I began my relationship with Drake when I was living out of a suitcase, rebuilding myself from the ground up after the unwinding of my first adult relationship. My best friend Josh would let me crash for weeks at a time on his couch in Fort Greene, which is how I came to be sitting at the burger spot one day when a woman named Tina materialized at the next table—looking like the most vivid personification of some platonic ideal. As it happens, she had styled herself on Kim Kardashian while doing some modeling and acting—a standard that was, at least to my eyes, entirely within her reach.
Had she had work done? It is entirely plausible. She was gorgeous, tall, slightly out of shape in a way that only humanized her and endeared her to me, with a lip-glossed smile like a spotlight when it landed on you. It landed on me for reasons I still don’t understand, while I was sitting there with my sweet-potato fries and my cheeseburger, not bothering a soul.
Tina passed me a flier for something I no longer remember, and I guessed that she must be light-skinned black or Hispanic, a local. Like a fool, I also assumed I’d somehow discovered her—a pretty, loquacious young lady who just likes to spend her Saturdays eating comfort food with her girlfriends. She told me her name, said I could find her on Facebook, and before she’d left I was already dreaming of a simple and quiet little Brooklyn life together. Tina was from suburban Toronto and Gujarati, “the Jews of India!” she later told me, not black at all, and that simple life would be harder to secure than I’d initially bargained because two famous rappers and one NBA All-Star were also vying for her attention.
I could not stand the ballplayer ever since he bested Allen Iverson’s Hoyas in the Big East finals, but I found the rappers more irritating still. I was in my late 20s, and hardly listening to hip-hop at all—deep in the hate phase of a love-and-hate relationship that had been going on for two decades. I’d spent the last four months of 2008 in Paris and Buenos Aires fleeing home in order to remember a few things about where I was from and write a coming-of-age memoir that was more like a Dear John letter to the cool-pose culture I’d come to feel had hoodwinked me. It was then that she introduced me, accidentally enough, to a young half-black, half-Jewish rapper from Toronto with a middle name almost as funny and unlikely as mine, and a first name that was even sillier.
“Oh my gosh, I love Drake,” Tina told me as we were driving from her apartment in Sunset Park to my parents’ house in New Jersey, “Best I Ever Had” blaring on the radio. “Who is Drake?” I asked her. “This is him. He’s going to be enormous.”
In hindsight, it seems inevitable that Tina and Drake were both from Toronto, which according to the BBC is now the most diverse city in the world. Canada never had slavery and as a result it never developed the all-encompassing black-white binary that continues to haunt America. What it does have is a patchwork of immigrant groups, along with the “old stock”—which differs by region, from Irish in the Maritime provinces to French in Quebec to First Nations up north and west, to Anglo-Saxons everywhere else. Jews as a class are in some way “the first immigrants”—or non-English or French immigrants—followed by non-Jewish Ukrainians and Poles, Chinese, British West Indians, Indians, North Africans, Vietnamese, and other Asians. Jews are the “original” prototypical Canadian 20th-century immigrant group, and Toronto has an especially large Jewish population.
To be part Jewish and part black in Toronto is to inhabit a natural, indigenous mix of established and rising immigrant groups. These identities are more easily seen—from the outside at least—as complementary, rather than opposing.
It is therefore not at all surprising to me that the world’s only superstar mixed-race rapper is not from the United States but from Toronto, or that the lane to success that he paved for himself passes directly through a redefinition of authenticity—a repurposing of that tired term to mean being true to yourself, as opposed to being true to your tribe, whatever that may be.
This vibe may help explain why, over the year of our courtship, as I finished that intensely anti-hip-hop memoir, Drake’s breakthrough mixtape So Far Gone paradoxically became an indispensable part of my sonic framework. The enthusiasm, the excitement, the sheer relatableness of his narrative persona, not to mention those instrumentals that seemed to hit me at every emotional register while I dreamed of Tina defined the time for me.
“I just want to be successful,” he declared proudly, even innocently, and the honesty moved me even as it embarrassed me.
