Old Man Grinding
Hugh Hefner tries to keep up with one of the Shannon twins in this picture from a party thrown in honor of Aubrey O'Day. Can you imagine these two having sex? Yikes.

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Playboy Party Pics
Hugh Hefner
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Hugh Hefner Biography

Holly and Hugh
Hugh Henfer is the envy of millions of men around the world. Despite not being close to a spring chicken, the Playboy founder has a... More »
Chicago, Illinois
Full Name
Hugh Marston Hefner