Chapter 1Toronto

Foreword

There is a version of this book that is about losing a rap battle, and it would be a shorter and much worse book.

I should declare an interest. I have written about Kendrick Lamar as well, and anyone who reads both will notice that they describe the same three weeks of 2024 and reach the same conclusion about the evidence, which is that almost none of what the two men said about each other is established by anything except their own assertions. I have applied that standard identically in both books. What differs is the vantage, and the vantage matters more here, because the exchange is a late episode in a career that had already reorganized the commercial structure of the entire form.

That reorganization is the actual subject.

Aubrey Drake Graham has more charting singles than any artist in the history of the Billboard Hot 100. He has done it by working out, earlier and more completely than anyone else, what streaming rewards. Streaming does not reward the album as a statement. It rewards presence: many tracks, many playlists, many moods, many collaborations, continuously, so that the listener never has to leave. He has released long albums with wide stylistic spread because a long album with wide stylistic spread is the optimal object in that economy, and the critical establishment spent a decade calling this bloat without noticing it was a strategy.

He also did something more interesting than that, and it is the thing I think will last.

Before him, the dominant mode in this music was declarative. You asserted status. What he brought, on So Far Gone in 2009 and completely on Take Care in 2011, was the opposite: a register of romantic inadequacy, late-night resentment, and self-pity, delivered without irony by a man who was winning. Nobody in rap had made that a viable posture. Almost everyone under thirty-five making the music now uses it. Whatever else is true about him, that is a genuine formal contribution and it is why the sales happened, not the other way around.

Then there is the biography itself, which is stranger than the persona.

A Jewish Canadian mother in Forest Hill and an African-American musician father from Memphis who was largely absent. A divorce at five. A bar mitzvah his father did not attend. Six years playing a paraplegic teenager on a Canadian high-school drama while selling mixtapes out of a car trunk. That is not a rap origin story in any recognizable sense, and the entire subsequent career can be read as a negotiation with the fact, sometimes gracefully and sometimes not.

Three things I hold myself to in the pages that follow.

The authenticity argument gets stated fairly before it gets examined. He has been accused of borrowing from every scene he has entered: Jamaican dancehall, London grime, Afrobeats, Houston, Memphis. The accusation is not baseless and the chapters lay out the specific instances with dates. It is also frequently made in bad faith by people who apply no such standard to anyone else, and it has a nasty edge to it about the Toronto and Caribbean-Canadian communities that were in that city long before he was. Both of those things are true and I say so in the same chapter.

The son is a person, not a plot point. His paternity was disclosed in 2018 in a diss record, which is a cruel way for a child to enter public life, and I have written what happened, and I have not written about the child.

And the ghostwriting question gets treated as a question about hip-hop's own conventions rather than as a scandal. The reference tracks, the credited co-writers, and the specific 2015 accusations are all here. So is the observation that the standard being applied to him has never been applied to the pop and R&B traditions he draws from, where collaborative writing is unremarkable.

On sources: the recorded output, credits and session accounts, the OVO business record, court filings including the defamation action he brought against his own label in January 2025, and twenty years of trade coverage. I conducted no interviews. Where I say what he intended, it is because he said it somewhere I can point to.

He named his city after a piece of municipal administrative history that most of its residents could not have recited. It stuck, globally, which is roughly what he does.

Chapter 1 · Toronto

Aubrey Drake Graham was born on October 24, 1986, at Mount Sinai Hospital on University Avenue in downtown Toronto. The hospital was the same one where most middle-class Torontonians were born in the mid-1980s. The city was a city of approximately three million people. The neighborhood his parents would settle in was Forest Hill, on the western flank of midtown, where the streets curved up the side of a hill and the houses had been built across the early decades of the twentieth century by Jewish families who had moved north from the older immigrant districts in the years following the Second World War.

His mother Sandi was Canadian. She had been born Sandra Sher (Sandra Graham after the marriage) into a Jewish family with roots in Eastern Europe, part of the Toronto Ashkenazi Jewish community whose midcentury history had produced a distinctive layer of the city's professional class. Sandi was a teacher. She would, across her career, work in Toronto-area public schools as an English teacher and later as a vice-principal. She was educated. She was bookish. She was, by every available account, the more stable parent. Her family had roots in Wawa, Ontario, a remote mining town in northern Ontario, before the Sher family moved to Toronto. The Sher family had, by the postwar decades, become part of the established Toronto Jewish community that centered on Forest Hill and its institutions.

