Estimated settlement: $100 million

Married from 1985 to 1989, they were on-again, off-again for many years after that, ultimately marrying in 1984 with the marriage dissolving in 1989 after Spielberg began dating Indiana Jones star Kate Capshaw. Irving contested their pre-nup (reportedly written on a napkin) on the grounds that she did not have legal representation at the time of its signing. She walked with $100 million. Spielberg seems to have bounced back, as the man is now worth $3 billion.