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Craziest Dresses in Oscar History (PHOTOS)

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What possesses great actors who are normally sane to appear in Halloween costumes in March? The Oscars, of course.

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What possesses great actors who are normally sane to appear in Halloween costumes in March? The Oscars, of course. 

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James Franco (2011): Hosting the Oscars is no easy task. 127 Hours nominee James Franco took paying homage to Marilyn Monroe quite seriously.

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Helena Bonham Carter (2011): This black Colleen Atwood dress wouldn’t be so bad if Carter didn’t wear that Union Jack Garter—more BAFTA than Academy Awards appropriate). Atwood also designed the costumes for Sweeney Todd and Alice in Wonderland (no surprise there).

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Jessica Biel (2009): Is that a Prada dress or did Biel wrap herself in her hotel room’s spare sheets after coming out of the shower?

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Amy Adams (2006): Yum, is that Carolina Herrara gown made out of chocolate?

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Melanie Griffith (2005): Unfortunately, she hobbled down the red carpet in with a huge cast on her leg.

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Uma Thurman (2004): A dancing pirate? One of the von Trapp children?

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Diane Keaton: (2004): Charlie Chaplin came back from the dead for the 2004 Oscars.

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Hilary Swank (2003): This pink Dior dress was junior prom meets cotton candy.

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Gwyneth Paltrow (2002): Just because her Oscar-winning Shakespeare in Love performance was risqué doesn’t mean she had to follow it up with this Alexander McQueen piece.

 

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Faith Hill (2002): Contrary to many media reports, Hill sang “There You’ll Be” at the 2002 Oscars, not “Somewhere Over the Rainbow.” But the confusion is understandable.

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Kate Hudson (2001): “So I called [the dress’ designer] Stella [McCartney] and we just laughed our arses off and she said to me, ‘Look babe, it was the hair wasn't it?’”

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Bjork Guðmundsdóttir (2001): Ladies and gentlemen, the greatest Oscar dress of all time.

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Angelina Jolie (2000): Not sure what’s scarier: Jolie’s Elvira look or infamously making out with her brother that night.

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Matt Stone & Trey Parker at the Shrine Auditorium in Los Angeles, California (Photo by Steve Granitz/WireImage)

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Celine Dion (1999): Was it the point to wear that tux backwards? Or did she just do that by mistake?

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Susan Sarandon (1996): The Dead Man Walking actress’ Dolce & Gabbana gown.

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Lizzy Gardiner (1995): The costume designer for The Adventure of Priscilla, Queen of the Desert should have known better.

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Whoopi Goldberg (1993): This Beverly Hills Boutique dress belongs on the set of Rodger and Hammerstein’s Cinderella, not the red carpet.

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Geena Davis (1992): The Ruth Meyers and Bill Hargate dress gave a Cinderella-esque look to the Thelma and Louise nominee, except for the lace-intertwined portion of it.

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Bon Jovi (1991): Nominated for best music and original song for Young Guns II, the purple tux Bon Jovi wore that night was indeed living on a prayer

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Demi Moore (1989): Designed by the actress herself, the bustier, bike shorts, and cape combination screamed Elizabethan biker. Moore accompanied then-husband and presenter Bruce Willis to debut her secret designing talent.  

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Cher (1988): The Moonstruck actress’ dress, designed by Bob Mackie, had actually distracted us from the fact that she did win an Oscar that year.

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