A complete timeline of Chris Brown's controversies and legal issues

We examine the singer's many controversies in the wake of ID's documentary 'Chris Brown: A History of Violence.'

Chris Brown has been in the spotlight for nearly two decades, but his career has not been without controversy.

The singer's eponymous debut album made him a fixture on the charts and the red carpet, but it wasn't long before Brown found himself embroiled in legal troubles. In 2009, Brown was charged with felony assault after a physical altercation with his then-girlfriend Rihanna. Similar accusations from a number of women have followed the artist in the ensuing 15 years, in addition to unrelated lawsuits, arrests, and detainments.

Brown's many legal issues are explored in a new documentary from ID and producers of Quiet on Set entitled Chris Brown: A History of Violence. In the astonishing series, a new accuser comes forth with allegations that Brown sexually assaulted her on a yacht belonging to Sean "Diddy" Combs.

Following the documentary's premiere on Oct. 27,  Entertainment Weekly examines Brown's most significant controversies and legal woes over the years.

Related: The View's Sunny Hostin 'shocked' by friend's teen asking if photos of Chris Brown's assault on Rihanna were AI-made

Feb. 2009: Chris Brown assaults then-girlfriend Rihanna

Brown was charged with felony assault after a verbal argument with then-girlfriend Rihanna escalated into physical violence, leaving the "Umbrella" singer hospitalized with visible injuries to her face.

Brown pled guilty to the charges and avoided jail time with a plea agreement, which included community service, five years probation, and domestic violence counseling.

Brown spoke about the incident on an episode of Chris Brown: Welcome to My Life (via BBC), explaining that his and Rihanna's relationship took a turn when she discovered he was having an affair with one of his employees. On the night in question, Rihanna had seen the woman at the party and it led to a heated argument during their drive home.

In his documentary, Brown admitted that the incident made him feel like a "monster" and would "haunt me forever."

For her part, Rihanna opened up about the incident during a 2009 interview on Good Morning America, saying that Brown threatened her life during the episode in order "to scare me." "All I kept thinking was, ‘When is it going to stop?’" she said, recalling that she "fended [Brown] off with my feet."

Rihanna added: “The more in love we became, the more dangerous we became for each other, equally as dangerous.”

March 2011: Brown melts down backstage during a 'Good Morning America' appearance

In 2011, Brown reportedly had a meltdown in the backstage area on Good Morning America after Robin Roberts repeatedly asked him about his relationship with Rihanna. Brown allegedly lost his temper backstage following a performance of his song "F.A.M.E.," leading to the show's hair and makeup team calling security after they heard a commotion from Brown's dressing room.

Reportedly, the singer smashed the window of his green room, raining shards of thick glass onto the crowded Manhattan street below. Police were summoned, but Brown and his entourage had left the scene by the time they arrived.

"As always, we ask questions that are relevant and newsworthy, and that's what we did in this interview with Mr. Brown," ABC News said in a statement after the incident.

Related: Soulja Boy opens up about his pals Chris Brown and Rihanna

Oct. 2013: Brown is arrested on felony assault charge; pleads to misdemeanor

Brown and his bodyguard, Christopher Hallosy, were arrested in Washington, D.C. after the two were involved in a “physical altercation” with two men outside of the W Hotel. At the time, the singer was still on probation following his 2009 assault of Rihanna.

Brown spent 36 hours in jail, and later plead guilty to misdemeanor assault. He was sentenced to time served in September 2014 for the incident.

Nov. 2013: Brown is ordered to leave rehab and sentenced to live-in anger management

Brown voluntarily entered a rehabilitation program after his D.C. arrest but was kicked out two weeks later after he violently lashed out during a family therapy session, smashing the window of his mother’s car with a rock.

Shortly after, he was ordered by a Los Angeles County Superior Court judge to spend 90 days in a live-in rehab facility for anger management.

March 2014: Brown is kicked out of a Malibu rehab center and arrested

Brown was kicked out of the court-ordered rehab program for violating the facility’s “internal rules,” per TMZ and subsequently jailed for violating the terms of his probation.

Two months later, he was sentenced to 131 days in prison for violating his probation. He was granted early release the following month provided he remained on probation and met with a psychiatrist twice a week.

July 2015: Brown is detained in the Philippines

Brown's legal troubles continued in 2015 after the singer was detained for three days in the Philippines in relation to a fraud complaint stemming from a canceled New Year's Eve concert at the end of 2014.

