Chris Brown is arguably one of the most controversial musicians in history. Although the singer gave us hits like “Residuals” and “Deuces,” you have to admit, his personal life is filled with drama and legal mess. Who else do you know was banned from several countries?
Brown is sitting in an U.K. jail after he was denied bail in connection to a 2023 incident. But in light of another legal woe added to Brown’s plate, The Root is revisiting the laundry list of past incidents, starting with perhaps his most notorious one.
2009: Rihanna’s Brutal Assault
The incident that arguably started it all is when Brown and his then-girlfriend Rihanna got into a physical altercation, resulting in Brown violently beating her. The Bajan singer was hospitalized with injuries to her face and body, and the pictures went viral.
Eventually, Brown pled guilty to a felony. His plea deal included community labor, five years of probation and domestic violence counseling, which he celebrated completing in 2010. “I have enough self respect and decency to be proud of accomplishing this DV class. Boyz run from mistakes,” Brown wrote on X. “Men learn from them!!!”
2012: Club Fight with Drake
Clearly, Brown wasn’t over his ex, Rihanna, because in 2012, he and RiRi’s then-boyfriend Drake got into it at a New York City nightclub. At least eight people were injured and Brown later tweeted a photo of a bloody gash on his chin, which he sustained during the fight.
Drake’s reps claimed the rapper wasn’t involved in the fight, but that didn’t stop the tension between the two artists from taking over the internet. Seven years after the brawl, Brown and Drake parodied their fight in the 2019 music video for “No Guidance.”
2013: Studio Fight with Frank Ocean
The “Sensational” singer must have a thing for fighting, because just months after fighting with Drake’s posse, he was back for another altercation with singer Frank Ocean. This time, the beef took place at a recording studio, according to TMZ. It was also reported that Brown initiated the fight, punching Ocean in the face over a parking space. Brown even threatened to shoot Ocean, according to police documents. Ocean declined to press charges.
2014: Bipolar Diagnosis
While in rehab— on judge’s orders after another violent incident— Brown was diagnosed bipolar with post-traumatic stress disorder. According to the facility’s reports, Brown’s violent and sometime irrational outbursts stemmed from his ongoing mental issues.
He was later kicked out of the rehab facility for for violating the facility’s “internal rules,” according to TMZ. Brown was also sentenced to 131 days in jail for violating probation, TIME Magazine reported.
2015: Assault in Vegas
The Grammy award winner was named in official documents from a 2015 assault case in Las Vegas. The accuser alleged Brown hit him after an argument over a basketball game. He declined to press charges against Brown.
2016: Brown Sued by Ex-manager
The manager, who Brown hired to help restore his image after Rihanna’s violent assault, sued him, claiming the singer had “brutally” attacked him, according to USA Today. The matter was later settled in 2019.
2017: Brown Allegedly Punches a Photographer
According to Tampa police, Brown “sucker punched” a photographer during a paid appearance at a well-known club. The victim claimed Brown attacked him because he took photos of the star’s arrival to the venue. The singer was never formally charged.
2018: Sued for Sexual Assault
An unidentified woman sued Brown and two others, alleging she was sexually assaulted at the singer’s home during a party. The court documents claimed Jane Doe was assaulted, using “drugs, alcohol, threats, and the presence of guns” to coerce her into unwanted sexual acts.
Brown’s attorney, Mark Geragos, denied the accusations in a statement to TMZ, saying, “In another era, we might have called this a shakedown. None of these allegations are true. Nobody has done anything with this… there’s no case here.” The lawsuit was ultimately settled out of court in 2020.
2022: Sued Again for Sexual Assault
In January 2022, an unidentified woman filed a $20 million lawsuit against Brown, alleging he raped her on a yacht in Miami. She also described two other incidents, including one in 2021 when she alleged Brown became “irate” when she refused his sexual advances, according to Radar Online.
The day after the lawsuit was filed, Brown took to Instagram saying, “Whenever I’m releasing music or projects, ‘THEY’ try to pull some real bulls**t.” In 2022, the woman’s attorneys dropped the case after Miami Beach police discovered messages between her and Brown. A judge officially dismissed the case in August 2022.
2023: Sued Over Fight at London Nightclub
In October 2023, Abe Diaw sued Brown for an alleged physical assault with a bottle of Don Julio 1942 tequila. According to the lawsuit, Brown knocked Diaw unconscious then continued to “ruthlessly stomp” on him. As a result, Diaw allegedly suffered head lacerations and torn ligaments in his leg.
2025: Brown Sues Warner Bros for $500 Million
Earlier this year, Brown filed a $500 million lawsuit against Warner Bros., Ample and the producers of the documentary “Chris Brown: A History of Violence,” as The Root previously reported. He claimed the documentary falsely portrayed him as a “serial rapist” and “sexual abuser.” In the suit, Brown refuted previous rape allegations made by Jane Doe accusers.
And Now...
Brown was arrested on Thursday (May 15), Brown was arrested in the U.K.— a country in which he was previously denied entry — over the 2023 incident involving Diaw. He was denied bond with an expected court date of June 13.