Anna Nicole Smith

Arguably one of the most talked-about gold diggers of all time Anna Nicole Smith made headlines when she married 87-year-old billionaire J. Howard Marshall after meeting in a strip club. Thirteen months after they were married Marshall died, leaving nothing to Anna in his will. Naturally, Anna took Marshall's son to court to snag a piece of his $1.7 billion estate. One judge initially rewarded her with half-a-billion dollars, and then another judge said she was entitled to nothing, leaving the case to drag on for a decade. Anna died at 39 of a drug overdose, so she couldn't see the end of the case.