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Insiders said the shoot was designed to be reminiscent of the magazine's inaugural shoot with Marilyn Monroe. Comedian Chelsea Handler appeared on the cover of Playboy's Christmas issue; the bigger shock perhaps not being that she bared it all, but that she did so in a rather serious context. While one might expect public figures like Madonna and Marilyn Monroe to grace the cover of Playboy, other celebrities' cameos were far more unexpected. It's probably one of the most memorable ones ever, though. In a cute play on her television personality, the two Y's in the magazine's name were left out, as if a contestant might soon spin the wheel and shout out that letter. Those, of course, were the days before she was a wife, a mother, and a pioneer of eco-friendly soap.

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Sierra. Age: 29.
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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.

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Brielle. Age: 21.
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Celebrities who posed for Playboy

Two months later, its poster girl, Kim, posted up on the cover of Playboy. In April , Bruno Mars appeared on a Playboy cover as well, albeit fully clothed. Comedian Steve Martin, for example, was a bit of a surprising choice for the January cover. Beginning in , her Playboy career spans 22 years.

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