His father Dennis was American. He had been born Dennis Graham in Memphis, Tennessee, into a Black working-class family that had produced, across multiple generations, professional musicians. Dennis was a drummer. He had played with Jerry Lee Lewis on the road in the late 1960s and early 1970s. Lewis was one of the founding figures of rock and roll, a white performer who had absorbed Black Southern musical traditions into a white-marketable commercial register, and the irony of a Black Memphis drummer backing him was not lost on observers of the subsequent Drake career narrative. The Memphis that Dennis Graham came from (the home of Stax Records, of Al Green and Isaac Hayes, of the soul and blues and R&B traditions that ran through the city's Beale Street corridor) was one of the great American music cities, a place that had produced more commercially significant popular music per square mile than almost anywhere in the country. That Drake would, decades later, absorb Memphis rap aesthetics (the Three 6 Mafia tradition, the chopped-and-screwed production that Juicy J and DJ Paul had developed) was a biographical loop of sorts: the Memphis-descended figure returning to Memphis sounds, however indirectly and however contested the cultural authority of that return. After the Lewis association dissolved, Dennis drifted through a series of session-musician engagements that took him from Memphis to Chicago and eventually, in the early 1980s, to Toronto, where he had met Sandi at a club. They had married. Aubrey was their only child.

The marriage did not last. By the time Aubrey was five, Dennis had left the household. He had returned to Memphis. He would, across Aubrey's childhood, be an intermittent and unreliable presence: a father who called sometimes, who visited rarely, who appeared in Aubrey's life when his own circumstances permitted it and disappeared when they did not. Sandi raised the boy alone in Toronto. The pain of that abandonment would, across the subsequent two decades, surface repeatedly in Drake's lyrical content: the absent father who had given him the Memphis bloodline and then vanished back across the border, leaving a half-Jewish boy in a Forest Hill basement to figure out what he was.

The story Aubrey would, decades later, tell on his records about his Toronto childhood was a story of poverty and struggle. The claim of the title line of Started from the Bottom was exactly that: he had begun with nothing and risen to the top. The line, from his 2013 single, became one of the most-quoted phrases of his career. The phrase was, in its factual register, not quite accurate.

The Forest Hill neighborhood the family settled in was an upper-middle-class neighborhood. Sandi's family had means. Her father had been a successful businessman. The house Aubrey grew up in (at the basement level of a Forest Hill home that the Sher family owned) was modest by the standards of the neighborhood, but the neighborhood was not modest. Aubrey attended Forest Hill Collegiate Institute, the same public secondary school the children of Toronto's professional Jewish-establishment families attended. He had access, across his childhood, to cultural and educational resources that the bottom framing systematically obscured.

The framing was not, however, entirely fabricated. The household was strained financially. Sandi was a single mother working a teacher's salary in an expensive city. Her health had been, across portions of Aubrey's adolescence, unreliable; she suffered from various health problems that her son would, in subsequent interviews, describe as occasionally leaving him to manage the household largely on his own. The illnesses were not detailed publicly with precision; what Drake communicated across various interviews over the years was that there were periods where Sandi's capacity to parent was diminished and Aubrey had functioned, effectively, as the responsible adult in the house. A teenager feeding himself, managing the bills, going to school, going to the Degrassi set, coming home to a mother who was not always well enough to be present. The baseline-level functionality he developed in those years was not the product of the bottom in any external objective sense. It was, however, the product of a kind of psychological pressure that leaves marks.

The basement-level housing arrangement, while located in an affluent neighborhood, was not affluent housing. Aubrey lived, across his childhood, with the consciousness that his family was less wealthy than the Forest Hill families whose children he attended school with. The relative deprivation, if not the absolute deprivation that the bottom line implied, was real. He had, in the psychological dimension that the line was reaching for, the experience of being the poorer kid in the rich school.

