The Good, the Bad, and the Ugly Side of Chris Brown’s Life

Many people only know Chris Brown because of his drama with Rihanna, but the singer had a successful career before their tumultuous relationship took over the headlines. After being discovered at age 13, Brown rose to become one of the “Kings of R&B” alongside Usher. He taught himself how to sing and dance.

Rihanna and Chris Brown / Chris Brown and his daughter / Chris Brown / Chris Brown
Source: Getty Images

It’s a shame that his career went down the drain after becoming public enemy number one in 2009. There was a time when people compared his talents to the late Michael Jackson. While he has tried to learn and grow from his mistakes, there is still a lot we don’t know about Chris Brown.

Music Was Always Part of His Life

Born on May 5, 1989, in Tappahannock, Virginia, Christopher Maurice Brown had a music-filled childhood. His mother, Joyce Hawkins, was a daycare center director, and his father, Clinton Brown, was a corrections officer. When his parents were at work, Brown would listen to his parents’ soul albums and dance around the house.

A middle school photo of Chris Brown
Source: Instagram/@chrisbrownofficial

His parents didn’t have much money, so Brown taught himself how to sing and dance. He would watch videos of Michael Jackson and imitate his moves. Brown wanted to become a performer, so he joined his church choir and entered the local talent shows. His mom quickly saw how gifted her son was.

He Used Music as an Outlet

When Brown sang Usher’s “My Way” at one of his talent shows, his mother was blown away by her son’s talent. She knew he could be a star and started to look for someone who could get him a record deal. Meanwhile, Brown’s home life was unpleasant, and music became his escape.

Chris Brown as a little boy hugging his mother.
Source: Instagram/@chrisbrownofficial

Brown’s parents divorced during his childhood, and his mom started dating again. One of her boyfriends terrified Brown because he was abusive. Brown once told his mother, “I just want you to know I love you, but I’m gonna take a baseball bat and kill him.” He wanted to protect her.

Discovered at a Gas Station

After his parents divorced, Brown went back and forth between his mom and dad. He started helping out at his father’s gas station, which helped his dreams come true. It was Brown’s lucky day when a production team from Hitmission Records happened to stop at the gas station while he was there.

A photo of Chris Brown as a teenager.
Source: Twitter

The producers were passing through on their search for new talent, and 13-year-old Brown was ready to perform on the spot. They were blown away by Brown’s voice and knew they had found a star. The team set him up with Lamont Fleming as a vocal coach, and Brown started to work on a demo.

He Went by “C. Sizzle”

Brown started working with Hitmission to arrange a demo package under the name “C. Sizzle.” They helped him approach contacts in New York to get a record deal. Tina Davis, a senior executive at Def Jam Records, was impressed when Brown auditioned for her, and she immediately took him to meet LA Reid.

The album cover art for C. Sizzle’s album.
Source: Amazon

Reid was the president of Island Def Jam Music Group, and he offered to sign Brown that day. However, Brown refused the proposal. Davis saw Brown’s talent and wanted to be part of his career. When she lost her job due to a corporate merger, Brown signed Davis as his manager.

He Had the Right Voice

Davis started promoting Brown to other labels, including Jive Records, J-Records, and Warner Bros. Records. Mark Pitts from Jive Records said he didn’t like the songs Brown had recorded, but he saw “huge potential.” All he needed to know was that Brown could sing.

Chris Brown stops by MTV's Total Request Live.
Photo by Paul Hawthorne/Getty Images

Ultimately, Brown decided to sign with Jive because they worked with the hottest singers like Justin Timberlake and Britney Spears. He initially was excited to mix singing with rapping, but Jive had a stronghold in the pop area, and they encouraged him to stick with singing.

He Dropped Out of School

While Brown was auditioning for record labels, he was still attending Essex High School in Virginia. However, he decided to drop out and move to New York when he was 16 to pursue his music career seriously. The decision certainly paid off.

Chris Brown relaxes in the recording studio.
Source: Imgur

Around the same time that he moved to New York, Brown started recording his debut album with Jive Records in 2005. Within three months, Brown had finished 50 songs, which had to be narrowed down to 14 for the final track list. Everyone believed in him.

