vintage Vintage Photos From Hugh Hefner's Playboy Glory Days  

Mick Jacobs
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List Rules Vote up the best portraits of the entrepreneur as a young playboy.

In addition to being the longest serving editor of a magazine, Playboy creator Hugh Hefner also held the Guinness World Record title for most prolific scrapbooker, with over 2,500 volumes to his name. Because Hefner so loved to document his life, countless vintage Hugh Hefner photos exist for fans to marvel over and witness the heyday of pop culture's original playboy. Hefner continued to photograph his life up until his death, and though more modern photos still capture his opulent and ridiculous lifestyle, old Hugh Hefner pictures depict a man in open revolution against conservative values of sex. The entire time, Hefner looks like a man who knew he was getting away with it, for better or for worse. While Playboy certainly loosened people up when it came to sexuality, it also restricted women to objects of desirability, and more than enough stories exist of Hefner being much less of a gentleman than his pipe made him out to be.

Many old Hugh Hefner photos depict Hefner's past loves and hookups, while others depict him meeting famous actors, writers, and even politicians from the past. As can be expected, quite a few of them feature Hefner's instantly recognizable pipe, an accessory that felt like an extension of the man himself. All of them showcase one of the most influential and controversial icons of modern pop culture, one who was a film producer, a civil rights activist, an alleged predator, and above all, a guy who gave a completely different meaning to an otherwise innocent word.

16 5

Introducing The Cuffs And Collars In 1960


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7 1

Fiddling With The Volume


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7 1

Sweettalker With A Sweet Tooth (1978)


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6 2

Catch Of The Playboy


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