Date: December 28, 2013
What they owed: A lump sum of $1 million

DMX failed to pay child support for 10 years to his the mother of his children, Patricia Trejo. When the case was in its developing stages, the man born Earl Simmons refused to bestow any amount of support without a DNA test. However, the L.A. Supreme Court forced the multi-platinum artist to pay up and provide his daughter.