A Complete Timeline Of Chris Brown's Legal Troubles

The following article includes allegations of domestic abuse and sexual assault.

If there's anyone who should've been scared in a post #MeToo world, it's Chris Brown. The singer's meteoric rise to fame has been largely overshadowed by a myriad of legal issues and abuse allegations, starting with his assault on Rihanna in 2009. The world saw the horrific photos. The singer, himself, admitted he "felt like a f***king monster." The Internet went through the trouble of calling out stars like Ed Sheeran and Kendall Jenner for appearing in the star's music video, and Snapchat's stock reportedly lost $800 million after an ad made fun of his infamous domestic violence incident. There have been petitions and think pieces urging for accountability, yet miraculously, Brown's career has largely been unscathed. In fact, it's thriving.

Spotify axed alleged abusers like R. Kelly and XXXTentacion from branded playlists as part of their hate content and hateful conduct policy, but Brown remains. His whopping eight platinum albums (four of which are multi-platinum) spawned 103 different singles on the Billboard Hot 100. Even in 2021, the singer is still as popular as ever. "Go Crazy," Brown's single with Young Thug, has been certified platinum twice — but will there be a breaking point?

As Brown's controversy continues to grow, here's a chronological look at his numerous legal troubles.

If you or someone you know is dealing with domestic abuse, you can call the National Domestic Violence Hotline at 1−800−799−7233. You can also find more information, resources, and support at their website.

Chris Brown pleaded guilty after assaulting Rihanna in 2009

2009 was a big year for both Chris Brown and his then-girlfriend Rihanna. At the time, they were the ultimate power couple — two fresh-faced Hollywood stars who met as teens and, by all accounts, would inevitably spend their 20s on the Billboard charts fielding a trail of paparazzi. That year, the pair were set to perform at the Grammy Awards, and both received numerous nominations, but neither of them made it to the ceremony.

According to The Guardian, Rihanna canceled her appearance following a pre-Grammy party after an argument with Brown over a text message from another woman turned violent. Per the police report obtained by CNN, Brown "punched" the singer in the left eye before driving away and continuing "to punch her in the face with his right hand while steering the vehicle with his left hand." Rihanna was hospitalized and left with visible facial injuries (the disturbing photos later circled around the internet) and Brown was arrested.

Brown pleaded guilty to one count of felony assault, and according to CNN, he was sentenced to "five years probation, community service," and "a year of domestic violence counseling." Rihanna eventually opened up about the incident — which was the first of many for Brown. "The more in love we became, the more dangerous we became for each other, equally dangerous," she told "20/20" (via CNN). "Because it was a bit of an obsession."

If you or someone you know is dealing with domestic abuse, you can call the National Domestic Violence Hotline at 1−800−799−7233. You can also find more information, resources, and support at their website.

In 2011, Chris Brown shattered a window at GMA during a violent outburst

For the next couple of years, Chris Brown more or less stayed out of trouble. The star focused on his career, which inexplicably didn't seem all that affected by his bad press. In fact, it managed to reach new heights. In 2011, when Rihanna agreed to downgrade her restraining order, Brown took home his first (and only) Grammy for his fourth studio album, "F.A.M.E." Unfortunately, the album's release was overshadowed by the star's violent behavior.

According to ABC News, the day the record dropped, Brown appeared on "Good Morning America" to perform the lead single "Yeah 3x." Things ended up taking a sour turn when co-anchor Robin Roberts asked the singer about his relationship with Rihanna in light of the newly relaxed restraining order. Though Brown tried to pivot the focus towards his music, Roberts kept pushing, and the star became noticeably aggravated.

The moment Brown finished his performance, he stormed off set and retreated to his dressing room, where he broke a window in a loud scuffle. The window was only discovered after some staffers "called security" because of the noise, but by then, Brown had already emerged shirtless from the wreckage and high-tailed it out of the building. No, he didn't even bother to put on a shirt before leaving (as documented in the now-infamous paparazzi photos). According to The Hollywood Reporter, Brown was informed of the questions beforehand, so Roberts was "shocked" by his response.

Chris Brown and Drake's bloody nightclub brawl ended in a $16 million lawsuit

Rihanna and Drake have a storied history, and Chris Brown directly inserted himself in the middle during a violent New York City nightclub brawl that left "at least" five people with injuries, according to The New York Times. The carnage — and the horrifying, bloody photos – aren't exactly surprising considering the fight was primarily sustained by an artillery of glass bottles, ice cubes, and cocktail glasses that were thrown by feuding rap entourages. Even Brown emerged with a gnarly gash on his chin, but what exactly happened isn't clear.

