As big as Lauryn Hill was in the 1990s, 50 Cent was just as big during the first ten years of the 21st century. The bad boy rapper was a pet project of Eminem and Dr. Dre, for whom anything they touched turned to gold during that decade. His fame transcended music; Jackson found his way into movies, and turned out to be a better actor than anyone expected him to be. That didn't translate into sustained financial success, though.
Being a bad boy rapper means doing bad things, and it was one thing in particular which crossed the line in a big way for Jackson. He decided to self-release what we'll refer to as an 'adult movie' with a woman who hadn't consented to appear in it, and didn't agree to releasing it. She took him to court, and won more than $7m in damages from him. Five years later a business venture with a company called Sleek Audio collapsed, leaving 'Fiddy' a further $16m out of pocket, at which point he filed for bankruptcy.