Hugh Hefner might be the only person on this list that is no longer with us due to health complications at the age of 91-years-old. But if anyone on this planet has lived the life of a true, playboy, it was Hugh Hefner himself who was the founder and editor-in-chief of the Playboy magazine franchise. The Playboy mansion in which he resided has become a historical landmark for some of the craziest celebrity parties and events to take place in Los Angeles.
What people don't know about the Playboy founder is that he almost lost his life in only one way you could imagine a man of his stature would. While getting it on, Hefner almost died choking on a sex toy. That's right... a sex toy. Hugh Hef spoke about his near-death experience stating the following, "What is the closest I've come to death? There was a moment when I was having sex with four Playmates and I almost swallowed a Ben Wa ball."