13. Justin Bieber
One of Billboard’s top defining artists of the millennial generation is hard pressed to find work in Hollywood too. Canadian pop star Justin Bieber was thrust into celebrity status once his debut single “One Time” reached airwaves in 2009. At 15, Bieber shattered records by becoming the first artist in history to have seven songs from a debut album appear on the Billboard Hot 100. He was on top of the world. But with success came a sense of entitlement. Bieber’s first run in with the law was in 2012 when he drove recklessly around his neighborhood. A year later he was charged for vandalism in Brazil. Bieber’s first arrest would be made the very next year in Miami Beach, Florida. The pop star admitted he had been drinking and was high on marijuana and Xanax while driving.