13. Michael Douglas’ divorce from Diandra Luker – $45 million

Michael Douglas married Diandra Luker in 1977 when she was only 19 years old, and had a son with her a year later.

After 18 years of marriage, Luker filed for divorce in 1995, walking away with $45 million, which was half of Douglas’s net worth at the time.

In addition to a cash settlement, Luker got to share the rights of some of Michael’s works produced during their marriage.

The reasons for their divorce became apparent after the split, when Douglas’s heavy drinking and partying became evident. After a very colorful life, which included everything from rehab to throat cancer, Douglas recently said in an interview his only regret was that his first marriage didn’t end sooner.