would really love to borrow sometime - animated or not.
#18: Sam Montgomery
“A Cinderella Story” (2004)
Top 10 Ugly Duckling Transformations in Movies
Hilary Duff does what she does best in “A Cinderella Story”: playing a totally awkward yet endearing teenager. In this rendition of the classic fairy tale, Sam wants to meet her online crush at a school dance but isn’t allowed to go by her evil stepmother. She goes anyway, with the help of her friends at the diner where she works, sporting an old wedding dress and a masquerade mask that somehow completely obscures her identity from everyone who knows her. Believable? Maybe not. But it’s magical nonetheless.
#17: 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.
#16: Vivian Ward
“Pretty Woman” (1990)
Let’s be real, Julia Roberts is always gorgeous, but at the beginning of “Pretty Woman” when she’s in her street-walking get up and blonde wig, she definitely doesn’t look her best. In one of the most satisfying scenes from this classic rom com, we get to see her character Vivian go from underdressed to perfectly in style when she returns to that snobby Rodeo Drive shop to tell them what a huge mistake they’ve made. The shopping montage that takes place before, set to the song that gives the movie its name, is beloved for good reason.
#15: Cinderella
“Cinderella” (1950)
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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.
#14: Danielle de Barbarac
“Ever After” (1998)
Another interpretation of the Cinderella story is this late ‘90s flick starring Drew Barrymore. Marketed as the supposedly real story behind the much-loved tale, “Ever After” introduces us to Danielle de Barbarac, whose father has died and who has long been mistreated by her stepmother and stepsisters. At the beginning of the film, she dresses like a common servant, but when the time comes for the big ball, she pulls out all the stops and looks absolutely ethereal in a white dress and pair of fairy wings.
#13: Josie Geller
“Never Been Kissed” (1999)
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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.
#12: Jo Stockton
“Funny Face” (1957)
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One of the greatest fashion movies of all time, “Funny Face” let audiences see Audrey Hepburn decked out in Givenchy for the duration of the film. The movie tells the story of an intellectual bookstore employee, Jo (played by Hepburn), who is discovered by a fashion photographer and brought to Paris to work on his new campaign. Jo is subtly elegant at the beginning of the film, but seeing her dressed up i the Parisian high fashions is pure eye candy that we just can’t get enough of.
#11: 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.
#10: Annabelle Fritton
“St Trinian’s” (2007)
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Annabelle doesn’t quite fit in at St Trinian’s, a school for wayward girls, because of her somewhat prissy attitude. So it comes as no surprise that her classmates kidnap her in the middle of the night to give her a new look that will fit the school’s aesthetic a little bit more. The audience gets to see each different clique trying out a makeover style for her, and the one they settle on is sexy, cute and a little bit edgy. Yes, Annabelle was beautiful before, but she’s got a lot more spunk after!
#9: 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.
#8: Katie Simpson
“She's Out of Control” (1989)
When 15-year-old Katie’s father leaves on a business trip, her typical look involves coke-bottle glasses, braces, and frumpy clothing. When he gets back however, his girlfriend has helped Katie transform into a full beauty, who ends up causing trouble because she has all the boys in town in a frenzy. This movie may not have done well with the critics, with the legendary Roger Ebert particularly panning it, but we still love this transformation, even if Katie’s father doesn’t!
#7: Tai Frasier
“Clueless” (1995)
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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.
#6: Charlotte Vale
“Now, Voyager” (1942)
Bette Davis is one of the greatest iconic Hollywood stars, but you’d barely recognize her at the beginning of this 1942 film. She plays Charlotte Vale, an unattractive spinster who is abused by her mother; and, because of her emotional distress, looks about twice her age. After spending time away from her family home at a sanitarium, and then on a cruise, she manages to flourish, and returns . . . looking completely unrecognizable. Her eyebrows alone are a before and after that would be inspirational to anyone!
#5: 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.
#4: Allison Reynolds
“The Breakfast Club” (1985)
One of the most iconic movies of the ‘80s also happens to feature one of the best makeovers in movie history. At the beginning of “The Breakfast Club”, Allison is the awkward and weird girl who is shown in sharp contrast to the pretty and popular Claire, played by Molly Ringwald. After spending their detention together though, the two girls bond and Claire gives Allison a completely transformative makeover. She always had good looks, but thanks to Claire, Allison finally got the confidence boost she needed.
#3: 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.
#2: Fran
“Strictly Ballroom” (1992)
Baz Luhrmann’s amazing debut may not be as well known as its successors, but that doesn’t mean it should be overlooked. This charming film focuses on the Australian ballroom dancing world, and in a plot somewhat similar to the classic “Dirty Dancing”, an experienced male dancer finds himself taking on a raw beginner to be his partner. Fran is the “Baby” of this story, and when we first meet her she’s one of the most awkward characters to ever grace our screens. By the end of the film though, she really comes into her own, and shows an elegance and poise we never could have imagined.
Before we unveil our top pick, here are a few honorable mentions:
Cady Heron
“Mean Girls” (2004)
Olive Penderghast
“Easy A” (2010)
Laney Boggs
“She’s All That” (1999)
Selina Kyle
“Batman Returns” (1992)
Gigi
“Gigi” (1958)
#1: Mia Thermopolis
“The Princess Diaries” (2001)
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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.
