2. Hugh Hefner
“Hef!” Yes, Hugh Hefner and his old age makes the list. When you sleep with thousands upon thousands of women desperate to be on the pages of Playboy, you get both the best and worst of life. First off, Hefner has pretty much had his pick of the litter over the years. But hot women doesn’t necessarily equate to clean women. The women Hefner has had the pleasure of bedding have generally been desperately attempting to latch on to a wealthy man in the hopes of dawning the pages of his magazine. That kind of desperation scares the heck out of us and raises numerous red flags. With all the partying at the Playboy Mansion, Hefner himself has no idea what the exact number could be. “I stopped counting a long time ago,” he said. “I’ve never thought in terms of quantity, but more in terms of quality.” Quality indeed, Hef.
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