Drake’s Rise to Fame and Fortune

On September 7, 2008, Lil Wayne stepped onstage at the MTV Video Music Awards and then stepped decisively away from the words on the lyric sheet circulating in the audience with the following lines:

I'm on my Disney thang, goofy flow/ I'm Captain Hook on the beat and my new car is Rufio/ Damn where my roof just go/ I'm somebody that you should know/ Get to shakin' somethin' cause that's what [deleted] produced it fo'/ I make mistakes that I don't ever make excuses fo'/ Leavin' girls that love me and constantly seducing hoes/ I'm losing my mind like, Damn where my roof just go/ Top slipped off like Janet at the Super Bowl.

Then, as Leona Lewis launched into the hook of Nina Simone's "Please Don't Let Me Be Misunderstood," he croaked, "Drizzy Drake: I love you, bwoy!" That namecheck was the only clue to most attendees that Wayne had just blatantly violated the unwritten rules of his own freestyle game by spitting another artist's words. Though almost lost in host Russell Brand's commentary on promise rings and presidential politics, it was a coronation moment rarely seen in the arena of rap, and with one verse, Wayne introduced the name of his protégé to the mainstream in dramatic fashion. Amongst those already familiar with the various Wayne-affiliated rookies collectively known as Young Money, the lines sparked a fierce debate over whether Drake was in fact ghostwriting for the master (he and Wayne both still claim he never has), but by the time the rap blog drama blew over, one thing seemed clear: Drake was the next big thing, heir apparent to Wayne's multi-platinum throne and Young Money's most likely flagship artist.

The buzz was confirmed by the radio phenomenon of "Best I Ever Had," a soft rock-sampling mixtape track that hit #1 on numerous charts without major label support or even a record deal in place. But a second look made this passing of the torch seem like an unlikely proposition. Drake shares with Wayne a certain manchild vocal tone, but their styles are almost antonyms. Where Wayne rides his stream-of-consciousness through drug and gunplay into Freudian—almost hallucinatory—nursery rhymes, Drake hews rigorously close to the guidelines of rap formalism, pumping an incredible volume of two- and three-syllable schemes out of the same subjects: girls, multi-colored whips and his skill in the booth. He seems to depart from this formula only to talk about his emotional state, an introspection that usually happens when he shifts from rap mode into catchy and sometimes haunting R&B. On his own records, he abandons Southern double-time to push genre boundaries more like Kanye, rapping over chopped-and-filtered snatches of Coldplay, Lykke Li and Peter Bjorn & John.

The differences only get starker if you compare Drake's bio to his project-raised, tattooed and codeine-addicted mentor. Though born in Memphis, Aubrey Drake Graham was raised in Forest Hills, an affluent enclave of Toronto that is about as far in mood and geography from New Orleans as you could get without a land bridge. Before he ever considered being a rapper, Drake was a child actor, portraying athlete Jimmy Brooks on the Canadian teen drama Degrassi: The Next Generation. His father, Dennis Graham, was a drummer for Jerry Lee Lewis, and he is nephew to both legendary bassist Larry Graham and Teenie Hodges—a guitarist best known for co-writing some of Al Green's '70s classics who's played with everyone from Talking Heads to Cat Power.

The more you know about him, in fact, the harder it seems to know exactly who Drake is. There is something almost chameleon-like about his talent. If his appeal can't be contained to a one-liner like "Wayne protégé," it's only because he invites a whole series of comparisons: to Wayne's inventiveness, Kanye's art-school eclecticism, Jay-Z's braggadocio and Lloyd's post-Kelly singsong. Though he reps Toronto, in interviews Drake has even said that a childhood split between his father's base in Memphis and his mother's house in Canada has allowed him to escape the territorial matrix of rap. He's parlayed this "from everywhere" quality into a burgeoning career as a guest verse specialist, always adjusting his approach to the demands of the host organism, a strategy that makes you wonder which Drake will step out on his own debut LP—slated to drop before the end of the year—a project that's not recorded yet but already titled Thank Me Later.

In some sense, Drake has already provided one answer in the form of So Far Gone, the mixtape that spawned "Best I Ever Had." Those who know him primarily as a Young Money soldier may be unaware that it had almost nothing to do with Wayne except for his vocal features, having been produced exclusively by Drake's Toronto-based crew, and appropriately, it's on his home court that I finally catch up with the moving target of so many expectations. We've both just flown in from New York on different flights and link for an after-midnight dinner on the roof deck of an Italian restaurant in which Drake is a silent partner. He's wearing a leather jacket and leaning on a cane with a gangsterish list, walking off the same basketball injury that had him propped up on a stool for his closing performance at the 2009 BET Awards. Posing for our camera with glass raised, he has the air of a newly made man trying on the don's overcoat for size, but in between snaps, he is quick to flash a grin to let you know he doesn't take himself too serious. In person, he has a face like mercury, sometimes opening wide with disarming vulnerability, then just as impulsively clowning, eyes seeking out everyone's reaction to see if they get the joke. If you don't, they move away instantly, flat and bored. Child-star handsome, at 22 he is still growing into his looks, with deep-set eyes that make his face somehow boyish and craggy at the same time, features almost too large for his slim shoulders in a way that heightens the youthful quality.

