Toni Braxton
After selling millions of albums, winning six Grammy’s and generating millions of dollars in sales, Toni Braxton famously filed for bankruptcy in 1998, citing her exorbitant spending habits and bad management as the cause. Sadly, Toni once again filed for bankruptcy in 2010, this time, citing her expensive health problems as the cause. In January, a court allowed US Bank to file a foreclosure suit against Braxton for money she still owed on the full price of her $1.5 million home in Duluth, Ga.