“How in the hell did I end up with you?” I asked Tina one day lazing on my parents’ couch, her lustrous black hair cascading through my fingers as my mother cooked breakfast for us upstairs. “I don’t know,” she laughed, “I think you bring me back to my middle-class values.”
For so long I’d tried to hide this aspect of myself, because in some real sense I knew it came down to me through my mother’s side. My father had manners and erudition and I would even say noble values, all of which my mother either shared or admired. But she had something that he’d been denied, which can really only ever be yours if you’re raised with it, and it seems completely unremarkable. It is not a racial thing—the tough Italian kids I grew up with did not have it, and many of the black kids I met later in college did—but it is a sensibility that is often mistaken for whiteness. I have learned to recognize it as a kind of existential unguardedness. It’s a quality capable of disarming prejudice—even as it sometimes invites resentment.
Perhaps it’s strange that it took me 10 years to finally see Drake live. But it took me even longer to reconcile myself to how much I wanted to.
The last time I’d been to a rap show at Madison Square Garden was back in 1997. Earlier that year, the Notorious B.I.G. had been murdered in downtown Los Angeles and not even a year before that Tupac Shakur, the idol of my generation, was gunned down on the strip in Las Vegas. The hip-hop world was simultaneously in upheaval and teeming with restless new talent. The culture had reached a tipping point: mainstream enough now that its elite had begun to get and display real wealth but still nothing like what would become standard for even the solidly mid-tier to earn some 10 and 20 years later. Back then, there was still, it seemed, an edge to it all.
Against that backdrop, my best friend C and I, two light-skinned mixed-black boys from New Jersey—his mother Puerto Rican; mine white Anglo-Saxon protestant—emerged from the depths of Penn Station and ascended to the bloodiest nosebleed heights of the Garden, where we marveled at our good fortune: two tickets to the Puff Daddy and the Family “No Way Out” world tour.
We’d covered ourselves in what was in fact the sum total of our net worth: Around our necks swung the thick gold Cuban link chains made heavy by the “Jesus-piece” and Pharaoh’s head medallions we’d nearly killed ourselves and our families to obtain; on our bodies, Iceberg sweats and Polo fleece; unlaced on our feet, construction Timbs and Nike Air Maxes. We were still two years away from college, and didn’t know anything. We lived 45 minutes by commuter train west of Manhattan, but only ever referred to it as “The City.” (As in, “Nah, you can’t find it out here—I heard you have to go into The City for that!”) I could count the number of times I’d ever ventured into The City on five fingers and have two to spare.
The night of the concert has been blurred in my memory for a long time now, but certain images do stay crisp: There is Lil’ Kim panting for breath and gyrating in matching lime green mink and panties; there are The Lox and Mase, and of course Puff Daddy, shimmying around in leather baseball jerseys and shiny metallic ensembles that would throw open the door to a subsequent grittier era. C and I certainly didn’t know any better—and, really, neither did the still-emergent genre. It was not a good concert, neither in terms of acoustics nor in the design of the set, and the artists themselves, while—with the exception of the headliner—mostly skilled lyricists, were terrible arena performers, wholly incapable of filling such a cavernous space (an art that Jay Z was the first hip-hop star to master and that Kanye took into the future). They simply cranked up the volume and shouted, and we were none the wiser.
Life’s vicissitudes soon uprooted both C and me from what I would call now the New Jersey of our minds—a simplistic and Balkanized confederation of Polish, Irish, and Italian white Catholics, assorted Latinos and blacks of all variations and skin tones who were descended from slavery in the South or from bootstrapping Caribbean immigration. (We were not aware of Jews back then.) These were ethnic tribes, with all the attendant chauvinism, xenophobia, and misunderstanding that should necessarily imply.
What strikes me most of all now about that scene are not our surface differences but the deep and common provincialism that was our true and collective identity. It was our provincialism that bound us to one another and ultimately rendered our backgrounds highly compatible, if not interchangeable. In spite of all the racism (traditional and reverse), ignorance, and casual disrespect, the lingua franca was hip-hop, the closest thing I’ve ever felt to secular religion. We came and went from our separate backyards to worship and pray together.
