The troubling events leading up to singer Chris Brown's arrest

By Bronte Coy

Recording artist Chris Brown during is court appearance on July 15, 2013. Photo / Getty Images
Recording artist Chris Brown during is court appearance on July 15, 2013. Photo / Getty Images

Bad boy singer Chris Brown is once again making headlines for all the wrong reasons.

He surrendered to police a short time ago following a nine-hour standoff outside his Los Angeles home, after claims he threatened a woman with a gun.

Los Angeles Police patrol the entrance to the street of singer Chris Brown's home in the Tarzana neighborhood. Photo / AP
Los Angeles Police patrol the entrance to the street of singer Chris Brown's home in the Tarzana neighborhood. Photo / AP

It's just the latest in what's been a troubling few years for the singer, stemming from his infamous assault of then-girlfriend Rihanna in 2009.

So where did it all go wrong for the 27-year-old?

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Here's a look back at the disturbing incidents that have led to Brown's downfall.

February 8, 2009: On the way home from a pre-Grammy Awards party, Brown attacked his then-girlfriend, Rihanna. He reportedly tried (and failed) to push her from a Lamborghini, slamming her head into the window and repeatedly punching her in the face.

March 2009: His attack on Rihanna lands him with two felony charges: assault and criminal threats. He pleaded guilty to assault and was sentenced to five years' probation and 180 hours of community service.

March 2011: After staying out of trouble for more than 18 months, Brown stormed out of an interview with a US TV show after questions about his assault conviction. He then trashed his dressing room and breaks a window.

June 14, 2012: A night out at a NYC nightclub ends in a bottle-throwing brawl between Brown and his rival Drake - reportedly over Rihanna. Police didn't have enough evidence to criminally charge either of the stars.

January 2013: Just six months later, Brown got into another fight with a different singer - Frank Ocean. It reportedly broke out over a parking space outside a recording studio in West Hollywood.

February 2013: LA police accuse Brown of faking his community service over his 2009 assault conviction, claiming he failed to provide "credible, competent or verifiable evidence" that he actually did the court-ordered 180 days.

May, 2013: Brown is involved in a traffic accident, after which he's accused of not providing the other driver with complete licence and insurance information.

July 2013: His probation is revoked thanks to that accident and faces actual jail time.

August 5, 2013: He turned himself in to police as a booking formality and is jailed for less than an hour. The cracks are really starting to appear though - the next day, he tweeted: "Don't worry, mainstream America. After this X album, it'll probably be my last."

August 16, 2013: Brown's probation is reinstated when the traffic charges are dropped, but he's still sentenced to do 1000 hours more community service.

October 2013: Brown is charged with felony assault after a brawl with a man outside a hotel in Washington DC and spends 36 hours in jail. He voluntarily checked into rehab but left just two weeks later.

November 2013: He is sentenced to 90 days at an anger management rehab facility. The deal was if he left rehab, he'd go directly to jail.

March 2014: Brown is kicked out of court-ordered rehab and sent to jail for violating internal rules.

May 2014: He's ordered to serve 131 days in jail for his probation violation.

June 2014: He's given early release because of jail overcrowding.

May 2016: Brown allegedly attacks his manager Mike G in a "drug-fuelled rage" - punching him in the face and neck. He'd been hired in 2012 to fix the singer's reputation after the infamous Rihanna beating.

June 2016: Brown's manager launches a lawsuit over the assault, claiming the star showed no remorse. "We did everything we could to resolve this in a non-public way to avoid damage to Chris Brown. Regrettably, as outlined in our complaint, Chris Brown has proven to be his own worst enemy," Mike G's lawyer told TMZ at the time.

August 30, 2016: Brown is accused of pointing a gun at a woman in his house, who raised the alarm, sparking a nine-hour "standoff" with local police.

- news.com.au

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