Hugh and His Girlfriends

Hugh and His Girlfriends

Hugh Hefner, Crystal Harris and the Shannon Twins sit and watch the action as Kendra Wilkinson marries Hank Baskett at the Playboy Mansion. Hilarious stuff.
Rating: 2.4 / 5.0
Whoa, Twins!

Whoa, Twins!

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
Hugh Hefner, New Girlfriend

Hugh Hefner, New Girlfriend

Yup, Hugh Hefner has another young, pretty girlfriend. Here she is, model Crystal Harris.
Rating: 2.1 / 5.0
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!
Rating: 2.0 / 5.0
Hef and Harris

Hef and Harris

Sorry, Hugh Hefner. Yell all you want. But it's over with Crystal Harris.
Rating: 1.8 / 5.0
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.
Rating: 1.0 / 5.0
Hugh Hefner in a Hat

Hugh Hefner in a Hat

Hugh Hefner loves to wear this captain hat. Which is really pretty hilarious if you think about it.
Rating: Unrated
Hugh Hefner in a Robe

Hugh Hefner in a Robe

Hugh Hefner shared this Instagram photo in the summer of 2016. He's been absent from the social media service for a long time.
Rating: Unrated
Hugh Hefner, Ahoy!

Hugh Hefner, Ahoy!

Hugh Hefner rarely goes anywhere without his captain's hat on. The man is doing pretty well at age 90.
Rating: Unrated
Hugh Hefner and His Wife

Hugh Hefner and His Wife

Hugh Hefner smiles here alongside Crystal Harris. We think she likes him for his money.
Rating: Unrated
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.
Rating: Unrated
Hugh Hefner and Family

Hugh Hefner and Family

Hugh Hefner is alive... and well? We hope. This photo was shared on Thanksgiving of 2016.
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 »
Born
Birthplace
Chicago, Illinois
Full Name
Hugh Marston Hefner