Teresa Giudice
If she thought that she would get out of financial trouble by starring in The Real Housewives of New Jersey, she was wrong. As a matter of fact, the show probably only made it harder for Teresa Giudice because it brought more attention to her money problems. It all started in 2009 when she and her husband allegedly had a debt of $10 million. They had to file for bankruptcy and tried to recoup their losses with fraud, which landed them in jail. She spent almost a year in jail before she got out.
Sinbad
Once upon a time, it felt like this comedian had everything one could ask for. Sinbad made it big by starring in A Different World. Things did not go smoothly for him, however. He had to declare bankruptcy more than once thanks to his business expenses among other things. In 2013, he reportedly had a debt of $11 million that he could not pay off since he only made $16,000 per month.