Instead of going glam to scoop up her Best Supporting Actress Oscar in 2000 for Girl, Interrupted, Angelina Jolie channeled Elvira in a shiny Versace floorlength.

The dress that launched a thousand jokes…Bjork showed up to the Awards in 2001, wearing the infamous swan dress, designed by Marjan Pejoski.

Nominated for Best Supporting Actress for Thelma and Louise in 1992, the gorgeous Geena Davis couldn’t decide between a long or short dress, so she opted to go 50/50. Wearing a white and black number, which looked like it belonged in one of those Western revival towns.

Cher is famous for her crazy couture, but shocked the red carpet of the Oscars in 1986, dressed like a Queen from outer space in an ensemble designed by Bob Mackie.

In 1988, Cher upped the unconventional ante, winning over the Academy, but not the fashion critics, in a barely there Bob Mackie ensemble.

Celine Dion looked like she was headed to the races….backwards! The singing sensation walked the red carpet in 1999, wearing a white tuxedo jacket in her own special way.

In 2004, Diane Keaton played homage to Charlie Chaplin, cross dressing on the red carpet!

Gwyneth Paltrow is known for her feminine grace on the red carpet, but in 2002, she baffled fashion critics by getting oddly outfitted in goth gear from the late Alexander McQueen.

Kim Basinger obviously wanted to stand out at the show in 1990, so she designed her own mess of a dress. Her shockingly, white creation was part strapless and part tuxedo, and featured an incredibly full skirt.

The Gap got haute in 1996, when Sharon Stone ended up wearing one of their frugal t-shirts with a Valentino skirt to the Academy Awards.

It doesn’t get any more unconventional than Demi Moore’s Oscar attire in 1986. The young star rocked spandex biking shorts with an attached train on bottom, exposing her bra under a corset on top.

Whoopi Goldberg hosted the Oscars in 1993, wearing an elaborate breakaway skirt and coordinating shrug over a pastel catsuit.