Per The Guardian, Brown was released after he obtained emigration clearance.

Jan. 2016: Brown is investigated over allegations of domestic violence

Police in Las Vegas launched an investigation into the singer after a woman alleged that Brown had stolen her phone and hit her after she had tried to take a photo with him during a party at the Palms Casino Resort.

Following the allegations, Brown posted and deleted an Instagram video denying he was involved and saying the accuser was “probably too ugly” to get into the party, per TMZ.

In a statement to PEOPLE, Brown’s reps called the victim’s statements “unequivocally untrue” and claimed the victim had “a total meltdown” before being escorted from Brown’s suite. "This seems like a clear case of retaliation for her bruised ego,” Brown’s reps said at the time.

The Clark County district attorney’s office later announced there was not enough evidence to pursue the case and Brown was not charged.

Related: Chris Brown finally gets his Michael Jackson tribute at BET Awards 2010. Amazing? Yes! Appropriate? Hmmm...

June 2016: Brown is sued by his ex-manager

In 2016, Mike G — whom Brown hired to rehab his image in the wake of assaulting Rihanna — sued the embattled musician for “viciously” attacking him. According to Variety, Mike G., whose real name is Michael M. Guirguis, alleged that Brown confined him to a room and punched him four times in the face and neck.

The suit noted that the assault was “unprovoked” and “just another attack in Brown’s long history of violent and abusive behavior.” The matter was settled out of court in 2019.

Aug. 2016: Brown is arrested following a stand-off with police; released without charges

The singer was arrested for assault with a deadly weapon following a nine-hour standoff at his home in Tarzana, California. The complaint stemmed from a woman who alleged Brown had threatened her with a gun after she admired some of his jewelry. The woman left the home, but Brown and his entourage reportedly refused to return her phone unless she signed a non-disclosure agreement. The victim was inevitably able to snatch her phone from one of Brown’s employees, after which she fled to a neighbor’s house and hid under a vehicle.

While police waited outside of his home with a search warrant, Brown posted three videos to Instagram in which he criticized the police for repeatedly coming after him. “When I call the police for stalker people that are endangering my life, they don’t come until the next day,” he said. “I ain’t did s—, ain’t gonna do s—. It’s always going to be f— the police. When you get the warrant, you can walk right up in here.”

Brown eventually met with authorities outside of his home while law enforcement searched the house. The singer was arrested for assault with a deadly weapon, but charges were never filed.

Related: Chris Brown releases new song after arrest What Would You Do?

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

Tran and Brown had an on-and-off relationship over the course of several years which ended in 2014. In 2017, a judge granted Tran a five-year restraining order against Brown after Tran testified that the singer became aggressive after she refused to return diamond jewelry he had gifted her.

Tran claimed in court (via PEOPLE) that Brown had repeatedly harassed her via text message, telling Tran he would “beat the s— out of” her. She claimed he also “threatened to kill me over text messages,” “threatened to harass my friends,” and “threatened to shoot me.”

Related: Rihanna slams Snapchat for controversial Chris Brown ad: 'Shame on you'

May 2018: Brown is sued for sexual assault; lawsuit settled out of court

An unidentified woman sued Brown and two of his friends for sexual battery, assault, and intentional infliction of emotional distress, amongst other charges. The victim alleged that she was forcibly held down against her will by Brown and his friend, Lowell Grissom Jr., along with an unidentified female cohort when she asked to leave a party. The trio also allegedly took the victim’s phone and would not return it.

When the victim’s mother became concerned, she phoned police who soon arrived at Brown’s home. At this point, Brown denied authorities entry and allegedly “ordered Grissom and others to hide a duffel bag filled with guns.” Later in the evening, the victim claims that the trio “entered into a conspiracy” to “use drugs, alcohol, threats and the presence of guns to intimidate, coerce and force unwilling female guests to perform sexual acts” for them.

The victim claimed that the unidentified woman “literally sat on top of” her head, “using her legs to pin Plaintiff down while forcing [her] to perform oral sex” as the doors leading out of the room were blocked and music was turned on “to cover up the sounds of any resistance.” Following that incident, the victim alleged that Grissom raped her twice more before she was returned her phone and allowed to leave the residence.

Brown’s lawyer, Mark Geragos, called the allegations “a shakedown” and noted that his client was “a target.”

The lawsuit was later dismissed in April 2020 after Brown settled out of court.

