Steven Spielberg & Amy Irving: ~ $100 Million Settlement

Celebrated director Steven Spielberg seems to have a thing for his actresses, as he married two of them! His first wife was Amy Irving, who auditioned for his movie, Close Encounters of the Third Kind. They were married for 4 years before divorcing in 1989.

The pair had hilariously signed a prenup on a scrap paper, said to be a random piece of paper napkin, where he promised to pay her $100 million. While it could have been dismissed by the court, she was eventually awarded the $100 million.