Chris Brown has worn many hats over the years—but when he makes headlines, it's usually not because of his smooth dance moves or his soulful light voice. Let’s take a deep dive into Brown's early fame, his hedonistic lifestyle, and of course, the scandals that have plagued him for almost his entire career.
1. He Is From A Disciplined Family
When your mom is a daycare center director and your dad is a corrections officer at a local prison, people expect you to be a tame, law-abiding citizen. This was the case for Christopher Maurice Brown, who joined the disciplined Brown family on May 5, 1989. But as we all know, little Brown chose a very unorthodox path—and he chose it surprisingly early.
2. He Loved Music
Brown discovered his love of music at a very young age when he started listening to his parents’ soul albums. Growing up in a small town in Virginia, Brown spent all his time discovering new styles of music. He knew that he had a passion for music, but did he have the talent? Well, there was only one way to find out.
3. He Was A “Self-Starter”
Still a child, Brown discovered his true gift—to sing and dance. In no time, he learned how to sing and dance, experimenting with different genres. He participated in several local talent shows, began to perform in his church choir, and did imitations of superstars like Usher and Michael Jackson.
At the time, Brown and his mother started searching for record deals. But at the same time, his home life was falling apart.
4. He Worried Sick About His Mom
At the time of the record deal search, Brown’s parents got a divorce. As if this didn’t affect Brown’s life enough, her mother got a new boyfriend—an ill-equipped stepfather who hurt Brown’s mom. Brown went through a phase of fear and fury—he desperately wanted to protect his mom, and he couldn't. Soon, it started taking a terrible toll on his mental health.
5. His Life Changed At a Gas Station
Most kids get discovered in a talent show or at an open mic. Chris Brown had a slightly more unique path. A team from Hitmission Records approached him...at his father's gas station. They were on the hunt for new talent, and the 13-year-old Brown was exactly what they were looking for. With Hitmission's help, Brown made his first record under the name C. Sizzle.
Ready, set, go!
6. He Moved To New York Alone
By the time he was 15, Chris Brown was ready to go “all in” to pursue his dream. Right after finishing his demo with Hitmission, Brown moved to New York and auditioned for Def Jam Recordings—who wanted to sign Brown immediately. I'm sure Brown couldn't believe his luck—but he was in for a rude awakening.
The senior executive who contacted Brown—Tina Davis—meant a lot to him. So when she lost her job at Def Jam after a corporate merger, the teenaged Brown had a big decision to make.
7. He Had To Choose Between Singing And Rapping
In a shocking move, Brown walked away from Def Jam. Instead, he paired up with Davis as his manager, and they signed with Jive Records. Jive had worked with stars like Britney Spears and Justin Timberlake, so he knew he was in good hands. But they had some demands. Brown was very excited to showcase his talent as a singer and a rapper, however, Jive Records made it clear that “it wasn’t acceptable yet” to sing and rap at the same time.
They gave Brown two choices, and we think he made the right one.
8. His First Album Was A Supernova
Chris Brown chose singing over rapping—and we'd say it paid off. His self-titled debut album hit the market in November 2005, selling 154,000 copies in its first week. Instantaneously, the album was number two on the US Billboard chart. It eventually hit triple platinum and earned Brown his first Grammy nominations. His career was on the rise, and he was only 16.
But a triple platinum album before you could drive wasn't enough. Brown wanted more.
9. He Joined The “Singer-Actor” Team
After becoming a household name as a singer, Brown joined the singer-actor train. He made his screen debut as a band geek in the fourth season of The OC. One role led to another, and in 2007, Brown found himself on the big screen, doing a movie with Ne-Yo: Stomp the Yard. He made other screen appearances here and there, but his acting career always remained as a side hustle—since his music career was on the rise again.
Stomp the Yard (2007), Rainforest Films
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10. His Life Was Extra
Chris Brown was not your ordinary teenager—I mean, he opened for Beyonce before he got his driver’s license. Therefore, when he turned 18, he didn’t shy away from the extravagant birthday party—which became an episode of an MTV show, titled Chris Brown: My Super 18.
His life was bound to be spectacular as long as he kept producing music. But Brown would soon learn that fame can be a double-edged sword.
Chris Brown: My Super 18 (2007), MTV
11. His Second Album Was A Winner
Brown was nervous about his second album, Exclusive. After the success of his debut, lots of fans had extremely high expectations. When Brown released the first single “Wall to Wall”, and it didn’t draw much attention, his fears piled up even more. However, with the album's second hit—"Kiss Kiss" featuring T-Pain, Brown was back on top.
Chris Brown was officially a superstar—and he saw just as much success in his dating life.
