R. Kelly
The IRS filed documents in 2012 that claimed the R&B singer owed the taxman almost $5 million in unpaid taxes dating back nearly eight years. Although the Chicago crooner paid $2.6 million in back taxes in 2008 and an additional $1 million the following year, he still owes Uncle Sam more than $4.8 million. Kelly also took another huge financial hit in 2013 when his Chicago home was auctioned off for less than a million dollars after he failed to pay his $3.5 million mortgage.
