(Source: Getty, Inset: Rolling Stone)
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21. Brooke Shields

Rolling Stone, October 1996

Rolling Stone loves to get people naked on its covers, and Brooke Shields is no exception. By the time she posed nude for the music mag, Shields was no stranger to racy photo shoots. When she was just 14-years-old she appeared in the controversial Calvin Klein ads that featured the tagline, "You want to know what comes between me and my Calvins? Nothing."