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Bette Davis, 1936

The Dangerous star was so convinced she wouldn't win Best Actress, she wore an old costume to the ceremony. After her surprise victory, rival Joan Crawford reportedly sniped, "Dear Bette! What a lovely frock."

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Barbra Streisand, 1969

Streisand made history tying with Katharine Hepburn for Best Actress, but that wasn't the only memorable moment that night. The Funny Girl star apparently didn't realize the bright lights would turn her sequined pant suit transparent. 

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Cher, 1974

Cher wore a midriff-baring ensemble the year before, but this flowery bandeau top exposed a lot more than just her abs.

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Edy Williams, 1974

So many questions: Is that a bikini? What's with the fur coat? And can someone please explain the dog? 

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Farrah Fawcett, 1978

The '70s style icon simply wowed in a slinky gown by Stephen Burrows. 

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Cher, 1986

Designer Bob Mackie didn't hold back making this legendary sequined ensemble complete with a sky-high feathered headdress. 

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Edy Williams, 1986

Some carefully-arranged strands of pearls leave very little to the imagination in this red carpet appearance. 

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Cher, 1988

None of the Kardashians can pull off a naked dress quite like this. The Goddess of Pop won her first Oscar for Moonstruck that year, wearing another Bob Mackie creation. 

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Demi Moore, 1989

It was the '80s, but Demi Moore really should have steered clear of bicycle shorts while designing this ensemble herself. 

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Kim Basinger, 1990

The Batman actress also tried her hand at fashion that year, dreaming up this, ahem, interesting suit-ballgown hybrid. 

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Cindy Crawford, 1991

The supermodel attended the 63rd Academy Awards with new boyfriend Richard Gere in tow. The plunging sheath by Versace still tops best-dressed lists more than two decades later.

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Geena Davis, 1992

She may have won acclaim for Thelma and Louise, but Davis didn't hear much praise for this bustier top, ruffled skirt combo. 

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Whoopi Goldberg, 1993

Underneath the comedian's purple satin skirt was a pair of paisley pants and a blindingly-green lining. Aaand that's how you end up on the worst dressed list. 

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Lizzie Gardiner, 1995

American Express didn't want the costume designer using their brand in The Adventures of Priscilla, Queen of the Desert, but they had no problem providing 254 expired cards for a one-of-a-kind Oscars dress. The real question is, how did she ever sit down? 

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Susan Sarandon, 1996

Something about the '90s inspired celebs to wear sunglasses both indoors and at night, but Susan's shades were the least of her problems in this shiny (and brown!) halter top. 

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Ashley Judd, 1998

Years before Janet Jackson's infamous wardrobe malfunction, Ashley Judd made headlines after an up-to-there slit revealed a little much for primetime television. 

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Cher, 1998

At this point, it would be more scandalous if Cher didn't wear something revealing to the Oscars. This shimmery number maintained the trend, from outlandish headdress to beaded hem. 

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Charlize Theron, 2000

Charlize Theron wowed in a tangerine gown by Vera Wang, but the actress later claimed the bombshell moment had an unintended effect. "I can't tell you how many times I've auditioned for a role, only to have my agent come back and say, 'Listen, Charlize, they saw you in the orange dress and they don't think you can do it,'" she explained. 

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Edy Williams, 2000

The consistently-daring actress was back at it again in what could only be described as a figure skater's ensemble gone wrong. 

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Matt Stone & Trey Parker, 2000

The South Park creators spoofed Jennifer Lopez's infamous Grammys moment and Gwyneth Paltrow's princess gown in an an extremely memorable Oscars debut. 

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Bjork, 2001

No Academy Awards article would be complete without Bjork's iconic swan dress. Ellen DeGeneres spoofed it. Kevin James wore one. Valentino even riffed the theme in its 2014 spring collection. But no one can ever top the musician "laying an egg" on the red carpet. Ever.

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Kate Hudson, 2001

Although she didn't wear a bird, the press skewered Kate Hudson's Oscars debut, hating everything from the Stella McCartney cape to the extremely-curly hair. But the young actress didn't realize the misstep at the time. "I felt so beautiful, and I have it in my closet still to the day," she said at a 2012 Vogue event. 

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Gwyneth Paltrow, 2002

Although she later regretted not wearing a bra, Paltrow still likes her "goth" look by Alexander McQueen. Unfortunately, few critics could get over the sheer top and heavy eyeliner. 

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Halle Berry, 2002

The Monster's Ball star also opted for a transparent bodice, but her Elie Saab dress (with strategic embroidery) received glowing praise. It's now routinely cited as one of the best Oscars dresses of all time.

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Hilary Swank, 2005

Thanks to a daring backless gown, the Best Actress nominee drew the inevitable comparison of looking like a million bucks. 

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Sally Kirkland, 2007

Former Best Actress nominee Sally Kirkland is always an Oscars personality, but a circus tent on top of some precarious pasties is a real headscratcher. 

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Tilda Swinton, 2008

Cosmo later wrote, "Please save Tilda from the black velvet garbage bags holding her body hostage." It's safe to say she did not make the best dressed list. 

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Charlize Theron, 2010

Charlize usually nails the red carpet, but bloggers hated the conspicuously-placed rosettes on her Dior gown. 

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Madonna, 2011

Fans wanted to know where Madge put her pants, but a black leotard under a see-through skirt seems quite tame by today's standards.

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Jennifer Lawrence, 2011

Jennifer Lawrence would go on to cement herself in Oscars history (Who could forget that fall?), but this Calvin Klein number attracted plenty of attention — and comparisons to Jessica Rabbit.

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