R&B Singer Chris Brown pleads not guilty on Monday to a charge of misdemeanor assault as a result of a fight on Sunday outside a Washington Hotel, the latest legal run in for the Grammy winner

R&B singer Chris Brown was arrested  on Sunday outside the upscale W Hotel, a few hundred yards from the white house. According to reports, it’s been said that there was another man in the incident he has been identified as Christopher Hollosy, while in court, Hollosy was described as Brown’s bodyguard, he was also arrested and charged with assault.

If found guilty of the assault charge, Brown faces up to six months in Jail and a $1,000 fine if convicted.

Brown, is known for his hits songs “Deuces” and “Look at me now” appeared handcuffed in District of Columbia Superior Court, with his lawyer entered the not guilty plea on his behalf.

The judge has set for a preliminary hearing for November 25.

The Metropolitan Police incident report said that two women had asked Brown for a photo with them outside the hotel. Brown declined them, when Parker Adams, 20, of Beltsville, Maryland, tried to get in the picture.

According to the report, Brown was heard saying, “I'm not down with that gay shit, and I feel like boxing”.

Brown, who was in Washington for a nightclub appearance on Saturday, punched Adams in his face and Hollosy did the same. Hollosy pulled Brown by the arm to the singer’s tour bus, the report said.

According to the report, Adams has  “swelling and bruising to the nasal area” with an apparent broken bones. Medics then took Adams to the hospital for treatment.

In 2009, Brown has been on probation for assaulting pop singer, Rihanna his then girlfriend. His probation was canceled over the summer due to the fact that he was charged in a hit and run traffic accident in Los, Angeles  after he reinstated agreeing to another 1,000 hours of community labor.

The Los Angeles district attorney office has accused Brown of cutting corners on his community labor sentences, which he has allowed him to finish in his home state in Virginia