16 Songs That Have Defined The Drake Era

On the eve of Views, a look at the songs that have helped to shape Drake’s legend so far.

Illustration Emily Keegin
April 27, 2016

In the 10 or so years since Drake first began making noise as a rapper, he has released three albums (and just as many mixtapes), won a Grammy, reigned atop the Billboard charts, become internet fodder for a horde of millennials adept at social media, graced the cover of numerous magazines (including FADER 100), and transformed the sound and face of Toronto’s music scene. Today, he is as dominant a force in our culture as 2Pac in the 1990s or Jay Z in the early-aughts. And so, on the eve of his album Views, we thought it best to take stock of 16 songs that have shaped his legend thus far. This is not a “Best Of” or a ranking of any sort, but an acknowledgement of the songs that represent Drake’s expanding influence in music, culture, and our lives.

"November 18" (2009)

Just seven years ago, Drake was largely unknown, more Canadian curiosity than bankable star. He was a mixed-race kid from the city of Toronto and former child-actor on a teen soap who sang as much as he rapped, and his songs were more like diary entries than big boasts. To say he lacked street credibility would not be inaccurate.

Arguably, it was the slow, syrupy “November 18” that eventually earned Drake accolades and acceptance from the streets. A deeply deferential nod to underground Houston rap culture, it name-checks UGK, Lil Keke, and Texas slang like boppa and candy paint. But what really laid bare Drake’s bonafides is the beat: a cleaned-up version of DJ Screw’s June 27 freestyle tape. It’s perhaps Screw’s most famous tape, using the slowed-down instrumental of a Kriss Kross deep cut (“Da Streets Ain’t Right,” which itself samples Biggie’s “Warning” and The Romantics’ 80s pop hit, “Talking In Your Sleep.”). In true Texas fashion, Drake whispers one verse and screws down another to fit the song’s woozy pace. He even credits DJ Screw as the song's producer. Proper respect.


In the end, Drake conflates Texas’s “slow” music culture with his approach to sex, declaring, memorably, Pussy’s only pussy and I get it when I need it. It’s what we now think of as quintessential Drake: dramatic, confessional, boyish, and charming all in one. And the place, for me, that serves as the quintessential example for the Peak Drake we now embrace. —JOSEPH PATEL

"Houstalantavegas" (2009)

In the half-dozen years since So Far Gone was released, Drake has gotten really good at singing. Listening back to "Houstalantavegas” today, he sounds almost entirely unrecognizable: his voice is thin and his tone hushed, as if he were signing to an audience of one. Beyond that, "Houstalantavegas"—which is named for the triad of cities which boast the richest strip-club culture—neatly encapsulates everything Drake was, is, and (probably) will be about. It’s sweet but selfish when he advices the dancer he desires, Until you find yourself, it’s impossible to loose you/ Because I never had you. But he's only being a bit naive if he truly believes that a flurry of ones will do it. The part where he offers to tattoo her name on his heart is corny as hell, even if this was before he got his first tattoo (the OVO owl on his shoulder blade). Yet here we are, all this time later, and he's still singing all the same things—only with more confidence and from someplace deeper in his diaphragm. —ZARA GOLDEN

"Successful" (2009)

Before the sad Drake meme there was just Sad Drake. And "Successful"—a slow-burning cut from So Far Gone—is a naked pity party for those of us who just want to be successful.

In 2009, I returned to New York after graduating school—I moved in with my boyfriend, found a studio space, and spent most of my waking hours wondering what the fuck I was doing with my life. Everything felt shiny and crisp and lonely. So Far Gone became the soundtrack to these early months, and “Successful” a late-evening favorite. It bumbled along and mixed perfectly with stale beer, but felt right for a post-grad school purgatory where dreams and desires felt both possible and highly unlikely.


Seven years later what strikes me is how honest "Successful" is. Drake is saying what he wants more than anything else, almost pleading for it. Now, knowing what happens, his gloominess seems so fragile. Money, money and the cars, cars and the clothes? He got them all. —EMILY KEEGIN

"Best I Ever Had" (2009)

The 100th and last episode of Degrassi: The Next Generation that a young Aubrey Graham appeared in was titled “Lost In Love Part 1.” The same day that episode aired in the U.S., Graham, as Drake, dropped his single “Best I Ever Had.” His TV character, Jimmy Brooks, was also a rapper—he and ex-girlfriend Ashley used to perform together, most notably at the talent show in season seven. It was like Lil’ Wayne had scooped him straight out of his TV wheelchair to join Young Money. I memorized I can make your pussy whistle/ Like the Andy Griffith theme song almost immediately.


