Since his debut single ‘Run It!’ hit the top of the US Billboard Hot 100 in 2005, Chris Brown has been a fixture in music. The singer, dancer, and songwriter has sold over 100 million records worldwide, and he has picked up several awards – including a Grammy for Best R&B Album in 2012. In addition to this solo success, Chris has been featured on several successful singles, like Jordin Sparks’ ‘No Air,’ T-Pain’s ‘Kiss Kiss’, Nicki Minaj’s ‘Only,’ and Lil Dick’s ‘Freaky Friday.’ However, for many, Chris Brown is most associated with his 2009 assault on his then-girlfriend Rihanna. Chris was sentenced to five years of probation and was ordered to complete 180 days of community labor and one-year anti-domestic violence program. Chris would have more run-ins with the law, and would be sent to jail in 2014 for violating his probation (he would be released that year after being credited 234 days of time served.) His continued legal trouble and unrepentant attitude has made Chris Brown the definition of ‘problematic fave.’