Brown has continuously been involved in various brawls and legal struggles since 2009

Chris Brown is no stranger to controversy and legal troubles.

In 2018, 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.

While the domestic violence incident with Rihanna as the most infamous of Brown’s legal troubles, he has been facing various other accusations over the years, including being charged with two criminal counts of having a restricted species — in this case, a capuchin monkey — without a permit in December 2018. His legal issues have even prevented Brown from performing in certain countries on occasion.

For context, here is a chronological list of Brown’s legal struggles.

February 8, 2009: Chris Brown physically assaults then-girlfriend Rihanna

Brown and then-girlfriend Rihanna had an argument that escalated into physical violence on the part of Brown. Rihanna was left with visible facial injuries and was hospitalized; Brown was subsequently charged with felony assault and making criminal threats on March 5. He pleaded guilty to a felony on June 22 of that year and accepted a plea deal of community labor, five years’ probation and domestic violence counseling.

After completing the yearlong domestic violence course in 2010, Brown posted to Twitter, “I have enough self respect and decency to be proud of accomplishing this DV class. Boyz run from [their] mistakes. Men learn from them!!!”

June 2010: Chris Brown is denied a visa to the U.K.

Brown was planning a short tour in the U.K. and Ireland but was subsequently denied a visa to the U.K. over the assault on Rihanna.

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: Chris Brown allegedly has meltdown backstage

Following an interview with Robin Roberts on Good Morning America, where Brown was 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: Chris Brown is involved in a New York City nightclub brawl

Eight people were injured in a brawl in an N.Y.C. nightclub involving Brown, Drake, NBA star Tony Parker and various members of the trio’s entourage. Brown later made a diss record about Drake (a remix of Chief Keef’s “I Don’t Like”), and Brown’s attorney claimed that Drake was the instigator of the brawl, though the pair later appeared together in a comedic skit at the 2014 ESPY Awards, suggesting they made up.

Seven years after the incident, Brown and Drake parodied the brawl as a dance battle in the 2019 music video for Brown’s song “No Guidance,” featuring Drake.

September 2012: Chris Brown tests positive for marijuana

According to a probation report presented in court, Brown tested positive for marijuana while fulfilling his community service in June in Viriginia, per Reuters.

Although mandatory drug testing was not required as part of Brown’s probation, a hearing was scheduled later on Nov. 1 to determine if Brown was in violation. He was given a warning a court, where Los Angeles Superior Court Judge Patricia Schnegg referred to him as a “role model.”

October-November 2012: Chris Brown violates his restraining order
As reported by Billboard, Brown attended a Halloween party dressed as an Islamic terrorist. Rihanna was also present at the party, which was a violation of the restraining order taken out against Brown in the wake of the assault. He appeared in court on Nov. 1, 2012.

January 2013: Chris Brown clashes with Frank Ocean

Brown and his entourage clashed with fellow singer-songwriter 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, according to an incident report TMZ obtained. However, Ocean declined to press charges.

July 2013: Chris Brown’s probation is revoked

Brown’s probation was revoked after his involvement in an alleged hit-and-run in L.A. 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 were eventually dropped, but Brown was served with an additional 1,000 hours of community service.

October 27, 2013: Chris Brown is arrested for felony assault

Brown was arrested for felony assault in Washington D.C., when he and his bodyguard, Christopher Hollosy, were involved in a “physical altercation” with two men outside of the W Hotel, according to police spokeswoman Gwendolyn Crump. Brown and Hollosy spent 36 hours in jail and appeared in court on Monday, Oct. 28.

According to CNN, the charges against Brown and his bodyguard were reduced to simple assault misdemeanors, and the two were released without bail. Brown was brought back to California to appear in court in L.A. and was ordered to stay at least 100 yards away from the man he was accused of assaulting in D.C.

