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Steve Martin Playboy While one might expect public figures like Madonna and Marilyn Monroe to grace the cover of Playboy, other celebrities' cameos were far more unexpected.

Comedian Steve Martin, for example, was a bit of a surprising choice for the January 1980 cover.

Sadly, Anna died tragically in 2007.

Pamela Anderson Playboy Model and actress Pamela Anderson has appeared on more Playboy covers than anyone else.

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Nun wagt Mimi Gwozdz den Schritt auf neues Terrain — und zeigt sich nackt im.

Hugh Hefner later hinted on his Twitter that the Lohan issue was one of the best-selling in Playboy history.

In a cute play on her television personality, the two Y's in the magazine's name were left out, as if a contestant might soon spin the wheel and shout out that letter.

Anna Nicole Smith: She was introduced to the American public on a Playboy cover in 1992 and Anna was chosen as 'Playmate' of the Year in 1993.