#21 Chris Brown
In February 2009, Chris Brown turned himself into the Los Angeles Police Department’s Wilshire station hours after he had an argument with his then-girlfriend Rihanna. Their fight escalated into physical violence which left Rihanna with visible facial injuries that required hospitalization. Brown was booked under suspicion of making criminal threats.
In April of that year, Brown pleaded not guilty to one count of assault and one count of making criminal threats. But two months later, Brown pleaded guilty to a felony and accepted a plea deal of community labor, five years of probation, and domestic violence counseling. His probation ended in March 2015, over six years after the violent incident that started it all.