“Best I Ever Had” was supplemented with a memorable music video where Drake coaches a women-only, booty shorts-wearing basketball team (“But Drake, all you did was teach us how to stretch!” one points out). The irony here, if you didn’t catch it, is that Graham is once again reprising a role. In addition to being his fictional school’s best and only rapper, Jimmy Brooks was the star of the Degrassi Panthers—that is, before another student brought a gun to school and shot him in the back, paralyzing him from the waist down and setting him on his path to become Degrassi’s coolest paraplegic basketball coach. After “Best I Ever Had” went three times platinum, Graham completed another seamless transition: from Jimmy Brooks to Drake. For those of us who always loved Jimmy, we rarely look back, but when we do it’s with warmth and nostalgia. And for me, You could have my heart or we could share it like the last slice remains the most romantic line of any Drake song to date. —LEAH MANDEL

"Find Your Love" (2010)

Drake was on the verge of dropping one of the year’s most anticipated albums, Thank Me Later, and still riding the wave from the album’s lead single, “Over,” when he dropped this mid-tempo R&B ballad. Its crooning shouldn't have come as a surprise, but it threw rap fans for a loop anyway. Was this hip hop? Was this R&B?


Eventually, it was embraced for what it actually was: a rapper wanting to win back the love of a past flame. “Find Your Love” ended up being a key launching point for Drake’s pop career—a reminder that he was, above all, just like the rest of us: prone to reminding an ex-lover that he was more than just a number. —BLAIRE MONROE

"Up All Night" (2010)

“Up All Night” is like a hit of cocaine: tinging with cold confidence, certain of its prowess. Having earned his place, on this song Drake takes pleasure in reaping the rewards of his new influence. He is waited on, the recipient of gifts: Kush rolled, glass full, I prefer the better things. If Sofia Coppola had made Marie Antoinette a decade later, “Up All Night” would have fit the film's soundtrack perfectly.


Like Drake’s threatened voodoo for you bitches, producer Boi-1da’s swelling strings and sharp snares give the track a grim murkiness, as if foreboding the inevitable comedown after the night’s end. This only makes Drake’s swagger feel more defiant: there's a sense not of living large despite the consequences, but because you know you’ll regret it later.

So the party goes on, with Nicki Minaj as its featured guest of honor. If the Young Money golden duo were flirtatious on 2009’s “Bedrock,” then here they play sparring partners in a face-off of power and influence. Minaj checks off her million-dollar mixtape earnings, gift for bars, and good looks with relish. (Still quotable, ad infinitum: Fuck I look like, hoe/ I look like yes and you look like no.) She is rightly thrilled to make broke bitches as bitter as the lemon rind garnishing the Hennessy cocktail you picture her sipping. —OWEN MYERS

"Headlines" (2011)

Drake was famously unhappy with Thank Me Later, his official YMCMB-released debut, so by the time his second label album Take Care came around, he'd spent a little more time writing, recording, and choosing singles that matched with his aspirations. That much is clear on "Headlines," the album's lead single. Dream production team of 40 and Boi-1da delivered an arpeggio-driven beat (which earned valid comparisons to songs by both Philip Glass and Santigold) over which Drake took on a new form, relaying an intentional, aggressive challenge to the Twitter-disseminated tropes about his music being strictly fodder for late-night texts to exes. Though there are plenty of emo moments all over Take Care—“Marvin’s Room,” “The Real Her”—”Headlines” was an introduction to Tough Drake.

