(WUSA) --- Chris Brown has faced a number of legal troubles before his arrest in Washington, DC for assault by the W Hotel.
Here's a list of five past times when he has made headlines for legal drama.
In 2009, Brown is charged with two felony counts after he beat Rihanna.
After pleading guilty, he's sentenced to five years probation and 1,400 hours of community service. The judge allowed him to complete those hours in his home state of Virginia.
Two years later in March, 2011, Brown goes on ABC's Good Morning America and host Robin Roberts asks him about the Rihanna incident.
After the interview, he storms off stage and destroys his dressing room throwing a chair out the window.
Brown gets into a fight with rapper Drake at a New York City club reportedly over Rihanna. Brown tweets a picture of a cut on his chin. Police decide they don't have enough evidence to make any arrests.
The Los Angeles police department open an investigation after reports he got into a fight with singer Frank Ocean over a parking spot in West Hollywood.
Two months ago a judge dropped a hit-and-run charge against Brown after he reached a "civil compromise" with the driver he hit back in May.