October-November 2013: Chris Brown enters a rehab facility

Brown voluntarily entered a rehab facility, only to be kicked out for violent behavior on Nov. 14, 2013. Brown reportedly smashed his mother’s car window with a rock during a family session, per his probation officer. Six days later, Brown was sentenced to three months at a live-in anger management rehab facility.

February 2014: Chris Brown is diagnosed with bipolar disorder and post-traumatic stress order

Brown was diagnosed with bipolar disorder and post-traumatic stress disorder by doctors while in rehab. The facility believed his past behavior stemmed from his attempts to self-medicate his troubles. A judge ordered Brown to stay another two months in a Malibu, Calif., rehab, though doctors noted he was making great progress and becoming less impulsive.

“It is evident that [Brown] has responded well” to the treatment, a probation officer wrote to the court. However, the officer said that Brown’s positive change in behavior “has occurred only recently,” and the court should be cautious about releasing him too soon and recommended Brown to remain on probation until November.

March 14, 2014: Chris Brown is kicked out of Malibu treatment facility

Brown was kicked out of the Malibu treatment facility where a judge had ordered him to stay. He was sent to jail for violating the facility’s “internal rules,” as reported by TMZ.

The Los Angeles Country Sheriff’s confirmed to PEOPLE that Brown was arrested and said in a statement that the singer “was cooperative when taken into custody.”

On May 9, 2014, he was sentenced to 131 days in jail for probation violation.

June 2, 2014: Chris Brown is granted early release from jail

Los Angeles Times reported that Brown was released early from jail. However, he remained on probation and was ordered to complete his remaining community service and see a psychiatrist twice a week.

September 2, 2014: Chris Brown pleads guilty to assault

Brown pleaded guilty to the assault from the October 2013 incident in Washington, D.C. He admitted to misdemeanor assault and was sentenced to time served. Brown spent two days in a District of Columbia jail.

“I would like to say to the court that I’m sorry,” Brown said during the hearing, though he didn’t provide further comment as he left court.

After the hearing, Brown’s attorneys released a statement on his behalf: “We are pleased with the outcome of today’s court proceedings. Mr. Brown’s guilty plea finally puts to rest a case that has been pending for almost a year. Today’s result will allow Mr. Brown to focus his attention back on his music and his career.”

January 15, 2015: Chris Brown’s probation is revoked

Brown’s probation was revoked when a judge learned he had traveled outside Los Angeles County without prior consent for a private performance at a nightclub in San Jose, Calif. An altercation during the performance escalated into gunfire, and five people were shot.

February 24, 2015: Chris Brown says he is banned from entering Canada

Brown confirmed that he was denied entry into Canada based on his criminal history just hours before he was set to perform in the first of two performances in Toronto.

“The good people of the Canadian government wouldn’t allow me entry,” Brown wrote in a since-deleted Tweet. “I’ll be back this summer and will hopefully see all my Canadian fans!”

Live Nation issued a statement, saying the “New Flame” singer’s ban was due to “immigration issues.”

May 5, 2015: Chris Brown allegedly hits a man in Las Vegas

Brown was briefly named in a misdemeanor battery case in Las Vegas, where a man alleged the singer hit him after an argument over a basketball game at the Palms Casino Resort. However, the man declined to press charges.

“A verbal altercation on the court led to a physical fight, and the victim was punched by another male subject who was later identified as recording artist Chris Brown,” police said in a statement. “The victim alleging that he was battered … has told LVMPD detectives that he no longer wants to go forward with criminal charges.”

Brown, however, denied any involvement in the incident, with his publicist, Nicole Perna, telling CNN in a statement, “Chris is currently in Las Vegas as he is performing at Drai’s on [Tuesday] and receiving a key to the Strip that day as well.”

She continued, “He has a suite at the hotel that has a basketball court and invited friends to come play. An unruly individual showed up uninvited and was removed from the premises. Chris was not in an altercation with this person.”

July 24, 2015: Chris Brown is detained in the Philippines

Brown was allowed to leave the Philippines after being detained for several days following a fraud investigation over his cancellation of a New Year’s Eve concert in 2014. The organizers alleged that Brown had canceled the show after he received the $1 million to perform.