12. He Was Best Friends With Rihanna
In 2007, Brown’s relationship with his reportedly “best friend” Rihanna—the queen of pop—took a different turn. Brown and Rihanna had met when Brown was only 15 years old. They both rose to stardom at the same time, so it was no surprise that their paths crossed often. When the two realized that fans like to see them together, they started collaborating.
It seemed like a match made in heaven. It wasn't.
13. He Fantasized About Rihanna
Brown and Rihanna released an alternative version of Rihanna’s smash hit “Cinderella”. Brown wrote his own verse to the song in the style of a response. He wrote a line that revealed his true intentions, where he fantasized about Rihanna being his “queen”. Both of their fans loved them performing this song and their on-stage chemistry. Everyone was begging for the two of them to get together.
Unfortunately, the two didn’t give the fans what they desperately wanted.
14. He Didn’t Deny Anything, But Rihanna Did
In response to the rumors about the two, Rihanna said something unexpected—and a little disturbing if you know where this story ends. She said, “We are best friends, honestly, like brother and sister”. But they were definitely hiding something. Paparazzi kept spotting them together at afterparties, birthdays, and so on.
Finally, the jig was up. After almost eight months, the two revealed that they were dating. Still, they had more secrets to hide—and a couple more skeletons in their closet.
15. He Never Learned How To Love
The fans thought that their characters would mesh together as elegantly as their voices had—but they were mistaken. This relationship was far from healthy—Brown cheated on Rihanna shortly after they started dating, and the couple never survived this infidelity. He reported that “She hated me after that. I tried everything, she didn’t care. She just didn’t trust me after that”.
Then, the fights began.
16. His Relationship Was Poisonous
When you meet a girl, love her, and want her to be your wife, you tend to overlook the damaging, unhealthy parts of the relationship. Brown confirmed that there were too many arguments and fights between the two—so much that they constantly contemplated what they were doing. They were in an endless cycle…which needed to be broken.
Unfortunately, the way it happened was a worst-case scenario.
17. He Mysteriously Cancelled A Performance
The marvelous romance quickly transformed into a hazardous relationship and there were rumors of the two arguing and fighting. So when Brown and Rihanna canceled their highly awaited performance for the 2009 Grammy Awards on the day of the ceremony, people assumed that they finally called it off…the fans were already excited about the amazing breakup songs.
However, the truth was much darker than that.
18. His Relationship Went Downhill
The reason behind the mysterious last-minute cancellation was Rihanna’s appearance. A couple of hours before the show, Brown and Rihanna had a fight, and Brown did something he regretted his whole life—he attacked his girlfriend. With bruises on her face, Rihanna was unrecognizable and in no shape to perform. Once she left the hospital the other day, she immediately took action.
19. His Next Date Was At A Courthouse
With bruises on her face, Rihanna left Brown and filed a lawsuit. Officials took Brown from his house, and soon he found himself alone wearing an orange jumpsuit instead of wearing his amazing Grammy costume and performing with his amazing girlfriend. Then, the verdict came.
20. He Was Ready For His Punishment
Brown didn’t try to deny his wrongdoing. When he went to court, he readily pleaded guilty. This landed him a lighter deal: He had to go through counseling, five years of probation, and many hours of community labor. He was okay with his punishment, but he had no idea what was coming.
21. He Had To Stay Away From His Ex
Despite this deal, Brown wasn’t yet done getting his punishment. In addition to the counseling, community service, and probation, the judge also issued a restraining order for Brown, which prohibited him from coming close to the woman he loved as long as it was active. But his misery was far from over.
22. He Felt Like A Monster
All Hollywood talked about was the scandal between Brown and Rihanna, which made Brown feel like a “monster” over and over again. Once again, it took a toll on his mental health. He didn’t like the person he saw in the mirror, so he tried to make a change in the best way he knew how.
23. He Changed It Up
Brown was ready to put aside the court drama and get back to the studio. Maybe because of the changes he went through, or because of the path his idols followed, Brown wanted to experiment with different musical styles in this album. He said, “I want to be like how Prince, Michael, and Stevie Wonder were. They can cross over to any genre of music”.
His idea to transform his musical style might have been the beginning of a “new Chris Brown”. Unfortunately for him, people weren't ready to forget about the old Chris Brown.
24. He Received Backlash
Following the drop of the new album, Brown and his team realized that media backlash was affecting the album’s success. He knew that the "incident" would haunt him forever if he didn’t face the public and speak about it openly. Therefore, Brown—with his tail between his legs—spoke about the incident in an interview.
25. He Faced The Public
In September 2009, Brown was on the Larry King show, his first public appearance after the incident. Brown’s mother was with him the whole time, and Brown shared his experience with hurtful behavior both as a kid and in a relationship. He said, "I'm in shock, because, first of all, that's not who I am as a person, and that's not who I promise I want to be".
