They've since reconciled, only to seemingly break up again.
Here's a look back at their rocky relationship: Brown stood beside his lawyer, Mark Geragos, at court in Los Angeles in March 2009.
While the couple has not been together in over a year, their past continues to inspire drama, most recently resulting in a beef between Chris and Soulja Boy.
While their history is pretty convoluted, we've attempted to map out a timeline of their very public on-and-off relationship.
Having signed with Jive Records in 2004, Brown released his self-titled debut studio album the following year.
It peaked at number two on the US Billboard 200 and was later certified double platinum by the Recording Industry Association of America (RIAA), selling an overall three million copies worldwide. " peaking atop the US Billboard Hot 100, Brown became the first male artist as a lead since Diddy in 1997 to have his debut single top the chart. earned Brown his first Grammy Award for Best R&B Album at the 54th Grammy Awards. However, after the release of Exclusive, Brown's albums have not been well received commercially or by music critics, with the exception of X, which received a normalized rating of 63.
His second album Exclusive (2007) spawned his second Hot 100 number one "Kiss Kiss", in addition to "With You" and "Forever". Apart from his work in the music industry, Brown has pursued an acting career.
Its successful lead single "Umbrella" became an international breakthrough in her career, as she won her first Grammy Award for Best Rap/Sung Collaboration with Jay Z in 2008.Check it out below.2011: Chris Brown and Karrueche meet on one of Tran's styling jobs, and the two begin dating.February 2012: Despite rumors of Chris Brown rekindling his relationship with Rihanna, it's reported that he and Tran are "doing quite well" and living together. Chris Brown and Karrueche Tran's relationship has been hard to keep track of over the last few years.Feuds and reconciliations have been frequent, and have often taken place through quickly deleted Instagram comments.