#6: Michael Douglas & Diandra Douglas
Relationship Duration: 23 years
Est. Divorce Cost: ~$45 million
Michael and Diandra Douglas’s divorce was among Hollywood’s most expensive at the time, driven by Michael’s decades-long acting career and lucrative film residuals. Married before he became a global star, Diandra was legally entitled to half of his earnings accumulated during their marriage, including profits from blockbuster films like Wall Street.

Their marriage reportedly deteriorated due to long separations, lifestyle differences, and personal struggles. Douglas’s intense work schedule and high-profile image contrasted with Diandra’s preference for privacy and philanthropy. After years of growing apart, she filed for divorce in 1995, later admitting they had been “living separate lives” long before the split.