Brown was sick of the shame and misery…and he was about to explode.
Larry King Live (1985–2010), CNN
26. He Had a Meltdown On Stage
In 2010, Brown scored a huge gig. He was going to perform a song by one of his idols—Michael Jackson—at a BET Awards tribute. Filled with many different emotions, Brown broke down while performing “Man in the Mirror”. He started crying and fell to his knees. Some people thought that he was grieving Jackson’s loss, and some thought that it was about his own problems or a mixture of both.
Either way, this was Brown’s wake-up call.
27. He Rekindled An Old Romance
Brown and Rihanna shocked the world yet again when they got back together in 2012. In an interview with Oprah, Rihanna confirmed that she had dropped the restraining order in 2011 and that she was ready to forgive him. The two jumped back into a relationship pretty quickly, but were they able to leave their past behind? Everyone wondered.
28. He Was In A Bar Fight
Brown might have redeemed himself in the eyes of Rihanna, but that doesn't mean things would be easy the second time around. Brown's jealousy didn't help matters either. On a Saturday evening in a New York nightclub, Brown found himself in the middle of a bar fight when Drake teased him about his relationship with Rihanna. The Brown-Drake brawl got out of hand pronto.
29. He Said He Didn’t Instigate The Fight
Later that night, both Drake and Brown’s entourage went to the hospital with lots of grave injuries while the NYPD tried to understand who started the fight: Did Brown suffer a beatdown or did he succumb to his impulses and instigate the brawl himself? Reportedly, Drake was the first one to throw a bottle and the last one to leave the scene.
No matter who was responsible, this was a red flag for Rihanna.
30. His Relationship Ended Quickly
The scandalous couple tried to start all over again, but Brown and Rihanna had lots of history and irreversible scars. Rihanna said that Brown was the “love of her life”, yet the couple realized that love isn’t always enough. Although the real reason behind their final breakup is unknown, Rihanna confirmed our hypothesis when she said, "When you add up the pieces from the outside, it's not the cutest puzzle in the world”.
Brown had now lost the love of his life for a second time. Little surprise, then, that he fell into darkness.
31. He Fought With Another Celebrity
Outside of a recording studio, in January 2013, Brown lost his infamous temper again over a parking space. This time, the other party was Frank Ocean—another singer/rapper. Do you see the pattern here? Well, this incident is more ambiguous than his other fights, since each side reported that the other party started it. The rumors are endless: Someone threw a punch, someone was armed, etc…
32. He Worked ‘Till He Collapsed
The fights, the allegations, and the fast life…Brown’s body couldn’t handle it all. On August 9, 2013, someone made an urgent call and reported that Brown had a seizure. The medical team arrived, but Brown insisted that he didn’t want to be transported to the hospital, stating that he didn’t need any treatment. Later when his doctor tended to him, he revealed the bitter truth about the seizure.
33. The Reason Behind His Seizure Was Poignant
According to the doctor, Brown had been through a “non-epileptic seizure”, and the cause was clearly “intense fatigue and extreme emotional stress, both due to the continued onslaught of unfounded legal matters and the nonstop negativity". It was clear that Brown needed to take a break, but he seemed to be in a state of denial…and this mindset was causing him new problems every day.
34. His Fans Began To Bother Him
One day in 2013, outside of the W Hotel in Washington, three people approached Brown to take a picture. Brown refused to take a picture with the man—Parker Adams—saying that “I’m not down with that gay [stuff]”. According to the officers, Brown thought his words weren't strong enough—so he had to combine them with his punches. People on the site intervened and took Adams to the hospital—while Brown found himself in handcuffs yet again.
35. He Crossed The Line
Apparently, Brown broke the fan's nose—and broke the internet with yet another incident. He spent the night behind bars, and if convicted, he could add six more months to that. He pleaded not guilty and was released until the court date. As he left the courthouse, he saw his fans screaming his name—but for the first time, it terrified him.
36. He Had A Break
Brown’s judge gave him an offer he couldn't refuse: He would behave, voluntarily enter into rehab, get his treatment, and he could stay free. Brown agreed and paused his album. For once, he decided to follow the rules and do the right thing for his mental health, his name, and his future. There was only one problem: Brown was never a rule-follower.
37. He Got Kicked Out
Unfortunately, Brown's time in the Malibu treatment facility was shorter than predicted. he had some trouble with the laws there, and the rehabilitation center kicked him out. According to the deal with the judge, the next stop was the Northern Neck Regional Penitentiary. Brown’s behavior was something to analyze, and a deeper look into him revealed the devastating truth.
