Image via Getty/Maury Phillips
Since his debut in 2005, Chris Brown has been a mainstay in the music industry, for some good and a lot of bad. Heralded for his vocal skills and dancing talent, his star power was virtually undeniable from as early as 16 years old; in the beginning of his career, he released two top five albums and five top 15 songs in the span of two years.
By 2009, though, Brown had become a pariah, shamed after a heartbreaking and horrifying assault on Rihanna. He began lashing out in public and on social media, earning a reputation for both assholerly and outbursts. While he retained an active fan base, his overall social standing in the hierarchy of pop culture began to fade. As a result, the Virginia native lost a lost of good will and a lot of good advertising deals.
He’s never had an album debut lower than number seven on Billboard’s charts, but later in his career, his personal life and actions have clouded and overshadowed his sales. From his relationship with Karrueche Tran, to a standoff with Los Angeles police, to being arrested in Florida earlier this year, turmoil has followed him throughout his career, the good majority of it invited by his own actions.
Chris Brown’s various dramas, which have played out over a series of 13 years, are detailed below.
Feb. 8, 2009: Domestic Violence
A few years into Brown’s career, the rumor mill swirled with speculation that he and Rihanna were romantically involved. Finally, they confirmed their relationship status and became the new royal couple of pop music. But unfortunately, things weren’t as magical as they may have seemed.
On Feb. 8, 2009, on the way home from a Grammy event, Rihanna expressed frustration over something that had occurred there (Brown says it was a former lover walking up to him). In response, Brown attempted to push her out of the car, slammed her head against the window, punched her in the face, and then repeated to do so as he drove. After she attempted to call her personal assistant and failed to get an answer, she faked leaving a voicemail in hopes that it would dissuade Brown from further action. In response, he threatened her with murder. He would go on to strike her several more times, as well as bite her ear and choke her to the point of near-unconsciousness.
Brown would eventually be charged with assault and receive five years of probation and six months of community service.
"Paris Hilton got more jail time than Chris Brown did for beating a woman to a pulp," said Kim Gandy, then-president of the National Organization for Women, to the Washington Post. "How could he not spend one day in jail? I find it shocking. There are things that celebrity should not protect you against."
March 21, 2011: Throws chair through window
Three days after the release of his fourth album, F.A.M.E., Brown made an appearance on Good Morning America. After getting visibly agitated by Robin Roberts’ questions about his assault on Rihanna, the singer threw a chair through a window in his dressing room.
2011: Involvement with Karrueche
From 2011 to 2017, Brown had an on-again, off-again relationship with Karrueche Tran, then a celebrity stylist, now a model and actress. Initially, the relationship had the same happy-go-lucky vibe that surrounded his time with Rihanna. Unfortunately, that was quickly shattered when he thrust Tran into a love triangle that involved constant breakups, tension and reunions between the couple and Rihanna.
Tran and Brown began dating in mid-2011, and lasted until 2012. Brown briefly reconciled with Rihanna, though, before settling down with Tran once more.
2011: Fights on Twitter with Raz and Tyler, the Creator
By 2011, Brown, once the clean-cut face of the next generation of pop, had formed a habit of getting into Twitter arguments, ranging from homophobic comments towards former B2K member Raz toward the end of 2010 to attempted disses at Tyler, the Creator the following year.
The latter feud occurred when Brown tweeted his disapproval of the trend of satanic references in rap. Tyler responded, in typical Tyler fashion, asking, “Why Is Chris Brown Talking So Much Shit About Metallica? Weird.”
June 2012: Beef With Drake Turns Violent
One of Brown’s most noteworthy beefs was his clash with Drake. In June of 2012, the vibe between the two had increasingly become hostile, and finally came to a head in New York City.
At a now-closed nightclub called Work in Progress, the respective crews of Brown and Drizzy overlapped when Brown decided to send a bottle of champagne over to the Champagne Papi. Drake responded by sending the bottle back, along with a note that reportedly said, “I’m fucking the love of your life.” A full-on brawl erupted; Brown was hit, as was Tony Parker, who was with Brown’s crew and received a scratched cornea as a result.
The beef has since simmered on and off, but one can assume it’s over, with the two hopping in the studio together in 2014 and Drake recently hyping up Brown’s basketball skills on Instagram.
