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The Worst Oscars Fashion Choices of All Time

Weirdest Oscars Dresses
David McNew/Hulton Archive/Frank Micelotta/Vince Bucci/David McNew, Getty Images

For those of us who don’t spend our lives and retirement funds making movies, the actual awards part of the Academy Awards isn’t the most interesting. The people we like hardly ever win and we don’t care how much anybody’s publicist helped them get where they are today. What we really tune in to see are the fashion statements. More specifically the fashions that state, “Clearly, I’m nuts. Aren’t you glad you invited me to your little party?”

In a good year, at least one, if not multiple celebrities will show up dressed in something so ridiculous it defies logic. And we love them for it. We love that we can mock them and we love that they had the guts to show up in public like that. We also love that they have been photographed for all history to gawk at them forever.

Here are 10 of the weirdest celebrity Oscar outfits we could find. For them, we know it’s an honor just to be nominated.

Cher (1986)

Cher's weird Oscars dress
Hulton Archive, Getty Images

Well, slap our faces and call us moonstruck, but what the deuce was Cher thinking? This isn’t an outfit, it’s some stuff she found in her garage. It seems to us she fell right off the cutting edge with this one, because we certainly didn’t see it on the racks at JC Penney six months later.

Demi Moore (1989)

Demi Moore's weird Oscars dress
Barry King, Getty Images

Remember when Bruce Willis and Demi Moore were an item? Remember when Demi Moore was invited to the Oscars? Well, we’d rather not remember this strange dress Demi wore to the 1989 ceremony. Was she auditioning for a role in Tim Burton’s ‘Batman’? What’s the deal with the cape thing attached to her?

Faith Hill (2001)

Faith Hill's weird Oscars dress
Frank Micelotta, Getty Images

We say if Faith Hill wants to show up at the Oscars looking like a sno cone, more power to her. She’s beautiful, talented, rich, has a rocking bod and a handsome husband. Impersonating frozen treats was obviously the only thing she had left to accomplish in life. Sadly, the lovely gown was probably quite a mess when it melted.

Matt Stone and Trey Parker (2000)

Matt Stone and Trey Parker's weird Oscars dresses
David McNew, Getty Images

For a minute we thought it was J-Lo and Gwyneth Paltrow, but if you look really closely, you can see that it’s actually Matt Stone and Trey Parker of ‘South Park’ fame enjoying their moment on the red carpet. There can’t possibly have been a single person there who expected them to show up in tuxes. We all know the real blame lies with Canada.

Bjork (2001)

Bjork's weird Oscars dress
Jeffrey Mayer, Wire Image

Who could forget the iconic swan dress that Bjork pretended to lay an egg in at the 2001 Oscars? Created by Macedonian fashion designer Marjan Pejoski, the swan dress is still a pop culture punchline today. Bjork said she wore the dress to coincide with her winter-y ‘Vespertine’ album, but we think she  was campaigning to be in ‘Black Swan’ a decade ahead of time.

Diane Keaton (2004)

Diane Keaton's weird Oscars dress
Vince Bucci, Getty Images

This was the year Diane Keaton laughed in the face of Oscar tradition and decided to show up looking like Buster Keaton. Ms. Keaton doesn’t usually like to show a lot of skin, but this gender bend was taking it a bit far. Although, she still looks pretty good and at least it doesn’t look like it came out of Cher’s garage.

Erykah Badu (2000)

Erykah Badu's weird Oscars dress
David McNew, Getty Images

If Ms. Badu was trying to make a bold statement, she was probably sadly overshadowed by the striking nature of the Matt Stone and Trey Parker appearance. She did hold her own pretty well with this odd and attention-grabbing outfit, though. While we assume she was aiming for some kind of traditional African tribal look, we’d hate to be whoever was sitting behind her during the ceremony.

Tyra Banks (2000)

Tyra Banks' weird Oscars dress
David McNew, Getty Images

2000 was such a great year for weirdness on the red carpet. Tyra Banks wanted to help raise the strange dress factor by arriving dressed as something you might use to dust your blinds and bookshelves. We’re guessing she planned to pilfer a few Oscars under that thing and then sell them on eBay.

Cameron Diaz (2002)

Cameron Diaz's weird Oscars dress
Frank Micelotta, Getty Images

Perhaps the beginning of 2002 was very busy for Cameron Diaz, or maybe they asked her to present at the very last minute. We don’t know. What we do know is that she clearly didn’t have time to shop for a dress and had to instead wrap herself in whatever wallpaper was left over from her most recent redecoration. It’s the jeweled chili pepper belt that really sells it though.

Gwyneth Paltrow (2002)

Gweneth Paltrow's weird Oscars dress
Frank Micelotta, Getty Images

Fashion icon turns fashion why-con. The woman who always adds an air of elegance and sophistication to the red carpet decided 2002 was the year to go Goth. Nobody told her that a beautiful, sparkling-eyed smile is not an appropriate accessory with a drab, emo dress. The only thing we can figure is that Cameron Diaz didn’t have any more spare wallpaper lying around.


Whoopi Goldberg (2002)

Whoopi Goldberg's weird Oscars dress
Getty Images

Whoopi Goldberg was set to host the show when she came down with a bad case of the avian flu, causing her to sprout a very noticeable set of tail feathers. It was too late to replace her with Billy Crystal, so the producers decided to just go with it. The only way to disguise tail feathers is to add as many sequins and sparkly embellishments to an outfit as possible. And then definitely show a lot of leg. To this outfit, we say, “Whoopee!”

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