When rappers team up for collaboration albums, fans get to hear their combined styles over a sustained project instead of a fleeting single.

Like Kanye and Jay Z’s Watch the Throne or Drake and Future’s game-changing If You’re Reading This It’s Too Late, collaboration projects can be career defining.

While Drake and Rick Ross have never made an album together, the two are frequent collaborators who have now amassed enough songs together to fill an album. One of the few repeat collaborators Drake has had who he isn’t in love with or has beef with, Rick Ross often makes appearances in Drake’s discography.


Their most recent single, LEMON PEPPER FREESTYLE, comes as part of Drake’s new EP, which is a teaser for the upcoming Certified Lover Boy. The new freestyle track reminds us that Rick Ross exists and adds to the pair’s catalogue, which spans both their careers and serves as a time capsule for eras of rap music (as well as the many past personas of Drake).

Taking a trip through the features is a nostalgia trip of mediocre rap songs, outdated videos, and genre-switch up. The two have been making music together for over a decade; and while some of the songs still hit, most of them feel like the vaguely memorable soundtracks to our awkward years: songs we only remember when their lyrics show up as Instagram captions.

Here’s how we rank them, from best and most redeemable to worst and most forgettable.

Money in the Grave (2019)

Famous Toronto Raptors devotee, Drake released a two song project to celebrate his team winning the 2019 NBA Championship. The song was the first collaboration from the two of them since Ross’s heyday in the early 2010s and one of their best.

The production may be simple, but it carries the high energy of both of their verses and emphasizes their token braggadocious flow. The song is simple, but addictive — the kind of song meant for workouts and parties. It brings out the best in both of them, the infectious energy that they both have the potential to rally behind them coming out in full force.

LEMON PEPPER FREESTYLE (2021)

The latest from the duo has the cadence of a song from Drake’s Views, but was produced by Ross’s label Maybach Music Group with the signature “Maybach Music’‘ vocal tag that was ubiquitous in the early 2010s. Now, not so much.

The song is easy listening, with a beat that samples the 2010 song “Pressure” by Quadron. It has one or two lines that stand out for their timeliness (cue the “practicing social distance from all these snitches” Instagram captions). Drake’s verse is the rap equivalent of his Architectural Digest tour — full of lavish status symbols but, ultimately, empty.

“Imagine me rapping ’bout if I never made it,” he says … effectively rapping about how it would be if he never made it. This kind of self-congratulatory bravado with barely concealed insecurity is classic Drake, which makes the song a classic for the fans who resonate with his typical, garnished but unoriginal flow.

It encapsulates all the elements of a Drake x Ross song because it’s exactly what you expect from both of them: not a wash, but the kind of song you listen to and immediately forget.

Gold Roses (2019)

Gold Roses is contemplative about the things Drake and Ross usually brag about — love, success, and their careers. Drake weaves tales of short lived relationships between lifestyle anecdotes (my favorite: “I never fly Spirit,” because same), while Ross reflects on the success he thought he would have versus his career reality, which he sees as being underrated.

“I was nominated, but never won a Grammy, but I understand they’ll never understand me” he starts with, then later says, “They’ll never love us.” Though overextended and self-indulgent, the single is compelling and stands alone in their discography for its distinct tone and overall quality.

Lord Knows (2011)

Although it’s not a highlight of the 2011 album Take Care, “Lord Knows” gets points just for being on it. The song is representative of Drake’s career-defining record in that it chronicles Drake figuring out his artistry, Ross at his peak, and both of them fantasizing about future success.

Drake also raps the line: “I know that showing emotion don’t make me a p*ssy,” which felt radical for a rapper at the time and solidified his reputation as the sadboy of rap music … a reputation he promptly discarded to get swole and make a trap album in 2015 — but: semantics.


I’m on One (2011)

The DJ Khaled/YMCMB lives up to its title — it’s on one. The track features Drake, Rick Ross, and Lil Wayne (who raps, “You’re a sell out, but I ain’t buying” but has since sold out as a Donald Trump supporter so there’s that.) The video looks extremely low budget, shot on a gloomy day in Miami in between a hotel room and a parking lot and DJ Khaled drinking a Four Loko … He was definitely on one.