Per the Times, it all went down at a birthday party for one of Ne-Yo's managers at the SoHo nightclub W.i.P. Apparently, tensions had been growing between Brown (who was in town for a "Today" show appearance) and Drake and Meek Mill (who were both fielding Rihanna romance rumors). From there, accounts vary. Some say Brown sent a bottle of champagne to Drake, who returned it. There may or may not have been a derogatory note about Rihanna involved. Other accounts say Drake's entourage stoked the fight as Brown left the club, and further reports say Drake started it by yelling at Brown (though Drake's camp told TMZ that fight was actually between Brown and Meek Mill).

All we really know is that bottles were smashed, and both Drizzy and Brown were sued for $16 million by the nightclub and its adjoining venue. The singers won the suit.

Chris Brown reportedly punched Frank Ocean over a parking spot

Chris Brown didn't limit his rap-related feuds to Drake. In 2013, he took aim at Frank Ocean. Again, it involved an entourage. This time, instead of a nightclub, the colosseum was a recording studio parking lot. Instead of ice and bottles, the ammo was reportedly homophobic slurs, gun threats, and fists.

According to TMZ, who obtained a copy of the police report, Ocean claimed the brawl began over a parking space and escalated when he refused to shake Brown's hand. The singer then allegedly "punched him in the face" before two members of Brown's entourage "pushed him into a corner and attempted to kick him." Ocean also claimed that someone called him a "f****t" and that "Brown threatened to shoot him." The fight lasted just two to three minutes, and Brown reportedly fled before cops arrived.

Once again, Brown managed to avoid accountability for his alleged violence. Ocean sustained a cut on his temple and index finger (the latter threatened his Grammy performance) but decided not to press charges. Though MTV reports that Brown was investigated for misdemeanor battery, the case was closed and no one was arrested.

Chris Brown couldn't run away from his probation problems

Chris Brown struggled to manage his five years of probation following his felony assault conviction — he was even forced to postpone his 2010 European tour after he was denied entry to the U.K. because of his violent behavior. In theory, all the singer had to do was lay low and wait for his probation to run out, but instead, he was allegedly involved in numerous brawls that were splashed across the tabloids. Weirdly enough, that wasn't what got his probation revoked.

According to the Los Angeles Times, Brown's probation was reviewed in 2012 after the singer's travel raised concerns and he tested positive for marijuana while doing community service in Virginia. Not long after, a District Attorney raised questions about whether or not he had faked his community service hours. Nonetheless, it wasn't until later in 2013 that Brown's probation was actually revoked after he was involved in an alleged hit-and-run accident in Los Angeles.

According to the Associated Press, Brown was charged with "misdemeanor hit-and-run and driving without a valid license." CNN reports that during the court case, the prosecutor claimed that Brown "went ballistic" after his Range Rover rear-ended a woman's Mercedes. The charges were ultimately dropped, and according to NBC News, Brown was slapped with an additional 1,000 hours of community labor, where he had the choice to either do "highway cleanup, beach cleanup, graffiti removal, or general maintenance work."

Chris Brown spent time behind bars after allegedly punching a fan in the face

Just as Chris Brown was smoothing out his probation problems from his first felony assault conviction, he was slapped with a second assault conviction. In 2013, the singer was arrested with his bodyguard in Washington D.C. after he allegedly punched a fan who tried to jump into a photo. Per Reuters, Brown allegedly broke the fan's nose.

According to The Washington Post, both Brown and his bodyguard were ultimately convicted. The bodyguard ended up having to spend a year on probation and complete 24 hours of community service, but Brown's sentence was far more serious because he was already on probation for felony assault. Pleading guilty to a lesser charge of misdemeanor assault helped him avoid a longer jail sentence, but Reuters reports that he was still sentenced to a year in jail for violating parole.

At the end of the day, there were no jailhouse recording sessions or record contracts like those seen by some of the rappers who served jail time before him. Brown didn't end up staying behind bars very long because, as Rolling Stone reports, he managed to cash in 234 days of time previously served. When it came to the actual assault, E! reports that Brown ended up serving no additional time.

