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20 Surprising Celebrities Who Took It All Off For Playboy

Sean Penn is Theron's current beau; he's one lucky man, as his ex-wife Madonna also appeared on this list, linking him romantically to two hot Playboy celebrity cover girls.

  • The 5ft 9inches beauty appeared in pure white gift wrap for the Christmas 1999 issue.

  • January 11, 2021: Kim promoted her new line of Skims hosiery using her most trusted model: herself.

  • It's safe to assume Homer breathed a sigh of relief at that.

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When she was still the hottest of hot property, this cover shoot was a serious coup for the men's mag.

  • It certainly worked and Quentin Tarantino appeared in the same issue.

  • Perhaps it was a career boosting move, or a rebellion against her parents, but in this case it was like mother, like daughter: In 1985, Jerry Hall had her own spread in Playboy too.

  • Not known to be a woman who hides her sexuality or is shy at the opportunity for a provocative photo shoot, she still turns some heads when people realise she once did Playboy.




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