It is Fourth of July weekend. In the past week or so, Michael Jackson died, and Drake finally inked a major label deal. But the conversation mostly centers on the Kanye West-directed video for "Best I Ever Had," which has just debuted. West's cinematography is being panned by a local video dude who doesn't like the lighting, though judging from his neon lumberjack and the hat awkwardly covering his baldy, his aesthetics are not necessarily to be banked on. Drake hardly blinks at the hometown hater, but the video—which features him playing coach to a female basketball squad in a league of their own, cleavage-wise—has invited negative feedback from other fans, ones whose opinion may carry more weight. Whether you like it or not, the video's tone definitely puts an ironic distance on the genuine emotion of the hook, thereby ruining the girlish daydreams of many a 16-year-old disciple. Of these there are more than a few, many of them fans he brought with him from his days as a cable TV heartthrob. Drake claims not to have put too much thought into it. "I started getting the straight cookie cutter treatments," he says. "The pretty boy, lovey-dovey shit that everybody wanted me to do." The Toronto accent is an extreme north version of flat Midwestern twang, sprinkled with Jamaican patois. In Drake's case, it's mediated by a soft Southern cadence picked up from his Memphis cousins. It balances out in the middle somewhere, and if you didn't know different, he could easily be from Detroit or Chicago. "I was just like, Man, let's do Kanye's video," he says. "Some crazy shit that could potentially offend people. Let's just fall out of this pattern of doing everything that everyone wants." Despite the nonchalance, it's the first inkling I get that his identity crisis is not so much a question about what makes him tick as a potential answer. The bait-and-switch of the video seems like a slo-mo version of a tactic he employs often in conversation and even in song, as when he raps, "I'm the next to blow…pause." He's always going out on a limb and then skewering himself before anyone else can, just to let you know that he could son himself more skillfully than you ever could—that he has the lyrical teeth to skewer you if you mistake introspection for weakness.

Toronto has been repeatedly recognized by the United Nations as the world's most multicultural city, and the security council of close homies assembled around Drake seems to echo this. There's Niko, with whom I don't talk much but who looks like the fifth member of Black Chiney Soundsystem. Oliver el-Khatib, a Lebanese-Scandinavian who grew up between Toronto and London, is Drake's brand manager. Tyrone "T-Rexx" Edwards promotes some of the trendiest parties in the city when he's not running a government-sponsored project that gives inner city youth access to a professional studio. Boi 1da produced the beat for "Best I Ever Had," while Noah "40" Shebib is Drake's engineer and main partner in the studio. Then there's Foots, whose main job seems to be taking Drake's car on epic missions to acquire Belmonts for el-Khatib to smoke and being dipped head to toe in Polo. Totally unsolicited, he lifts his pantcuffs and shirt-tail to display the logos on his socks and boxers, just in case you doubted the thoroughness of his game. "I mean," he says, "It do have a horse pon it too right? Respeck." Even the brown-skinned girls who float around the table boast family trees that include Carib, Arawak, Syrian and African branches. Also, everybody is nice. In fact, to judge from this crew, everybody in Toronto is a creative individual with a pleasant-ass demeanor, racially integrated, well-adjusted, has free health care and is not broke.

All of which begs the question: What the hell do they have to rap about? Driving through, the city itself feels modern, clean and spacious, with no visible ghettos or overcrowding. If rap music often feels like a reverse SATs, an intellectual exercise inherently—if not intentionally—biased in a way that favors the skill sets of kids from oppressed minorities and dilapidated zip codes, it seems almost natural for a newcomer to edit out the squeaky clean parts of their resume. But Drake does not seem particularly pressed to play down the middle class and Jewish half of his biracial upbringing and frequently mentions his mother's central role in his life.

The next day he even lets us tag along to visit his bubbe, his mother's mother, in the nursing home she recently moved into. She obviously adores her Aubrey, and is not even mad when we interrupt her card game with her boyfriend. "Don't call him that, we just say he's a friend," she says, as she is apparently not the type of bubbe to have her biz in the streets. "I have a girlfriend like that too," Drake replies. "We say she's just a friend, cause she doesn't want anybody to know." He could be talking about Rihanna, whom he's been hanging out with a lot lately, or maybe his ex, Canadian diva Keshia Chante. Or really, any one of a number of world-class dimes he seems to have on the hook these days. We go to sit with Bubbe in her suite, where she has a Drake splash page from the Toronto paper taped to the wall. "Well, what's new with you?" she asks, and Drake starts off like any other college age grandson. "Just traveling, mostly." But then, "I signed a record deal. For a million dollars…" Bubbe makes him repeat this a few times before she is sure she heard right. "Actually, more than a million," he confirms.