Dedicated to His Craft

Brown worked with producers and songwriters, including Scott Storch, Cool & Dre, Sean Garrett, and Jazze Pha. Brown also wrote half of the tracks. He wanted his music to be relatable, so he wrote about things that all 16-year-olds were going through.

Chris Brown poses for a photo with his new CD.
Photo by Scott Gries/Getty Images

The whole album took less than eight weeks to finish, and the self-titled album was released in November 2005. The album was an instant hit and reached number two on the Billboard 200. It was a commercial success with iconic singles like “Run It” and “Yo (Excuse Me Miss).”

Dabbling in Acting

Shortly after his first tour, Brown landed a small role as a band geek on Season 4 of The O.C. He also made his film debut in Stomp the Yard with Ne-Yo, Meagan Good, and Columbus Short. He might not have had the biggest roles, but Brown proved himself.

Chris Brown and Columbus Short in a still from Stomp the Yard.
Source: Sony Pictures

Brown’s character was killed at the beginning of Stomp the Yard, but his performance was very convincing. He was used to being in front of the cameras after his journey through Japan and England was captured for the documentary Chris Brown’s Journey.

The Biggest Birthday Bash

When Brown turned 18, he wanted to go all out for his birthday party. He threw not one but two parties, which were featured on MTV’s My Super Sweet 16. They renamed the episode Chris Brown: My Sweet 18. One party was for his friends and family.

Chris Brown receives his birthday cake from Jennifer Hudson.
Photo by Jemal Countess/WireImage/Getty Images

His second party was a massive extravaganza for anyone who wanted to come. Everyone wanted to celebrate with the hottest singer of the time. Brown was also easy on the eyes, and he had a clean record then. He seemed like the perfect guy.

Only Girl in the World

Long before Brown was romantically linked to Rihanna, the two became friends around 2005 when they tried to make it in the music industry. They started as friends who collaborated on music, and three years later, they confirmed that they were dating.

Rihanna and Chris Brown pose on the red carpet.
Photo by KMazur/WireImage/Getty Images

The two had plenty of on-stage chemistry. Brown and Rihanna arrived separately at the 2008 Grammys, but they got cozy inside. Two days later, Brown sang for Rihanna at her 21st birthday party. He ended the song with a kiss, and the two jetted off to Barbados.

The Trouble Begins

A year after the two confirmed their relationship, Brown and Rihanna’s relationship took a horrifying turn. They were scheduled to perform together at the 2009 Grammys, but it was announced that they wouldn’t appear at the awards show. Rumors began to swirl about why the two pulled out.

Rihanna is in the hospital with bad facial injuries.
Source: Reddit

It was later revealed that Brown and Rihanna got into a physical altercation the night before the Grammys. She had two black eyes and multiple bruises, and he had a cut lip. Photos revealed Rihanna in the hospital with a bloody face. Brown was then arrested for felony battery.

He Pled Guilty

When the pair went to court in mid-2009, Brown pled guilty to the charges and was sentenced to five years of probation. He also had to do community service and go through domestic violence counseling. Rihanna also filed a restraining order against him.

Brown covers his face as he sits in court.
Photo by Lori Shepler-Pool/Getty Images

The news completely rocked the entertainment world. Everyone thought they were an adorable couple, and no one understood what led to the fight between them. The details of their altercation were also kept quiet for years. It wasn’t the end of their story.

It Damaged His Reputation

Brown became public enemy number one after people saw the pictures of Rihanna’s beaten face. A year after the incident, Brown was denied entry to the UK because of his assault charges. He had to cancel his short tour in England and Ireland.

Chris Brown takes part in an interview with Robin Roberts.
Source: YouTube

It hurt his career, and he lost many fans. In 2011, he showed his temper again after an interview with Robin Roberts on Good Morning America. He was asked about Rihanna, and Brown blew up in his dressing room, allegedly throwing a chair at a window.

A Second Chance

To most people’s surprise, Rihanna forgave Brown a few years after the incident. The pair rekindled their romance in 2012 after Rihanna confessed to Oprah that Brown was her “true love.” She claimed they rebuilt the trust between them, and they would always love each other.

