3. Toni Braxton
Most of the music lovers will remember the unstoppable Unbreak My Heart track, released in the late 1990s by Braxton. However, after this song she did not have many hits that lead to a couple of bankruptcy filings and some overspending. Braxton twice filed for bankruptcy, which were not quite far apart from each other. One took place in 2010 and the other happened in 2013. She says that the first was because of the low royalties that she received from her record label and the second was due to canceling her Vegas show, after she fell ill. Despite being in a debt of $50 million, Braxton purchased a house, worth $3 million, in Calabasas, California. At this rate, it seems that Braxton will soon be filing for a third bankruptcy.