Whitney Houston | $20 million

Whitney Houston is an American actress and singer who’s been certified as one of the best-selling recording artists of all time, as well as the most awarded female artist in history, by the Guinness World Records. She has sold more than 200 million records all around the globe. She released two soundtrack albums and seven studio albums, all of which have attained gold, multi-platinum, diamond, and platinum status by the RIAA.

Having nearly $20 million in debt to Sony when she passed away back in 2012, she now has, in fact, a negative net worth. It’s a known fact that she has achieved so much success throughout her career, but maybe because of some bad investment planning strategies, she lost all her fortune. She was flat broke back in 2001 when she signed a contract with Arista/Sony for a whopping $100 million. It’s a surprise to so many people that during the peak of her career, she was earning $30 million each year from tours.