Toni Braxton
Source: ABC News
The famous singer rose to fame in 1990’s when she sold millions of her albums across the world. However, according to her explanation, the huge sales of her albums didn’t translate to extreme wealth as many people thought. In fact, she said that she received less than $2,000 in royalties from her first recording and she already owed her recording company a lot of money. She filed for bankruptcy in 1998 after compulsive shopping for her fancy home strained her finances. She tried to mount a comeback, but she ended up canceling a planned Las Vegas revue due to health complications something that forced her back to bankruptcy.