14. Charlie Sheen’s divorce from Denise Richards – $40 million

Charlie Sheen and Denise Richards had a tumultuous marriage followed by a nasty divorce. Sheen and Richards have two children together, and after years of bickering are reportedly on friendly terms now.

However, at one point they had sunk as low as Sheen evicting Richards and their children from their family home.

In the end, Richards was awarded a $40 million settlement, which included assets and syndicated royalties from Sheen’s Two and a Half Men TV show. As part of their divorce settlement, Sheen will pay Richards $10 million in child support for the first 15 years after the dissolution of their marriage.