Demi Moore (Vanity Fair)

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In 1991, while she was seven months pregnant, Demi Moore posed nude for the August issue of Vanity Fair. Some retailers were so taken aback by the photo taken by Annie Liebovitz (yes, her again), that they sold the issue in a brown paper bag, as if it were a copy of Penthouse. Although the shot did cause a few grumblings amongst the more conservative cranks, it's now seen as one of the most iconic magazine images of all time. Unfortunately, the shot has also spawned an array of copycats including Britney Spears, Claudia Schiffer, and a dude named Johnny Vegas -- BING at your own risk.