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This 1985 Madonna cover is just one of the most famous. When Playboy was first published in 1953, the inaugural issue featured nude photos of Marilyn Monroe. Comedian Steve Martin, for example, was a bit of a surprising choice for the January 1980 cover. Between the time she came out with "All I Want For Christmas Is You" and when she married Nick Cannon, Mariah Carey appeared on the cover of Playboy.