Whoopi Goldberg – 1993 Academy Awards

Whoopi Goldberg has been one of America’s favorite comedians for decades now. But in 1993, she pulled a practical joke that few people understood. That’s not to say she wasn’t laughed at: in fact, her outrageous 1993 dress is still an iconic Oscar fail moment today.

Goldberg’s daring dress has a Halloween costume quality that makes it very hard on the eyes. It’s a sort of dark purple cape that opens up to show a gaudy blue pantsuit and a shockingly bright green lining. We love Goldberg, and we think she’s great, but it’s hard to believe she left the house wearing this.