Date: October 13, 2010
What they owed: $123,000

In 2010, reports surfaced about Houston rapper Scarface owning money in four child support cases. The unpaid obligations led to Scarface sitting in a jail cell in Texas from October 2010 to August 2011 after he owed $123,000. "It was a learning experience, and my advice to any father out there is that if you send anything, you send it through the courts," said Scarface, in a 2012 interview with MTV. "That's the best way to do, because at the end of the day, you not gonna get no credit for it."