Chris Brown and Rihanna attend a basketball game.
Photo by Noel Vasquez/Getty Images

Apparently, Rihanna dropped the restraining order against Brown in 2011 after forgiving him. She held a grudge for a long time. The pair were spotted sitting courtside and looked cozy on vacations. They seemed to have worked through their challenging problems.

Nightclub Brawl

Brown’s legal troubles were far from being over after his altercation with Rihanna. In 2012, eight people were injured in a fight at a New York nightclub involving Brown, Drake, and NBA player Tony Parker. Brown claimed that Drake instigated the fight.

blurry photos from the night at the bar / The shattered remains after the fight.
Source: YouTube / Twitter

There was tension between the singers before the incident, and things boiled over after Brown sent a bottle of champagne to Drake’s table, but the Canadian rapper told the waitress to return it to Brown. The two eventually made up and did a comedy skit at the ESPYs in 2014.

It’s Up for Interpretation

Brown has gotten many tattoos over the years, but none caused as much controversy as his 2012 neck tattoo. The large inking featured a woman’s face that appeared to be badly beaten. Many instantly assumed it was supposed to be Rihanna’s face after their fight.

A photo of the tattoo on Chris Browns neck.
Source: Twitter

The singer received plenty of backlash for the tattoo because it seemed like he was making light of domestic violence. However, Brown’s representatives clarified that the tattoo was a sugar skull, not his ex-girlfriend. The clarification didn’t stop the criticism against Brown.

They Broke Up… Again

After reconciling and trying to make their relationship work, Brown and Rihanna ended their romance for good in 2013. He confirmed their split during a radio interview, sharing that Rihanna was “doing her own thing,” but he would always love her.

s Rihanna and Chris Brown perform on stage.
Photo by Theo Wargo/WireImage/Getty Images

Brown said he was ready to move forward. Rihanna reflected on their relationship in a 2015 article stating she always wanted the best for Brown, but she put up with too much because she wanted to protect him. In 2017, he opened up in his documentary Welcome to My Life.

What Really Happened?

In Brown’s 2017 documentary, he shared his side of the story and gave people a look into what happened the night he and Rihanna got into a physical fight. He said there were many verbal and physical fights leading up to the incident.

Rihanna and Chris Brown attend a event.
Photo by Rick Diamond/WireImage/Getty Images

Brown said, “She would hit me, I would hit her, and it was never OK.” On the night of their fight, Brown admitted to cheating on Rihanna. She got angry and started screaming and hitting him while they were driving. Then, he did the unthinkable.

It Went Downhill

As she was yelling and hitting him, Brown turned and punched Rihanna. When he saw her busted lip, he couldn’t believe what he had done. She then reached for his crotch while grabbing his phone, and Brown said he bit her in retaliation because he was trying to drive.

Chris Brown talks about that night in his documentary.
Source: YouTube

Brown stated he wanted to resolve the situation because he loved her and didn’t want to hurt her. When he pulled over, Rihanna got out of the car and screamed for help, and the police intervened eventually. The documentary only shared his side of the story.

He Felt Like a Monster

There is no excuse for what Brown did to Rihanna, but he said he felt like a “monster” after the assault. In his statement after the altercation, Brown said his actions were “inexcusable,” and he felt ashamed for disappointing his mom and those who “taught him better.”

Chris Brown and Rihanna attend the 55th Annual GRAMMY Awards.
Photo by Christopher Polk/Getty Images

Brown apologized to Rihanna several times, but that didn’t change what he did to her. In his documentary, he also told the story as if all his actions were just responses to her actions. As someone who grew up around domestic abuse, he should have known better.

He Went to Jail

Brown has had many run-ins with the law, and he was sent to jail in October 2013. While in Washington DC, Brown and his bodyguard were involved in a fight outside his hotel. They were arrested for felony assault, and he spent 36 hours behind bars.

Chris Brown appears in court for a probation violation hearing.
Photo by Paul Buck-Pool\Getty Images

Brown was brought back to California to appear in court for the charges. During his hearing, Brown voluntarily entered rehab. Unfortunately, he was kicked out shortly after for violent behavior. He was then sentenced to three months at an anger management rehab facility.

