Hugh Hefner is such an old man, but the guy still dates and marries Playboy models. Owning the magazine helps, but still. Playa.
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Hugh Hefner and Crystal Harris are so cute together. They have such chemistry. She and money are like magnetized to one another.
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Is it all over for Crystal Harris and Hugh Hefner? Sources say the former walked out on the latter five days prior to their wedding date.
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Sorry, Hugh Hefner. Yell all you want. But it's over with Crystal Harris.
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The Playboy boss pats his top girlfriend on the (pregnant?) belly. This rumor proved to be false, as Holly Madison was never knocked up.
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Yes, Hugh Hefner practically got dumped at the altar. But life isn't so bad for this Playboy mogul.
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Hugh Hefner loses one fiancee and gains two girlfriends. Life isn't so bad for this billionaire.
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Hugh Hefner came really close to marrying Crystal Harris. But we say he's better off without her!
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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 »
Born
Birthplace
Chicago, Illinois
Full Name
Hugh Marston Hefner