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Craziest Dresses in Oscar History (PHOTOS)

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

Kevork Djansezian/AP

Kevork Djansezian/AP

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

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2011

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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2011

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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2009

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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2006

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

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2005

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

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2004

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

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2004

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

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2003

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

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2002

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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2002

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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2001

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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2001

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

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2000

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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2000

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

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1999

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

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1996

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

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1995

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

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1993

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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1992

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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1991

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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1989

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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1988

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.