He Had Problems

While in rehab, Brown was diagnosed with bipolar disorder and PTSD. The judge ordered Brown to stay another two months after his diagnosis because the doctors said his past violent behavior stemmed from previously undiagnosed disorders. He was apparently making great progress in the facility.

Chris Brown enters the H. Carl Moultrie I Court House.
Photo by Kris Connor/Getty Images

In the past, Brown had tried to self-medicate his troubles. The doctors worked to help him become less impulsive. While Brown said he was happy with the program, he reportedly felt disappointed when the judge extended his stay. The court wanted to make sure he was really changed.

He Violated the Rules

In March 2014, Brown was kicked out of the rehab facility before the end of his court-ordered stay. He reportedly violated the facility’s rules and was sentenced to 131 days in jail. He was credited the 234 days he had already served and had to finish the rest of his sentence.

Chris Brown is interviewed backstage at Power 105.1.
Photo by Brad Barket/Getty Images

After a few months, Brown was released early in June 2014. However, he was still on probation and had to complete community service and see a psychiatrist twice a week. The judge hoped the psychiatrist could help him for the better.

He Didn’t Learn His Lesson

Although he is a celebrity, laws still apply to Brown. When he left LA County to perform at a nightclub without consent from his probation officer, his probation was revoked. An altercation that left five people shot occurred at Brown’s concert, only making things worse.

 Chris Brown performs during the 'Between the Sheets' tour.
Photo by Chelsea Lauren/WireImage/Getty Images

A month later, he was denied entry into Canada because of his criminal history. Brown’s treatment clearly didn’t change him, and he learned nothing from his time in jail. Unsurprisingly, this wouldn’t be his last time in front of a judge.

He Became a Dad

In the midst of his legal woes, Brown became a father for the first time in 2014. He was friends with model Nia Guzman for years before they started dating, and she got pregnant. Guzman gave birth to their daughter Royalty in May 2014.

Chris Brown and daughter Royalty arrive at the 2015 Billboard Music Awards.
Photo by Gregg DeGuire/WireImage/Getty Images

With Brown in rehab and then in jail, the two didn’t stay together romantically. They also battled in court over child support and custody issues. Despite their issues, they worked through them to co-parent Royalty. Brown even named an album after his daughter.

Trapped in the Philippines

Although he was still on probation, Brown was permitted to fly to the Philippines in July 2015. Unfortunately, the trip was not worth it because he was held there for three days due to a fraud complaint against him for a canceled concert the previous New Year’s Eve.

Chris Brown attends the NYLON Midnight Garden Party.
Photo by Chelsea Lauren/Getty Images

The claim stated that Brown canceled after he was paid in full. Brown said he had nothing to do with it. When he tried to leave the country, Brown was stopped and had to wait three days to leave. Brown pleaded on social media for help.

Banned From Australia

While some people count the countries they have visited, Brown should count how many he is banned from. In December 2015, Brown was forced to cancel his Australia and New Zealand tour a week before the first show due to his visa troubles.

Chris Brown performs at Drai's Beach Club
Photo by Bryan Steffy/Getty Images

The Australian immigration minister, Peter Dutton, warned Brown that his visa would be denied if he tried to enter the country. The minister didn’t approve of Brown’s criminal history and didn’t want to risk any issues by allowing Brown into the country.

He Bought His Mom a House

While Brown has done many horrible things, there was a time when he wasn’t such a bad guy. When he was just 15 years old, Brown bought his mom a $1 million house. He had just made some money from his music career and wanted to thank his mom for everything she did.

A photo of Chris Brown and his mother.
Photo by Johnny Nunez/WireImage/Getty Images

When we were 15, we could barely afford to buy gum, let alone a million-dollar house. Brown’s mom was so grateful for the gift and her son’s generosity. She probably never imagined that he would go down such a dark path.

He Threatened Her

When Guzman announced that Brown was Royalty’s father, his then-girlfriend, Karrueche Tran, broke up with him. However, that wasn’t the end for them. In 2017, Tran filed a five-year restraining order against Brown after he sent threatening texts to her and demanded his gifts back.

hris Brown and Karrueche Tran attend Teyana Taylor's VII listening event.
Photo by Chelsea Lauren/WireImage/Getty Images

Tran testified that Brown asked her to return the diamond rings he gifted her. He reportedly texted her, “I can get my money back, and I’m tired of playing games. I will beat the sh*t out of you and make your life a living h*ll.”

