Toni Braxton
R&B giant Toni Braxton earned two mammoth multiplatinum albums and six Grammys during the ’90s. But by 1998, the singer went from singing about broken hearts to broken bank accounts when she famously filed for bankruptcy, 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.
