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!








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Grandma says "Hi" .... are you in Ohio?
he's hugh hefner the founder of the playboy mansion this old man has had more women around him than the 72 virgins awaiting muslims lol
The women were downright flacid. These pictures obviously predate the invention of the stair-stepper and pilates. Thankfully, women are now more toned.
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These women are NOT fat! People may not have been obsessed with aerobic exercise like they are today but these women were REAL women with real curves and they are all very attractive
Gustav, if you wanna use big words and sound smart at least spell them correctly!!! FLACCID NOT FLACID
Don't you mean airbrushed, lipo'd, tucked, botoxed, body make-up, implants, laser treatments....on and on and on.
just look at the second part of your name. it gives a great explanation to why you said that. "ballsack." they aren't fat at all. you may like butts and boobs on a stick, but that isn't reality. its fake. sorry to burst your bubble. and most men like some curves.
Yeah right...all that was before anorexia was King....or Queen? and way before when people walked on shoes, Now helthy and beautiful people favored Flip-Flops, and baggy pants showing off underwear with brown marks, that's chic right? but anyway by then girls were not fat but well built, probably you and all of your generation will be living forever and ever lean and beautiful thanks to pilates and aerobics..just wait and see....and dream on baby
Congratulations, Mr Hefner: for decades an icon for millions of unhappy men.
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I bet this man has had more sexually transmitted deseases
than Emilda Marcos had shoes..!!
Personally he made women look like Ho's,
I would shun him...
with all of my radiant beauty..!!
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your scary !!!!!!!!!
I think it was Imelda....
He made women look like hoes? Lol? I dont believe he twisted anyones arm to be in his magazine? So whos the hoes here? The pics was all taken with concent so dont even go there. If they didnt want the pics posted they wouldnt have posed for them? And if u got a problem with that then dont read the magazine?
These are the ladys that I remember, not self obsessed tramps, I am really surprised he is getting remarried, the women were really pretty back in the day, everything goes in a circle, wait and the skinny women of today will be remembered as these women around the ashtrays are remembered today.
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A jealous tilt on the female responses, an admiring tilt on the male side, imagine that.
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Honestly it's not all jealously with women. It's just there is more to us then just objects (especially as we age) I may not turn heads like I use to(yes I was hot) but I still want to feel like a person and be treated like I still matter.
Very jealous....Maybe they need to spend alot more time on the treadmill and less on the pc.
Curvy means fat. No matter how many times you say it. Its sad....if someone is toned and not fat the fatties call them anorexic.
I think the women look amazing. As a woman who struggles to stay fit and thin- it is wonderful to see real women- look at the models that are in playboy now- fake breasts and plastic surgery. All the women are natural in the above photographs, no fake anything.
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i agree they looked good to me i dont like the fake look or skinny rail type
a nerd that found a way to change people around him so he could get layed and have men want to be him [brillant]if you ask me its lasted for years
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