The Definitive Ranking of Every Drake and Rick Ross Collab

Last night, one of hip-hops most enduring duos added a new song to their oeuvre. Drake and Rick Ross have been appearing on songs together since 2009 and making one-on-one collabs since 2011, and they bring something special out of each other—all of these songs would be counted among their best by fans. As Drake put it on The Rap Radar Podcast, they’re always on the same, unspoken wavelength—he can send Ross something soulful like “Gold Roses” or upbeat like “Money in the Grave” and get the complimentary feature he’s looking for without any direction.

Their chemistry stems from the extensive time Drake spent in Ross’ native Florida, back when he lived in Miami for a spell in the early aughts. With Drake entering his imperial phase working on his critically acclaimed Take Care, and Ross in the midst of his own Teflon Don, the two were on similar creative peaks that yielded a lot of studio time and winning collaborations. “Whenever we get in the booth, I always play the big brother role. And he always be the young fly brother,” Ross once told me. “From day one, when I met him, he was just one of them people that I really fuck with. He knew I would've gotten my shoes muddy for him. We all became family and it just continued to be that way.”

There was even talk of a proper joint album, which Ross tentatively dubbed The YOLO Tape at the time. Obviously that never materialized, but short of a brief spell in the late 2010s when Drake was beefing with Ross protege Meek Mill, the two have never failed to deliver heaters that run the gamut from bodying Chicago drill beats to imploring women to get their names tattooed as the ultimate sign of devotion.

That run continues with Drake’s new song “Lemon Pepper Freestyle,” and if you believe Chad Ochocinco, just might lead to the elusive tape we’ve been waiting for. Until then, they already have enough to fill a playlist: here’s every song they appear on together, ranked.

17. “Fed Up” (2009)

DJ Khaled has an ear for connecting a range of artists on his collaborations. On 2010’s Victory, Khaled gets Jeezy, Rick Ross, Drake, Lil Wayne, and Usher for an all-star anthem about being tired of being tired. Renzel shouts out Khaled saying he’s got him for life; Drizzy raps about Weezy telling him not to retire on ‘em. Some bonds are forever, however this song pales in comparison to what these two and Khaled would do together and apart in the years following.

16.“Empire” (2011)

A song that leaked during the 2010s, “Empire” officially appeared on producer team J.U.S.T.I.C.E. League’s J.U.S.T.I.C.E. for All. Ross’ hook isn’t necessarily appropriate in the diversity, inclusion, and equity era, but Drake’s consistency even back then is impressive: “And to my city, I’m the two-three/Drug dealers live vicariously through me/No bench time, nickname Starter Drake/Franchise player, I don’t even get a water break.”

15. “She Will” (2011)

Rick Ross appears on Lil Wayne’s The Carter IV single “John,” which led to Wayne cutting his verse on the album cut “She Will.” But the original version with Renzel’s feature leaked and it clearly should’ve made the cut. Over T-Minus’ thunderous beat, Ross provides booming authority and luxurious bon-mots (“Craps table, Bellagio, I’m a big tipper”) while Drake handles hook duty.

14. “Deuces (Remix)” (2009)

Chris Brown and Tyga have their own musical chemistry, as seen on their joint album Fan of Fan. But on the remix to their song “Deuces,” Drake and Rick Ross appear alongside friends T.I., Kanye West, Fabolous, and André 3000, who was on a guest verse run at the time. It’s a vintage posse cut from the blog era, and one of the first times the two appeared on a track together. Great song but considering half a dozen people are on it, Drake-Rick Ross collab isn’t the first thing that comes to mind when talking about it.

13. “Money in the Grave” (2019)

By 2019, Drake and Ross had set such a high standard for their collaborations that sometimes the bar was just a little too high to clear. “Money in the Grave” is perfectly fine, but conditionally so. It will definitely send a party up, but on its own, there’s little to write home about save for a solid Drake flow. Considering Drake released this as a part of a two-song package (alongside the instantly forgettable “Omerta”) to celebrate the Toronto Raptors NBA championship win, you can forgive fans for expecting him to mirror that triumph on wax more definitively than the casual flexing he does here.

12. “No New Friends” (2013)

While “No New Friends” is typically associated with the meme of an awkward pose Drake unintentionally pulled off in the video while wearing Dada, the song itself is another one for DJ Khaled. It’s essentially a remix to “Started From the Bottom,” with the same players that made “I’m on One” an instant classic. Is that a bit formulaic? Sure, but when Drizzy, Ross and Wayne come together, as assembled by Khaled, the results are undeniable.

11. “Diced Pineapples” (2012)

Drizzy only handles hook duty here but “Call me crazy, shit—at least you callin” is among the best R&B work he’s ever done and the production, with its twinkling piano keys, is so cinematic it sounds like the score to a romantic drama set in the tropics. Bonus points for a killer Wale verse that brings the song home.

10. “Pop That” (2012)

“Pop That” was the soundtrack for standing on couches in the club for the entirety of summer 2012 and then some. There was a sustained period where you couldn’t drop an event posse cut without a sturdy 16 from Ross somewhere in the mix—mostly because two of his close personal friends French Montana and DJ Khaled were the ones pumping them out. But Ross never disappoints and neither did the songs, especially when they were in the midst of a crazy feature run like the one Drake was on while in-between albums in 2012.

