Courtney Love
Over the years, Courtney Love has been in tax trouble more than once. In 2012, she had to pay the IRS hundreds of thousands of dollars. On top of that, she had to pay her legal counsel $27 million. It might sound like a great sum of money but let us not forget that her late husband Kurt Cobain left her a lot of money. While she had to cut back on spending, she is probably going to do all right no matter what.
Toni Braxton
You were wrong if you assumed that a person is financially set for life just because they have a Grammy. Toni Braxton allegedly only received $2,000 in royalties despite selling her album sales reaching millions of dollars. In 2010 and then in 2013, she declared insolvency. When she and her sisters appeared on a reality show, she admitted that she had to watch her spending because she is trying to follow a budget.