Before the beard and the muscly thirst traps, back when he was still soft in the face and round in the belly, “Headlines” gave space for Drake to publicly reckon with having successfully made the transition from stealing his mother’s debit card to having millions for real. Today, he has no problem uttering threats or invoking the goons on the OVO payroll who will allegedly carry them out, but back in 2011, Drake’s raps about catching a body were the beginning of jokes, and serious questions, about his authenticity. Was the former child actor from Canada really declaring that he might end someone’s life? Yes, yes, he was. The drum programming and over-processed vocals might sound a little dated in retrospect, but “Headlines” remains quintessential: a mix of confidently delivered, deceptively simple boasts and crew loyalty shout-outs, paired with multiple hooks that’ll stick like glue to any listener’s head. They knowww, they knowww, they knowww. —RAWIYA KAMEIR

"Marvin's Room" (2011)

As a cry of loneliness polished into something worthy of millions of likes, and an ugly drunk phone call made aspirational, “Marvin’s Room” was not new for Drake. He'd already long been known as the “emo” rapper. But it was new for popular culture, and foreshadowed the widespread aestheticization of anxiety and depression on Twitter and Instagram. “Marvin’s Room” came before so sad today and before the rise of Sad Boys. I'd argue that it's gloriously unabashed misery feels like it paved the way for both.

It also seems worth noting that a year later, "humblebrag" was added to the dictionary, as we sought to describe the ways in which people were trying to garner pity and envy simultaneously on social media. It’s not merely that Drake is bummed on “Marvin’s Room,” or even that he’s relatably bummed, but that he’s self-consciously, and extremely lavishly, bummed.

Take the third verse of the song, where things get really desperate, and Drake pairs a jumped-up staccato flow with bars that are delivered as low-key as a phone conversation you don’t want anyone to overhear. He turns luxury and despair into a rhyming couplet: I was just calling ‘cause they were just leaving/ Talk to me, please, don’t have much to believe in. He makes himself into the villain, and he depicts it heroically, sprinting from the aggressive brag (Bitches came over, yeah we threw a party) to the pathetically humble (Too many drinks have been given to me). He asks for thankless emotional labor from a woman in his life—and he acknowledges it, too: I need someone to put this weight on. Drake doesn’t come out of “Marvin’s Room” looking good. And yet he also came out of it looking better than he ever had before. —AIMEE CLIFF

"The Motto" (2011)

Drake’s whole ethos in 2016 is culture-mashing; on tracks like the leaked “Controlla” (featuring Popcaan) and the Views single “One Dance," he plays the role of dues-paying fan and possible cultural interloper.

But before he was dipping into the sounds of Kingston, London, and Lagos for inspo, The Bay was among Drake’s regional influences of choice. On Take Care bonus track-turned-single “The Motto,” he and Lil Wayne take a ride through Oakland, referencing Bay Area pioneer Mac Dre in both lyrics (Rest in peace Mac Dre/ I’ma do it for The Bay) and sound (T-Minus’s sparse, shuffling production is hyphy-adjacent). For the video, Drake and Wayne filmed scenes in Oakland and recruited Mac Dre’s mom for a shout out—a precursor for all the right people in any given culture that Drake would go on to befriend.


“The Motto” also set the precedent for another Drake quality we’ve come to accept as the norm: Drake as meme. The phrase “YOLO” appears elsewhere on Take Care—Rick Ross raps YOLO, you only live once on “Lord Knows” and Drake later tweeted that Rozay had put him onto the acronym—but it was Drake’s hook on “The Motto” that turned the simple phrase into a global phenomenon. In the years since, turning casual references into internationally recognized catchphrases or images has become a calling card of his. Back in 2011, OVO’s clothing line existed just as a handful of T-shirts with owls emblazoned on them. In 2016, Drake-isms are a cottage industry of their own, popping up on both official and unofficial merch almost overnight; “The Motto” all but foreshadowed that. —RAWIYA KAMEIR

"Over My Dead Body" / "Too Much" (2013)

Drake was always supposed to be this sensitive rapper, but his most emotional pleas aren't delivered with much emotion. On “Over My Dead Body” and “Too Much”—twin songs with sentimental lyrics, rangy guest vocalists, and solo piano to signal seriousness—every sound and sentence is more dynamic than Drake's own voice. His performance is not convincing. But in his hollow, disaffected tone there is a truer meaning; he's only more resonant in monotony.


