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In May 1987, "Wheel Of Fortune" co-host Vanna White bared her behind on the cover of Playboy. The first was in May 1996. Country icon Dolly Parton posed for Playboy in October 1978. It must have been good luck because, shortly afterward, she unleashed a stream of pop-country hits that topped the singles charts, including "9 to 5" and "Islands in the Stream. Nancy Sinatra earned the "sin" in her last name when she posed for Playboy in May 1995, just one month shy of her 55th birthday.