5. Hugh Hefner
Hugh Hefner is not just the brains behind the wildly successful Playboy magazine, he is also one of THE, if not THE original playboy. At all times he has a bevy of women around him and only a few are lucky enough to be called his girlfriend. His playboy lifestyle is documented through the eyes of his first, second and third girlfriends at the time on a reality show called The Girls Next Door. Hef may be old but he is not dead and apparently neither is his taste for beautiful women, a party mansion and of course, his love for money.
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