Hill is one of the most fascinating people on our list. Famous, successful and critically acclaimed at 21, living in self-imposed exile at 25, and jailed for tax evasion at 37. After over a decade of being almost completely out of the public eye, Hill popped up again in 2012 after being investigated for tax evasion. She owed nearly $1 million dollars on income earned in the mid-00's. Unlike others on the list, Hill was far from destitute. In fact, she simply didn't pay what she was ordered to and was sent to the slammer for three months. During that time, she paid off her debts. She's also supposedly releasing an album soon. The world waits with bated breath, Ms. Hill.
