Estimated settlement: $80 million

Kevin Costner and Cindy Silva, who met in college, were married for 16 years, during which time Costner earned a spot on the Hollywood A-List with movies like Dances with Wolves, Bull Durham and Field of Dreams. When the marriage ended, Cindy walked with $80 million while Costner went on to star in a series of big budget dissapointments, including the infamous Waterworld and The Postman, sending his career into a steady decline from which it has never recovered.