22. Michael Douglas and Diandra Luker
Embed from Getty ImagesAfter 23 years as husband and wife Michael Douglas and Diandra Luker divorced in 2000.. Douglas says the one regret he has is that he wishes he had divorced first wife Diandra, sooner. ‘I know I’m going to get into trouble here. I have nothing against her and in fact I’m very fond of my first wife. But we should have ended that marriage eight or ten years earlier,’ Douglas has said. The couple married in March 1977 after Douglas proposed marriage to Luker after only two weeks of courtship. They got married that same year and had their son Cameron the following year. They separated in 1995 before ultimately divorcing. Douglas went on to marry much younger, Welsh actress, Catherine Zeta-Jones on November 18, 2000. They were both born on September 25, though 25 years apart.