3. Lauryn Hill
Laurnyn Hill, the Grammy winner, ended up in prison for three months for not paying almost $1 million in back monies for nearly a decade. The singer justified her non-payment of taxes in the court proceedings, by saying that she wanted to protect herself and her children when she quit the music business. Hill tried to pay off her tax debts during the days before her sentencing, but she was still not able to pay the penalties and interest. She was released from prison in October 2013.