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Comedian Steve Martin, for example, was a bit of a surprising choice for the January cover. Despite its raciness and the controversy that occasionally surrounded it, countless celebrities posed for the groundbreaking adult magazine as a sort of Hollywood rite of passage. 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. Hugh Hefner later hinted on his Twitter that the Lohan issue was one of the best-selling in Playboy history. It's probably one of the most memorable ones ever, though.

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Addison. Age: 29.
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Country icon Dolly Parton posed for Playboy in October

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Harper. Age: 28.
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Vanna White's Vintage Playboy Photos

It's probably one of the most memorable ones ever, though. Comedian Chelsea Handler appeared on the cover of Playboy's Christmas issue; the bigger shock perhaps not being that she bared it all, but that she did so in a rather serious context. It was notably left undated because the magazine's founder, Hugh Hefner, didn't know if there would be a second issue.

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