Rarely Seen Photos of Hugh Hefner at Chicago Playboy Mansion

We're used to seeing Hugh Hefner surrounded by a bevy of beauties and old pictures of the Playboy mogul from 1966 show much of the same.

Rarely seen photographs of Hef's early years, however, are a little different -- it seems back then, judging from the pics, he preferred brunettes.

Don't get us wrong, blondes are definitely represented. (And all of his recent girlfriends, including fiancee Crystal Harris, have been towheads.)

But in this photo of Hefner by the pool, brunettes clearly dominate.

So as we prepare to watch Hef get married again, take a walk down memory lane at his Chicago mansion. Check Out the Pics Below!

Cinthia Moura Samantha Mumba Melissa Howard Brittany Lee Monika Kramlik