Rapper Chris Brown (C) leaves the US District Court in Washington October 28, 2013.[Photo/Agencies]

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R&B singer Chris Brown pleaded not guilty on Monday to misdemeanor assault after a fight that broke a man's nose on Sunday outside a Washington hotel, the latest legal run-in for the Grammy-winner.

After spending the night in jail, Brown left the courthouse in a crush of security and press as fans crying "Chris, Chris" tried to rush the artist. He faces a maximum of six months in jail and a $1,000 fine if convicted.

Brown, 24, was arrested early on Sunday outside the upscale W Hotel, a few hundred yards from the White House. Brown's bodyguard, Christopher Hollosy, 35, was also arrested, charged with assault and released after pleading not guilty.

Brown won a Grammy for best R&B album for F.A.M.E. in 2011 and is known for hits including "Deuces" and "Look at Me Now." He appeared handcuffed in District of Columbia Superior Court, where a defense lawyer entered the not guilty plea on his behalf.

After the not guilty plea, the judge ordered Brown released, touching off a smattering of applause from fans in the courtroom. The judge also set a preliminary hearing for November 25 for both defendants.

"Christopher Brown committed no crime," his lawyer, Danny Onorato, said in a statement. "We understand that his security acted to protect Mr. Brown and Mr. Brown's property as he is authorized to do under District of Columbia law. We are confident that Mr. Brown will be exonerated of any wrongdoing."

The episode began when two women asked Brown to be in a photo with them outside the hotel, a Metropolitan Police Department incident report said. Brown objected when Parker Adams, 20, of Beltsville, Maryland, tried to get in the picture.

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

Brown denied punching Adams, and Hollosy said he intervened when Adams tried to get on Brown's bus, according to a court charging document.

Adams was taken to the hospital and treated for a broken nose, the charging document said.

Brown has been on probation since 2009 after assaulting pop singer Rihanna, his then-girlfriend. Brown's probation was revoked over the summer after he was charged in a hit-and-run traffic accident in Los Angeles, but reinstated after he agreed to another 1,000 hours of community labor.

The Los Angeles District Attorney's office has accused Brown of cutting corners on his community labor sentence, which he was allowed to complete in his home state of Virginia.