Madonna & Guy Ritchie — $76-92 Million

After 8 years of marriage, Madonna and the British director split in 2008. The settlement was estimated between $76-92 million — making it one of the largest divorce payouts in UK history. Ritchie received their London pub, their Wiltshire country estate, and reportedly $76 million in cash and assets. Madonna kept their New York properties. The irony: Ritchie's career (Snatch, Lock Stock) was already successful, but the Madonna settlement made him richer than most of his films combined. Their custody battle over son Rocco played out in tabloids for years afterward.