Chris Brown Spends 25th Birthday In Jail: His Top 10 Most Shocking Moments

Chris Brown will spend his 25th birthday behind bars today. This time last year a newly single Brown was partying with on/off girlfriend Karrueche Tran in Las Vegas.

It’s been another drama-filled year for the star with arrests, court appearances and more girl drama, he just can’t stay away from trouble. Check out his most shocking moments so far:

10. Frank Ocean

Grammys sunb When Frank Ocean won the Grammy for Best RnB album in 2013 Chris, who was sitting in the front row refused to stand up after the stars had a run in in a recording studio carpark months before. He was widely condemned for his behaviour.

Chris Brown won’t stand for Frank (WENN)

9. Calling The LA District Attorney Racist

In Summer 2013, Brown was given additional community service hours relating to the 2009 assault charges of then girlfriend Rihanna as there was some disagreement over whether he’d actually carried them out. He went on a Twitter rant after, which he quickly deleted, calling the DA “racist”.

He wrote: “Ni**a done 6 months community service with police and the DA racist a** crying to the judge that I didn’t do it. F**k the SYSTEM!”

Chris Brown at one of his many court appearances (SplashNews)

8. Broken window

When questioned about the 2009 assault of girlfriend Rihanna on Good Morning America in 2001, Brown lost his temper and punched through a glass window.

7. Grammy Backlash

Chris controversially was awarded a Grammy in 2012, when some people on Twitter, including celebrities objected, he went on a full blown Twitter rant. He wrote at the time: “HATE ALL U WANT BECUZ I GOT A GRAMMY Now!

That’s the ultimate F**** OFF!” “IM BACK SO WATCH MY BaCK as I walk away from all this negativity #teambreezygrammy.”

6. Explicit Twitter exchange with comedian Jenny Johnson

When Jenny Johnson called out Brown about assaulting Rihanna in November 2012 the singer replied with some pretty explicit content. Not only threatening to “shart” in the comedians face, but also alluded to her performing a sex act on him. Nice.

Chris and Jenny’s explicit exchange (TWITTER)

5. Rihanna and Chris Back On

In 2012 it became pretty obvious that Brown and RiRi’s toxic romance was back on. She sat down with Oprah and admitted she felt protective of him after the infamous assault and proclaimed him as her soul mate. Their romance ended in May 2013 with Brown straight back to his former girlfriend Karrueche Tran.

Rihanna and Chris spend Christmas Day together (London Entertainment / Splash)

4. Drake Fight

In June 2012 Chris and another of Rihanna’s on/off lovers Drake just happened to be in the same New York nightclub, W.i.P. A brawl broke out between their entourages after Drake allegedly sent Brown a note about the Diamonds singer.

Drake and Chris have been in a long running fued over Rihanna (Wenn)

3. Washington Arrest

In October 2013 Chris was arrested and charged with misdemeanour assault after allegedly punching a man outside a Washington D.C. hotel at around 4am. The man claims he had tried to take a photo with Chris, with the star objecting. Chris’ bodyguard has already been found guilty of the offence, with Brown’s trial delayed until after the appeal has gone through.

2. Ejected From Rehab

Chris Brown was kicked out of rehab (SplashNews)

When Chris was arrested in October 2013, a judge in his probation case revoked his freedom and placed him in rehab to deal with anger management issues. After four months of treatment he was kicked out the facility for breaking fundamental rules on March 14, which included making threatening remarks in group therapy sessions. He was then taken to jail where he’ll be staying for at least another week.

1. February 2009 Assault

For sure the most shocking moment, which is linked to several on our list is the infamous assault of then girlfriend Rihanna on the way home from a pre-Grammy party in February 2009.

A shocking picture of a bruised and battered Rihanna was leaked by TMZ and the whole world appeared to turn on the young Chris Brown. Brown pleaded guilty to a felony and accepted a plead deal of community labour, five years’ formal probation and domestic violence counselling.

In a statement following the assault, Brown said: “Words cannot begin to express how sorry and saddened I am over what transpired,”

“I am seeking the counselling of my pastor, my mother and other loved ones and I am committed, with God’s help, to emerging a better person.”


Rihanna and Chris Brown perform together in 2008 (WENN)


He spoke about the assault during an interview on Larry King Live in September 2009 along with his mother Joyce Hawkins.

He said of the assault: “When I look at it now, it’s just like, wow, like, I can’t believe that that actually happened.”

Brown was convicted of federal assault and given a five year probation. The shocking assault led to Chris being dropped by radio stations, condemned by fellow artists and has had repercussions for his career and personal life ever since.