5. Chris Brown
Chris Brown’s reputation was nothing more than a peaceful, sweet and caring teenager who was often compared to the likes of Michael and Janet Jackson. His music was selling incredibly well and everything was going great, up until he decided to put his hands on Rihanna and leave her bruised and battered. The incident, which took place in 2009, had a significant effect on Brown’s career because, though Chris continues to sell reasonably well when it comes to his music, he will always be reminded about the Rihanna assault by others. Chris has faced the judge over twenty times since the incident, so keeping himself out of trouble has been a real struggle for the singer.