If money can (or can’t) buy happiness, then is mainstream pop music success able (or not) to guarantee you some real estate in conversations anointing the greatest rapper?
Regardless of how much weight you place on artistic integrity and respecting ones street-bred roots, on paper, Drake’s success using that very formula is hard to dismiss. With multiple Grammys and a stable of Billboard chart records to his name, the Toronto native has gone from relative obscurity to one of hip-hop’s most commercially dominant artists of all time. In fact, with nearly 200 non-mixtape cuts alone to his name, it’s hard to escape the clutches of the OVO founder’s sound.
It’s not hard to see why either. Ever since he self-released his debut mixtape, 2006’s Room for Improvement, Drake’s marketability was never in doubt. A former small screen star on the Canadian teen drama Degrassi: The Next Generation, 2009’s So Far Gone was the real beginning of his superstardom, the heir apparent to Young Money Entertainment’s throne. Less than 10 years later and it’s clear he’s made good on the promise signaled by his early potential.
A lot has changed for Drake during that time but the essence of what makes him one of the most in-demand performers of this generation remains the same. With the help of a frenetic release schedule and some shrewd promotional techniques, he’s grown into a brand unto himself, keeping a tight stranglehold on the pop and hip-hop charts in the process. The past two years alone have seen him take over the streaming landscape with Views, More Life and Scorpion, putting together a two-year run that, from a numbers standpoint, feels unmatchable.
However, statistics are like swimsuit models: They show you a lot, but not everything. In Drizzy’s case, his detractors point to underwhelming lyricism and a monotonous, repetitive flow as two of the major reasons why he can’t be considered the genre’s undeniable king. There’s even a case to be made that, in his best work (which mostly shows up on Take Care, arguably his only long-form effort that will carry any historical significance with it in 20-30 years), he positions himself as more of a laid-back R&B crooner type than a man who spits one memorable bar after another.
In truth, Drake’s legacy really does circle back to that opening question – do commercial adulation and financial success as a crossover force buy you legend-type status? It’s a question that, with him or any other artist, can never be definitively answered; I mean, what if both sides are right? Is it possible to be so good at pop-rap that even the staunchest of heads can’t ignore you? Or will that person, regardless of their success level, be relegated to the wallflower status, allowing “real” emcees to take center stage?
Maybe Aubrey’s music is more akin to the dessert you have after a hearty main course. Lighter, far less substantial but no less memorable. Different taste buds are activated and you’re not necessarily putting those two dishes in the same category of culinary complexity or artistry, yet no one can deny that, as a confection, Drake’s tracks still (mostly) taste good going down.
Honestly, maybe I’m just hungry.
10. Take Care
Drizzy and Rihanna were a romantic couple once, with the former recently admitting that he wanted to start a family with the R&B empress. Of all their collaborations over the years, this one is still arguably the best showcase for their chemistry on (and presumably also away from) the mic. His smooth, understated delivery is punctuated by her equally memorable refrain: “If you let me, here’s what I’ll do/I’ll take care of you.” I’m sure he would’ve liked that.
9. Nice For What
Drake’s written more than a couple of floor-fillers during his time in the spotlight. From “The Motto” to “One Dance,” he and his production team definitely have an ear for the kind of hooks that mainstream audiences will instantly love. Such is the case for “Nice For What,” a high-energy cut that uses a classic Lauryn Hill as a backbone for the rapper to stretch his legs and step outside the confines of his normally more melancholic lyrics. Turns out happy Drake is still the best Drake.
8. Cameras/Good Ones Go Interlude
Coupled together on the Take Care tracklist, these two songs combine to add some pointed commentary about celebrity and the emptiness behind that kind of public facade to Drake’s lovelorn lyrics. “Only on camera, only on camera/Don’t listen to the lies, I swear they all lies/You know I could be your knight in shining Armor All tires,” he insists, trying to prove to an ex-girlfriend and perhaps even to his fan base that, behind all the trappings of fame, he’s still just the same regular guy.
7. Hold On, We’re Going Home
There may be a few that scoff at this pick, but let’s be real for a second: this buttery smooth single captures Drake at the height of his R&B sensibilities. Boasting a Majid Jordan feature that compliments the instrumental really well, Drizzy takes a page out of the R. Kelly songbook (a man he also surpassed in terms of top ten hits with this track), turning on the charm and romantic flair to craft a singularly sexy pop outing.
