Six Hollywood Swans in their Ugly Duckling Roles

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Nobody loves to show off their beauty more than female celebrities. You can find them dressed to the teeth on any red carpet Hollywood has to offer. There are a few, however, who don’t mind dressing down for a job. It’s amazing to see how plain (and sometimes scary) movies can make some of the most gorgeous women on earth.

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And sometimes they feel the need to make the scary down right terrifying.

Let’s face it, making most Hollywood beauties look bad cannot be an easy job. Here are six chicks who showed their ugly duckling side, along with pictures of the way we prefer seeing them.

Rachel Leigh Cook in “She’s All That”

Donning some baggy clothes to hide her awesome body and growing a uni-brow that almost rivals that of Frida Kahlo, Rachel transformed herself into boring plain jane Laney Boggs for this 1999 romantic comedy.

The way we prefer Rachel:

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Brittany Murphy in “Clueless”

An almost unknown Brittany Murphy played Tai in the 1995 air head flick “Clueless”. Half way through the movie, her character is given a make over, and we discover she’s female.

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On the left, a nearly manly Brittany Murphy.

The way we prefer Brittany:

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Sandra Bullock in “Miss Congeniality”

Sandra went above and beyond the call of duty in 2000’s “Miss Congeniality”. Not only did she wear men’s clothes and not shave her legs, she also can be witnessed gulping beer, letting food fall from her mouth and snorting while she laughs.

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The way we prefer Sandra:

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Drew Barrymore in “Never Been Kissed”

Drew portrays a chubby, insecure, fashion impaired reporter who’s posing as a high school student in the 1999 movie “Never Been Kissed”. Of course, she gets herself a makeover before it’s all over with. Before that point, however, you’ve really got to look twice to believe it’s Drew.

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The way we prefer Drew:

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Anne Hathaway in “The Princess Diaries”

Sleek, graceful Anne Hathaway has been called the Audrey Hepburn of her generation. In Disney’s 2001 “The Princess Diaries”, however, it’s easier to compare her to a cross between Bozo the Clown and Oscar the Grouch.


The way we prefer Anne:

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Charlize Theron in “Monster”

In probably one of the most dramatic transformations from beauty to beast, Charlize Theron did more than dress down for her role as Aileen Wuornos in 2003’s “Monster”. She also gained thirty pounds.

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The way we prefer Charlize:

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