5. Crystal Harris (Hugh Hefner)
Basically the only real things anyone recalls about Hugh Hefner tend to be which he founded Playboy, and he is often internet dating women. Amazingly Harris is regarded as their newest conquests, and even though he could be nearly 90, he married the 28-year-old. But having done this just about every year when it comes to previous 2 full decades, he has an ironclad pre-nup that keeps Crystal from getting any such thing when they divorce.