The financial instability would eventually push Sandi and Aubrey out of Forest Hill entirely. They moved to Weston Road, a neighborhood in the northwest of Toronto that was substantially more working-class, more racially diverse, and more genuinely precarious than Forest Hill had been. The contrast between the two neighborhoods (the Forest Hill Jewish enclave with its Collegiate and its manicured streets, and the Weston Road corridor with its West Indian and African immigrant communities, its crime statistics, its different set of ambient threats) gave Aubrey a dual-neighborhood biography that he would draw on for the rest of his career. He had been the biracial kid in the Jewish neighborhood. He had then been the Jewish kid in the Black neighborhood. He had been, across his adolescence, the same person in two completely different social environments, and he had been a marginal outsider in both.

He was also biracial. He was Black. He was Jewish. He was Canadian, which in the hip-hop context meant he was technically an outsider to the American tradition that defined the genre's commercial and cultural infrastructure. He was the son of an absent American father and a present Canadian mother whose Jewish-immigrant family had absorbed him as their own. He was, at any given moment of his childhood, in some dimension of the available identity categories, the outsider. The Forest Hill Jewish kids did not quite see him as one of them. The Black community in Toronto, which was substantial but more diffuse than the Jewish community, did not quite see him as one of them either. He was the child between categories. The psychological consequence (the lifelong attempt to construct a coherent identity from elements that did not naturally cohere) would, across his subsequent career, be one of the engines of his commercial success and one of the sources of his sustained vulnerability.

The Bar Mitzvah, in October 1999, was the moment at which the Jewish dimension of Aubrey's identity received its formal articulation. He was thirteen. The ceremony was held at a Toronto-area synagogue. He read his Torah portion. He gave the short speech that thirteen-year-old Bar Mitzvah boys give. The family (Sandi, the Sher grandparents, various aunts and uncles) celebrated. Dennis was not present. He had not flown up from Memphis for the ceremony. The absence at the Bar Mitzvah would, decades later, become the emblematic fact about Dennis Graham's role in his son's life: the Jewish holiday he missed, the performance he skipped, the recital he ignored, the birthday phone call that didn't come. The Bar Mitzvah was the crystallization of all of that. The moment when a Jewish boy becomes, by his community's definition, a man, and his father couldn't be bothered to buy a plane ticket from Memphis.

The Bar Mitzvah established Aubrey, in the religious-genealogical sense the Jewish tradition operates in, as a Jewish adult. He would, across his subsequent career, periodically reference his Jewish identity (in lyrics, in social-media posts, in public observances of Jewish holidays). The references were sincere. They were also commercially convenient. The Jewish dimension gave him a cultural-cross-over angle that the Black-American hip-hop industry's assumed religious-cultural register did not easily accommodate. He was, in the terms of identity-marketing, more interesting than a straightforwardly Black artist would have been because he was straightforwardly Black and also straightforwardly something else.

The dual identity had a daily-life texture that the broad biographical framing tends to flatten. He was the kid at Forest Hill Collegiate who got invited to Bar Mitzvahs on Saturday mornings and who also could, when he wanted to, navigate the Weston Road corners where the Jamaican-Canadian and Somali-Canadian teenagers ran their own separate social infrastructure. He had access to both worlds and full membership in neither. The Forest Hill social world was organized around cultural codes (family money, hockey, the Jewish calendar, the summer camps) that he could approximate but not fully inhabit. The Weston Road world was organized around different cultural codes (neighborhood loyalty, a Toronto Blackness with Caribbean roots) that he could also approximate but not fully inhabit. The boy in the middle. The kid who could move but couldn't quite belong.

The something-else dimension would, across his career, expand. He would become, over the years, fluent in Jamaican patois (used on his collaboration with Rihanna and others). He would adopt UK drill phrasing (after spending time in London). He would deploy Afrobeats production (across the More Life and Scorpion periods). The aggregate cultural-chameleon practice would become, for some critics, the defining feature of his career and the central object of their critical attack. Drake doesn't create cultures, he colonizes them. The line, attributed to various critics across the years, captured the persistent objection that Drake's cultural-borrowing practices were extractive rather than collaborative. The objection had merit. It was also, when applied to his career across decades, the single most-overused critical observation that anyone made about him. The cultural-colonization charge was true. It was also, in the commercial terms his career operated by, the strategy that had built the empire.

