8. Trey Songz
Trey Songz was slapped with a lien from the federal tax department for failing to pay his monies in 2013. The singer saw Uncle Sam knocking his door for his tax debts of more than $748,000. However, it is interesting to note that in the year in which Trey Songz did not pay his taxes, that is 2013; he agreed to live in a Hollywood Hills manor, for which he gave $35,000 per month. It seems like Songz is not good with his cash.