After another run-in with the law, Chris Brown has checked himself into rehab to combat his ongoing issues with anger management. Breezy’s quick temper has gotten him into a bit of trouble over the past four years maintaining a bad boy image in the public eye. With the rap sheet of the R&B artist beginning to run long with hostile incidents, let’s take a look back at Chris Brown’s affairs with the legal department.

February 9, 2009

Unfortunately this date may be the most standout of any in Chris Brown’s career. That day marks the infamous beating of then girlfriend Rihanna. According the reports, an argument between the two superstars escalated into physical violence, which left Rihanna bruised and battered. Chris Brown was later sentenced to five years probation, one year of counseling and hours of community service. Years later the couple would make up to break up.

June 14, 2012

In one of the most shocking club incidents in recent memory, Chris Brown and Drake got into a bottle-throwing altercation at NYC night spot., W.I.P. During the brawl NBA star Tony Parker and other partygoers received numerous injuries. Both rap-singers were slapped with lawsuits in the aftermath.

January 2013

The turn of the New Year didn’t mark a lot of fun for Chris Brown as trouble approached him to start off the year. Brown was involved in an altercation with Frank Ocean at a Hollywood recording studio over what was stated to be a parking spot. After striking the singer behind Channel ORANGE, Brown and his entourage allegedly threatened to shoot Ocean and threw around a few homophobic slurs in the process.

July 2013

People weren’t the only thing that Chris Brown was hitting in Los Angeles. Back in the summer of this year, Brown was involved in a fender bender that soon became a hit-and-run, according to the other driver. Although the charges were later dropped, the affect of the accident would provide another blemish on an already flawed record.

October 27, 2013

Just a few days ago, Chris Brown found himself in his latest round of trouble as he and his bodyguard were arrested on a felony assault charge. The incident occurred outside of the W Hotel in Washington, D.C. as the singer was taking a picture with a female fan and a male passerby attempted to photo bomb the two. Brown hit the man, allegedly breaking his nose. Luckily for the singer–if you want to call it luck–the charge has been dropped down to a misdemeanor.