Elaine Tan, a spokeswoman of the Immigration Bureau, told the Associated Press that Brown was cleared after “verifying that Chris Brown has no other derogatory record apart from the [immigration lookout bulletin]” that had been issued.

December 2015: Chris Brown cancels his tour

Brown canceled 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: Chris Brown is investigated by police

Brown was investigated by police in Las Vegas after a woman alleged he beat her and stole her cell phone during a party at the Palms Casino Resort.

“The victim was alleged to have been battered by Brown, who at the same time took her cell phone,” the Las Vegas Metropolitan Police Department stated in a press release. “A verbal altercation took place as the victim was escorted out of the room by private security and into the hallway.”

In a statement to PEOPLE, Brown’s rep called the victim’s statements to police “unequivocally untrue” and that the victim was escorted out of the hotel by security because of her “wild behavior” while allegedly having a “total meltdown.”

“Her claim that she had her phone in her possession inside the after party and was able to take a photo causing an altercation with Chris Brown is a complete fabrication,” said the rep. “This seems like a clear case of retaliation for her bruised ego.”

June 2016: Chris Brown is sued by his ex-manager

In June 2016, Michael Guirguis (a.k.a. Mike G), a manager who Brown hired to help him rehabilitate his image after Brown assaulted Rihanna, filed a lawsuit against Brown claiming the singer had viciously attacked him on May 10.

In June 2016, Michael Guirguis (a.k.a. Mike G), the manager Brown hired to help him rehabilitate his image after he assaulted Rihanna, filed a lawsuit against Brown, claiming the singer had “brutally” attacked him on May 10.

According to The Blast, the matter was settled out of court in 2019 after several years of litigation.

August 2016: Chris Brown is arrested on suspicion of assault

Brown was arrested on suspicion of assault with a deadly weapon following a nine-hour standoff with police at his L.A. mansion after a woman called 911 claiming he had allegedly threatened her with a gun, according to the Los Angeles Times. Charges were never filed.

April 2017: Chris Brown allegedly punches photographer

Tampa police said Brown allegedly “sucker punched” a 28-year-old club photographer 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. Brown was not arrested at the time.

In July 2018, Brown was arrested for felony battery after a performance in West Palm Beach, Fla., for the April 2017 incident in Tampa. However, the Tampa Bay Times reported that the charge was dropped in August 2019 because of “insufficient evidence to prosecute.”

June 2017: Chris Brown is ordered to stay away from ex-girlfriend Karrueche Tran

PEOPLE confirmed that a judge granted Brown’s ex-girlfriend Tran a restraining order against the singer for five years. The model alleged 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, “B—- I will beat the s— out of you” and “I promise you I will make your life hell.”

Tran also alleged Brown punched her in the stomach twice and pushed her down the stairs several years ago, but no police report was filed during that time. These alleged incidents would have occurred while he was on probation for his assault against Rihanna.

After a tumultuous on-and-off-again relationship, Tran and Brown officially split in late 2014.

May 2018: Chris Brown is sued by unidentified woman for alleged sexual assault

An unidentified woman sued Brown and two others after she was allegedly held down and sexually assaulted in the singer’s home during a party on Feb. 23, 2017.

The woman — identified only as Jane Doe in court documents obtained by The Blast — claimed the group used “drugs, alcohol, threats and the presence of guns to intimidate, coerce and force unwilling female guests to perform sexual acts.”

She sued the trio for sexual battery, battery and assault and intentional infliction of emotional distress. Brown’s lawyer denied the allegations to TMZ.

“In another era, we might have called this a shakedown,” Geragos said of the lawsuit. “None of these allegations are true. Nobody has done anything with this … there’s no case here. Chris is a target.”

In April 2020, the lawsuit was dismissed and settled out of court.

