(Source: Getty, Inset: Vanity Fair)
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17. Demi Moore

Vanity Fair, August 1991

Demi Moore's 1991 Annie Leibovitz shoot for Vanity Fair was so shocking that the magazine was distributed in some cities with the paper bag covers they usually reserve for Playboy and Hustler. Since then the naked pregnancy cover has been copied by everyone from Britney Spears to Claudia Schiffer to Christina Aguilera.