After spending 36 hours in jail -- his longest time behind bars to date -- Chris Brown was released on Monday (October 28) when a judge in Washington, D.C. reduced his federal assault charge to a misdemeanor.

The singer and friend/bodgyguard Christopher Hollosy were arrested early Sunday morning after an altercation outside D.C.'s W Hotel. A man identified in court documents as 20-year-old Parker Adams told cops that he had tried to take a picture with the singer and two women when Brown told him "I ain't down with that gay sh--, I feel like boxing" and punched him in the nose, according to reports.

According to court documents, both Brown and Hollosy pleadded not guilty and were released Monday afternoon. They were ordered to return to court on November 25 and stay at least 100 yards away from Adams.

Brown, 24, is still on probation after his 2009 assault of then-girlfriend Rihanna. As part of a plea deal in the Rihanna case that allowed him to avoid any jail time, Brown was sentenced to five years of probation and more than 1,400 hours of community labor.

This is just the latest of many run-ins with the law for Brown, but he has avoided any serious jail time in both his fight with Frank Ocean in an L.A. parking lot (Ocean didn't press charges) and the infamous bottle brawl with Drake last year.

MTV News reached out to Brown's lawyer for comment but had yet to hear back by press time.