Chris Brown got kicked out of rehab – twice

The same year that Chris Brown allegedly punched both Frank Ocean and a photo-hungry fan, he voluntarily checked himself into rehab. According to People, the star aimed to "gain focus and insight" into his violent behavior, but this was apparently a short-lived endeavor. The star was booted from rehab for — you guessed it — the same type of violent behavior that sent him there in the first place.

CNN reports that Brown was kicked out of the facility after he "smash[ed] his mother's car window during a family session." This landed him in court-ordered rehab for 90 days, where it seemed like the singer was finally going to get some actual help. According to People, doctors diagnosed Brown with PTSD and bipolar disorder, and he spent his stay learning how to become "less impulsive." He was actually making real progress when his stay was extended by an additional two months in early 2014. Those two months were never completed because, according to TMZ, Brown was booted for violating a number of rehab rules.

What happens in Vegas stays in the tabloids

Not long after leaving jail, Chris Brown found himself in the midst of a handful of assault investigations — two of which took place at the Palms Casino Resort in Las Vegas. First, in 2015, the star was accused of punching a man at a basketball game, but according to Billboard, the man dropped the charges. Then, on the weekend of New Year's Day, the singer was accused of battering a woman who tried to take his picture and stealing her cell phone during a party at one of the resort's hotel rooms. According to People, Brown claimed the accusations were "unequivocally untrue" and that the woman was booted by security for "wild behavior" and a "total meltdown." He was never charged.

In between those two incidents, Brown popped over to Denver, Colorado to film a music video with French Montana and Fetty Wap. That's where the third incident went down. According to TMZ, a woman claimed she was "forcibly thrown" off the singer's tour bus outside of a strip club after violating the production's "no cell phone" rules (though, she wasn't actually part of the video). The scuffle was allegedly rough enough that her phone became a casualty, and she filed a report for "third degree assault." 

Again, Brown was never charged. According to Fox31, the woman in question opted against pursuing the case. The moral of the story, don't try to take Brown's photo.

Chris Brown was sued by his manager after a brutal alleged attack

Chris Brown has seemingly built a rapport with various police departments across the country — and his career was more or less impervious to his bad behavior. Sadly, the same did not allegedly go for his team. That year, the singer was sued by Mike "Mike G" Guirguis, the big-time manager who Brown supposedly hired in 2012 to repair his sullied image after the Rihanna assault, for "assault, false imprisonment, intentional infliction of emotional distress and breach of contract," according to USA Today.

Per Variety's report, Guirguis claimed that he not only helped Brown regain a favorable public opinion, he also helped the star seek treatment for his various anger and substance use issues. In other words, Brown bit — or rather, "viciously attacked," as Guirguis claimed — the hand that fed him. The manager alleged that, during the horrific incident, the star trapped him in a room and punched him "four times in the face and neck," unprovoked. The alleged assault was so brutal that Guirguis was hospitalized.

In response to the suit, Brown claimed that he had fired Guirguis for stealing money. This prompted Guirguis to mull over a defamation charge. According to Yahoo! Entertainment, the matter was privately settled in 2019.

Chris Brown's bizarre SWAT team standoff

By 2016, Chris Brown's rap sheet was so long and convoluted that even his lawyer probably had a hard time keeping track of his run-ins with the law. All we know is that his bad behavior eventually culminated in a SWAT team standoff — which seemed like it would be the climax of the singer's supervillain downfall. In truth, most people don't remember it even happened.

According to Consequence, who captured the star's litany of Instagram posts taunting the cops as he was sequestered inside his home like Julian Assange at the Ecuadorian Embassy, it all began when Baylee Curran, a beauty pageant contestant, called 911 claiming the singer "pulled a gun" on her during a party in his Los Angeles mansion. As police surrounded the property waiting for a search warrant, the singer allegedly threw a duffel bag containing "at least one gun, other weapons, and drugs" out of his window while antagonizing officers via Instagram with pithy one-liners like "Come and get me" and "F**k the police." 

According to TMZ, Brown's entourage (including Ray J) eventually began filtering out of the house one by one. It took about 11 hours but police finally received their warrant and searched the property as Brown emerged from his fortress. Per The New York Times, Brown was arrested and "charged with assault with a deadly weapon." Despite the drama, the case never appeared to go anywhere.