9. “Gold Roses” (2019)

2019 was an interesting year for this duo, in that they gave listeners something for everyone. If you prefer club banger Drake & Ross, there’s “Money in the Grave” for your turn-up pleasure. But if you like to hear these two trading introspective bars over soulful beats, this is the one. Inspired by a conversation they had surrounding Nipsey Hussle’s untimely passing, Drake and Rozay reflect on their legacies and all they’ve accomplished, and plead with their critics to appreciate them while they’re still here.

8. “Us” (2012)

One of the most enjoyable aspects of Rick Ross’ imperial phase was his willingness to hop on the beat for any great, popular song and make it his own unofficial remix, from rap hits in his wheelhouse like 2 Chainz’ “Spend It” to bizarre choices that still somehow work like Lorde’s “Royals.” “Us” is one such Random Rozay Remix, wherein he brings Drake along to help him toe-tag Chicago rapper and Chief Keef affiliate Lil Reese’s banger “Us.” Ross sets the tempo and Drake comes through and smashes it with one of his most effortless verses to date.

7. “Made Men” (2011)

The only thing holding this song back from perfection is a superfluous third verse from Ross tacked on to the end. But those first two, my God. Ostentatious theater is Rick Ross’ whole raison d'etre and it’s always fun listening to him hype Drake up to match his boasts. Drake sees Ross’ “My yayo Usher Raymond, that bitch just keep on dancing” and raises him “One of my baddest women ever, I call her Rihanna—but that’s ‘cause her name is Rihanna.” It’s another collab of theirs that doesn’t have a proper album to call home, but quietly, it’s one of their best.

6. “Free Spirit” (2011)

Drake spent much of the run-up to Take Care dropping songs fans still consider among his best that he then just...neglected to put on the actual album. “Free Spirit” was the first time he and Ross collaborated on a song that’s just the two of them, and their chemistry is palpable. They’re the only two rappers who could fully lean into a concept as tongue-in-cheek ridiculous as “tat my name on you, so I know it’s real” and make the joke land with a wink and a smile. This was a beloved loosie lost to the streaming era until Drake finally gave it and other songs like it a proper home on his 2019 B-sides collection Care Package.

5. “Lemon Pepper Freestyle” (2021)

When Drake said “ten years in and you yet to hear my most impressive verses” on “Gold Roses,” he really meant it. And therein lies the reason for all the hype that comes with a Ross and Drake duet. They bring the best out of each other. From a slick bar about Ross’ ex-fiance to curving thirsty moms at Adonis’ PTA meetings, this is the Drake verse that just won’t stop—and he makes every bar count. It’s an ode to and an exercise in excellence, hence being titled after wings that taste like perfection.

4. “Aston Martin Music” (2010)

J.U.S.T.I.C.E. League and Renzel never miss. One of his and Drake’s earliest collaborations is the cinematic “Aston Martin Music” (not to be confused with Ross’ more bombastic “Maybach Music” series) from Teflon Don, wherein Ross enlists R&B Drake to get the Boss in his romance bag. The album version finds Drake, who at that point still hadn’t even dropped a studio album yet, relegated to hook duty but of course Drake couldn’t resist rapping on a beat this lush. He dropped a standalone verse fans still consider among his best today and titled it “Paris Morton Music” (Drake is never above pandering to a model or video vixen he’s infatuated with) and you can find an extended cut that puts his verse with the original song on Soundcloud and YouTube.

3. “I’m on One” (2011)

This isn’t just one of Drake’s best songs with Ross, it’s one of his best songs period, and arguably the birth of the “Drake featuring Drake” phenomenon he’d later brag about on “5AM in Toronto”: “Give these niggas the look, the verse and even the hook.” It takes a special rapper to wrestle some shine on a song that Drake otherwise eclipses like this one, but Ross manages to do it, with lines talking about burying money and calling Marc Jacobs personally.

2. “Lord Knows” (2011)

Take Care takes a lot of sonic and stylistic risks, but for the straightforward rap tune Drake put a call into Just Blaze for a soulful Roc-a-fella era beat and Rick Ross for one of the album’s only guest verses. Who else glides over bombastic, swelling, triumphant sounds as comfortably as Rozay? Drake does his thing on this track, but when Ross steps into the spotlight the song is his. Coming in one year after “Devil in a New Dress,” he was beginning to carve a role out for himself as an album scene-stealer. His influence is certainly felt across the rest of the album—Drake would take his “Y.O.L.O, you only live once” line and run with it on one of the breakout singles, “The Motto.” While “Free Spirit” endured as a fan favorite, “Lord Knows” is the song that cemented Drake and Ross as a formidable duo.

1. “Stay Schemin” (2012)

Some would call this Drake’s best feature verse, and one of his top five or ten overall. Take that heat and place it within the window of the Teflon Don - God Forgives I Don’t era, in other words Rick Ross at the height of his powers, and you have two stars colliding (with a damn near scene-stealing French Montana verse to boot). Ross loves to call his tracks movies, and this one sounds like Miami Vice or Bad Boys. In the span of 90 seconds, Drake went from the guy who once said “Diss me and you’ll never hear a reply for it” to the brash young gun who scored a flawless victory against the veteran Common, foreshadowing how he’d handle situations with Meek Mill and Pusha T years later. But even with that stellar verse and French’s hypnotic hook, this is still Rick Ross’ film and he sets the scene beautifully.

Originally Appeared on GQ