Hef and his Twins

Hef and his Twins

This would be a lot cuter if Hugh Hefner was the grandfather of the Shannon Twins. Instead, he's their lover.
Rating: 3.2 / 5.0
Hugh Hefner Wedding Photo

Hugh Hefner Wedding Photo

Hugh Hefner and Crystal Harris are married! Send in your best wishes to the couple now.
Rating: 3.2 / 5.0
Holly and Hugh

Holly and Hugh

The Playboy boss pats his top girlfriend on the (pregnant?) belly. This rumor proved to be false, as Holly Madison was never knocked up.
Rating: 3.1 / 5.0
Hugh Hefner Clothed!

Hugh Hefner Clothed!

In regular clothes, that is. Dude normally wears pajamas, or probably less when he gets naked with his many girlfriends. But here, he almost looks like a regular old guy! Almost.
Rating: 3.0 / 5.0
Aubrey O'Day and Hugh Hefner

Aubrey O'Day and Hugh Hefner

Aubrey O'Day and Hugh Hefner look thrilled to be hanging out at this Playboy party, don't they? It's okay to smile, guys.
Rating: 3.0 / 5.0
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.
Rating: 3.0 / 5.0
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.
Rating: 3.0 / 5.0
Old Man Grinding

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.
Rating: 2.9 / 5.0
Holly and Hefner

Holly and Hefner

Holly Madison and Hugh Hefner are having a lot of sex as they try to have a baby. Sorry. We're just reporting the facts, as relayed to us by Holly herself. Hard to blame Hugh, she's kind of a looker.
Rating: 2.9 / 5.0
Sherlyn Chopra and Hugh Hefner

Sherlyn Chopra and Hugh Hefner

Sherlyn Chopra gives Hugh Hefner a squeeze in this photo. The former will become the first Indian to get naked in Playboy.
Rating: 2.9 / 5.0
Hugh on the Red Carpet

Hugh on the Red Carpet

Hugh Hefner looks almost alive in this picture. It's courtesy of the Iron Man 2 premiere in Los Angeles.
Rating: 2.6 / 5.0
Aubrey and Hef

Aubrey and Hef

Pssst, Hef. Thanks for putting me in your magazine. I'll repay you later... if you know what I mean!
Rating: 2.5 / 5.0

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