The empire, when it came, was anchored in Toronto. Not in Memphis, which Dennis had given him by blood and withheld in practice. Not in the abstract American hip-hop geography that the industry's commercial architecture was organized around. Toronto. The 6. The city that had made him. The city he would, in turn, remake. But that was still twenty years away. In 1999, Aubrey Graham was thirteen years old, freshly Bar Mitzvahed, fatherless at the ceremony, and about to start a television acting career that would define his adolescence and nearly ruin the adult career that followed.

The acting career began before the rap career. Aubrey was twelve when his mother (looking for ways to supplement the household income, and informed about the audition through a connection in the Canadian entertainment community) took him to an audition for a Canadian teen drama called Degrassi: The Next Generation. The franchise was a continuation of an older Canadian television property that had been producing teen-drama content since the 1980s. The new iteration, beginning in 2001, would focus on the high-school students at the fictional Degrassi Community School in Toronto. The casting team was looking for a young Black actor to play a basketball-star character named Jimmy Brooks.

The original Degrassi franchise had aired in Canada from 1987 through 1991 as Degrassi High, itself a continuation of Degrassi Junior High which had begun in 1986. The franchise had been the Canadian Broadcasting Corporation's most significant youth-drama property and had developed, across its iterations, a creative philosophy: dramatic realism, current social-issue content, teenage actors performing teenage situations without the sanitized resolution-arc that American teen drama typically imposed. The franchise's decision to hire a twelve-year-old Aubrey Graham and to eventually give him the school-shooting-and-wheelchair storyline was entirely consistent with the franchise's creative philosophy. Degrassi handled what was actually happening to teenagers. It had always handled it.

Aubrey auditioned. He was cast. He was fourteen at the start of filming in 2001. The role would extend across seven seasons, from 2001 through 2008: a run of 145 episodes that made Jimmy Brooks one of the central characters in the show's history. Across the years he transitioned from a recurring character into one of the central ensemble figures of the show. The developmental arc the character would follow (beginning as the popular athlete, surviving a school-shooting episode, navigating the subsequent paralysis-and-wheelchair years) gave Aubrey, across his early adolescence, a television-acting platform that virtually no other Canadian teenage actor of his cohort had access to.

The work was steady. The pay, by Canadian Actors' Equity standards, was substantial. By the time Aubrey was sixteen, he was contributing meaningful income to the Sher household. Sandi could, on the Degrassi income, manage the household more comfortably than the teaching salary alone had permitted. The financial improvement that the show provided would, in subsequent years, be obscured by the started from the bottom framing. The framing was, on one register, accurate to the pre-Degrassi household situation. It was not accurate to the household situation across Aubrey's late adolescence, when the Degrassi income had substantially improved the family's economic circumstances.

The acting career was also, in a register that would become central to the subsequent rap career, the authenticity-vulnerability that hip-hop culture would never let him fully escape. He had been, on Canadian basic-cable teen drama, Jimmy Brooks. He had been the character in the wheelchair. The image of the actor in the wheelchair would, across the rap-industry insults that subsequently accumulated against him, be one of the most-deployed weapons against his hip-hop credibility. You used to be on Degrassi. The line, in various configurations, would appear in dozens of subsequent diss tracks. He had been a child actor. The hip-hop culture, which valued the street-credentialing it valued, would not stop reminding him.

What none of the insults could undo, however, was what the Degrassi years had actually provided: the commercial infrastructure, the professional relationships, the income stream, and the North American audience recognition that allowed Drake to enter the rap industry with advantages that his Toronto-rapper peers simply did not have. The show aired in the United States on The N cable channel (later TeenNick) which gave him recognition among American teenagers who were, by the late 2000s, exactly the age of the early-internet hip-hop-mixtape audience. When So Far Gone circulated in 2009, a substantial portion of that audience already knew who Aubrey Graham was. They had been watching him play Jimmy Brooks for years. The credibility liability and the commercial-recognition asset were the same television career. He had spent seven years accumulating both simultaneously.

What Aubrey was doing while he was acting on Degrassi, however, was preparing the rap career that would eventually displace it. He had begun, in the early 2000s, to record demos. He was using the household equipment (a basic computer, a USB microphone) and the early file-sharing networks of the period to distribute the recordings. He was teaching himself to rap, to sing, to produce. He was, by the standards of any serious assessment of his prep period, working substantially harder than the casual Degrassi actor frame would have suggested.

