When it comes to hip-hop of the last decade, Drake and Rick Ross are about as good as it gets. With 12 No. 1 albums between them, a plethora of platinum plaques, a résumé of sold-out shows and a multitude of memorable verses, both artists have tenured spots at the top of rap's food chain. While Carol City, Fla. is a long way from Toronto, Canada, when Drizzy and Rozay link up there is a synergy that is rarely seen by artists who don’t rep the same area, clique or even the same country.
Aubrey and Ross’ musical relationship is one that started around the dawn of the decade, following the release of Drizzy’s lauded So Far Gone mixtape. And over the years, it has blossomed. Since 2010, the two have been featured on an album’s worth of songs together. At one point they were even working on a joint project that never materialized.
That’s not to say things have been all gold roses through the years. Drake’s beef with MMG artist Meek Mill, which started in the summer of 2015 before being officially squashed last year, naturally caused a rift, with Ross and Drake throwing subliminals toward the other on tracks during that time period. Ross’ calling out of Cash Money head Birdman surely didn’t help things.
In honor of Rozay and Drizzy recently rekindling their relationship with two new collabs—and possibly getting back to work on that joint project they thought we all forgot about—XXL chronicles the two rappers’ musical relationship.
Drake Speaks on Cosign From Rick RossMay 2010
Drake appears on the May 2010 cover of XXL magazine alongside labelmate Nicki Minaj. Following the release of his critically acclaimed mixtape So Far Gone and prior to the release of his debut album Thank Me Later, Aubrey reveals Rick Ross has reached out to collaborate.
“I just want to make the music,” he says. “For anyone that doesn’t believe in me, your favorite rappers do. They call me for hooks, features and all that. [Rick] Ross, Jeezy…For the people that don’t believe, the people that you do believe in got love for me. That’s all that matters.”
Rick Ross Collabs With Drake on “Ashton Martin Music”July 2010
Rozay taps Drake to appear on the third single from his Teflon Don album, “Ashton Martin Music,” also featuring Chrisette Michele. It would be the first of many collabs between the two rappers.
Rick Ross Collabs With Drake on “Made Men”Dec. 2010
Ross again recruits Drake to appear on his song “Made Men.” The 2 Tall Beats-produced song appears on the Miami rapper’s debut mixtape, Ashes to Ashes, which also features other memorable cuts like “9 Piece” and “John Doe.”
DJ Khaled Drops “I’m on One” Featuring Drake, Rick Ross and Lil WayneMay 2011
The second single off DJ Khaled’s fifth studio album We the Best Forever features Drake, Ross and Lil Wayne’s “I’m on One.” The song is nominated for a Grammy award in 2012 for Best Rap/Sung Collaboration.
Rick Ross Performs at 2011 OVO FestJuly 2011
Only in its second year, Drake’s OVO Festival goes down at the Molson Amphitheater in Toronto. Drizzy is able to get Rick Ross, The Weeknd, Lil Wayne, Nas, J. Cole and other stars for the big event.
Drake Teases Joint Project With Rick Ross Aug. 2011
“One of the people I enjoy rapping with most in this business is Rozay,” he says. “Me and him have talked about potentially doing something after our albums come out. I just love making songs with him. Every time we make a song it just seems to be something I love listening to after the fact when I’m in my car.”
Drake Drops “Free Spirit” Featuring Rick Ross Sept. 2011
The fourth of four promo tracks Drake put out in anticipation of his Take Care album, the non-commercial release "Free Spirit" features the rappers spitting over a Sade sample contorted by Drake’s go-to producer, Noah "40" Shebib.
Drake Reveals He's Working on Joint Mixtape With Rick Ross Nov. 2011
A week before Take Care drops, Drake announces a joint mixtape with Rick Ross is imminent.
“I have been working on a mixtape with Ross,” Drake tells XXL. “A mixtape called Y.O.L.O. [That means] You Only Live Once. I've been working on that for the last couple of weeks. We haven't really connected because he's been going through this thing with his health. I’ve been stashing my little beats and verses.”
Drake Puts Out Take Care Featuring “Lord Knows” With Rick RossNov. 2011
Drake releases his sophomore album Take Care, which features a Rozay guest 16 on the track “Lord Knows.” The dynamic duo preaches on the Just Blaze beat.
Rick Ross Releases “Stay Schemin’” Featuring Drake and French MontanaJan. 2012
Rick Ross gets Drake to hop on his Rich Forever mixtape track “Stay Schemin,’” which also features French Montana. Drake, then beefing with Common, uses his airtime to test the Chicago rapper.
The song also features the now famous Drake line and Ross adlib, “Bitch, you wasn't with me shootin' in the gym!”
