17. Michael Douglas and Diandra Luker
Hollywood star Michael Douglas met and married 19-year-old Diandra Luker in 1977. Douglas was 32-years-old at the time and was doing quite well in Hollywood at the time. The couple had one son, but divorced in 1995. Diandra walked away with $45 million as part of the divorce settlement. Douglas would later regret not divorcing Diandra earlier. He went on and married his current wife and fellow celebrity, Catherine Zeta-Jones, but that was after he won his battle with alcohol and women.