December 2018: Chris Brown is charged with possession of a restricted species

Brown was charged with two criminal counts of having a restricted species — in this case, a capuchin monkey — without a permit. Each count carried a maximum sentence of six months in prison, TMZ reported. The outlet said the Los Angeles City Attorney’s Office is taking Brown to court on Feb. 6 and that the California Department of Fish and Wildlife was also investigating.

Patrick Foy, captain with the California Department of Fish and Wildlife, told PEOPLE they obtained a search warrant earlier in 2018 and visited Brown’s home in January. The singer wasn’t home at the time, but others there relinquished the monkey. The California Department of Fish and Wildlife filed their evidence with the LA City Attorney, who then filed charges.

According to AP News, prosecutors later dropped charges against Brown for possessing the monkey without a permit after the artist agreed to forfeit his rights to Fiji and pay $35,000 for the monkey’s care.

In June 2022, the Florida-based owner of the exotic animal breeding business who allegedly sold the monkey to Brown was sentenced to five years’ probation. Monkey breeder Jimmy Hammonds was ordered to pay a $90,000 fine to a fund operated by the U.S Fish & Wildlife Service and to serve eight months of his probation in home confinement.

January 2019: Chris Brown is detained in Paris

PEOPLE confirmed that Brown was detained in Paris on potential charges of aggravated rape and drug infractions after a woman filed a complaint with police.

“We confirm the detention in custody of Mr. Chris Brown and two other individuals on charges of aggravated rape and narcotics offenses. Police custody is still in progress,” the Paris Public Prosecutor’s Office told PEOPLE in a statement at the time.

Brown denied the accusations. The probe was later dropped, and Brown filed a defamation suit against the woman.

April 2021: Chris Brown’s housekeeper claims his dog attacked her sister

Brown’s former housekeeper filed a lawsuit in Los Angeles Superior Court stating that she and her sister were cleaning Brown’s house on Dec. 12, 2020, when Brown’s dog — a Caucasian shepherd, a breed which is also known as Caucasian Ovcharka and can weigh anywhere from 110 to 200 lbs. — “viciously” attacked her sister.

According to the lawsuit, the sister’s injuries required multiple days in the hospital and two surgeries.

In November 2022, Radar Online reported that a judge pushed the trial back to September 2023 after the sister had not yet undergone medical examinations related to the injuries.

May 6, 2021: Police break up a large party at Chris Brown’s mansion

In the early morning of May 6, 2021, L.A. police were called to Brown’s home, where “hundreds” of attendees were celebrating Brown’s 32nd birthday. According to police, the crowd was compliant, and no arrests were made.

When asked for comment by PEOPLE, the Los Angeles Police Department replied that “officers responded to a loud noise call” and “dispersed a large crowd.”

June 18, 2021: Chris Brown is accused of striking women at his home 

On June 18, 2021, L.A. police responded to a call from a woman at Brown’s home claiming that a male suspect — which several outlets, including TMZ and ABC7, reported being Brown — struck her in the back of the head. Brown was no longer at home when police arrived, but the officers recorded a crime report.

January 27, 2022: Chris Brown is sued by woman claiming he raped and drugged her in Miami

A woman identified as “Jane Doe” filed a $20 million lawsuit against Brown on Jan. 27, 2022, alleging that he drugged and raped her on Dec. 30, 2020, on a yacht in Miami. The woman also detailed two subsequent encounters with Brown, including an instance in August 2021 when Brown became “irate” because she would not respond to his alleged sexual advances.

While not directly addressing the claims, the day following the lawsuit, Brown shared a message on his Instagram Story saying, “Whenever I’m releasing music or projects, ‘THEY’ try to pull some real bulls—.”

However, Radar Online reported in March 2022 that the accuser’s lawyers dropped her case after Miami Beach police shared months of text messages between Brown and Doe. There were messages in which Doe repeatedly asked Brown if she could see him again after the alleged rape.

In August 2022, a judge dismissed the case, per NBC Palm Springs.