It is 2014 and the Toronto Raptors are playing the Brooklyn Nets in an NBA Eastern Conference playoff game. The camera pans to follow the action on the basketball court, stopping when a Raptors player is fouled. In the background, sitting court-side is arguably the world’s most famous rapper, Drake. He is using a lint roller to tend to his fleece trousers while watching the action unfold. The next day, a 20-second clip of this act of self-grooming spreads like a rash across the internet. It sparks a wildfire of memes and conversations across mainstream and social media. A few games later, a Drake-themed lint roller is unveiled by the Raptors and handed out to 1200 audience members, one of whom sells it for $55,100 on eBay.

In July 2023, British rapper Central Cee, looking effervescently cool, a reflection of his youth and status as one of the world’s biggest artists, sways in the background of a freestyle video while Drake, looking like an uncle at a family reunion trying to fit in with the teenagers, is decked out in a bright cherry-red jacket and reading glasses. He takes to the mic and cocks his eyebrows ever so slightly, looking up at the camera, stating “it’s a madness… and a badness” before pausing, and in a faux-patois accent, saying “combinayshaan”.

Within hours, the clip proliferated throughout the internet and the way Drake says 'combination' is permanently etched into my brain. Pause the video just as he says the word and even Central Cee is smirking. These days, Drake’s cultural value is present as more than a rapper: he may still bend culture to his will, a voracious vacuum which sweeps up anything relevant, but his power lies in his ubiquity. He is inescapable, a meme that seems to never disappear.

But, before he grew to be a cultural behemoth, Drake was the one carving a path, epitomised by his 2009 mixtape, So Far Gone.

I remember when the project dropped. We were all turning 18 and in our final months of high school. I was in love. I had never felt this way before: consumed constantly by thoughts of someone, to be aware that there was someone out there in the world who cared for you too, who also wanted to spend an excessive amount of time holding your hand, walking the streets and staying up until 4am on the phone talking about your hopes and dreams. That year, and the summer, in particular, felt electric. There were endless possibilities ahead of us, and So Far Gone soundtracked our collective hope. Drake was playing out of car windows as the heat rose in the city, and the sounds of the mixtape wafted from house parties as you approached them.

Despite living in Toronto, I had never watched the TV show Degrassi and didn’t know who Drake was, but all the rap blogs were talking about this mixtape. Reading the track listing, I was curious. How did this kid from down the road get Lil Wayne, Lykke Li and Bun B on a tape? He was just a few years older than me; how had I not heard of him?

Once I downloaded the tape and hit play, I was hooked. From the opening bars of the first track, ‘Lust For Life’, the mixtape possessed a skeletal, atmospheric production while the sparse, minimalist beats underpinned it. There were skittish, lean snares throughout. I felt then – and still do feel – like it encapsulates the rawness of winter in Toronto. Listening to So Far Gone for the first time was akin to driving through the city’s arterial veins with the windows rolled up, heater on blast while brown snow streaked the sidewalks.

The way Drake rhymed felt natural. He didn’t use clever wordplay or double entendres or wicked metaphors. He wasn’t a wordsmith like Lil Wayne nor did he have the authenticity of Jay-Z. Rather, Drake possessed a certain relatability and charisma. He simply narrated his thoughts and feelings, discussing his life while admitting to his insecurities and failings. Within his rhymes, there was a self-assured modesty. His vulnerabilities rendered him approachable yet his ambitions rendered him admirable — this was a nimble tightrope act he pulled off ably.

Admittedly, at 18, I struggled to express my emotions. Instead, I'd convey my feelings to the person I loved through Drake lyrics. Lines like “Sweatpants, hair tied, chillin' with no make-up on / That's when you're the prettiest” became my way of expression, while tracks like ‘Successful’ with an infectious chorus of “I want the money, money and the cars / Cars and the clothes, the hoes / I suppose / I just wanna be, I just wanna be successful” fuelled my fantasies of making it. I remember vividly shouting it on many walks home after a night out.

On ‘Say What’s Real’, he rhymes in the opening bar “Why do I feel so alone?” while later discussing his insecurities with his mother, rapping “she wonder where my mind is, accounts in the minus”. He had managed to take the emotional depths of Toronto’s indie music scene and layer it over a Kanye West beat. It echoed my own feelings of loneliness and insecurity. Drake's music, how it was both aspirational and delicate, resonated with me deeply. It symbolised where Toronto felt as a city: fresh, hopeful, a home for immigrants.

My family moved to the city from New Delhi, India on 31 December 2003. Maybe it was leaving a city whose population was 10 times bigger than that of Toronto’s, but Toronto always felt like a small town, as if it would be dwarfed by American cities like New York and Chicago, due to its proximity to both. Call it ignorance or Toronto not having a global significance, but I hadn’t even heard of the city until I was informed I was moving there. Those first few years felt awkward as I wasn’t sure what my new home offered other than a very tall building (the CN Tower) downtown. It was, in many ways, attempting to feel itself and find its identity.

