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Her cover also came out shortly after her second book "Are You There, Vodka? Her cover, in which she was years-old, became the magazine's best-selling issue of the decade. Her most recent cover shot in July came just before her her 40th birthday. After the release of her first Playboy picture, Guess Jeans signed her on the spot as a model. Her American cover shot was taken just five months after giving birth to her second child, Lola Rose. Her critically acclaimed films were all released after her Playboy appearance.

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Jaylin. Age: 22.
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Keep reading for a look at the most famous women who graced the cover, and some who appeared in Playboy more than once.

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Livia. Age: 25.
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The 50 Hottest Celebrities Who've Posed For Playboy

Marilyn Monroe was famously the first model on Playboy's cover and probably the single most famous woman to appear in the magazine. Keep reading for a look at the most famous women who graced the cover, and some who appeared in Playboy more than once. This American cover shot was also her promotional image for film "Into the Blue.

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