Marston Hefner, Claire Sinclair

Marston Hefner, Claire Sinclair

Marston Hefner and Claire Sinclair (seen here with Hugh Hefner) have been dating off and on for a year and a half.
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Hugh Hefner on Piers Morgan Tonight

Hugh Hefner on Piers Morgan Tonight

Why is Hugh Hefner smiling during this appearance on Piers Morgan Tonight? We can think of a few, large-breasted reasons.
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Hef on The Hollywood Reporter

Hef on The Hollywood Reporter

Hugh Hefner says something very important to The Hollywood Reporter in this issue: he totally had sex with Crystal Harris!
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In His Bathrobe

In His Bathrobe

Hugh Hefner came really close to marrying Crystal Harris. But we say he's better off without her!
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A Smirking Hef

A Smirking Hef

Hugh Hefner loses one fiancee and gains two girlfriends. Life isn't so bad for this billionaire.
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The Hef

The Hef

Yes, Hugh Hefner practically got dumped at the altar. But life isn't so bad for this Playboy mogul.
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Hef and Anna Sophia Berglund

Hef and Anna Sophia Berglund

Hugh Hefner is seen here with Crystal Harris and Anna Sophia Berglund. Sources say he moved on from the former with the latter.
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Hef and Harris

Hef and Harris

Sorry, Hugh Hefner. Yell all you want. But it's over with Crystal Harris.
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Crystal Harris and Hugh Hefner Image

Crystal Harris and Hugh Hefner Image

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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Hugh Hefner and Crystal Harris Picture

Hugh Hefner and Crystal Harris Picture

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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Old But Still a Playa

Old But Still a Playa

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 and His Women

Hugh and His Women

There's a decent chance that Hugh Hefner has had sex with all these women. Just consider that for a few moments.
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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