Because the single thing Drake best expresses, for me, is not love or hurt or power or humor but a failure to communicate. I do not think Drake is in touch with his feelings. Instead, fame and competition and relationships and phones have dulled the sharp edges of raw emotion, corrupted his ability to commit to even his own thoughts. He says I love you like he's thanking the guy who delivered his Seamless. I think it’s like that for a lot of people now: you say more than you mean, hoping the words make you mean something. —DUNCAN COOPER

"Hold On, We're Going Home" (2013)

If you write and read about music with any regularity, you’ll probably notice the word “timeless” pops up a lot. I’ve used it myself, but I still think it’s a mostly empty descriptor, or at the very least a vague one. Is the elemental piano melody on Rihanna’s “Stay” timeless because it’s generally unconcerned with the frills of contemporary pop? Is a fuzzy rock song by Sheer Mag timeless simply because it feels exciting but sounds vintage? Does timeless mean trend-proof, or something more? In a new-ish profile of OVO beat-maker Nineteen85, FADER contributor Nick Sylvester described Drake’s “Hold On, We’re Going Home,” which Nineteen85 co-produced alongside 40 and Majid Jordan, as a “timeless” song. It wasn’t the first time that word felt true, but I definitely didn’t question it. An early preview of the hopeless romance that pervades Nothing Was The Same, the song featured Drake singing and not rapping at all, only backed by Majid Al Maskat’s airy falsetto and a mostly uninvolved disco beat.


The lyrics are straightforwardly lovesick. Drake wonders: why are you one way when we’re alone and someone else out in the world? I know exactly who you could be, he croons, cementing the track’s position on wedding reception playlists from now until the sun explodes. It’s perfectly paced for that situation—lively enough for dancing and mellow enough to warrant holding someone close to your chest while you do it. I remember when it first hit radio, my childhood friend praised its unhurried tempo and the production’s soft, subtle glow. “This song is the exact vibe I want to live in always,” she said. Maybe that’s what timeless means: when a song’s so perfect that you can’t ever picture yourself living without it. —PATRICK D. MCDERMOTT

"Worst Behavior" (2013)

June Jordan, the black feminist writer and poet, was in search of an attitude. She said as much in Some of Us Did Not Die, her 2002 collection of essays, writing: “I am seeking an attitude. I am trying to find reasons for pride.” Jordan’s heady pronouncement mostly concerned discussions around gender identity and the disavowal of projected notions of female weakness, but her posture is important to keep in mind, because it is a sentiment and a mood that has connected some of our most important pop epics: from Whitney Houston’s early-’90s edict “I’m Every Woman” and 2Pac’s DJ Quik-assisted “Heartz of Men” to Kanye West’s thundering choreo-gospel, “On Sight.” This posture, again, appeared most memorably in 2013 on “Worst Behavior," the thump-crazy, DJ Dahi-produced cut from Nothing Was The Same. On it, Drake is all attitude, all flex—taking a symbolic victory lap at his most celebratory and his most seething. They used to never want to hear us/ Remember? he barks, cocky and assured, jolting past digressions to the present. He wants you to remember how you never believed, how you never thought he'd make it. Mothafucka never loved us/ Remember?/ Mothafucka/ Remember?


What Drake had come to represent before this song (a sort of post-macho rap archetype who found agency in his feelings) and who he would grow into after its release (a more hard-bodied, lovable anti-hero) find an axis point on “Worst Behavior” to thoroughly situate these dueling identities. The song becomes an ideal vehicle for both Drakes to exist side-by-side, because at its best "Worst" straddles vulnerability and hard-won pride more beautifully than any other Drake song. And it succeeds in doing so because it is triumphant in a way “Headlines” or “Energy,” for example, will never be. Here Drake doesn’t just seek an attitude, the song itself becomes an attitude—a call to arms, the feeling of sporting Superman’s cape in a dimly-lit club surrounded by phony friends and hangers-on. I can tell you many a time I have drunkenly rap-yelled the lyrics on sweaty Brooklyn dance floors. I, too, wanted everyone to know the hurt and obstacles I had overcome, the attitude I sought out, the man I had become and was still becoming. Mothafucka never loved us, remember? Remember. —JASON PARHAM

"Trophies" (2013)

The first time we heard Hit-Boy’s stately horn loop for “Trophies” was in a brief trailer signaling the imminent release of Nothing Was The Same in September 2013. That same month, Drake attended the announcement that All Star Weekend would be coming to Toronto and was photographed sitting next to a chortling Mayor Rob Ford. It was his first truly civic photo op, and just over two years later, a new mayor would present him with a key to the city. Much of his career had been him angling to become the face of the city—the sweetheart of the Screwface—and the vision had finally manifest. “Trophies” didn’t make the album but it dropped a few months later on New Years Eve Eve, an apt moment to toast victory.


