The Most Ridiculous Oscars Dresses Will Always Be the Best

The urge to make fun of Björk’s swan dress was so immediate that by the time the 2001 Oscar ceremony was underway the fowl creation had made its way into host Steve Martin’s schtick.

After the Icelandic singer took the stage to perform “I’ve Seen it All,” the devastating song about a woman with a degenerative eye disease from Lars von Trier’s Dancer in the Dark for which she was nominated, Martin quipped: “I was going to wear my swan, but to me they are so last year.” Later that year, Ellen DeGeneres came out on the Emmys stage wearing a replica of the garment designed by Marjan Pejoski. “I guess this is business casual,” she said to laughs.

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The swan dress with its tutu and his bosom-grazing plush animal is arguably the most mocked red carpet look of this century. It’s been mimicked in White Chicks and lampooned on 30 Rock.

It’s also a piece of art that has been displayed in both the Museum of Modern Art and the Metropolitan Museum of Art, but that’s not to say that it isn’t very funny—to think that Björk was not aware of that fact is to seriously underestimate Björk.

When interviewed about the ensemble as she walked the press line, Björk was demure, but in subsequent interviews she talked about how the public misread her intention. Hell, she even brought eggs to “lay” on the carpet. “C’mon, you don’t bring eggs unless you want to take the piss, right?” she told the Sunday Times in 2004. “I was actually amazed at how many people thought I was serious. I didn’t mean to cause a riot!”

What we think of as “worst dressed”—codified in countless issues of People magazine and by the talking heads on E!—is skewed by society’s perceptions of what celebrities, specifically female celebrities, should wear to the Oscars. Our image of a star accepting a trophy best supported by Julia Roberts in vintage Valentino or Halle Berry in Elie Saab.

But “worst dressed” doesn’t leave room for having a sense of humor about all the pomp and circumstance, and in 2001 Björk was already part of a tradition of Oscar guests using fashion for fun on a night synonymous with staid glamor. These bold and intentionally amusing looks pre-date fashion experiments like Lady Gaga’s meat dress at the 2010 VMAs.

Now these kinds of kooky plays on formalwear are de rigueur at the Met Gala where Billy Porter enters on a platform carried by buff, shirtless men and Katy Perry cosplays Lumière from Beauty and the Beast. Only these ensembles are immediately celebrated whereas Björk was bashed.

When Barbra Streisand received her first nomination in 1969 for playing Fanny Brice in Funny Girl, she chose her infamous glittery Arnold Scaasi pantsuit because she just figured she’d be more buttoned up the next time she was nominated. (If you’re Barbra, you can have that kind of confidence.) As she climbed the stage to accept the Best Actress she won in a tie with Katharine Hepburn the bell bottoms turned out to be see-through, showing her tuchus to the entirety of the Dorothy Chandler Pavilion.

She didn’t know the get-up was sheer, but she did know she chose it over a more “conservative” option. Sure, it wasn't an intentional joke like the swan dress, but she took Scaasi’s advice to “forget that elegant bit,” as he once told the Los Angeles Times.

“Elegance” was arguably never on the mind of the underrated queen of Oscar provocation: Edy Williams. Williams was always an unconventional guest at the Academy Awards. She was best known for her bit part as a porn star in the delightfully trashy movie Beyond the Valley of the Dolls directed by her one-time husband Russ Meyer, but for almost two decades she regularly came to the Oscars in absurd, nudity-forward looks. Occasionally she would bring along a dog as an accessory.

In 1986, she wore a sheath of pearls barely concealing, well, anything. It's hard to argue that Williams’ consistent appearances in bikinis and animal prints were anything but an extensive joke played upon the stuffy institution she somehow gatecrashed year after year. After the ’86 ceremony, she went on a talk show hosted by conservative commentator Wally George who said she dressed “disgracefully” at what was supposed to be a “classy upbeat affair.” She responded: “I have a good sense of humor.”

That very same year, Williams wasn’t even the biggest attention grabber out there. After all, her status was minor compared to the person with the most outrageous outfit of the night. Cher was pissed she wasn't nominated for her work in Peter Bogdanovich’s Mask despite winning Best Actress at Cannes, and she was even angrier that she was then asked to present at the ceremony.

So she called up her friend, the designer Bob Mackie, and had him create what would become an iconic example of over-the-top Oscar fashion. She wore a feathered headdress and a top with jagged edges that looked like teeth bearing the entirety of her midriff. She told the New York Times in 1987, “I decided, ‘I’m going to remind them of what they don’t like about me.’” Two years later, she won Best Actress for Moonstruck. It’s Cher. She’s hard not to like.

The best red carpet jokes aren’t obvious jokes. These women are stepping out with a straight face like true provocateurs, baffling people along the way just like Celine Dion did when she wore a backwards tuxedo to the 1999 Oscars. (A year before she wore the Heart of the Ocean from Titanic. It was time to get a little funky.) When the rebellion looks too obvious it's, well, just kind of lame.

Take for instance, when South Park creators Trey Parker and Matt Stone showed up, high on acid, to the 2000 ceremony dressed, respectively, as Jennifer Lopez at the Grammys in her low cut Versace and Gwyneth Paltrow at the previous years’ Oscars in pink Ralph Lauren. Their stunt was not at the expense of the institution of the Academy Awards, but at the women who take it, and other awards shows, seriously.

Like Parker and Stone, Björk and Cher and Edy and Barbra were Academy Awards interlopers. All—save for Edy—had seen their careers flourish outside of the film industry. (Edy, alas, never really saw her career flourish.) Except, unlike Parker and Stone, they all took their Oscar attire incredibly seriously while at the same time knowing that what they were wearing would raise some eyebrows and provoke some giggles.

To put them on “worst dressed” lists removes their agency. “Worst” is only in the eye of the beholder. Without these ladies, the red carpet would be no fun at all.

Esther Zuckerman is the author of Beyond the Best Dressed: A Cultural History of the Most Glamorous, Radical, and Scandalous Oscar Fashion (Running Press). You can pre-order here.