Chris Brown’s 23 Most Controversial Moments Ever


Last modified 12th May 2023.

Chris Brown…a name that can spark conversation (and controversy) in any room. We suggest you bring his name up with your friends and comment below how many heated conversations just started, we’re nosy! 

He’s a non-stop trending celebrity and dubbed one of the world’s best-selling male artists of all time. Breezy clearly has natural talent, once having been compared to Michael Jackson, but he has a knack for getting himself into some trouble. Sometimes, this bad boy behavior can really overshadow his achievements. 

So, what has the Run It hit-maker done to have his immensely successful career tarnished by negative headlines? Here’s a list of Chris Brown’s most controversial moments… 

1. Assaulting Rihanna 

February 2009

A whole slew of controversies would begin to surround Chris Brown following this infamous incident. In 2009, Brown and Rihanna’s fight inside a Lamborghini on the night prior to the Grammys made headlines across the globe.

Pictures circulated online of Rihanna with a split lip, a black eye and severe bruising all over her face, revealing the devastating effects of her boyfriend’s assault on her. Brown was eventually sentenced to five years of probation, a year of domestic violence counselling and six months of community service. 

2. Denied Entry to the UK and Canada 

June 2010/February 2015

Just over a year and some months following the physical violence incident with Rihanna, Breezy was denied a visa to the U.K. 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.”  

That’s not all. When Brown landed in Canada in 2015 for a series of gigs he had coming up, he was denied entry due to the criminal record he received after assaulting his ex-girlfriend. 

3. Breaking Down on Stage at BET Awards 

June 2010

At the end of Brown’s Michael Jackson tribute at the 2010 BET Awards, the star broke down on stage. He ended the tribute with an emotional performance of Man in the Mirror, dropped to his knees in self-reflection and later choked up whilst performing the self-improvement anthem.

He later said whilst accepting the AOL Fandemonium award that he was aware he let his fans down and wouldn’t ever do it again. 

4. Smashes Window on Good Morning America 

March 2011

More trouble for Chris! Good Morning America’s Robin Roberts asked Chris Brown about the progress of his life since the incident with Rihanna, which triggered the singer and struck a nerve. He performed a song and shortly after, stormed off the stage into his dressing room, where he smashed a window with a chair and made so much noise, that hair and makeup had to call security. 

5. Fighting with Drake 

June 2012

Both Chris Brown and Drake have had a thing with Rihanna, so it was only a matter of time before this celebrity feud would begin. After a Twitter war, things got physically violent in a New York nightclub a month later, which left them sued for $16 million. 

The bar sprawl which left eight people injured, kicked off when Brown sent a bottle of Champagne over to Drake’s table, which Drizzy then sent back with a note that read, “I’m fu**ing the love of your life.”

Shortly afterwards, the entourages began brawling and Drake punched Brown and smashed a bottle over him, leaving the Loyal singer with a ripped chin. Following the fight, Breezy posted a photo of his bruised face on social media.  

The duo have since made up and have collaborated on music together.

drake chris brown
champagnepapi | Instagram

6. Dressing as a Terrorist 

October 2012

What crazier way to attend your ex-girlfriend’s party than in a full terrorist costume fit with fake bullet casings wrapped around your robe? There isn’t one according to Brown, who showed up at Rihanna’s 2012 Halloween party in the full kit along with his triage.  

A picture of his controversial costume was posted to Instagram and Twitter which, unsurprisingly, received a lot of backlash. Thankfully for Brown, his mother, Joyce Hawkins, defended him, tweeting, “HALLOWEEN IS FOR FUN NOTHING MORE THAN JUST FUN. GET A LIFE PLEASE”.  

7. Punching Frank Ocean  

January 2013

When Brown unwelcomely took Frank Ocean’s parking spot outside his studio, there was a cause for a scene. Breezy tried to shake hands with Ocean and brush it off, but he must’ve still been bitter, as he refused the handshake.

How did Brown take this? Well, he threw a punch, allegedly threatened to shoot Ocean, saying “We can bust you too”, and left Ocean with a cut on his right index finger and left temple. It’s also said that one of Brown’s entourage used a homophobic slur against Ocean, heightening the situation.

So, in-case you ever get offered a handshake by Chris Brown, we suggest you don’t leave him hanging. 

