Michael Douglas and Diandra Douglas

Now married to Catherine Zeta-Jones, Douglas wed a then-19-year-old Diandra in 1977 after just six weeks of dating. As the actor's career took off as a result of roles in Wall Street and Basic Instinct, rumors of infidelity surfaced, resulting in the couple's 1998 split. A court awarded Diandra an estimated $45 million, in addition to homes in Beverly Hills and Majorca, Spain.