5. Tionne T-Boz Watkins
Tionne T-Boz Watkins filed for bankruptcy twice, once in 1995 and the other in 2011. In fact, last year, a judge declined her third bankruptcy case, since the TLC singer reportedly made no attempts to pay off her debts, to settle her affairs, or to appear at a creditors’ meeting. Fortunately, T-Boz’s recent TLC network show, that is Totally T-Boz, produced some cash. She claims that she lives within her means. In spite of that, T-Boz is nearly $700,000 in debt, largely for the unpaid mortgage payments of her lavish home.