Chris Brown is no stranger to controversy and legal troubles.
Most recently, stars like Ed Sheeran and Kendall Jenner, who appeared in Brown and Lil Dicky’s music video, came under fire for supporting “an abuser” — referencing the time Brown assaulted then-girlfriend Rihanna in 2009. The domestic violence incident was also alluded to in a 2018 Snapchat ad for a game called “Would You Rather?”, which asked users if they would rather slap Rihanna or punch her ex. The market value of the app’s parent company dropped almost $800 million due to the ad, according to CNN.
And in terms of his recent run-ins with the law, Brown was arrested on suspicion of assault with a deadly weapon in 2016, and his ex-girlfriend Karreuche Tran was granted a restraining order against him the following year.
For context, here is a chronological list of Brown’s legal struggles.
February 8, 2009
Brown and then-girlfriend Rihanna have an argument that escalates into physical violence on the part of Brown. Rihanna is left with visible facial injuries and is hospitalized; Brown is subsequently charged with felony assault and making criminal threats on March 5. He pleads guilty to a felony on June 22 of that year and accepts a plea deal of community labor, five years’ probation and domestic violence counseling.
Brown is denied a visa to the U.K. over the assault on Rihanna. He had been planning a short tour in the U.K. and Ireland. In a statement, the U.K.’s home office wrote, “We reserve the right to refuse entry to the UK to anyone guilty of a serious criminal offense. Public safety is one of our primary concerns. Each application to enter the UK is considered on its individual merits.”
March 22, 2011
Following an interview with Robin Roberts on Good Morning America in which Brown is asked about the incident with Rihanna, the singer allegedly blew up in his dressing room during a commercial break and threw a chair at a window overlooking Times Square. He confronted several members of the show’s production staff and exited the building, shirtless.
June 14, 2012
Eight people are injured in a brawl in an NYC nightclub involving Brown, Drake, NBA star Tony Parker, and assorted members of the trio’s entourages. Brown later makes a diss record about Drake (A remix of Chief Keef’s “I Don’t Like”) and Brown’s attorney claims that Drake was the instigator of the brawl, though the pair appear together in a comedic skit two years later at the ESPY Awards, suggesting they’ve made up.
Brown tests positive for marijuana while working at his community service.
Brown attends a Halloween party dressed as an Islamic terrorist. Also present at the party is Rihanna, which is a violation of the restraining order taken out against Brown in the wake of the assault. He appears in court on November 1.
Brown and his entourage clash with fellow singer Frank Ocean and his group outside a West Hollywood recording studio, reportedly over a parking space. One of Brown’s entourage reportedly used a homophobic slur against Ocean and Brown allegedly punched Ocean and threatened to shoot him, though the latter declines to press charges.
Brown’s probation is revoked after his involvement in an alleged hit-and-run in Los Angeles. Earlier in 2013, reports surfaced that questioned the validity of Brown’s community service – he appeared to be credited with having served time during periods in which he was out of the country. The hit-and-run charges are eventually dropped, but Brown is served with an additional 1,000 hours of community service.
October 27, 2013
Brown is arrested for felony assault in Washington D.C. when he and his bodyguard are involved in an altercation with two men outside of a hotel. He spends 36 hours in jail and is brought back to California to appear in court in Los Angeles.
Brown voluntarily enters a rehab facility, only to be kicked out on November 14 for violent behavior. Six days after that, he’s sentenced to three months at an anger management rehab facility.
Brown is diagnosed with bipolar disorder and post-traumatic stress disorder by doctors while in rehab. The facility believes his past behavior stemmed from his attempts to self-medicate his troubles.
March 14, 2014
Brown is kicked out of the Malibu treatment facility where a judge ordered him to stay after serving his 90 days. He is sent to jail for violating the facility’s rules and on May 9, 2014, is sentenced to 131 days in jail for his probation violation.
June 2, 2014
Brown is given early release from jail. He remains on probation and is ordered to complete his remaining community service and see a psychiatrist twice a week.
September 2, 2014
Brown pleads guilty to assault related to the incident in D.C.
January 15, 2015
Brown’s probation is revoked when a judge learns he’d traveled outside Los Angeles County without prior consent to perform at a nightclub for a private performance. An altercation during the performance escalated into gunfire and five people were shot.
February 25, 2015
Brown confirms that he’s been denied entry into Canada based on his criminal history.
May 5, 2015
Brown is briefly named in a misdemeanor battery case in Las Vegas in which a man alleges the singer hit him after an argument over a basketball game. The man declined to press charges.
July 24, 2015
Brown is allowed to leave the Philippines after being detained there following a fraud investigation over his cancellation of a New Year’s Eve concert in 2014 after already receiving $1 million to perform.
Brown cancels his tour of Australia and New Zealand a week before the first show. In late September, Australia’s immigration minister, Peter Dutton, warned Brown his visa would be denied, based on his criminal history, if he could not show just cause to the contrary.
January 2, 2016
Brown is investigated by police in Las Vegas after a woman alleges he beat her and stole her cell phone during a party at the Palms Casino Resort. Brown’s rep calls the charges “Unequivocally untrue.”
Police say the singer allegedly “sucker punched” a 28-year-old club photographer in Tampa during a paid appearance at AJA Channelside. The alleged victim claimed that Brown attacked him because he was taking photos after Brown arrived at the venue for an after-party “showing,” police said. He is not arrested.
A judge grants model Karrueche Tran a restraining order against the singer and ex-boyfriend for the next five years, PEOPLE confirms. The model alleges in court that Brown texted her violent threats, such as, “I can get my money back and I’m tired of playing games,” along with, “Bitch I will beat the s— out of you” and “I promise you I will make your life hell.”