Hugh Hefner is a confused old man. He appears shocked to learn that the Shannon twins look exactly alike. Crazy!
Rating: 2.3 / 5.0
Yup, Hugh Hefner has another young, pretty girlfriend. Here she is, model Crystal Harris.
Rating: 2.1 / 5.0
Hugh Hefner says something very important to The Hollywood Reporter in this issue: he totally had sex with Crystal Harris!
Rating: 2.0 / 5.0
Sorry, Hugh Hefner. Yell all you want. But it's over with Crystal Harris.
Rating: 1.8 / 5.0
Why is Hugh Hefner smiling during this appearance on Piers Morgan Tonight? We can think of a few, large-breasted reasons.
Rating: 1.0 / 5.0
Remember these days? Holly, Bridget and Kendra pose with ex-boyfriend Hugh Hefner.
Rating: Unrated
Holly Madison no longer talks to Hugh Hefner, but she sure is spilling the beans in her new memoir Down the Rabbit Hole.
Rating: Unrated
Hugh Hefner loses one fiancee and gains two girlfriends. Life isn't so bad for this billionaire.
Rating: Unrated
Hugh Hefner is such an old man, but the guy still dates and marries Playboy models. Owning the magazine helps, but still. Playa.
Rating: Unrated
Hugh Hefner came really close to marrying Crystal Harris. But we say he's better off without her!
Rating: Unrated
Yes, Hugh Hefner practically got dumped at the altar. But life isn't so bad for this Playboy mogul.
Rating: Unrated
Hugh Hefner and Crystal Harris are dressed like Robin Thicke and Miley Cyrus for Halloween. This is disturbing.
Rating: Unrated

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