The Making of a Legend: How Drake Became the Greatest Rapper of Our Generation

By: Paul Cantor
Drake performing at Governors Ball 2015
Photography by Maria Jose Govea
  TAGS:   Article, Exclusive

On a cool spring night, while well-heeled urbanites get on with their post-dinner debauchery—a calming glass of pinot at a wine bar; tasty froyo at one of those wacky places with the sixteen handles; or something similarly cheeky—the line outside of the famed S.O.B.’s nightclub snakes wildly around the block. Critics, DJs, tastemakers, and rap fans alike have traveled far and wide to this grand metropolis, this rapidly-gentrifying Gotham City, for far more exciting things. The year is 2009, the month is March, and Aubrey Graham, a rapper and sometimes singer who just wants hip-hop to get more in touch with its sensitive side, is set to make his long-awaited New York debut. It is on this night, with rap legends like Eminem, Kanye West, and Bun B looking on, that the seeds are sown. It is here, barely a month after his mixtape So Far Gone has gone viral and weeks since its first single, “Best I Ever Had,” has become a radio staple, where the legend begins. It’s on this small stage, in this cavernous club, where we are finally introduced to the greatest rapper of our generation—Drake.

It has been six years since that fateful night and, in that time, Drake has out-rapped, outperformed, and, ultimately, outlasted almost everyone who he might have once considered his superior. Lil Wayne, his label boss and occasional touring mate, hasn’t been the same since jail. Eminem is in a years-long, post-rehab malaise. When he’s not backing up Beyoncé, Jay-Z is saving the music business. And Kanye, the rapper whom he began his career by emulating, is more preoccupied with branding his new family than cutting records. Hip-hop these days is increasingly becoming a one-lane highway, with Drake at the steering wheel. It’s well-earned. He has three critically-acclaimed and universally celebrated LPs under his belt—Thank Me Later (2010), Take Care (2011), Nothing Was the Same (2013)—that see the Toronto native in the pocket with clever wit, syrupy melodies, and meme-ready quips on each one. Last year, songs like “0-100” and Tha Carter V teaser single “Believe Me” defined the rap lexicon merely by being uploaded to Drake’s Soundcloud account. And earlier this year, the mixtape/album If You’re Reading This It’s Too Late debuted at #1 on the Billboard 200 despite it being released directly to iTunes without any promotion or even a single. While we were sleeping, Drake became king.

Drake performing at Governors Ball 2015

Photo by Maria Jose Govea

The great tennis legend Arthur Ashe once said, “Success is a journey, not a destination,” and if anyone can attest to that, it’s Drake. A biracial child, his parents divorced when he was 5-years-old and, despite this, he lived in Toronto with his Jewish mother and grew up middle class. Unlike a rapper with a traditional narrative arc—broken home, poverty, drug dealing, and finally an escape through music—Drake found success as a teenager playing the wheelchair-bound character Jimmy Brooks on the show Degrassi: The Next Generation. While he was on the show, he began connecting with different artists and producers through MySpace and subsequently released a pair of mixtapes, Room for Improvement (2006) and Comeback Season (2007). Although adored by diehard fans, the projects were somewhat sophomoric and lacking the breadth of his later material. But this was early in his career and he hadn’t yet found his sound. And he wasn’t getting written off based on his music alone, but also because he wasn’t, at least to the hip-hop largess, real. He was an actor, a rich kid, a pretty boy. Mostly, he was strange—a Canadian who straddled the line between hip-hop and R&B. Aubrey Graham was an outsider. Aubrey Graham didn’t belong.

But in hip-hop, you’re only as hot as who you’re standing next to, and everything changed for Drake in 2008, after a mutual industry connection introduced his music to Lil Wayne. Weezy, then arguably the biggest rapper in all of music, was impressed with the kid’s melodic sensibilities and charming ladykiller demeanor, so he put Drake down with his Young Money crew, a roster he’d just begun filling out with the likes of Nicki Minaj. The pair began experimenting with Drake’s sound, developing it more, and a year later, So Far Gone hit, its ambience and emptiness a sort of calming presence in a genre often more preoccupied with what goes in the club than the contemplative thoughts of someone who has just left it. Still, Drake was a tough sell. His sensitive bonafides didn’t easily mesh with rap’s in-your-face ethos and he was still the new kid on the block. He hadn’t yet earned his stripes. Luckily, the music industry was beginning to collectively shift its attention to the performative aspects of music above all things, and it was here, on the road—not necessarily in listeners earbuds, in which an artist is at the mercy of the skip button—where Drake began converting naysayers to believers. Whether it was with Lil Wayne or with Jay-Z, city after city, night after night, Drake began slowly chipping away at what he’d become. Little by little, bit by bit, he earned his fans.

