Kim Basinger
Oscar-winning actress Kim Basinger is most-known for her marriage and divorce with legendary actor Alec Baldwin. She purchased a huge piece of real estate for roughly $20 million during her prime years in Hollywood, but as time went on, she had to sell parts of it off to pay off her debts and whatnot.
Things got worse when she pulled out of the film Boxing Helena and ended up paying the studio $3.8 million for the trouble. She had to file bankruptcy because of this, but since then, she appears to be on her feet once again. With $20 million to her name, she has enough to live more than comfortably.