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Rarely Seen Photos of Hugh Hefner at Chicago Playboy Mansion

By PopEater Staff Posted Apr 17th 2011 06:00AM

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!

Tags: hugh hefner

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Sunday 17 April

By larry

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Hefner found a knack to get rich and famous for being a sleazeball.

Sunday 17 April

By marcia

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Heff is living proof that little boys need to play with Barbie dolls. That way when they get older they won't be fixated on them.

Sunday 17 April

By nalia & friends

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The woman in the green bikini is simply twisted around. She is not out of shape and probably never had a baby. You are also all judging by airbrushed photos of today of women that heavily exercise. But if you sat down with one and observed the natural folds you would see ripples and lumps.

We draw from models every week and even the youngest most well exercised person has ripples, lumps and bumps and muscle definition.

The smooth Barbie doll persona you guys are all whacking off to is fake and heavily photoshopped.

Sunday 17 April

By bahoobi

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If I recall, one of "Hef's" long lasting GF was Barbi Benton, a non blonde.

Sunday 17 April

By DJMW

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Be realistic. This womanizer would screw anything with the proper orifice no matter what color hair was on their heads or even if they were bald. The man is disgusting.

Sunday 17 April

By zappa

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Of cousre, most young woman would find him gross and creepy. Huges latest girlfriend look like crack hos from North Hollywood. Me thinks he is about running on empty.

Sunday 17 April

By Larry

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Hugh Hefner is sssssoooooooooooooooo disgusting. I can't imagine any woman with self respect and/or dignity having anything to do with him, unless she is a "gold digger" for financial gain.

Sunday 17 April

By Dennis Shelton

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What other reason would all those women be in his magazine? If i had his money and fame why not go for the younger women? Noone is putting a gun up to their heads?? I never seen a Brinks truck follow a funeral? He mind as well have fun with it cause he cant take his money with him? Any guy would do the same thing if they had the chance to. Who cares if they are after his money? At least he will die a happy man!

Sunday 17 April

By Larry

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I totally agree with you, Hugh Hefner must be running close to empty but, more than likely he's running on Viagra !

Sunday 17 April

By Thomas

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Anybody remember Barbie Benton, Hef's main squeeze in the early 70's? Adorable little natural-figured brunette, a real girl next door. He should have stayed with her.

Sunday 17 April

By Pat

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There was no such thing as liposuction back then, plastic boobs and nose jobs, and cheek implants etc. You went with what God gave you. No one obsessed about their bodies the way they do now, curves were what a woman had. Women really were feminine and womanly in every since of the word. You had the twiggy model, but that wasn't the norm, most people thought she looked odd. Sad to see young women fall for the skinny no hip boy look that magazine push..I don't think real men like the look. Hef was a very shy very intelliant gentlemen.

Sunday 17 April

By Gloria

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He is now an old goat, who has always had the morals of a roach.
Man....can PopEater say "filler" on a slow news day?

Monday 18 April

By Daniel

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Excuse me are you one of the person that were not accepted by the magazine to be a bunny Girl?

Sunday 17 April

By lindamc

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Anyone think of digital photography, the girls now are all not so slender and smooth, what you see now is not what you get.

Sunday 17 April

By AnonEmous

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All gorgeous women, no matter what colour their hair :) Very interesting to see what Heff looked like back then and the predominant style.

Sunday 17 April

By Bill Cherry

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I miss the old Hugh Hefner from the Chicago Playboy Mansion days. My very favorite Playmate was a brunette, too. Her name was Christa Speck. In fact, I've written about her. Google her name to see my piece.

Sunday 17 April

By danclrksvll

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HEFNER HAS NO IDEA THAT GOD'S JUDGEMENT WILL FIND HIM GUILTY SOON.HE WILL BE VERY POOR IN HELL AND WILL WEEP OVER THE THOUSANDS OF MARRIAGES AND LIVES HE HAS RUINED

Sunday 17 April

By Dennis Shelton

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Marriages and lives he has ruined? Wtf? If you dont like the magazine then dont read it??? Theres only one judge out there and i dont think that is you!

Monday 18 April

By TERRY

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THERE IS NO GOD

Sunday 17 April

By Bunny Kathy

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I was a Playboy Bunny and lived at the Chicago Mansion in 1968-69. There was dormitory space for 22 bunnies at the mansion. Men were never allowed up there. Now that I'm over 60, I am so grateful that I had the guts to do that. It was considered very risque back then with those skimpy costumes, but waitressing in 3" heels was hard work. Now I think Hef is more than a little goofy sometimes, but he always treated all of us with respect. Don't believe all the hype about the craziness that happened there, it was all part of marketing Playboy and the lifestyle.

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