Drake performing at Governors Ball 2015

Photo by Maria Jose Govea

Drake’s introductory show in 2009 may have won him the hearts of the tastemakers, but it was hardly a memorable gig. “I was nervous,” he said, looking back. “It just had so much pressure behind the show. Not only that, but I had no band. I had no sense of what makes a great performance.” A year after the fact, he was still struggling. His Away From Home tour in 2010 found him on the road for months, playing over 70 different dates. And while he was the most buzzed-about new artist at the time, with a bevy of hit singles and features under his belt already, he hadn’t yet found the right groove on stage. Partly, it was because he wasn’t in good enough shape. Performing, particularly when it requires singing, is more physically challenging than most artists realize, and belting out lyrics is practically impossible when you’re winded. Add to that the fact that Drake’s music, at times, requires a certain degree of intimacy, and you can see how he might have gone wrong.

Two years later, Drake was back at it, on the Club Paradise tour, playing similar venues—college arenas, mostly—and in far better physical shape. Backed by a better band, and with a much deeper catalog of hits due to the release of his second album Take Care, the string of dates reportedly took in $42 million and became the most successful rap-oriented tour of 2012. At the same time, his own concert series—the Toronto-based OVO Fest—began hitting its stride as well, roping in talent like Nicki Minaj, 2 Chainz, The Weeknd, ASAP Rocky, French Montana, Waka Flocka Flame, Meek Mill, Rick Ross, and Snoop Dogg, among others. Drake was now more than just a performer—he was a curator and tastemaker as well. Last year, he added a wry little wrinkle to the ordinary tour experience, co-headlining a tour with Lil Wayne which saw the two powerhouses putting their hits against each other’s night after night, with fans voting on the winner via a downloadable app. The formula proved to be deeply engaging and galvanized their shared audiences equally.

Drake performing at Governors Ball 2015

Photo by Maria Jose Govea

There is the old comic book adage that goes, “With great power, comes great responsibility,” and, nowadays, Drake feels that in his bones. Particularly because his music is so expressive, so emotive, and he’s been so successful selling it to people, the stakes for everything he does are impossibly high. So while his only real competition in hip-hop fades off into middle age—or mediocrity, if we’re just being honest—he is, at this point, in a world of his own, running a race against himself, trying to do better, if only because he knows he can. Take his Coachella performance, for example. Perhaps not attuned to the complexities of dealing with a crowd numbering over 100,000 people deep—and outdoors, as opposed to the intimacy that arena walls can proffer—his pair of slow, lumbering sets kicked off this summer’s festival season with a thud (an awkward kiss with Madonna didn’t help). But like a true millennial, he put his head down and refocused, coming back at Governor’s Ball with a far more powerful set: more upbeat, faster-paced, with better energy. As a chance to right his wrongs, he made it count. There was no disappointment to be had, only joy.

Perhaps true legends are defined more by how they respond to failure than to success, and when you’re winning, it’s easy to stay in your comfort zone. But nearly a decade into his career, Drake is so far gone from where he was at the outset but still occasionally fails because—like Kanye and Jay-Z and Eminem and Lil Wayne and all the other truly great ones—he gets held to a higher standard. And because he actually tries. And yet year after year, he returns, still iterating, still developing, building on that dark, ominous OVO sound. It comes deftly pulsating from up north, and slinks in like an earworm, until we’re all #withmywoes and #0-100 and #squad on social media, all in our feelings, singing Drake’s praises, even when what we’re really trying to do is just sing our own. And maybe that’s Drake’s true power, the real reason why he’s the greatest rapper of this generation. Because he is truly of this generation, making music for this generation—the poster boy for all the quietly-confident boys and girls out there, the ones who have something to say and just need a little place to say it. When Drake is on, we are all running through the 6 with our woes or, at the very least, with our lord and savior—Drake

*prayer hands emoji*

Drake performing at Governors Ball 2015

Photo by Maria Jose Govea

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