Date: November 25, 2013
What they owed: $25,000; a monthly payment of $2,500

Chief Keef got hit with a slew of lawsuits in 2013—around the same time he was waiting out a 90-day, rehabilitation stay in California. Upon DNA confirmation that he was the father of a ten-month-old infant, a Cook County judge ordered the GBE leader to pay a hefty lump sum of $25,000 and monthly payments of $2,500. Keef faced a similar lawsuit concerning another child last year, in that case he ended up paying $11,000.