Chris Brown: How latest charges further complicate his legal woes

Singer Chris Brown flashes a peace sign as he departs the H. Carl Moultriel courthouse in Washington, Monday, Oct. 28, 2013. (AP / Cliff Owen)

WASHINGTON -- Chris Brown's misdemeanour assault charge in Washington, D.C., could further complicate the R&B singer's unsettled legal situation. Additional time behind bars remains a possibility for the singer -- both in the District of Columbia and California -- where Brown remains on probation for his 2009 beating of his on-again, off-again girlfriend Rihanna.

Brown emerged from a Washington court on Monday flashing a peace sign after spending more than a day in custody on a charge filed after a man accused the Grammy winner and his bodyguard of punching him and breaking his nose outside a local hotel.

Brown's arrest early Sunday comes at a crucial time for the singer, who is releasing an album this winter and is under a deadline to complete hundreds of hours of community service to satisfy his sentence for the Rihanna attack.

His day and a half in custody are the longest time the scandal-plagued singer has spent behind bars and the case represents the most serious accusations he's faced since his attack on Rihanna. Brown left the courthouse to cheers from supporters, some of whom clapped when a judge announced he would be released.

His time in custody was much longer than the few hours he spent at a Los Angeles jail after the Rihanna attack. In contrast to Brown's LA court appearances, which routinely happen in the afternoon when his case is the only one on calendar, Brown appeared in a crowded D.C. courtroom and had to wait until the end of the day for his case to be called and his release granted.

Brown is accused of punching a man who tried to get a picture with the singer and two other people near Washington's W Hotel early Sunday, according to the man's account in a police report. The report states Parker Isaac Adams, 20, said Brown told him, "I'm not down with that gay s---" and "I feel like boxing." The exact context of Brown's remarks was not immediately clear.

The man told police Brown punched him in the face, and a court filing states the man's nose was fractured. Brown's bodyguard, Chris Hollosy, stepped between them and also punched the man before grabbing Brown by the arm and leading him toward his tour bus, according to the report.

In an interview with police, Brown denied hitting the man and said he was on his tour bus when Hollosy got into a fight with Adams.

"We understand that his security acted to protect Mr. Brown and Mr. Brown's property as he was authorized to do under District of Columbia law. We are confident that Mr. Brown will be exonerated of any wrongdoing," Brown's lawyer, Danny Onorato, said after Monday's hearing.

Brown, 24, had a squeaky clean image before his attack on Rihanna on the eve of the 2009 Grammys, but since then has had several flare-ups that have been reported to authorities and noted by Los Angeles prosecutors. Brown broke a window after a 2011 "Good Morning America" interview in New York and was accused of snatching a woman's cellphone in Miami after she tried to snap pictures of the singer. He was also slightly injured in a New York nightclub brawl and earlier this year, was accused of being involved in a fistfight with Frank Ocean's entourage over a parking spot at a West Hollywood recording studio.

He was not charged in any of the incidents, but they have kept his public image tarnished, even as legions of fans continue to support him. Many of Brown's more than 13 million Twitter followers continue to come to the singer's defence and attack his critics on the site.

The release of singer's latest album, "X," was delayed earlier this year and is due to be released in the coming months. Brown's career since the Rihanna attack has been a mixed bag: his 2009 album "Graffiti" bombed but he found success with the back-to-back pop hits "Yeah 3x" and "Deuces," which was -- one of 2010's top R&B songs.

He also earned his first Grammy win for his album "F. A. M. E." and received several nominations for his follow-up "Fortune." The album featured 2011's most popular rap song, "Look At Me Now."

While jail time would put a dent in his career, others -- from the ultra-successful Lil Wayne to T.I. -- have made it to the top of the charts after prison stints.

Brown faces an August 2014 deadline to complete 1,000 hours of graffiti cleanup or other community labour. The additional service was added earlier this year after prosecutors accused Brown of failing to properly complete his service in his home state of Virginia.

In addition to penalties Brown would face if convicted in the Washington case, he also faces the possibility of up to four years in prison if a Los Angeles judge determines he violated his probation for the Rihanna attack.

Probation officials would need to investigate the new arrest for it to become an issue in California, which could happen before Brown's next probation progress hearing on Nov. 20.

Judges typically wait to see if a person on probation is convicted in a new case before imposing new punishments, said Los Angeles defence attorney Steve Cron, however Brown's notoriety may prompt earlier scrutiny.

LA prosecutors cited the "Good Morning America" and Miami cell-phone snatching incident in court filings earlier this year seeking modifications to Brown's probation. The office had no comment on the Washington arrest.

Cron said while Brown's fate depends on the facts in the Washington case, the singer's history might lead to some more time behind bars. "If the guy got hurt at all, I think he's looking at some jail time," he said.

McCartney reported from Los Angeles. Entertainment Writer Mesfin Fekadu and Writer Eric Tucker contributed to this report.