9. 1966
Well, there isn’t a lot you can say about this. When you are the man in the middle of this picture, surrounded by tons of half-naked women, things are looking up for you. By 1966 for Hugh Hefner, well…the world was his oyster. He was a man making tremendous strides with his business and was also single.
He was an available man who made sex his hobby. He was coming off a notorious 1963 case in which he was arrested for selling obscene literature from a Playboy issue centered around a naked Jayne Mansfield. Hefner wasn’t found guilty of any crime.
A single Hugh Hefner had women falling at his feet left and right. Hefner admitted that during this time he was sleeping with 11 out of every 12 Playboy bunnies. Now that’s the definition of a good time!
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