I’ve since learned that almost everyone C and I grew up with has stayed within a 50-mile radius of where we’d been born, a fact that astonishes me. But there were a few of us even then whose aspirations were different. I’m not sure I’d be among that number were it not for my father—a black man who as a precociously autodidactic child had fallen in love with Maimonides’ Guide for the Perplexed and studied his way out of segregated Texas. He met my mother while running War on Poverty programs in Southern California. Neither of them had meant to rear their children in a social context like the one in which we found ourselves, and my father made it his business to make sure that we would not stay in it.
C put in his proverbial 10,000 hours in my father’s library alongside me. He ended up at Oxford then Wall Street then Harvard. For my part, I inherited my parents’ love of books and Paris and wrote my way into a life there. Although Pappy was biologically and financially responsible for me, he was an intellectual and spiritual father to both of us. C and I were less like friends and more like brothers in his nurture, seeing the world together through his very particular viewfinder.
I don’t know at what age it became hard to deny that the lightness of our mothers’ skin mingled into our own might have had something to do with some of the luck and opportunities that found us but had eluded him. At the time, I was more focused on the difficulties this sometimes brought me. The rudeness it could provoke in some of my classmates. C’s mother was Puerto Rican—which at the time meant to me that he didn’t have to deal with all that I dealt with. It was too late by the time I came to understand some of my own advantages passed along to me by virtue of my mother’s identity. By then I knew it was Nas who rapped that “a thug changes, and love changes, and best friends become strangers,” and that is a fair enough description of what had to happen to C and me, with the qualification that we were not really thugs not even a little bit, even when we so desperately wanted to be.
The thing that finally froze our friendship after years of intermittent cooling was so complicated and multifaceted that even I do not fully understand it. But if I were pressed, I’d say it had more than a little to do with the fact that I could no longer abide having another person in the room who had witnessed me as I’d been before a series of interventions and refinements. Perhaps he couldn’t either. In any event, it is one of my lingering regrets that I felt the need to penalize him for knowing who I had been, just as I’d felt the need to repudiate the culture that shaped us.
Memories of that Puff Daddy and The Family concert more than 20 years and what feels like another lifetime ago sprang into my mind uninvited as I made my way, with my flesh-and-blood brother this time—past the little fur sellers in some of whose windows Tina’s image still hung, modeling their wares—back into Madison Square Garden for the Manhattan leg of the Canadian rapper Aubrey Drake Graham’s ongoing “Aubrey & the Three Migos” tour. In the time between the two concerts, hip-hop, now fully middle-aged and having survived numerous minor identity crises was a world apart from what I’d known it to be in those more innocent years when I’d so self-consciously tried to channel its aesthetics and mores into my own self-worth.
As we bought sandwiches and beers, my brother and I—ourselves in middle age or fast enough approaching it—marveled at the ferociously committed younger concertgoers. There were the girls of all ethnicities who looked as if they’d stepped directly out of an Instagram filter, melding together into a brand-new polychromatic hybrid type defined only by its silky blown-out hair, blown-up lips, hip-and-bust hugging spandex and those asses … those death-defying asses that were pumped up and swollen to extraordinary, inhuman proportions. And then there were their dates, the Drake look-alikes of all races. Italian, Jewish, Latino, and mixed-black kids with perfectly tapered low fades and puffed-up dark beards in loose T-shirts and tight black jeans. Many had gone to far greater lengths for their jewelry than C and I had known was possible.
The pathos of the physical mimicry among the devotees dress-rehearsing their hyperspecific fantasies—this earnest yearning was familiar enough. But the porosity of the boundaries on the level of physiognomy felt novel indeed. Drake is an actor, a child actor at that, and perhaps this is the most important detail of all about him, before the hybridity and the Canadian-ness and the middle-class values he clearly also inherited through his mother (his often absent father being a Memphis bluesman). Perhaps starting from a point of obvious phoniness freed him in the end to tap into something so shockingly real.
