Lauryn Hill
In 2013, Lauryn Hill started a three-month prison sentence after failing to pay around $1 million in taxes over a decade, reported the Associated Press. The singer pled guilty to the charges in June 2012, admitting to not paying taxes on $1.8 million in earnings from 2005 to 2007, according to Rolling Stone.
The publication reported that her sentence also included unpaid taxes from 2008 to 2009, which brought her total tax debt to $2.3 million. After prison, she was to serve one year of probation, including three months of home confinement, reported People Magazine.
