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Hugh Hefner later hinted on his Twitter that the Lohan issue was one of the best-selling in Playboy history. When Playboy was first published in , the inaugural issue featured nude photos of Marilyn Monroe. Beginning in , her Playboy career spans 22 years. Comedian Steve Martin, for example, was a bit of a surprising choice for the January cover. Those, of course, were the days before she was a wife, a mother, and a pioneer of eco-friendly soap.

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Josephine. Age: 29.
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She appears on numerous covers, in several centerfolds, and even wrote the foreword to the coffee table book, "Playboy's Greatest Covers.

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Leona. Age: 28.
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Celebrities who posed for Playboy

Country icon Dolly Parton posed for Playboy in October In , she was chosen as Playmate of the Year and parlayed her success into an acting career. Model and actress Pamela Anderson has appeared on more Playboy covers than anyone else. Those, of course, were the days before she was a wife, a mother, and a pioneer of eco-friendly soap.

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