Karrueche Tran won a restraining order against Chris Brown after he allegedly threatened to kill her

A SWAT Team standoff seemed like the ultimate Hollywood ending to Chris Brown's story arc as a music industry supervillain — but alas, he kept trudging forward. In 2017, the singer's on-and-off girlfriend Karrueche Tran won a five-year restraining order against the star after testifying in court.

According to TMZ, the actress shared numerous threatening text messages and voicemails that Brown had left her in the wake of their breakup. He reportedly started getting aggressive when she refused to return the diamond rings that he had given her. Eventually, it escalated to violent threats, including "b***h I will beat the s**t out of you" and "I promise you I will make your life hell." Tran also testified that Brown "told a few people that he was going to kill me" and threatened to "take me out" and "shoot me."

This apparently wasn't the first time Brown was violent towards his ex, either. Tran told the judge that Brown "punched me in my stomach twice" and "pushed me down the stairs" a few years prior.

If you or someone you know is dealing with domestic abuse, you can call the National Domestic Violence Hotline at 1−800−799−7233. You can also find more information, resources, and support at their website.

Chris Brown's 2018 misdemeanor charges were serious monkey business

In 2018, Chris Brown took a break from his string of violent crimes to try something new. In an offense that served as a faint homage to Justin Bieber's wild-child phase, Brown allegedly was caught with an illegal pet. Monkeys — which appear to be quite popular in the world of celebrity animal-related crimes — require strict permits, none of which Brown allegedly had when brought home a baby capuchin monkey named Fiji and started posting pictures of it online with his daughter, Royalty.

According to TMZ, the photos sparked concern from fans, who were worried that the exotic pet — a so-called "wild animal" — was a danger to Brown's three-year-old. Someone ended up tipping off the California Department of Fish and Wildlife, who discovered during an investigation that Brown, indeed, did not have a permit. Rather than another SWAT team standoff, the singer handed over the monkey before cops had to raid his house. He was charged with "two counts of having a restricted species without a permit" and faced up to a year in prison.

Brown ultimately avoided serious repercussions by giving up the monkey for good, paying "for its care," and agreeing to never purchase a monkey ever again, according to the Los Angeles Times. Perhaps Royalty would like a dog instead?

Chris Brown was involved in two sexual assault investigations

For most of Chris Brown's career, his alleged risky substance use has taken a backseat as tabloids focused on his violent behavior. It wasn't until 2017 that Billboard blew the lid on the singer's alleged issues with cocaine, "Xanax, marijuana, Molly and lean." This seemed to play a role in two sexual assault claims that involved the singer.

In 2017, Brown allegedly held a drug-fueled sex party where a woman claimed she was raped by one of Brown's friends and "forced to perform oral on another woman who was menstruating," according to TMZ. The woman also alleged that "Brown's friends forced women to hook up" with the singer "and another man." Cops ultimately couldn't determine if the acts were consensual, and E! reports that Brown privately settled the matter.

In 2019, TMZ reported that Brown was arrested in Paris, along with two other people, for "alleged aggravated rape and narcotics offenses." Per the report, a woman claimed that Brown — and his bodyguard and friend — raped her in the Mandarin Oriental Hotel after they met at a club near the Champs-Élysées. According to The New York Times, Brown claimed the woman was "lying." Though the investigation was on-going, he was "released without charges."

If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN's National Helpline at 1-800-656-HOPE (4673).

In 2021, Chris Brown was accused of slapping a woman hard enough that her weave fell off

Since 2012, it seems like Chris Brown hasn't gone a single year without getting into legal trouble. Only in 2020 — when the music industry ground to a halt and people sheltered indoors — was there a rare sense of calm in the singer's world (or at least the version of his world that we see through the tabloids). Judging by his Instagram account, he spent a lot of that time being a dad and hanging out with his two children, but that sense of calm was quickly shattered in 2021.

According to NBC News, in late June, police "responded to a report of an argument" at Brown's home in San Fernando Valley. This turned into a battery investigation after a woman claimed she was hit by the singer. According to TMZ, the slap was allegedly so hard that it "made part of her weave come out," though there were no reported injuries and no arrests. E! reports that Brown wasn't even home when police showed up on the scene, and the rapper hasn't responded beyond an Instagram Story where he wrote, "Y'all so d*mn [baseball cap emoji]" (for reference, cap is slang for a lie). At the time of this writing, the matter is still being investigated. Will he finally face a reckoning? Probably not.