6. Look What You’ve Done
A delicate, low-key and incredibly touching Take Care highlight, “Look What You’ve Done” has Drizzy paying tribute to his mother Sandi, his grandmother Evelyn and his Uncle Steve. It gives listeners some deeply personal insight into the rapper’s formative years, especially when it came to spending habits that were deemed irresponsible by other members of his household.
5. Hotline Bling
It was the video that became one of the most meme-able pop culture moments of the decade and the track that kicked off Drake’s unprecedented run of chart-topping dominance in 2016. I’ll admit that, yes, the lyrics have always felt more than a little on the basic side here, but what really makes this a gorgeous song is that instrumental, a glittering island rhythm that transports you right to the heart of the rapper’s late-night angst.
4. Too Much
One of several outings that Drake has had with British-born Sampha, “Too Much” goes introspective as the Six God grapples with his own anxiety as he continues to push himself to become one of the genre’s most respected talents. “Most people in my position get complacent/Wanna come places with star girls, and they end up on them front pages/I’m quiet with it, I just ride with it/Moment I stop having fun with it, I’ll be done with it,” he spits, painting himself as someone who’s anything but complacent but, oddly enough, also stoic and seemingly joyless in his pursuit of greatness.
3. Best I Ever Had
The first meteoric hit to grace Drake’s catalogue, “Best I Ever Had” was inspired by Nebby, his on-again-off-again flame who supposedly is also the subject of “Hotline Bling.” “She was just the best,” he said during a Toronto radio interview shortly after the track dropped online. “[The] best woman that, that I’d ever had, period I guess. She represented everything about the city that I loved.”
If we’re talking about representation, “Best I Ever Had” not only stands out as Drake’s best pre-2016 crossover effort but also as the specific moment in time where he (along with Nicki Minaj) transitioned over to being the creative force that upheld Young Money Entertainment’s reputation as one of the most influential labels in hip-hop history.
2. Marvin’s Room
Named after Marvin Gaye’s studio where the recording session took place, “Marvin’s Room” is the most emotional and possibly the angriest track from a popular subsection of Drake’s work where he vents about loneliness, the girl who got away and why she should come back to him. The trippy, bass-heavy beat underscores the feeling of drunken instability as the rapper wanders around the more dangerous corners of his own psyche.
If the decision had been left up to Drizzy, “Marvin’s Room” may have been left on the cutting room floor during the assembly of Take Care. However, Noah “40” Shebib pushed back and may be the main reason it’s become one of the Canadian’s most respected cuts. “I challenge Drake when it comes to decision making,” 40 told Vibe. “He didn’t want to put ‘Marvin’s Room’ on Take Care and I was like, ‘Bro, f*ck you, you’ve gotta put this on there. It’s a moment.'”
1. Know Yourself
One of the less flashy tracks from If You’re Reading This it’s Too Late, “Know Yourself” makes good on the promise of its title. Drake knows where he comes from, knows where his sweet spot is as a rapper and, most of all, knows how to put it all together into an instantly relatable and easily accessible package.
Effortlessly laying down slinky vocals over top of a brooding, almost menacing-sounding trap beat, Drake positions himself as both a lover and victim of fame, making him a target for both artists and pundits in the hip-hop world. “N*ggas want my spot and don’t deserve it/I don’t like how serious they take themselves/I’ve always been me, I guess I know myself/Shakiness, man, I don’t have no time for that,” he explains during an early section of the song, crafting a biting mission statement with every breath.
There’s also a noticeable Toronto connection in his lyrics, admitting to The Fader that his inspiration came from a pretty unlikely source:
“I always used to be so envious, man, that Wiz Khalifa had that song “Black and Yellow,” and it was just a song about Pittsburgh. Like, the world was singing a song about Pittsburgh! And I was just so baffled, as a songwriter, at how you stumbled upon a hit record about Pittsburgh. Like, your city must be elated! They must be so proud. And I told myself, over the duration of my career, I would definitely have a song that strictly belonged to Toronto but that the world embraced. So, ‘Know Yourself’ was a big thing off my checklist.”
Top-drawer pop aspirations or not, “Know Yourself” is effective purely as a rap song but also as a nod to Drake’s tireless work ethic and indefatigable drive.
Honorable Mentions: Uptown, Light Up, Underground Kings, Energy, Legend, Jumpman, One Dance, Too Good, With You, Free Smoke, God’s Plan, Started at the Bottom, The Motto
Did your favorite Drake track fail to make the list? One of the rankings too high or too low for your taste? Drop those opinions in the comments section or call into our voicemail hotline to share your thoughts!