The reality hanging over the concert and the entirety of his fifth album, Scorpion, was the ugly spat between Drake and the older rapper Pusha-T, a walking anachronism from an earlier, angrier era. It was a beef that felt both tamer than the two extraordinary conflicts of the ’90s that forever marred the genre and was also somehow far more personal, and meaner. That viciousness touched something deep inside me. These are millionaire entertainers, I know, and yet a part of me was suddenly back in high school at the cafeteria lunch table, learning again what proximity (real or perceived) to whiteness is worth and what costs it may impose.
The conflict between Drake and Pusha-T unfolded according to a familiar conceit. On his mini-album Daytona (a project small in every way), Pusha-T, occupying the role of the “authentic” black rapper, goaded Drake with barbs about ghostwriting practices that are in fact entirely unremarkable. (Drake also provided ghostwriting services for Pusha-T’s producer and label boss, Kanye West.) But as soon as Drake responded on the ostensible merits, seeming to win in the process, the terms of debate shifted to a despicable level of ad hominem, as they had to, because that in fact was the point of the argument to begin with. West himself, the one indispensable transitional figure in hip-hop culture who did the most to enable the rise of artists like Drake, gave up the game when he rapped “calm down,” after Drake had stopped responding, “you light-skin!”
After nearly two hours, Drake emerged through the floor of the phantasmagoric stage positioned in the center of MSG, a tiny figure in that vast space with that signature ersatz drawl—more Southern than a real Southerner thanks to his acting chops and his dad. He began to rap and sing his heart out, never facing one side for too long for wont of excluding the rest, it seemed improbable that a single body could fill that much arena for 90 minutes. But he filled it. The concrete floors heaved when the hook to “Know Yourself” struck, and the crowd rapped along word-for-word to it all. Drake led them through a snippet medley of his greatest hits and even covered Michael Jackson’s “Rock With You” like a hypertalented karaoke or bar mitzvah singer more than anything else. He spoke to the crowd between songs about his father’s presence in the rafters and loving your family and following your dreams. Platitudes, all of it—“Talking all the good things,” he once rapped, “that’s all I’m really good for”—but the kind that made me turn to my brother and hug him tightly. These parts ought to have been awfully corny but somehow they weren’t.
Drake did not seem to work in the same profession as the three-man ensemble Migos, who opened the show and joined him during his set for their earworm collaboration “Walk It Like I Talk It.” These were rappers, larger than life but ultimately pedestrian, identifiable; Drake, by contrast, seemed like a man who had willed himself into another dimension. “I am in The Matrix, and I just took the blue pill,” he also once rapped, and this may be the best metaphor for his trajectory that I can think of. Unlike Jay Z, who earned the right many times over to call himself the Mike Jordan of rap, or Kanye West, who is something like its Andy Warhol (and far too strange to ever be anything other than sui generis), or all the scores of talented and disposable upstarts that Drake does features with and siphons energy from, it occurred to me that Drake is simply what it looks like when a thoroughly normal kid becomes the biggest rap—and possibly even the biggest pop—superstar in the world. I found myself rooting for him.
If racism is a cognitive error, as the artist and philosopher Adrian Piper argues, a failure to see the thing itself instead of an abstract category it is filtered through, it occurred to me that Drake performs and exudes his blackness without triggering most people’s learned anti-black responses. He slips the yoke, and does so in a way that not even Tiger Woods or Barack Obama equally mastered. Unlike either of them, he works in a predominantly black field, which is not insignificant. And unlike the white rappers who face their own obstacles in that work environment, there is no attendant guilt factor involved in admiring him. Claims of appropriation don’t stick.
In a real and increasingly common fashion as the country and culture continue to beige around the widening edges, Drake occupies a position on the social Venn diagram where he can easily engage black and mainstream culture while feeling inside yet also superior to both. He is a hybrid. Hybridity, of course, is nothing new, but the reception to its presence is evolving, and the compromises that are asked of it are less obvious or demanding. Though events of this past summer tested this premise severely, in the end they did nothing to disprove it.
Drake really does get to have it both ways, and that is a feat that can almost never be forgiven.