Monkeying Around

While most of Brown’s criminal history has been violent, in 2018, he received a unique charge. He was charged with two counts of having a restricted species for having a capuchin monkey without a permit. Each count carried a maximum sentence of six months in jail.

A monkey is pictured with Chris’ shoes.
Source: Instagram/@chrisbrownofficial

As a result, Brown was ordered to give up his monkey. He also had to pay $35,000 to the facility where it would be held and couldn’t visit without special permission. Brown couldn’t own any other restricted species, and his home was randomly searched.

Father of Three

Brown started dating model Ammika Harris in 2015. They rekindled their relationship in 2019 when Harris gave birth to their son Aeko. While Brown was allegedly dating Harris, he was also in an on-and-off relationship with Diamond Brown. If two baby mamas weren’t enough, Brown got a third.

Chris gets a hug from his son.
Source: Instagram/@chrisbrownofficial

In January 2022, Diamond gave birth to her daughter. Initially, Diamond didn’t confirm that Brown was the father, but Brown posted a picture of their daughter on his Instagram in April 2022. The father of three has a lot of child support to pay.

Add France to His List

The countries Brown can travel to these days are becoming more and more limited. He probably won’t be welcomed back to France anytime soon after the 2019 incident in Paris. Brown was detained after a woman reported him to the police for sexual assault.

hris Brown attends 'The Lost Warhols' Collection exhibit.
Photo by Tibrina Hobson/Getty Images

He was held for a few days while investigators gathered evidence. Brown denied the accusations, sharing a photo saying the woman was lying, and none of it happened. He added that it was disrespectful to his daughter (his other children weren’t born yet) and family.

King of Burger Kings

Besides his music career, Brown has had a lucrative career as a fast-food chain owner. He owns 14 Burger King chains, which is pretty impressive. Those who want to own one of the chains have to have a net worth of at least $1.5 million and $500,000 in liquid assets.

Chris Brown attends the 1st Annual Xmas Toy Drive.
Photo by Imeh Akpanudosen/Getty Images

Luckily, Brown has a net worth of about $50 million, so he has more than enough to open more Burger King chains. He must have made a lot of money from those 14 restaurants. Brown was surprisingly smart about his investments.

Michael Jackson Is His Inspiration

When it comes to singing and dancing, Brown has always been inspired by Michael Jackson. He taught himself to dance by watching videos of Jackson, and his moves have impressed many people over the years. Brown’s admiration was somewhat mutual.

A fake photo of Chris Brown and Michael Jackson.
Source: Instagram/@chrisbrownofficial

Brown was starstruck when Jackson once called him to say he was a fan of his song, “Shortie Like Mine.” It’s not every day that your childhood idol tells you they are a fan of your work. Brown was so happy to hear from the King of Pop.

Once a Nominee, Always a Nominee

While many people say it is just an honor to be nominated, we can imagine that Brown is pretty tired of being nominated and not winning. The singer has been nominated for 19 Grammy Awards, but he only won once.

Chris Brown poses with his award for Best R&B Album.
Photo by Rick Diamond/WireImage/Getty Images

Brown won his only Grammy in 2012 for Best R&B Album for F.A.M.E. He has been nominated as an artist, featured artist, and songwriter, but he has only gotten lucky once. Brown has also been nominated for over 25 Billboard Music Awards but has only won four.

In Hot Water Again

Just when you thought Brown’s legal troubles couldn’t get any worse, they did. In January 2022, a woman filed a civil suit against Brown, falsely accusing him of sexual assault while on a yacht in Miami in December 2020. Brown denied the allegations and proved he didn’t do it.

hris Brown attends the 62nd Annual GRAMMY Awards.
Photo by Amy Sussman/Getty Images

He had text messages to prove that the relationship was consensual. Brown plans to sue the accuser for defamation for making false accusations. She reportedly kept asking to sleep with him and didn’t stop texting until he made plans to meet up with her.

Making Music

Besides his legal woes, Brown is best known for his music. He has released nine studio albums during his career and loves making music. In 2007, he took his passion further and founded the record label CBE (Chris Brown Entertainment or Culture Beyond Evolution) under Interscope Records.

