Chris Brown | $50 MILLION

Christopher Maurice Brown, who is more popularly known as Chris Brown, was born in Tappahannock, Virginia, and is now a world-renowned R&B and pop artist. He is famous for his hit songs, Run It, Kiss Kiss, No Air, and Forever. Not only that, but he’s also known for his songwriting skills and top-notch dance moves that have succeeded in swaying audiences over the course of his career. Chris Brown has had his fair share of ups and downs as well as success and issues over the past couple of years.

If you don’t remember, he dated his co-artist, Rihanna, back in 2008 until he was arrested for having been violent with her over a heated argument. He and his lawyers then pleaded guilty, and he was sentenced to 180 days of community service as well as five years probation. In 2013, he got himself arrested for an assault charge and was ordered to finish a 90-day rehabilitation session in Malibu but had to be taken out of the center and put into custody in 2014 for violating his probation. With all these troubles, we hope he doesn’t go into bankruptcy.