The urge in some—but it must be said, never all—quarters to police the boundaries of acceptable blackness in hip-hop is as understandable as it is shortsighted and familiar. West himself rose to prominence in defiance of the class if not the color archetype in hip-hop at a time when the culture genuflected to drug dealers. “We all grew up street guys who had to do whatever we had to do to get by,” Jay Z remarked. “Then there’s Kanye, who to my knowledge has never hustled a day in his life. I didn’t see how it could work.”
In 2002, that really was unthinkable. Now we’re a decade into the reign of Drake, and perhaps nothing better encapsulates the scale of the paradigm shift he has both ushered in and normalized than the remarkable—and underremarked-upon—2012 music video for the song “HYFR” from his second album, Take Care. “On October 24th 2011 Aubrey ‘Drake’ Graham chose to get re-bar mitzvah’d as a commitment to the Jewish religion” the opening text reads before shifting to footage of him as an Afro’d child, and then to the present, where we see him as the sole black member among a group of otherwise white Jews standing with yarmulkes on their heads and loosened ties and collars in front of the Temple Israel of Greater Miami.
The nimble rap verse starts and then, spliced with what looks like an entirely authentic Torah-reading ceremony, wherein Drake finds his place in the Hebrew scroll, the video cuts to rap scenes in the synagogue with DJ Khaled (whose parents are Palestinian), and the indubitably street-credentialed Brian “Baby” Williams backing him up. He is celebrating becoming a man in twinned binaries—black and white, young and old, Drake and Lil Wayne, the suburbs and the street, a Jewish kid rejoicing in a synagogue with his Palestinian friend. He looks fully at ease in all these scenarios.
It is not frivolous to dwell on this exercise in dualism a little longer. Of the video, Drake has observed that it simply marked the moment in his life when he felt rich enough to throw himself the kind of bar mitzvah his mother couldn’t afford when he was a boy. But his decision to pair the video with this specific song offers a clue to something even deeper. “Today,” these images announce, “I am a man for real”—an assertion not just of his maturity in the world of hip-hop, but of his right to use his own unique birthrights (white, black, Jewish, Canadian, whatever) in a world where some might rather he not. “As of right now, all the responsibility is mine,” he seems to be telling us here, “and all the credit is, too.” There has never been a white rapper with as many white and non-black friends as Drake. Not even Eminem—especially not—has displayed anything approaching such a degree of comfort in the presence of whiteness. “What have I learned since getting richer?/ I learned working with the negatives can make for better pictures,” Drake rhymes on “HYFR” with what feels like unusual wisdom in the realm of pop music. (This line is typically understood as a double entendre, though I detect a third meaning there in addition to the play on developing film and processing setbacks: Is he not also shrewdly implying there is a payoff in moving toward that which is opposite of oneself?) The result is that he blends seamlessly between the seemingly incommensurate poles of his personal identity. As a viewer you do not object to any of it because the cultural groundwork has been laid before he got here.
By the time Drake flitted across that gorgeous stage in the middle of Manhattan and pretended to be a Southern rap star, we all gladly met his pretense and raised him tenfold in the process, just as in recent years, as he has ventured into faux-Jamaican patois and black British “road rap” styles and sing-rapping in more than passable Spanish, we have for the most part suspended our disbelief.
We do this, I think, because that ventriloquism is damn pleasurable, perhaps even healing. It shortens vast distances that seem, on further reflection, arbitrary to begin with. It is Drake’s love of the United Kingdom, in fact, that is most difficult to imagine a famous American rapper—even A$AP Rocky—equaling. It is risky, but it is also evidence of an impressive humility that is actually a voracious appetite for human possibility.
As the show drew to its close, there was yet one more twist in store. “I feel like we’re all living in a country where they try and tell us every single day, on our cell phone, on our news, they try to tell us that we’re living in a divided country, that we don’t understand unity,” Drake told the audience, in a new politically woke mode he has seldom tried on before but that felt authentic enough in the moment. “And we’re listening to this fucking idiot that’s in office … and meanwhile right here in New York City, we got 17,000 people from all races and all places. No matter how they tell us the world is goin’, this is how the fucking world is supposed to be.”
Thomas Chatterton Williams is a contributing writer at the New York Times Magazine and a national fellow at New America.