February 2009: Brown, then 19, is arrested for assaulting then-girlfriend Rihanna, then 20, during a confrontation the morning before the Grammys. Both nixed their scheduled appearances at the award show. A probation officer's report filed for his sentencing showed that Brown was involved in two previous domestic violence incidents with Rihanna in months prior to the arrest, in Europe and in Barbados.
"I remember she tried to kick me, just like her beating s--t, but then I really hit her. With a closed fist, like I punched her and it busted her lip. And when I saw it I was in shock, I was like, f--k why did I hit her like that?" Brown said in his 2017 documentary Welcome to My Life: The Official Chris Brown Documentary.
Brown added, "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. I felt like a f--king monster. I was thinking about suicide, I wasn't sleeping, I barely ate."
June 2009: Brown pleads guilty to one count of assault with the intent of doing great bodily injury in connection with his February confrontation with Rihanna, as part of a plea deal.
August 2009: Brown is sentenced to five years of probation for his assault of Rihanna, and is also ordered to complete 180 days of community labor and a one-year anti-domestic violence program.
Rihanna meanwhile obtains a restraining order against Brown.
December 2010: Brown completes his court-mandated anti-domestic violence course.
February 2011: Rihanna's lawyer tells E! News that she has agreed to allow the current restraining order against Brown to be bumped down to a level one, which would mean that the two would be allowed to contact each other as long as he doesn't harass or annoy her.
March 2011: Brown has a meltdown in his dressing room following an interview on Good Morning America with Robin Roberts, during which she asked him about his assault of Rihanna. He later apologizes, saying in a different interview that he had to "let off steam."
June 2012: Police investigate a New York City club fight that allegedly broke out between Brown and Drake, a friend of Rihanna, and their entourages. Brown is one of five people injured. He later alludes to the brawl and to Drake in a diss track.
Brown and Rihanna, meanwhile, continue to date on and off until 2013.
February 2012: Brown is accused of snatching a woman's cell phone after she allegedly tried to take his photo outside a Miami club. The case is later dismissed.
June 2013: Brown is accused of assaulting a woman at a San Diego nightclub. She tells police he pushed her in the VIP section and later filed a lawsuit against him.
August 2013: Brown is ordered to complete an additional 1,000 hours of community labor, while the Los Angeles District Attorney agrees to dismiss a request to rescind his probation over his hit-and-run charge, which was dismissed. The singer is not happy.
"Ni--a done 6 months community service wit police and the DA racist ass crying to the judge that I didn't do it. F--k the SYSTEM!" Brown tweets.
October 2013: Brown and his bodyguard are arrested and charged with felony assault after getting into an altercation with a man outside a hotel in Washington D.C. Brown's charge is later reduced to a misdemeanor and he soon enters rehab for anger management.
November 2013: Brown is discharged from the rehab center after throwing a rock through his mother's car window while she was visiting him. Probation officials say he also failed to "comply with the rules and regulations" of his program. The singer is ordered to complete 90 days of anger management treatment at another facility, submit to drug testing and perform at least 24 hours of community labor a week.
Brown tells authorities that he had suffered a "setback, mentally and emotionally," when he was not credited for all the community service hours he initially completed, and also "had issues with his attention deficit disorder and underwent a period of depression."
December 2013: A Los Angeles judge revokes Brown's probation due to his assault arrest and orders him to continue his anger management treatment.
February 2014: A letter from Brown's rehab facility explains his recent behavior, saying he "became aggressive and acted out physically" due to untreated bipolar II disorder, "severe sleep deprivation, inappropriate self-medicating and untreated PTSD."
April 2014: U.S. Marshals take Brown into federal custody ahead of a trip to Washington, D.C. to stand trial on his misdemeanor assault charge.
May 2014: Brown is sentenced to a year in jail in Los Angeles after admitting to violating his probation, which was recently revoked over him being kicked out of rehab. The singer receives credit for 234 days of time served and court-ordered rehab, and officially has 131 more days to go. The judge also reinstates and extends Brown's probation to January 2015.
June 2014: Brown is released early from jail.
October 2014: Brown pleads guilty to misdemeanor assault in his Washington D.C. case. He is sentenced to time served after having been jailed for two days in the case and is also been ordered to pay $150 in court costs.
January 2015: Eight days before Brown's probation is set to end, it is revoked again, this time because he traveled to San Jose, California without getting permission from his probation officer to leave Los Angeles and still had 200 hours of community service left to perform in just over a week. His attorney says his office had mistakenly informed the singer he could go to Northern California without the judge's permission. The singer is allowed to remain out of jail until March, when he has a probation violation hearing.
March 2015: Brown's probation formally ends after a judge rules the singer has completed 1,000.5 hours of community service and the Probation Department concludes there were no violations.
"IM OFF PROBATION!!!!!!!! Thank the Lord!!!!!!" Brown tweets. "Hopefully this is my last day in court..... Pray for me.."
May 2015: A man tells Las Vegas police he was beaten during an altercation with Brown and his friends during a late-night basketball game at the Palms Casino and Resort. The person later decides not to press charges.
January 2016: Las Vegas police investigate Brown over possible misdemeanor battery and theft after a woman claimed he assaulted her and took her cell phone during an altercation at a party in a hotel room. He denies the accusations.
June 2016: Brown finds himself inside an Amsterdam police station after cops detain him for driving what appears to be a dirt bike without a license plate. He is released after paying a fine. Brown documented the incident on Instagram, calling the police "cool as s--t."
August 2016: Baylee Curran, Miss California Regional 2016, tells police Brown threatened her with a gun while she was admiring a piece of jewelry in his kitchen. He is arrested and charged with assault with a deadly weapon. He is soon released from jail after posting a $250,000 bond and denies any wrongdoing. The case is later dropped due to lack of evidence.
February 2017: Brown's ex Karrueche Tran obtains a temporary restraining order against him, saying he threatened to kill her. It was made permanent in June. At the time of the filing, Brown tells his followers in a since-deleted post not to listen to "all this bulls--t."
April 2017: Brown is accused of punching a photographer at a Florida nightclub and police open an investigation.
May 2018: A woman files a civil lawsuit against Brown, claiming she was sexually assaulted at the singer's home. Brown's attorney denies the allegations.
June 2018: A woman named Cassandra is granted a temporary restraining order against Brown, who she claims has been harassing and stalking her. The singer's attorney says Brown doesn't even know the woman.