With the rise of this child actor-turned-rapper, Toronto piggybacked on Drake’s success and welcomed the successful rebrand he instigated. Drake carved the path for fellow Toronto superstar The Weeknd to walk down while people globally started calling Toronto the “6”, a reference to the city’s area codes as well as to its six original boroughs. OVO, Drake’s record label and clothing brand, signed up and coming R&B and hip hop artists, launching the careers of Canadians Majid Jordan, Roy Woods, Dvsn, PartyNextDoor and many more.

I left Toronto in 2012, skipping across countries and continents before landing in London, England at the tail-end of 2018. During that time, Drake grew exponentially and so did Toronto’s visibility. Wherever I was in the world, when people found out I was raised in Toronto, their reference point became Drake: usually, it was “running through the 6 with my woes”, taken from ‘Know Yourself’, off his 2015 mixtape, If You’re Reading This It’s Too Late. Otherwise, references to “the 6” were – and still are – made constantly. I was happy to play along. I felt proud. Toronto was now officially a global city, as ubiquitous as Drake.

Throughout So Far Gone, Drake plays the underdog — mostly, because he had to at that time in his life and career. When he emerged, critics and the industry were sceptical. Here was a half-Jewish half-Black rapper who was unfairly derided for playing a kid in a wheelchair on TV, attempting to lay a claim to the throne. In a hip hop scene still steeped in machismo, Drake's blend of R&B and rap, coupled with his vulnerability, was initially dismissed. Yet, in hindsight, the mixtape was groundbreaking, bridging the gap between genres and setting the stage for future artists. Drake's rise to fame was meteoric, but with success came scrutiny. As he transitioned into superstardom, his music became more formulaic and more manufactured. He became less an artist and more an industry unto himself, churning out hits that lacked the depth of his earlier work.

After the release of So Far Gone, he spent the next decade of his career becoming the most successful artist of the 2010s. He had a cultural ubiquity that rivalled Michael Jackson, The Beatles and Taylor Swift. His ability to manufacture hits was relentless. Like a factory production line, he churned out infinite phrases and slogans which entered the cultural vernacular. Everything he said became an Instagram caption: yolo, nice for what, no new friends, god’s plan. He had tapped into something advertising brands spend millions to devise.

Since 2009, more than 75 skyscrapers have been built in Toronto proper with another 30 currently under construction, a figure that rivals the entire European Union. To visit the city now is to see an endless sea of skyscrapers surrounding pockets of American-style suburban neighbourhoods. I have gone back to Toronto a handful of times since I left in 2012. The longest time I spent there was a few months in 2018, before moving to London. Each time, my nostalgia for 2009 grew. The possibilities felt endless, hope defined us. Now, when I head back, my family and friends tell me how it has gone from a haven of immigrants to an unlivable city.

While the financial crisis of 2008 hammered nearby American cities like Detroit and Buffalo, Toronto, and much of Canada, dodged the tsunami of foreclosures. Rob Ford, a conservative party member, was elected mayor in 2010. Unfortunately, long past his mayorship, the repercussions of his time in office, and his successor John Tory, are still felt today. A city governance favouring conservative austerity neglected investment in shelter systems and public housing. Simultaneously, multiple provincial [state] governments disregarded the impacts of their policies on housing prices, driving up real estate prices. Suddenly, as the city propelled forward, driven by immigration and a booming tech industry, decades of poor preparation were exposed. Toronto had become a world-class city in housing costs, but a mid-tier city in infrastructure, transit and culture.

Drake was never going to end up next to Kanye West or have a generation-defining career like Kendrick Lamar. So Far Gone wasn’t an Illmatic, heralding a new genius like Nas. But, upon its release, there was a sense of hopefulness that Toronto had a bonafide artist to promote. Instead, he became the soundtrack to clubs and house parties; mindless background music with a singable chorus — his relatability never vanished, but it just became sad. A man in his late 30s singing to college-aged kids, creating TikTok dances felt painful when he could’ve matured and grown up with everyone else. He’s become everyone’s guilty pleasure, rather than their core desire.

When he emerged on So Far Gone, I felt like I knew Drake: from his mum’s height to his deepest darkest insecurities, but now he feels hollow, lacking the authenticity that once defined him. Those who know are still waiting for that generation-defining project, the one that we can look back on with pride. Instead, with dozens of infectious singles to his name, he's become a caricature of himself, pandering to trends rather than pushing boundaries. And much like Toronto's transformation into a soulless metropolis, Drake's artistic evolution mirrors the city's descent. Both have lost their way, drowning in a sea of mediocrity and complacency.