Drake and Rick Ross Appear on French Montana’s “Pop That” June 2012
French Montana reunites Rick Ross and Drake on his hit single “Pop That,” adding Lil Wayne for good measure. The summer banger peaks at No. 2 on Billboard’s Hot Rap Songs chart.
Drake Reveals Collab Project With Rick Ross May Undergo Title ChangeJune 2012
Aubrey gives in update on the Y.O.L.O. joint album he is creating with Ross, saying the title may change due to the success of his song “The Motto,” which popularized the phrase.
"That title has become so—it's like an epidemic," Drake says. "I hope by the time we finish [the project], it would still hold weight and substance. We might have to call it something different now, 'cause that's just so attached to 'The Motto.'”
Rick Ross Drops “Diced Pineapples” Featuring Drake and Wale Aug. 2012
Ross and Drake link up once again on the sultry single “Diced Pineapples.” The track appears on Rozay’s fifth studio album, God Forgives, I Don’t. Wale also guests on the track.
Rick Ross’ “Us” Featuring Drake and Lil Reese Comes Out Oct. 2012
The Bawse puts the 6 God on yet another track, this time, adding him along with Lil Reese on the Young Chop-produced “Us” off The Black Bar Mitzvah mixtape.
DJ Khaled Drops “No New Friends” Featuring Drake, Rick Ross and Lil WayneJune 2013
DJ Khaled brings the gang back together for an “I’m on One” reunion of sorts, as he handpicks the trio of Drake, Ross and Lil Wayne again on the Suffering From Success single “No New Friends.”
Rick Ross Salutes Drake’s OVO MovementAug. 2013
On the heels of Drake dropping the new single “Hold on, We’re Going Home,” Ross hops on Twitter to give the Toronto transplant props.
“Salute mybrother @Drake on a classic hip hop moment #ovo,” he types.
Rick Ross Remixes “Hold on, We’re Going Home” Oct. 2013
Rick Ross Takes Shot at Drake on “Color Money” Track Dec. 2015
Following Drake and Meek Mill’s beef, which started in July 2015, Rozay has to choose sides. He rolls with the home team and takes a shot at Drake on the Black Market track “Color Money.”
“Color money got your bitch out on a world tour/My lil homie made a million on his girl tour,” Ross raps, referencing Drake’s “Back to Back” diss. “We back to back and down to whack a nigga unborn/Miami niggas got 'em changing all the gun laws/So run Forrest, got some shooters and they dying, too/I got more money than that pussy that you’re signed to.”
J.U.S.T.I.C.E. League Unearths Rick Ross and Drake Track Jan. 2016
Drake Takes Shot at Rick Ross on “Weston Road Flows” April 2016
While the heat is still on between Drake and Meek, Drizzy counters Rick Ross’ shot with a subliminal of his own. On the Views track “Weston Road Flows,” Drake appears to reference a former fling with Ross’ ex-fiancee Lira Galore.
“Yeah, I brought your wifey out to Saint Martin/She violated, I sent her back where it all started,” Drake raps. “How quick they are to forget about their bachelor apartment/Leave it to niggas like you to show em' light in the darkness.”
Rick Ross Is Ready to Go After DrakeAug. 2016
Ross is interviewed about the ongoing Drake and Meek beef on N.O.R.E. and DJ EFN's Drink Champs Podcast. He reveals he will be more than willing to get more involved if need be.
"If it's gotta go there, Renzel gonna jump off the porch on your ass," says Ross.
Rick Ross and Drake Meet to Try and Squash Beef Sept. 2016
“I heard Drake and Ross met in Prime 112 to squash the beef between Meek Mill and Drake. Listen, if that rumor is correct, that’s what we need to happen. Meek Mill, Drake, Ross, fuck beef. I’m just saying, I got the word, I don’t even think I’m supposed to blow it up. Let’s leave that shit the fuck alone, I love both of y’all, both of y’all my people’s, y'all both got my phone number, Ross got my phone number. But let’s leave that beef in the past."
Rick Ross Reveals Beef With Drake Is Squashed May 2017
“It was really just… We wasn’t even discussing anything negative because by the time we get in the room, it’s so much other things going on that it’s already, ‘Let’s get on some money,’” Ross reveals of the sit-down. “But I had to just make sure we at sat down and have some sort of understanding. It’s all about trying to touch nine figures.”
Drake Releases “Money in the Grave” Featuring Rick RossJune 2019
In celebration of the Toronto Raptors winning the franchise's first-ever NBA Championship, Drake drops a musical two-pack titled The Best in the World Pack. One song, “Money in the Grave,” features Aubrey reuniting with Rick Ross for the first time in years.
Rick Ross Releases “Gold Roses” With Drake July 2019
For the second time in back to back months, Ross and Drake connect. This time, Ross gets the OVO head honcho on board for the Port of Miami 2 single “Gold Roses.”