April 8, 2021 R. Kelly – The R&B star seems to have a painfully cavalier attitude about taxes and payments in general. According to IRS documents from 2012, Kelly racked up tax debt of almost $5 million. This is on top of $2.6 million in back taxes paid in 2008 and $1 million paid in 2009. In 2013, he failed to make mortgage payments on his $3.5 million home in Chicago, which sold at auction for below $1 million. A few years back, the singer reportedly owed the IRS more than $4.8 million in back taxes.