Feb. 2013: Fights with Frank Ocean
Stemming from the original Twitter spat between Brown and Tyler, the former engaged in a war of words with Frank Ocean after a complimentary tweet from Brown was interpreted as insincere. Tyler jumped in this time as well, joking that Amber Rose had stolen Brown’s style. Eventually, though, Tyler declared an end to the beef after a group of Brown’s associates started stalking Ocean in Los Angeles.
Spoiler alert: the beef was not over, and three years later, Twitter fingers turned to trigger fingers. Upset that Brown had taken his parking spot at a recording studio in Los Angeles, Ocean confronted his entourage, which lead to a brawl, during which Ocean says he was called homophobic slurs by Brown. Ocean declined to press charges for the incident.
Two weeks later, Ocean beat Brown out for Best Urban Contemporary Album at the Grammys, and received a standing ovation, during which Brown remained seated.
2013: Brown Enters Rehab (And Gets Kicked Out)
Brown’s legal troubles would continue into 2013. Two months after being assigned an additional 1,000 hours of community service following a charge for a hit-and-run, he and his bodyguard were arrested and charged with felony assault in relation to a fight outside of a Washington D.C. hotel.
With the charge reduced to a misdemeanor, Brown elected to enter rehab for anger management. However, he was kicked out a month into his treatment for throwing a rock through his mom’s window. He would re-enroll at another facility, a requirement after his role in the D.C. fight.
May 9, 2014: Sentenced to Jail Time
After being kicked out of his second rehabilitation facility, Brown was jailed and in May of 2014. He was sentenced to 131 days in prison. He’d be released a month later, and a few months after that, he’d plead guilty to misdemeanor assault and pay just $150 in court costs.
March 21, 2015: Off Probation
After staying relatively out of trouble since his release from jail and completing his court-mandated community service, Brown was ruled off probation from his 2009 assault arrest.
Aug. 31, 2016: Arrested After Standoff
In perhaps the strangest chapter in the saga of Chris Brown’s legal struggles, in 2016 he found himself in a standoff with Los Angeles police.
Baylee Curran, a former Miss California winner, was over at Brown’s house when she and a friend began, according to her, admiring the singer’s jewelry. This lead to an alleged brandishing of a firearm by Brown and a call to the police, who arrived at Brown’s house and waited until they received a warrant to enter.
The entire time, Brown was posting Instagram videos, angrily reacting to the police’s presence. He would eventually be arrested, though charges were dismissed due to a lack of evidence.
Feb. 21, 2017: Karrueche Files A Restraining Order
Even with Rihanna out of the mix and Tran and Brown together, the cycle continued, and things reached a breaking point after Brown fathered a child with another woman. A few months later, Tran posted on Instagram following an interview between Brown and Ryan Seacrest, saying, “Don't be mad at me because our relationship is over due to your lack of loyalty. You know what's weak?? You forcing yourself into my car.. my broken window.. blowing up my phone.. trying to shower me w gifts.. Man the fuck up and change the bs in your life like I've told you several times.”
In 2017, after alleging Brown “threatened to kill me to others, threatened me via text messages and threatened to harass my friends" and that he had struck her several times, Tran was granted a five-year restraining order, something she felt was necessary for her safety.
July 5, 2018: Arrested in Florida for Battery
In June of 2018, Brown embarked on a nationwide tour in support of the album. In July, he headed to Florida for shows in West Palm Beach and Tampa. Following the first performance, Brown was taken into custody, the arrest stemming from his assault of a photographer in Tampa a year before. He would later be released on bail and allowed to perform the next night in Tampa.
Feb. 2019: Beef With Offset
21 Savage getting locked up by ICE was an event that affected people in the music community in different ways. Some stars sent lawyers, some sent prayers. And, at least in Chris Brown's case, some sent memes.
The singer turned 21 Savage's situation into a joke, but Offset didn't take it lightly. The Migos member responded to Brown sharing a meme setting a video of 21 to Big Shaq's "Man's Not Hot" by saying "Memes ain't funny lame."
Things got worse from there. Offset and Chris Brown traded shots back and forth. Insults about age (surprisingly coming from Brown, even though he's the elder of the two), invitations by Brown to pull up and duke it out at his house, references by Offset to Brown's violent past ("only people you go toe to toe with is women"), accusations of drug abuse, and even comparisons to Pootie Tang abounded. At least for now, Brown has the last word.