That deal is the end result of what has been described as one of the biggest bidding wars the music industry has seen in ages. No one party is willing to share all the details, but Atlantic Records and Interscope's Jimmy Iovine were certainly both in the mix, and at one point, Universal Motown president Sylvia Rhone apparently threatened Drake with legal action to prevent him from going elsewhere. In the end, he signed directly to Aspire, a company co-run by his manager (and Young Money CEO) Cortez Bryant, with major label distribution through Universal Republic. Although his Wikipedia entry and various news items list his label as Cash Money/Universal Motown, Drake is quick to say, "I went through Universal Republic because I don't fuck with Motown. At all." The details are more than academic, since the Universal affiliation is what allows Lil Wayne and Young Money to own a piece of the project. But even though Wayne has been touted as an executive producer in previous interviews, Drake indicates that putting a YM logo on the disc is more of a nod to his mentor than a structural reality. "I respect the fact that Wayne put me in this position," he says. "But as an artist, I have to do my own thing at this point. I'm not sure if that's gonna be a struggle in the next couple months, to set myself apart. I don't want it to feel like a disrespectful thing, but I know it's a bridge that I'm going to have to cross as far as becoming my own person."

Our next stop is the house Drake grew up in, which turns out to be one floor of a modest duplex on a block of Forest Hills that feels suburban but hardly wealthy. We're here to continue the dubious project of pretending not to be photographing Drake at whatever activities he would be up to anyway. By that measure, he would be lamping under the birdbath in his smallish backyard, wrapped in a newly purchased Hermés blanket against the chill of a Canadian summer evening, staring at the purple flowers that overhang the steps and celebrating a million-plus advance with a bottle of Opus One and a droopy spliff. Although it's meant to be a contemplative moment, there are lot of "pause" jokes between pics, and a lot of "respecks"—a conversation ender meant to convey exactly the opposite of what it says. "Which one" is another recurring theme, a particular way of phrasing friendly disrespect as an open-ended question, as in: "Foots, is that Polo Mansion or Polo Warehouse? Which one?" Drake's mother arrives, to make sure we followed her detailed instructions and found the keys where they were hidden in a blue plastic prescription drug canister under the planter on top of the barbecue grill. She looks at her son wrapped in the Hermés blanket and says, "Are you cold, or are you just trying to look cool?" prompting much discussion of her natural "which one" skills. Drake has just about taken an entire Swisher Sweetfull to the face when Kanye West calls to say he's done a re-edit of the "Best" video he wants him to see. T-Rexx is holding Drake's phone and there's an awkward interlude when he answers, "Ye? Kan-Ye?" because the association is still so new it doesn't seem real.

This highlights yet another x-factor in play around this album project, which is the fact that Kanye—according to the people around Drake, anyway—is so open on his talent that he is more amped to work on Drake's project than his own, dangling the possibility that he might step in as executive producer. That night at Cherry Beach studio, the crew runs through two or three newly recorded songs which are in contention for Thank Me Later. There's "Shut it Down," a pure R&B burner that's so close to the sound he's going for that Drake "probably almost can't see it not making it"—though it still needs a rap verse and maybe a guest. There are tracks with Rihanna and Pharrell. "Forever" may be for the album or possibly a forthcoming soundtrack, a Kanye collabo in which he and Drake bring out the best in each other, elevating their respective rap games in a way that's only happened with Drake and Wayne on tracks like "Ransom." It's the kind of verse that lends real credibility to his fans' claims that Drake is the best lyricist on the set in 2009. Despite the obvious implication, he does not seem inclined to substitute one mentor for another, preferring to develop the sound for the album himself, drawing beats from his engineer, "40" Shebib, and other members of his crew, loosely known as October's Very Own. It's not that he doesn't want Kanye's input, but he feels that, "We've got to build a vision that's strong enough for Kanye to come and say, 'Okay, I see it.' That Pharrell can say, 'Okay, I see it.'"

It's the following day now, and Drake is laid out on the king-size of a luxury hotel suite, resting the injured leg. With a tape recorder and chair pulled alongside, I can't help but feel a little like a psychiatrist, and I am in fact asking him about his childhood. "Well I have always sorta been alone in my world," he starts off. "I have great relationships with my parents and stuff, but I've never really been connected to anything, and it caused me to think a lot." We talk about the relationship that first provoked him to try singing and his Memphis cousin's obsession with Usher; about his misfit status amongst the rich kids of the Forest Hills high school where he lasted exactly one year, the biracial kid with the single mom and the dad "who was more like a little brother." We talk about what aspects he drew from each: his father's "overcool, Shaft-like personality," his mom's ambition, her generosity.

He is remarkably able to see and articulate all this in himself. But by this point, I don't need anybody to tell me he's got a whole hell of a lot to rap about after all; that probably since he even had an identity, he's been using his exceptional verbal ability to navigate uncomfortable situations, sometimes finding common ground, sometimes striking out to defend himself, but always having to decide where to fit in when there is no automatic place for him. I give one last shot at getting Drake to define the place he wants to carve for himself with the album, his official stepping out moment. His eyes go wide with that throw-you-off vulnerability and he says, "I don't think I ever want to find my place."