The producer he was working with, from approximately 2004 forward, was Noah Shebib (40), a Toronto-born producer of Lebanese-Irish descent (his father was the filmmaker Donald Shebib) who had grown up in the Toronto film and music world and who had, from an early age, been developing the production aesthetic that would eventually define the Drake commercial sound. Shebib was diagnosed with multiple sclerosis in 2005, at twenty-two, an autoimmune condition that would impose physical limitations across his career while never stopping his studio work. He and Drake had met through mutual Toronto connections and had recognized immediately that their abilities (Drake's vocal and lyrical instincts, Shebib's production aesthetic) were mutually complementary. The two began working together with the collaborative depth that serious artistic partnerships require: spending hours in studios, building tracks from scratch, developing through iteration the sound that would eventually produce the So Far Gone breakthrough.

In February 2006 (at nineteen) Drake self-released his first mixtape, Room for Improvement. The release was conducted via his website and through direct distribution; he sold copies from the trunk of his car to people who would actually buy a local rapper's CD in Toronto. The reception was minimal but encouraging. A local buzz began to form. By 2007 (twenty-one) he had released a second mixtape, Comeback Season. The breakthrough on Comeback Season was Replacement Girl, a single featuring Trey Songz whose video was featured as the "New Joint of the Day" on BET's 106 & Park on April 30, 2007. This was a documented first: Drake became the first unsigned Canadian rapper to have a music video featured on BET (Black Entertainment Television, the American cable network), without the backing of a major American label. The moment was small by commercial-chart standards. In the context of what it meant for a Toronto rapper to penetrate the American cable infrastructure, it was significant.

The Replacement Girl BET exposure also established, for the first time in Drake's career, a commercial fact that would define the subsequent decade: American audiences were willing to receive him. The Degrassi recognition advantage (American teenagers who had been watching him on TeenNick for years) combined with the BET exposure to create a name recognition in the American market that comparable Toronto rappers simply did not have. He was not, when he arrived in American hip-hop spaces, an unknown quantity. He was the kid from Degrassi. He was the Canadian rapper who had gotten BET play. He was already known. The So Far Gone breakthrough was, in this framing, not a discovery but a confirmation: American audiences recognizing a figure they had already been watching from a distance.

He was, by 2007, a working Canadian rapper whose career was at the development stage that hundreds of comparable Canadian rappers were also at. Most of them would not break through. He would.

What he had that the comparable Canadian rappers did not have was the Degrassi commercial platform combined with the industriousness that the dual acting-and-music career required. He could, in 2007, work the Degrassi set during the day and record demos in the evening. He had been training, across approximately six years of overlapping acting-and-music work, for the moment at which the music would, eventually, become his full focus. The moment came in 2009. The next chapter is about So Far Gone, the mixtape that finally produced the breakthrough.

What Toronto meant to Drake (the city that built him, the city he would rebuild) deserves a final remark in this opening chapter. Toronto in the 1980s and 1990s was a city in the process of becoming what it would eventually be: one of the most demographically complex cities in the world, with immigrant communities from the Caribbean, East Africa, South Asia, Southeast Asia, and East Asia building neighborhoods in the west end, the east end, and the northwest corridors that bore very little resemblance to the Forest Hill and Rosedale enclaves at the city's wealthy center. Drake grew up in the geographical center of one of the most diverse cities in North America while being substantially insulated, by the economic and social architecture of Forest Hill, from most of that diversity. He knew, from the Weston Road move and from crossings his social life required, that Toronto was multiple cities layered on top of each other. He knew, from his biracial position, that identity was a negotiation between territories rather than a fixed address. The city's structural complexity (its demographic diversity and its persistent economic stratification) was the environmental substrate of everything he became.

The 6, as he would brand it (the Toronto area code, 416, the six) was never the single unified entity his commercial mythology made it. It was a city of neighborhoods that did not always speak to each other. Drake's gift was in moving between those neighborhoods, in the apartment buildings of Weston Road and the mansions of Forest Hill, in the synagogues and the studios, in the Degrassi set and the late-night basement sessions with 40. He was the figure between categories in a city built on categories. It turned out to be the ideal preparation for a career spent building bridges between cultural registers that were not supposed to connect.