Settlement: $76 to $92 million
After eight years of marriage, the pop icon filed for divorce from her director husband, citing his "unreasonable behavior." More than a decade older and considerably wealthier than Ritchie, Madonna's publicist confirmed that she ponied up the lump sum — almost a fifth of her estimated $500 million net worth — to end the union.
Reported settlement: $40,000 a month
Even before the divorce, Spears was no stranger to shelling out cash for Federline — his occupation at the time of their marriage was listed as "pizza delivery boy and dancer." She reportedly even paid for her own five-carat diamond double-banded engagement ring.