8. Getting Involved in a Hit-and-Run  

July 2013

When Chris’ car hit a Mercedes in 2013, the officer dealing with the incident claimed that the singer refused to hand over his license and gave false insurance information. However, Brown stated in a tweet that “it’s not a hit and run if you get out of the car and exchange information”, later claiming that the woman saw a “payday from Chris Brown” even though he “followed the proper procedures”.

In the end, Brown came to a civil compromise with the victim, but was handed an extra 1,000 hours of community service. 

9. Assaulting Men in Washington 

October 2013

Just a few months following the hit-and-run incident, Breezy was arrested for felony assault, following an altercation with two men outside a Washington D.C. hotel. The victim was sent to hospital and Chris Brown was slapped with a charge reduced to a misdemeanor, 36 hours in jail and a stint in rehab for anger management. 

chris brown instagram
chrisbrownofficial | Instagram

10. Kicked Out of Rehab, Goes to Jail 

March 2014

Breezy is no stranger to shocking moments! A month into his treatment at the Malibu Rehab facility, he attended a family session which led him to throw a rock at his mom’s car window. The artist was immediately kicked out of rehab and sent straight into custody (131 days in jail) for violent behavior and probation violation. Strangely, he got upset because his mom wanted him to get the complete course of treatment.  

11. Reuniting with Rihanna 


Shortly after rumored to be dating Karrueche Tran, pictures began to surface of Breezy and his ex-girlfriend, Rihanna at a Lakers game, looking too close for comfort. 

Although Brown and Rih insisted they were “just friends” and nothing more, additional cozy photos together on Instagram began circulating and they even recorded a few collaborations (Birthday Cake, Nobody’s Business) together.

There was more controversy surrounding this reunion when Rihanna later revealed in an interview with Oprah that the pair still “love each other and we probably always will.”

Chris Brown and Rihanna broke up for good in May 2013. 

rihanna chris brown back together
badgalriri | Instagram

12. His Relationship with Karrueche  


Chris Brown’s relationships haven’t exactly been easy, with break-ups, fights and feuds all around. His love triangle with Karrueche and Rihanna has always made front-page news. Chris reportedly cheated on Karrueche with RiRi, which later led to Twitter feuds galore.  

RiRi initiated the verbal feud after she dissed Tran in her song Birthday Cake through lyrics such as, “Sweeter than that rice cake”, after which, she posted a picture online of her holding a pack of rice cakes with the caption, “ima make you my bitch”.  

Tran responded to the attack tweeting a famous Nicki Minaj lyric, “‘I’m Angelina, you’re Jen/C’mon you see where Brad is at.” Rih then took a final jab quoting Minaj’s rival, Lil Kim, “I’m a leader, y’all on some followin sh*t/Coming in dis game on some modelling sh*t.” 

Brown loves the girls, and the girls love him…but not each other apparently. Although he and Karrueche rekindled their romance after Rihanna’s involvement, the relationship remained toxic.

He split with her again after she met up with his (then) enemy Drake, telling fans at Power 106’s Cali Christmas, “I’m single… Fu*k that bi**h.” After getting together once more, the final straw for Karrueche was when she discovered via social media that Chris had a daughter, Royalty, with another woman. 

13. Fighting at Basketball Game 

May 2015

Another legal trouble is faced by Chris Brown. An unwelcome and “unruly individual” was said to have turned up at a basketball court where Chris and his friends were playing, which landed Brown in another legal altercation. The victim accused Brown of punching him, leading him to be treated in hospital. The singer’s publicist denied Brown’s involvement, as did Brown, and the man declined to press charges. 

14. Stuck in Philippines for Fraud Investigation 

July 2015

In 2015, fraud claims left Brown barred from leaving the Philippines for three days. The accusations said that he had received a full $1m pay check for a gig he cancelled on New Year’s Eve in 2014. However, the charges were dropped and Brown was given the green flag to leave once it had been verified that he had “no other derogatory record”.  

The artist took to social media shortly afterwards to profess his frustration at the situation, tweeting, “This is a very serious situation, and someone needs to be held accountable for mixing my name up in all this. I’ve done nothing wrong.” 

