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20 Celebrity Women Who’ve Been in Playboy: From Marilyn Monroe to Kate Moss & More

Since its inception in the mid 1950s, Playboy magazine has courted fascination as well as controversy. Whether the magazine’s founder, Hugh Hefner, was positioning the outlet as a pioneer of the sexual revolution, or if history and investigative pieces uncovered the misogyny that was happening behind the scenes, Playboy has been a longstanding cultural pillar for decades. The outlet has ushered in a new era within the past few years, and even in the years prior to Hefner’s death in 2017, the magazine has catered to thought-provoking essays.

But Playboy’s roots are deeply embedded in the covers that made the outlet such a lightning rod for controversy and conversation. Dating all the way back to its first issues in the ‘50s, a number of famous women have appeared on the cover and in the photo spreads of Playboy. Of course, it’s no surprise that one of the very first women to make an appearance on the cover was Marilyn Monroe.

The stunning blonde beauty was, and largely remains, the epitome of sex appeal. As time went on, Playboy featured even more stars like actress Drew Barrymore, models Brooke Shields and Naomi Campbell, comedian Chelsea Handler, and one of Kim Kardashian’s first major covers was with Playboy, too.

There have been so many famous faces on the cover of this magazine, and some of them might surprise you. Take a look at our roundup of 20 famous women who posed for Playboy.

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