4: Curtis Jackson aka 50 Cents
He sold drugs as a teenager and allegedly took nine bullets in a 2000 shooting that nearly killed him but he survived that. Curtis Jackson, also known by his stage name, 50 Cent is one of the most popular artists in current times and has sold more than 30 million albums while earning dozens of music awards, including a Grammy. Soon after tasting success in the music industry, he ventured into other non-musical business and made a fortune of $ 100 million selling one of his businesses.
As other High-rollers, 50 cents was accustomed to the ultra-lavish lifestyle and uncontrolled spending. Much to his dismay, after the decline of his musical career, he was involved in a string of lawsuits from his former love flame and business partners which cost him a fortune. As per reports, he was used to supporting a small army of friends and also gave money generously for charity purposes. All this spending took a toll on him and racked up more than $20 million in liabilities against assets of less than $15 million. He declared bankruptcy in 2015 and was forced to mortgage his Farrington Estate.