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7. Bruce Willis’s divorce from Demi Moore – $90 million
Willis stated he felt he failed as a father (they have three daughters) and husband, while Moore quickly moved on with a much younger Ashton Kutcher, whom she also divorced in 2013.
Willis has since been dating model Emma Heming, with whom he has a daughter. Moore walked away with $90 million from her first marriage, but didn’t do nearly as well in her second marriage, even failing to get spousal support despite the fact that Kutcher cheated on her.