Possibly the most notorious case of gold digging in recent memory, Anna Nicole Smith was a 20-something Playboy model and stripper who met millionaire oil baron and (super hot 89-year-old) Howard Marshall. He was smitten and verbally promised her proceeds from his estate, a legal battle that is ongoing ever since both of their deaths. Owing to her drug overdose, it's Smith's boyfriend and children who are attempting to get money from the Marshall estate these days. Unlikely they will be successful however, as Marshall's family have plenty of money to fight any court actions.