15 Gold Diggers Who Got Big Paydays From Celebs

5. Crystal Harris (Hugh Hefner)

Basically the only things anyone remembers about Hugh Hefner are that he founded Playboy, and he is always dating young women. Crystal Harris is one of his latest conquests, and even though he is nearly 90, he married the 28-year-old. However, having done this just about every year for the past two decades, he has an ironclad pre-nup that keeps Crystal from getting anything if they divorce.