The song is actually still good and features the chorus of the previously unreleased “Trust Issues,” by Drake. The resulting track has the opposite vibe to the originally melancholy heartbreak song and is instead a self-aggrandizing song about their own success.

If it feels like every Drake song is him talking about how far he’s made it, it’s because that might be true. “I’m on One” is unapologetic, though his future persona makes the beardless, younger version of him seem a little too premature, while both Ross and Wayne’s fame have depleted since.

No New Friends (2013)

“No New Friends” was undeniably iconic in its time and remains a staple in social media lexicon. In hindsight, the repeated “no new friends” lyrics is pretty much the only thing worth remembering in the song. The DJ Khaled/YMCMB production features Lil Wayne and shows pretty forgettable, yet well produced, performances from Wayne, Ross and Drake. But nostalgia wins this round, because something about it still hits.

Stay Schemin (2012)

“Stay Schemin” appeared on Ross’s 2012 mixtape Rich Forever and features Drake, French Montana, and Ross’s terrible vocals in the chorus. French Montana and Drake also have their share of collaborations, like “No Shopping,” and “No Stylist,” which came later.

“Stay Schemin” was controversial for the line that mentioned Vanessa and Kobe’s divorce filing: “B**ch, you wasn’t with me shootin’ in the gym.” It was also a response to Common’s diss of him in the song “Sweet.” The controversy and the brewing beef have become par for the course, but the young rapper at the time seemed audacious. The song marks an early sign of what we now know as Drake’s agitated, ego-driven personality that makes him ever-ready to defend himself on a verse.

Aston Martin Music (2010)

Aston Martin Music really is Aston Martin music for the 2010s, the kind of half-R&B, half pop, half rap, vibe that dominated the charts in 2010 alongside Usher, Jason Derulo, and Young Money. The song has the vibe of the kind of person who says they want someone to ride or die for them … while bringing nothing to the table except maybe big talk and big dreams of having an Aston Martin because they heard it in a Drake song.

Diced Pineapples (2012)

The piano-heavy track has a different energy compared to most Drake x Ross collabs. The song is sensual and an attempt to be romantic, though it veers towards objectifying and still can’t resist mentioning status symbols and money. The video is essentially an ad for Ciroc and is similar to “Aston Martin Music” for its R&B vibe. Drake sings the chorus but the song’s standout is actually Wale, who raps the opening and ending verse and brings life to the otherwise bland track.

Free Spirit (2011)

The song starts with the repeated cry of “tat my name on you so I know it’s real,” which Drake later sings on the chorus, followed by the ending quip, “When I go you’ll still be mine.” The song is just a description of a toxic relationship, but in a way that felt romantic in 2011. So, more “ride or die” vibes.

The stripped back production is mostly just a looped beat track, a pumped up bass, and a sax that comes in mid-chorus — oh to be a producer in 2011. The song is forgettable beyond its anthemic first demand, and its lyrics are better left in the past, not to be exhumed.

Pop That (2013)

“Pop That” feels so apt for 2013 — the overwhelming club-ready production, the overt oversexualization of women, and the anchoring line “what you twerkin with.” 2013 marked a change in mainstream rap, which went from R&B dominated, to more engineered and shamelessly wild, accompanied by the twerking trend.

Though this was a few years before the trap takeover, the song marks a phase of Drake that was less defined by the romance of Take Care and instead saw the birth of “Champagne Papi.” Alongside French Montana, Drake and Ross revel in hedonism and objectification in a song made up of unharmonious noise and forgettable, unimpressive lyrics.

Deuces Remix (2010)

All I can say is, yikes!

The 2010 remix of Chr*s Br*wn’s “Deuces” features Drake, T.I, Kanye West, Fabolous, Rick Ross, and André 3000. The lineup is stacked and the song approaches seven minutes — and for what? None of them deliver career performances, and it all happens in service of … Chris Brown? Not something we need to revisit.


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