38. He Was Diagnosed With Bipolar Disorder
A lot of people were concerned about Chris Brown, and everyone who took a deeper look into his case started realizing that his behavior might stem from an untreated mental disorder. His probation officer reported that Brown “became aggressive and acted out physically due to his untreated mental health disorder” and the court documents confirmed that he had bipolar two. But would a diagnosis finally put him on the right path?
39. He Released A Song Behind Bars
Brown might have disappointed a lot of people, but never the people who enjoyed his music. Even behind bars, Brown wanted his team to release his latest song, “Loyal”. The song became one of his most successful releases, making it to the top 10 on the Billboard Charts.
Too bad Brown wasn’t there to enjoy it, physically and mentally.
40. He Was In A Love Triangle
In 2014, while trying to work on an album, Brown's love life was still full of drama. By now, Brown was in an on-again-off-again relationship with Karreuche Tran—a beautiful model and actress. The couple had been on a one-month break when Brown met Nia Guzman—another model. The two got along together instantly, and they had a short fling. At least, Brown thought it was short.
41. He Made A Decision
Brown still loved Tran, so he wanted to get back together again with her. But it wasn't that simple. He knew that if Tran knew about Guzman, it would be the end of his chances with her. So he did what all men do: He kept his mouth shut and hoped the past would never come back to haunt him. But life had other plans for him.
42. A New Girl Came To His Life
Almost a year after his fling with Guzman, Brown received some news—he became a father! Good luck keeping your fling a secret when she comes back with a kid! Immediately, Brown's whole life turned upside down. He broke up with Tran for good. He wanted to make it work, but he screwed that up when he slept with Guzman. But, at least he has some perspective:
He got one thing out of the fling that he would never take back: His daughter, Royalty.
43. People Got Used To Blaming Him
Brown was constantly working, recording tracks, and staying out of trouble. But a lot of people out there still hated him, and he couldn't stay out of the headlines for long. In August 2016, a woman called the officers and reported that Brown threatened her. When the officers came, Brown didn’t let them in. Although he was innocent at first, his confrontation with the LAPD was about to put him in the wrong, again.
44. He Never Learned How to Keep His Calm
While LAPD surrounded the house, Brown started posting videos on Instagram—shouting, and calling them “idiots”. He was furious because he was innocent, and he believed that the officers were “defacing his name and his character”. Still, you can’t call law enforcement “the worst gang in the world” if you don’t want to be in trouble.
In the blink of an eye, Brown was behind bars, waiting to pay the bail.
45. He Filed A Lawsuit
After his little showdown with the LAPD, Brown filed a lawsuit against his accuser to clear his name. It turned out that Brown was right, and the court found texts from the accuser saying that “I'm going to set him up and call the officers and say that he tried to shoot me and that will teach him a lesson”. Brown bitterly reported that these fake news and allegations keep coming because of his past and that he wants people to see the truth.
46. He Reconciled With His Old Enemies
After yet another detour, Brown was back on track for his new album. Brown enjoyed mixing up styles and working with different people, but people never imagined Brown working with Drake after the notorious bar fight back in 2012. When the new album—Indigo—came out, the song that featured Drake instantly shot to the top of the charts.
It was a nice footnote in Brown's career—but the bad news started to pile up yet again.
47. He Was On The News, Again
For once, Chris Brown got attention for his music, and his music only—until January 2022. Like a recurring nightmare, a woman appeared with allegations. The woman wanted to sue him for attacking her on his yacht in Miami. Brown denied the allegations and retaliated—but this time, only with the law.
48. He Lawyered Up
Brown planned to counter-sue the woman for defamation—after numerous cases similar to this, his lawyers were familiar with the logistics of the case. In this case, the accuser’s lawyer dropped the case after realizing that the allegations were not true, and Brown was off the hook due to lack of prosecution. He was in the clear before the court, but not before the public eye.
49. His Michael Jackson Tribute Performance Was Disappointing
In November of the same year, 2022, Brown announced that he would be performing a song in another Michael Jackson tribute at American Music Awards. His fans were tired of Brown canceling performances, and they were in for another disappointment. On November 18, Brown posted rehearsal footage from the performance and announced that he would not perform due to unknown reasons.
The second mysterious cancellation received even more backlash than the first.
50. He Made History
There are countless rumors and incidents about Brown’s private life—people talk about his values as a person all the time. However, his musical achievements were not up for debate. Brown made history by selling 197 million records and becoming one of the best-selling music artists. He changed the R&B scenery by becoming one of the highest-paid African American artists of all time.
Will he be remembered for that in the end? Only time will tell—but his odds don't look so good.
