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Issue: May Elle Macpherson covered the May issue in nothing but a pair of black pantyhose. Sharon Stone will do down in history as one of the biggest sex symbols in Hollywood history. Joan Collins was full Dynasty glam on her December Playboy cover. Geri Halliwell was there to help Playboy readers spice up their lives in the May issue. Case in point: Charlize Theron's May cover.

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Charli. Age: 22.
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Mansfield's peek-a-boo cover is iconic—and not even her first appearance in the magazine.

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Rose. Age: 23.
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Marilyn Monroe kicked off the trend in as the first-ever Playboy cover star, and dozens of icons since have adorned the cover of the magazine, now a byword for unapologetic sexiness. The cover, naturally, went down in Playboy history. Let's take a trip down memory lane, shall we? Issue: March Bo Derek has always been a perfect 10—so she was a natural fit for Playboy.

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