15. Accused of Punching Woman 

January 2016

In what was yet another controversial moment for Chris Brown, Brazilian model Liziane Gutierrez accused the star of punching her in a Las Vegas hotel and stealing her phone after the incident. Brown has always maintained his innocence, but it’s believed the pair settled for $70,000. The star’s lawyer stated that Gutierrez had been “making false accusations” and that “her statements are unequivocally untrue.” 

chris brown on stage
chrisbrownofficial | Instagram

16. Arrested for Pointing Gun at Baylee Curran 

August 2016

Beauty queen Baylee Curran accused Brown of pointing a gun at her face and demanding she leave the premises after she had been admiring diamond jewelry in his home. After the woman called the police “screaming”, a nine-hour standoff with the cops occurred outside Breezy’s home which eventually followed with him being taken into custody.

He was later released on bail for $250,000 and his lawyer took to Twitter to defend him, claiming that the accusations were “demonstrably false”. 

17. Punching Club Photographer 

April 2017

A photographer at Aja Channelside nightclub in Tampa was left with a bloody lip after snapping pictures of Brown. The artist insisted on no photos being taken and after getting frustrated, he reportedly “jumped over the couch and punched him in the face while he was cornered”. Video footage later supported these shocking claims. 

18. Karrueche Gets Restraining Order 

June 2017

As cute as they looked together, we told you Breezy’s relationship with Karrueche was toxic. The model and actress was granted a restraining order against her ex-beau for five whole years.

Apparently, Brown got aggressive when she refused to return diamonds he had bought her during their relationship. The star was also said to have messaged her multiple times, threatening to have her banned from all events, kill her, and that he would “beat the sh*t” out of her.  

Chris retaliated on Instagram writing, “I want nothing to do with her. You think I wanna chase or still be with someone who would try to destroy me??? She doesn’t need a restraining order from me. I need one from them.” 

chris brown karrueche
chrisbrownofficial | Instagram

19. Owns a Restricted Species 

December 2018

Chris Brown’s controversies never seem to end! When Brown posted a video of his three-year-old daughter, Royalty, playing with a Capuchin monkey, the California Department of Fish and Wildlife launched an investigation.

Upon finding the restricted species in his home for which he did not have a permit for, the star faced a possible jail term of six months, but was merely banned from owning more primates and given a $35,000 fine. 

20. Accused of Rape in Paris 

January 2019

In early 2019, a 24-year-old woman accused Chris Brown of rape which is said to have occurred at the Luxury Mandarin Oriental hotel. The artist was taken into custody for “potential charges of aggravated rape and drug infractions”, but was later released, with no charges filed against him.


chris brown hat
chrisbrownofficial | Instagram

21. Accused of Hitting Woman 

June 2021

He’s been involved in a string of violent episodes, so when he was once again accused of abuse in 2021, people were not surprised. A woman claimed that she and the singer had got into an argument which ended in Brown striking her hard enough for her hair weave to fall out.

There weren’t any injuries reported and no charges were faced by Brown. 

22. Accused of Sexual Assault 

January 2022

Just when you thought these accusers would leave Breezy alone, the singer gets embroiled in controversy again. In early 2022, the Grammy award-winning artist was accused of drugging and raping a woman on a yacht in Florida.

The woman who reportedly “feared for her life and career” claimed that Brown offered her an intoxicated drink which left her “disoriented, physically unstable”, before being led to a bedroom where he allegedly raped her.

The singer defended himself on Instagram writing, “I hope yall see this pattern. Whenever I’m releasing music or projects, ‘THEY’ try to pull some real bulls**t.”

It wasn’t long until Breezy was proven right and not guilty – he revealed text messages from the accuser proving his innocence, affirming that there was a consensual relationship between the two. She was quick to drop the case against him, but Chris will undoubtedly sue the accuser for defamation for making false accusations.

23. Fighting With Usher

May 2023

There’s no confirmation this fight actually happened, but if we’re to go by TMZ‘s word, it totally did. At Chris Brown’s 34th birthday celebrations, the hitmaker apparently got into a physical fight with singer Usher.

Rumor has it Usher tried to intervene when Chris was yelling at fellow singer Teyana Taylor for not wanting to talk to him. This apparent physical fight left Usher with a bloody nose.

chris brown usher
chrisbrownofficial | Instagram

There we have it, Chris Brown’s most controversial moments so far. What do you think? Does Breezy deserve to have his troubled past clouding over him, or should the public be more forgiving of his mistakes? 

Although he has made many poor choices, there is no denying his musical and artistic talent. Hopefully Chris Brown continues to work to become the best version of himself from here on out.  


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