Drake + Chris Brown: A Timeline Of Their Tumultuous Relationship

Chris Brown and Drake’s friendship has seen some serious twists and turns over the years. Although they started off as friendly associates, their relationship began to sour in 2010 when the Toronto-based rapper was linked to Breezy’s ex-girlfriend, Rihanna. From social media jabs to the bar brawl heard around the world in 2012, it’s easy to forget that these two were friends before they were foes. And now it looks like they’re back to being friends again? It’s definitely hard to keep up with their saga! That’s why VH1 has broken it down for you.

New photos on Instagram show that the two have been working together in the studio, leading us to believe that they’ve buried the hatchet following Brown’s release from prison. We hope this rekindled friendship lasts for a long time because we’re anxious to hear their latest collaboration. While we wait, here’s a look at Chris Brown and Drake’s relationship over the years.

December 2009

Chris Brown and Drake were both featured on Vibe’s revived issue after the urban magazine folded a few months prior.

February 2010

Drake brought out Chris Brown during a headlining performance at Virginia Commonwealth University (VCU) in Richmond, Virginia. This would mark their first performance together.

June 2010

Drake revealed in an interview with ExtraTV that he and Chris Brown were in the studio together. The two were also spotted clubbing in a New York nightclub. Drake and Rihanna dating rumors also started to make the rounds at this time.

November 2010


Drake is featured on the official remix of Brown’s song “Deuces” that also featured Kanye West, Rick Ross, T.I., Fabolous, and Andre 3000. The two were also spotted sitting close to each other at a Miami Heat game alongside Birdman, Mack Maine, Lil Wayne, and Bow Wow.

June 2011


Chris Brown remixes Drake’s “Marvin’s Room.”

November 2011

In a UK radio interview, DJ Whoo Kid says Chris Brown elbowed Drake in the chin only to tweet later that it was a joke.

May 2012

Chris Brown and Meek Mill got into a Twitter beef, supposedly over Rihanna. Drake chimed in tweeting “Oh that’s your ho? That’s our ho too. Lol,” to add insult to injury.  An unheard track called “Yamaha Mama” featuring both Brown and Drake unexpectedly hit the Internet.

June 2012

A brawl broke out between Chris and Drake’s entourages at New York City nightclub, W.i.P. It’s unclear what sparked the fight, but it’s rumored that it was a dissing match over Rihanna. In any event, Chris tweeted the result -a bloody gash on the side of his face.

April 2013

Drake addressed his feud with Brown, boasting that he “makes better music than him,” and admitting to dating Rihanna in an interview with East Village Radio’s “Keep It Thoro” host Elliott Wilson. Chris Brown tweets “Lol” response.

July 2013

Drake addressed the feud again in a GQ magazine interview stating that “I don’t want my name to be synonymous with that guy’s name” and that he wishes he and Brown “could talk it out man-to-man”.

June 2014

CB posted a video on Instagram of him rapping to Drake’s “0 to 100,” which was eventually deleted from his profile. 

July 2014

Chris and Drake were spotted in the studio together via Instagram. Brown also made a cameo in the Drake vs Blake ESPYs Awards skit. Another Instagram video surfaced of Chris playfully singing Drake’s “0 to 100.”

August 2014

The two were supposed to perform together on stage Monday night of Drake’s annual OVO Fest in Toronto but Chris’ legal troubles were allegedly the reason his management canceled the appearance at the last minute. [Photo: Getty Images]

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