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1. Chris Brown
This guy is constantly getting into trouble. His first run in with the law is still the one he is most famous for. Of course, we are talking about when he assaulted pop star and then-girlfriend Rihanna in 2009. But ever since then, Brown has continued to get in trouble with the law.
In October 2013, he was arrested and charged for assault related to a fight that broke out in front of a hotel in Washington DC. This landed him in prison for a shirt stint, because he was already on probation because of the incident with Rihanna.
According to reports from the incident in front of the swanky hotel, Brown punched someone and broke his nose. It’s was also said that the singer used a homophobic slur before hitting the man. Brown was not the only person arrested in the scuffle; his bodyguard was also taken in after the incident. However, brown had some luck and the charge was reduces from a felony to a misdemeanor.
He had some more luck when the court stated that he could get out of jail by going to a rehab clinic instead. Brown has been in and out of rehab and since the beating of Rihanna; he has seen the inside of anger management classes many times as well. It remains to be seen whether the singer is going to be changing his ways anytime soon.
His people are saying that he is very sorry about the violent incidents and that he is trying to get back to his career and live a healthier life as a result. He might have to get really serious about it if he wants to stay in jail, but it surprisingly has not done much to ruin his career since his fans seem to be incredibly forgiving.