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While one might expect public figures like Madonna and Marilyn Monroe to grace the cover of Playboy, other celebrities' cameos were far more unexpected. Madonna In October , after losing millions of readers to easily available Internet pornography, Playboy announced that it would be doing away with nudity in favor of partially clothed, raw intimacy. 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. Long before Uma Thurman slayed countless men with martial arts in "Kill Bill," she did it with pictorials in the Australian incarnation of Playboy. Her father was Frank Sinatra, so she learned how to do things "her way.

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Rory. Age: 30.
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Those, of course, were the days before she was a wife, a mother, and a pioneer of eco-friendly soap.

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Azariah. Age: 21.
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Her father was Frank Sinatra, so she learned how to do things "her way. Insiders said the shoot was designed to be reminiscent of the magazine's inaugural shoot with Marilyn Monroe. Despite its raciness and the controversy that occasionally surrounded it, countless celebrities posed for the groundbreaking adult magazine as a sort of Hollywood rite of passage.

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