Afterward, Rihanna told Oprah Winfrey that she forgave Brown, and insisted he "made that mistake because he needed help."
Brown's problems haven't stopped.
On Tuesday, the singer was back in the news, this time accused of aggravated rape and drug violations in Paris, a French judicial source told CNN.
CNN has reached out to Brown's attorney for comment.
Brown's musical career has been marked with as much controversy as success.
When he burst onto the music scene in 2005 at the age of 16, Brown was touted as "the new Michael Jackson."
His fame grew when he and Rihanna began dating in 2008. With their matching places on the charts, the pair quickly became music's "it" couple.
But their romance took a dark turn just hours before the 2009 Grammy Awards, when Brown assaulted Rihanna, whose birth name is Robyn Fenty.
"Robyn F. turned to face Brown and he punched her in the left eye with his right hand," a police report of the incident read. "He then drove away in the vehicle and continued to punch her in the face with his right hand while steering the vehicle with his left hand. The assault caused Robyn F.'s mouth to fill with blood and blood to splatter all over her clothing and the interior of the vehicle."
Brown pleaded guilty to a felony assault charge and received five years probation, community service and an order to attend a year of domestic violence counseling.
The high profile nature of that crime a decade ago -- along with circulation of a photo of Rihanna's battered face -- has continued to color public perceptions of Brown.
What followed has not helped to restore his image.
He has feuded with fellow recording artists, done stints in rehab and has landed in jail for violating probation.
A 2014 report from his rehab facility attributed Brown's aggression to bipolar disorder, post traumatic stress disorder and drug use.
"Mr. Brown will also require close supervision by his treating physician in order to ensure his bipolar mental health condition remains stable," a letter from the facility reportedly stated. "It is not uncommon for patients with Post Traumatic Stress Disorder and Bipolar II to use substances to self-medicate their biomedical mood swings and trauma triggers."
Some of Brown's other troubles include:
- Being accused of threatening a woman with a gun at his Tarzana, California home in 2016. A nine-hour standoff with police ended in Brown's arrest on suspicion of assault with a deadly weapon. His attorney at the time, Mark Geragos, called the charges "demonstrably false" and the case has not gone to trial.
- Brown's ex-girlfriend, actress Karrueche Tran, obtained a restraining order against him in 2017, alleging he had threatened her with violence.
- In May 2018, an unidentified woman reportedly filed a civil lawsuit against Brown, alleging she was sexually assaulted at the singer's home by one of his friends. Brown's attorney denied the allegations.
- And in July, Brown was arrested after a concert in Florida for an outstanding felony arrest warrant stemming from an allegation he punched a photographer at a Tampa nightclub in 2017. That case is still pending.
Brown addressed some of his issues in the 2016 film, "Welcome to my Life: The Official Chris Brown Documentary."
He said he contemplated suicide after the incident with Rihanna.
"I wasn't sleeping, I barely ate. I just was getting high," Brown said in a trailer for the film. "I went from being on top of the world, No. 1 songs, being kind of like America's sweetheart to being Public Enemy No. 1."
For many, that label has stuck.
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