Chris Brown and Rihanna faced some serious ups and downs in their relationship before they called it quits.
The fellow pop stars originally met as teenagers in 2004, but it wasn’t until four years later that Brown and Rihanna sparked romance rumors. Brown was charged in 2009 for physically assaulting Rihanna. He pleaded guilty to one count of felony assault and was sentenced to five years of probation, as well as community service and domestic violence counseling.
Brown and Rihanna controversially rekindled their romance in 2012 before splitting again for good one year later.
“It’s in the past, and I don’t want to say, ‘Get over it,’ because it’s a very serious thing that is still relevant; it’s still real,” Rihanna told Vanity Fair in October 2015. “A lot of women, a lot of young girls, are still going through it. A lot of young boys too. It’s not a subject to sweep under the rug, so I can’t just dismiss it like it wasn’t anything, or I don’t take it seriously. But, for me, and anyone who’s been a victim of domestic abuse, nobody wants to even remember it.”
During his 2017 documentary, Chris Brown: Welcome To My Life, Brown recalled how infidelity played a role in the explosive fight that led to his arrest.
“My trust totally was lost with her,” he recalled at the time. “She hated me after that. I tried everything, she didn’t care. She just didn’t trust me after that. From there, it just went downhill because there were too many verbal fights, physical fights as well. Mutual sides.”
Rihanna was subsequently linked to Drake and Saudi billionaire businessman Hassan Jameel before finding love with A$AP Rocky. The couple started a family with two sons born in May 2022 and August 2023. Brown, for his part, welcomed daughter Royalty with Nia Guzman in 2014 and son Aeko with ex-girlfriend Ammika Harris in 2019. Brown and Diamond Brown welcomed their first child together in 2022 with the birth of daughter Lovely.
Keep scrolling to see Rihanna and Brown’s ups and downs over the years:
2004
The duo met at the Z100 Jingle Ball concert and continued to cross paths in the music industry as their individual careers were on the rise.
2008
“We are best friends. Honestly, [we are] like brother and sister,” Rihanna told MTV News after denying a romantic relationship with Brown. “He’s an amazing person, but we are not dating. We’re very close friends though. Very, very close.”
Later that year, Rihanna and Brown quietly started dating after months of speculation.
2009
Brown made headlines when he was arrested for physically assaulting Rihanna in his car on the night of that year’s Grammys. He pleaded guilty to the felony charge and served five years of probation, in addition to community service and domestic violence counseling.
“I’m pretty sure we can always be friends,” Brown told Larry King in his first interview after his arrest. “I don’t know about our relationship, but I just know definitely that we ended as friends.”
2012
Brown started seeing Karrueche Tran after his split from Rihanna. Brown and Tran briefly called it quits when he reconciled with Rihanna in 2012.
“We’ve built a trust again, and that’s it. We love each other and we probably always will. That’s not anything that we’re going to try to change. That’s not something you can shut off if you’ve ever been in love,” Rihanna said in a 2012 interview while calling Brown her “true love.”
Rihanna went on to say that she had forgiven Brown for assaulting her, adding, “It took me a long time. I was angry for a long time. I was resentful, I held a grudge. I was dark. I was angry. It was coming out in my music and my clothes and my attitude. I didn’t like that feeling. It was heavy.”
2013
One year — and two new song collaborations — later, Brown and Rihanna called it quits for good. “I mean, at the end of the day, she is doing her own thang. She is on the road,” he said during a 2013 interview with the Kyle and Jackie Show. “It’s always gonna be love. I’m a grown man, just gotta fast forward.”
2015
“I was very protective of him. I felt that people didn’t understand him,” Rihanna told Vanity Fair in 2015 about why she publicly protected Brown. “But you know, you realize after a while that in that situation you’re the enemy. You want the best for them, but if you remind them of their failures, or if you remind them of bad moments in their life, or even if you say, ‘I’m willing to put up with something.’ They think less of you — because they know you don’t deserve what they’re going to give.”
2017
Brown addressed the arrest — and the infamous photos of Rihanna’s injuries — in his 2017 documentary, Welcome to My Life, saying, “I look back at that picture and I’m like that’s not me, bro, that’s not me. I hate it to this day. That’s going to haunt me forever.”
According to Brown, he and Rihanna spoke about their combative energy before his arrest.
“There was always a point where we’d talk about it like, ‘What the f— are we doing?” he recalled. “Like, ‘I don’t like you slapping me.’ If I go on stage I got a scratch on my face and I gotta explain it like, ‘Oh, no I fell.’ If you got a scar or a bruise you gotta put makeup on. I’m not ever trying to put my hands on any female. I felt like a f—– monster.”
Brown continued: “I remember she tried to kick me, but then I really hit her, with a closed fist, I punched her. I busted her lip. When I saw it, I was in shock. I was like, ‘F—, why the hell did I hit her?’ From there, she just spit in my face, spit blood in my face and it enraged me even more.”
2018
A source exclusively told Us Weekly in January 2018 that Brown and Rihanna were still “good friends” and would “talk all the time.” At the same time, Brown surprised the public when he made a public birthday shout-out to Rihanna.
2018
Rihanna slammed Snapchat for an advertisement that included images of her and her ex-boyfriend and asked users if they’d rather “slap Rihanna” or “punch Chris Brown.”
“You spent money to animate something that would intentionally bring shame to [domestic violence] victims and made a joke of it!!!” she wrote via Instagram at the time. “This isn’t about my personal feelings, cause I don’t have much of them … but all the women, children and men that have been victims of DV in the past and especially the ones who haven’t made it out yet …. you let us down! Shame on you.”
2019
Rihanna posted an Instagram photo of her posing in her Savage x Fenty lingerie, to which Brown replied, “TO BREAK DA INTERNET! KEEP RISING QUEEN. MUSIC SOON PLEASE.” Brown quickly received backlash from fans for the comment and it wasn’t the first time since he also publicly reacted to her posts in 2017 and 2018.
Brown and Rihanna later celebrated Drake’s 33rd birthday at separate events days apart. “They’re still friends and have continued to stay in touch and talk,” an insider told Us at the time. “Chris will always love her and she’ll always be his No. 1.”
2022
Brown seemingly offered Rihanna his well wishes after news broke that she welcomed her first child with Rocky.
“Congratulations,” Brown wrote in his Instagram Story in May alongside emojis of a red heart, prayer hands and a pregnant person. The post didn’t mention Rihanna directly but it was posted soon after Us confirmed that Rihanna gave birth to her first baby boy with A$AP Rocky.
2024
Investigation Discovery’s Chris Brown: A History of Violence revisited the incident report from Brown’s arrest.
“Chris tried to shove her out of the car by opening the door and throwing her out. She had her seatbelt on so that didn’t work. Then he punched her in the eye. He kept punching her and her mouth was filling up with blood,” broadcast journalist Sharon Carpenter recalled about the night of the arrest. “Chris Brown had said to her, ‘I am going to beat the s— out of you.’ Then he said, ‘Now I am really going to kill you!’ He then put her in a chokehold so tight that she began to lose consciousness.”
Neither Rihanna nor Brown participated in the docuseries.
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