3. Chris Brown
Chris Brown’s rise to fame was matched by a chaotic fall marked by courtroom battles and a brief stint behind bars. After a widely publicized assault on Rihanna, his legal troubles only deepened; culminating in jail time for violating probation and a violent outburst in D.C. Once the heartthrob of pop, Brown’s story turned into one of talent shadowed by turmoil, with his name repeatedly resurfacing in troubling headlines.