July 2018: Brown is arrested on felony battery warrant after a Florida concert; charges dropped due to insufficient evidence

Moments after wrapping up his show in West Palm Beach, Florida, the singer was taken into custody for an out-of-county warrant for felony battery. The warrant stemmed from an April 2017 incident in which police said Brown allegedly “sucker punched” a club photographer.

Brown was released after posting bond. He then appeared to address the arrest on Instagram by sharing a shirtless photo of himself on stage. “What’s NEW???” he wrote alongside an eye-roll emoji. “Show tomorrow!!!!”

Prosecutors later dropped the charges in August 2019 due to insufficient evidence.

Jan. 2019: Brown is detained in France

The singer was detained in Paris after a woman filed a report alleging that Brown had sexually assaulted her. "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 at the time.

Brown denied the allegations. When the charges were later dropped, he filed a defamation suit against his accuser.

Oct. 2021: Brown is sued on allegations of copyright infringement over several hit songs

Brown was sued by a U.K.-based music label who accused the singer of stealing elements of Red Rat’s 1997 Jamaican dancehall track “Tight Up Skirt” for his 2017 track “Privacy.” Brown inevitably reached a settlement with the company.

Around this time, Brown was twice sued for similar allegations that he stole elements of other artists’ music for use in his songs “Pills and Automobiles” and his duet with Drake, “No Guidance,” but those cases were dismissed.

Related: Drake, Chris Brown, Chance the Rapper support Lil Wayne after emotional tweets

Jan. 2022: Brown is sued by a woman who claims the singer drugged and raped her; judge dismisses case

On Jan. 27, 2022, a woman identified as “Jane Doe” filed a lawsuit against Brown alleging that the singer drugged and raped her on a yacht in Miami on Dec. 30, 2020.

In the filings, per PEOPLE, the woman claimed she met up with Brown two subsequent times following the assault and that he became “irate” when she refused his sexual advances.

In August 2022, a judge dismissed the case.

July 2024: Brown is sued by concertgoers for $50 million

Brown and Live Nation were named in a $50 million lawsuit by four concertgoers who attended the singer's "11:11" tour stop at the Dickies Arena in Fort Worth, Tex. on July 19, 2024. The plaintiffs allege that the singer and members of his entourage "attacked and brutally beat" them following the show.

The plaintiffs were awarded a temporary restraining order from Brown and the other named defendants. They also sought a temporary injunction to prevent Brown and the other defendants from deleting or otherwise tampering with documents and data relating to the alleged assault.

The case has not yet proceeded to trial.

Oct. 2024: Brown is accused of sexual assault in new documentary

In Chris Brown: A History of Violence, a woman identified only as Jane Doe comes forward with allegations that Brown sexually assaulted her in 2020 on a yacht belonging to Sean "Diddy" Combs, who is currently being held in federal prison without bail on charges of racketeering, sex trafficking, and transportation to engage in prostitution. Doe claims that on a trip to Miami in December of that year, a mutual acquaintance invited her to a party on Combs' boat. Doe, who at the time had recently moved to Los Angeles to pursue dancing, saw Brown at the party and took it as a "sign" that the artist might "be able to help me or guide me or give me some advice."

“We had talked, and he had handed me a drink. I'm not even sure...this is when my memory starts getting a little bit weird," Doe claimed. "I don't remember if I saw him pour it, but I just drank it and he just hands me another drink. As I'm standing there, I did start to feel tired and my body was feeling a little heavy."

Doe claimed that Brown took her to one of the yacht's bedrooms and proceeded to have nonconsensual sex with her.

Following the incident, Doe admits she spoke with Brown to gain "more clarity" about the encounter. "None of the text[s] disproved the occurrence of the sexual assault," Doe told PEOPLE. It wasn't until she went to therapy that Doe could admit to herself what occurred was a sexual assault. "I know it for a fact. Instead of telling myself that it wasn’t. It was. It was rape," she claimed.

Doe shared that she had a legal team assisting her with a case, but in 2022, a judge dismissed the matter "without prejudice" citing a lack of prosecution. But one of Doe's former attorneys, Ariel Mitchell, is currently representing her again.

In the documentary, Doe claimed that she received death threats following the assault. "Even coming forward as a Jane Doe, some people still found out who I was," she claimed. "Coming forward with this now, I just hope I can shed light on what really happened."

Chris Brown: A History of Violence is streaming on Discovery Plus.

Related: Chris Brown gets stuck midair at concert, has to be rescued with ladder