Chris Brown is in the recording studio.
Source: YouTube

Brown signed Kevin McCall, Sabrina Antionette, and Sevyn Streeter under his label. Additionally, he signed singer-songwriter Joelle James and the rock group U.G.L.Y. However, after 2014, the label exclusively signed Brown’s work. The artists went on to work with other labels.

He Writes for Other Artists

Brown has had a lot of success on his own, but he has also written top hits for other popular artists. He has written songs for Rihanna, Joe Jonas, Pitbull, Tinashe, and David Guetta, to name a few. Brown has proven then he is not just an extraordinary performer.

Chris Brown performs onstage.
Photo by Kevin Winter/Getty Images

He has been nominated several times for his songwriting abilities. Brown is undeniably talented, but it’s unfortunate that his bad behavior has often overshadowed that. We wonder how much farther he could have gone if he hadn’t done some things from his past.

Hidden Talent

Everyone knows Brown can sing and dance, but he is also a skilled graffiti artist. Brown has painted since he was a child. He feels that it gives him a chance to express himself in whatever way. He creates street art under the pseudonym Konfused.

Chris Brown poses beside his graffiti.
Source: Tumblr

Brown partnered with street artist Kai to create work for Miami Art Basel. He painted buildings of different radio stations such as Hot 97. In 2015, Brown worked on some of the walls of the Grammy Museum. He mixed spray paint drawings with images of iconic musicians.

His Obsessed Fan

Many people have a singer or celebrity they look up to, but we don’t break into their homes. However, Brown had a fan who was so obsessed with him that she broke into his house and vandalized it in May 2015.

A photo of the woman who broke into Chris’ house.
Source: Instagram/@chrisbrownofficial

Brown went on Instagram to talk about the incident, saying his fan wrote “I love you” on the walls, cooked food in his kitchen, and painted her name on his cars. The 21-year-old woman was charged with burglary, vandalism, and stalking. His house was also robbed.

Bad Luck Brown

Maybe it was karma coming back to get him, but a few months after Brown’s stalker broke into his home, it was burglarized. A group of men with guns broke into his home and stole money and valuable items. Brown wasn’t upset about the money.

Chris Brown attends The 57th Annual GRAMMY Awards.
Photo by Christopher Polk/WireImage/Getty Images

Brown was more upset because the gunmen forced his aunt, who was home, into the closet. They threatened to kill her if she called the police, and she was traumatized by the experience. Brown felt horrible that his aunt went through such a terrifying thing.

Framed by a Beauty Queen

Brown must have horrible luck because he was framed by a lying beauty queen in 2016. Brown was arrested after an 11-hour stand-off with the police because a woman claimed he was threatening her with a gun inside. He refused to let the police in without a warrant.

Police talk to Chris Brown outside his home.
Source: YouTube

When the police returned with one, Brown refused to let them enter, causing a stand-off. The charges were eventually dropped against Brown after it was revealed that the woman had a history of making up death threats. The allegations were completely false.

It Came Back to Haunt Him

Although it has been 13 years since his assault on Rihanna, Brown’s past still follows him. His ex recently got married to A$AP Rocky in his music video, in which the rapper dissed Brown. In a noteworthy lyric, Rocky said, “I don’t beat my b**ch, I need my b**ch.”

Chris Brown / Rihanna and ASAP Rocky
Source: Getty Images

While Brown has yet to respond to the diss, hearing that his past is still being brought up must hurt. He hasn’t changed much over the years and is still getting into trouble, but Brown has tried to move forward. We can only hope he learns to control his anger and impulses.

Breezy Isn’t Done

Brown, who often goes by Breezy, announced his new album will be released in June 2022. The album title Breezy will be his tenth solo studio album. He has been teasing fans about his new music for a while, and everyone has been patiently waiting.

Chris Brown holds up a bra that was thrown on stage.
Photo by Scott Dudelson/Getty Images

Brown said his new album has “a different type of love mixed with heartbreak.” He also shared that the album will have the same amount of songs as his debut album from 2005, which had 16 songs. It will be refreshing to see Brown go back to his R&B roots.