Had hit records on my demo, Drake screams at a specific no one in particular. This a fuck-them-boys-forever, hold-a-grudge song. He’s doing his best Lil Fame, rapping with a puffed out chest (foreshadowing his own physical transformation). That goading, goon flow—Bitch, I use a walkie talkie just to get a beverage—is a continuation of NWTS’s bravado, and its message of transformative ascendancy foreshadowed that season’s unexpected playoff run for the Toronto Raptors. “Trophies” isn’t the song everyone remembers forever, but it is a timestamp that marked and hinted at a personal and industry-wide coup by Drake. Or maybe it was just the song you played at midnight to welcome 2014. Either way, that’s Drake doing what he does best: setting up the moments you’ll remember for years to come. —ANUPA MISTRY

"Hotline Bling" (2015)

Does any other Drake lyric stick to the brain as much as you used to call me on my cellphone? It's the kind of opening line that automatically plays in your head, sung by a stadium of fans, reminiscent of Journey's Just a small town girl or Biggie's It was all a dream. Like "Don't Stop Believing" or "Juicy," "Hotline Bling" never managed to hit No. 1 on the Hot 100. And yet these songs serve as mission statements for their respective artist's catalogues. "Hotline Bling" is bigger than 690 million YouTube views, or Super Bowl commercials, or SNL parodies, or No. 2 chart positions. It's a song that shook the culture. And it's not just Drake's biggest hit, it's undeniably his best. Every single bar is perfectly and deliciously memorable. (OK, maybe the bridge isn't the most spectacular moment, but it gives you a chance to take a breath, to sway a little bit to Drake being sad, and get ready to go back in twice as hard.) The beat, crafted by producer Nineteen85, is pulled from Timmy Thomas's 1973 song "Why Can't We Live Together," a sparse and affecting melody about the politics of peace. In the distant future, when a gray-haired Drake is live-streaming his Las Vegas residency on Facebook, he will, no doubt, get the most likes during his performance of "Hotline Bling." It's a signature song, now and forever. —MYLES TANZER

"Diamonds Dancing" (2015)

“Diamonds Dancing” was featured on What A Time To Be Alive, a mixtape with Future many felt would have benefited exponentially from Drake’s absence. But on “Diamonds,” Drake matches and even surpasses the pop-star-turned-Monster’s capacity for selfishness, manipulation, and abuse. You know what I need from you when I get home, Drake demands, thick with honey. You better not be on the phone/ Talking to your friends like you usually do/ Tellin’ that I never spend time with you/ It’s hard to find the time. This, even after Future describes the lifestyle that’s killing them and draining his relationships. Self-awareness left with his sobriety. His insecurities are covered with a patina of masculine pride made deliberately flimsy. Such bad tendencies are the negative image of “Good Ones Go,” the psyops of “Hotline Bling” distilled to its essence. He rambles for nearly two minutes on the outro—a place where he has bared his soul before—casting off vicious epithets with the same gorgeous voice that would write “little songs” that you could build self-worth around. If he’s balling in the middle of the club, no jersey, it’s because said jersey has been set ablaze on a lawn somewhere along with most of his belongings. And rightfully so. Love has become something meant to serve him. But it’s dishonest to condemn. We celebrate “Diamonds Dancing” as the work of an artist who, time and again, taps into the places most of us retreat from. —JORDAN DARVILLE

"Know Yourself" (2015)

Like my man, the wise country star Eric Church, just said, “My favorite artists are the ones that I can take their eight or ten albums and I can see the arc of their life.” Like my man, the wise rap star Drake, said himself: Please do not speak to me like I’m that Drake from four years ago/ I’m at a higher place. This song, thus far, to me, is Drake’s crowning achievement: his what-we-perceive-as inexorable maturation. If You’re Reading This It’s Too Late sounds so fundamentally different from the old stuff—leaner, more nimble; darker and harder—that it’s hard for me, right now, to even go back and listen to the old stuff. Eventually I will: years and years from now, I’ll take all the albums, line ‘em up, take stock of the arc of The Boy’s life. For now, I’m stuck in present-day Drake, for whom the frigid nights of Toronto seem to somehow feel increasingly chillier, more prone for treachery, and who then must pull his old friends around him like riot police in Testudo formation. I’ve always been me/ I guess I know myself he says, in words quite possibly written by someone else. I believe him completely. —AMOS BARSHAD

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16 Songs That Have Defined The Drake Era