Chris Brown: Looking ROUGH at Court Hearing, to Remain in Jail at Least Another Week

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After spending the last seven weeks behind bars since being kicked out of rehab and jailed, Chris Brown definitely looked worse for the wear in court yesterday.

The singer looked haggard and tired during a hearing in the Rihanna case. Take a look:

When the judge ruled he will remain in jail, again, the 24-year-old looked defeated.

His next hearing is May 9, and at that point, both sides will come back to court and determine if they can strike a deal over the star's probation violation.

If not, he'll remain in jail for another month as he awaits trial in Washington, D.C.

If you're unfamiliar with Chris Brown's legal woes, this is one complicated mess. He's charged with assault on the east coast, but on probation out west.

With his probation - for the 2009 assault on Rihanna - revoked, he's had to endure two brutal Con Air flights from L.A. to D.C. and back again recently.

All so he could attend his assault trial in the District ... and have it be postponed.

The D.C. trial has been delayed because of the singer's bodyguard, Christopher Hollosy, a key witness who was just convicted in the same incident.

Chris Brown Smoking Weed
Chris Brown smoking weed - 3 joints at the same time no less. What a class act as always.

Hollosy says unless he is granted immunity, he will not testify in Brown's case until he has exhausted the appeals process, which could take six months to a year.

Hollosy had been widely expected to take the fall for his boss, accepting responsibility for attacking Adams, but this new delay might suggest otherwise.

D.C. Superior Court Judge A. Franklin Burgess Jr. set a status hearing for the Chris Brown assault case for June 25, the same day as Hollosy's sentencing.

In addition to its own legal ramifications, the D.C. case could lead to major penalties - potentially YEARS in prison - in the probation violation case.

The terms of his probation, after assaulting Rihanna, include that he obey all laws. Obviously, he has an issue establishing if he can do this effectively.

In the meantime, Brown sits in an L.A. jail, with the prospect of going to prison for up to four years if the judge decides the singer violated his probation.

On an unrelated note ... can you believe he cheated with Kim Kardashian?!

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Gee, what a way to spend your 25th birthday, Chris. One can only hope that you're starting to see that being a badass isn't all that's cracked to be and that it comes with consequences. As far as looking worse for wear, well that's what jail and hard living can and will continue to do to you if you keep this BS up. Dude get it together, you're better than this and you're too smart for this.