A little over eight years ago, I had dinner with Drake. It was the first and the last time that would ever happen. These days, getting to Drake involves traversing rings of head of state-like protection. Interviews are controlled, stage-managed, engineered towards an end. And now that the man is a monolith, everything about our meal seems unlikely. Above all: It was for Heeb magazine, a spiky publication that imagined itself as the home for discerning, self-effacing Jewish hipsters. (The word “heeb” itself is a light Jewish slur. They once photographed the Beastie Boys playing a game of dreidel as if it was cee-lo).
I recently dug up my original pitch, and it. Is. Atrocious. “Don’t know if you’ve heard of this guy Drake, but he’s probably the most buzzed about young rapper these days,” my young, foolish, plucky self wrote. “The first interesting thing about him is that he was on ‘Degrassi,’ the Canadian teen soap, for like eight years. The other thing, which I just found out, is that he’s apparently a practicing Jew, bar mitzvah’d and everything.” Then I tantalizingly mentioned both “rumors of hookups with Rihanna” and my belief that “no Jewish media has approached him yet.” And the worst part: “So, Asher Roth didn’t work out, but maybe I could get you a rapping Jew after all!” I have completely repressed this memory. But apparently, I had then-recently pitched, and then-subsequently failed to gain access to, Mr. I Love College himself.
But Heeb still said yes! So over the next few months, I flailed towards landing Drake. I was blogging at the time and happy to be employed, but also insanely desirous of any assignment that’d let me write longer than 299 words. I’d never profiled anyone before but knew, vaguely, that if I were to one day progress towards something resembling a journalism career, that that career might entail regular profile-writing. I also was really, truly obsessed with Drake in 2009. I listened to So Far Gone on a loop; I injected every spare verse and NahRight nugget into my veins. I wanted this really badly.
After a bunch of false starts, I eventually found the right media liaison. More miraculously: I heard “yes.” I was told that, if I wanted, I could come to Toronto to do the interview.
Heeb had already let me know that my payment for the piece would be... literally nothing. But I was a little bummed to hear they couldn’t float the price of a flight, either. Still: I knew I had to go north. I cleaned out my mom’s airline miles and took off. Heeb, kindly enough, did offer to put me up at the editor-in-chief’s girlfriend’s parents’ house.
Instead, I opted for independence. I booked the absolute cheapest possible lodging I could find: a $17 dollar bed in a shared bunk room in the HI Toronto Hostel. I stayed one night and, because I didn’t really trust the shoddy-looking lockers, slept literally clutching my Sony VAIO laptop.
At night, a young man named Oliver texted me to see what hotel I was at—they were coming to pick me up for the interview. I had no recourse but to admit that I was at the hostel. They rolled up in a Bentley Continental Flying Spur. So, for what I have to imagine was probably the first and certainly the last time, a Drake-owned and/or operated luxury vehicle pulled up to Toronto’s HI Hostel.
I scrambled into the back seat with Oliver. Drake was in the passenger’s seat, ignoring me while fielding phone calls. Another friend, introduced as T-Rex, drove. We were headed to Sotto Sotto, an Italian restaurant described as “Drake’s favorite.” Then it happened: flap-flap-flap-flap-flap. Perfectly intro-level rap star problems: There was a flat tire on the Bentley. “This is like the fourth time that’s happened,” I would later quote Drake as saying. “The guy at the dealership threw in these fucked up rims.”
Eventually we did make it to dinner, via taxi, and eventually Drake would acknowledge me, via shoulder squeeze, and eventually I would have an honestly great time. We got free shrimp cocktails and free pre-dinner aperitifs. Drake used the phrase “fuck it, let’s get sloshed.” And to my great relief I didn’t have to pay for the rest of the food. At the end, when the check came, I really was ready to take out my debit card and stretch myself thinner. But Drake beat me to it with aplomb. I remember that he was, like, nice in general. When we got back in a car after the dinner (this time a Range Rover), he swept the guts of a blunt off the backseat for me.
It’s not like my conversation with him during dinner was revelatory. If I was better at my job, I certainly would have asked different, better questions. But I will take credit for “breaking” one piece of “news”: Drake himself told me that the “song of the night” at his bar mitzvah was Backstreet Boys’ “I Want It That Way.” And ultimately, I don’t really regret anything. I had a fumblingly candid conversation with Drake in some of the last months in which that was humanly possible.
In June 2010, Drake would put out his smash debut album, Thank Me Later. Since then, between studio LPs, mixtapes, “playlists,” and full-length collaborations, he’s released at least one major project a year. That doesn’t include the dozens of one-off hits and guest verses and “SNL” hosting gigs and general undefined ubiquity. Scorpion, presaged by the massive singles “God’s Plan” and “Nice for What,” is out this month. And his beef with Pusha-T had us all Googling “secret Drake love child photos.” Basically: Since showing up, he’s never really gone away.
Willingly or otherwise, due to professional obligations or otherwise, I’ve almost certainly spent more time thinking about Drake in the last decade than I have about any non-nuclear-member of my family. (Sorry, Uncle Ricky, I will call you right after I’m done writing this.) I do feel a certain sense of pride, bizarre and unearned as that is, for the monolith he’s become. And that he may be quietly entering the very early beginnings of his late-empire phase doesn’t escape me, either. As Drake finds himself embroiled in the biggest crisis of his career, I wonder what he’s thinking. Did he really believe he’d be able to dictate his fate forever?
That meal is memorable to me still, but not because anything particularly illuminating happened. I’d never, ever claim to understand something about Drake because of it. It’s just that he had no perception to tend to back then. Or, at least, the perception hadn’t ossified into a shell. And that’s impossible to imagine now.
To Drake die-hards, Oliver El-Khatib, the dude who texted me to come outside the hostel, is a legit celebrity now: He even gets his own sultry GQ photo shoots. As Drake’s manager and the keeper of the OVO flame, he helps his famous boss evince a sense of ineffability. Together, they’ve accomplished a grinding sense of destiny. Together, they’ve set us up to believe that loving Drake or hating Drake is immaterial, because either way Drake will just produce more bangers forever. Everything thorny that Drake and his art can, purposefully or otherwise, represent or reflect—from questions of class to questions of cultural appropriation to questions of racial identity—ultimately gets crushed down by the weight of his successes. It’s a hermetically sealed operation, with victory the only option.
But once, he got a request for an interview from a “hipster Jewish” publication and impulsively he said, “Fuck it, let’s get sloshed.” In the many years since, Heeb shut down its print edition. Actually, it happened before my piece even published! There was supposed to be a photoshoot; one of the publicist’s only requests was that Drake be able to “control his own styling.” But in the end, my article—my first-ever profile—ran online only. (In a beautiful sign of the times, the editors included a bit below the story: “To find out more about Aubrey ‘Drake’ Graham, check out his MySpace.”)
The ensuing reader comments were appropriately on-brand for the Heeb readership. Like: “I really do hope he follows his mom’s desire and marries a nice Jewish girl—and I really hope that girl is me!” and “I’m a Black Jewish Canadian mom with a beautiful son of my own. Drake’s story is a 1-in-a-billion fairytale. If he continues to be proud of who he is, the success will always follow.”
We know now how the story goes. He did not marry that one Jewish girl. But he did succeed and succeed and succeed until—at some point, maybe around a half-a-decade ago—he became totemic. He’s not unassailable, of course. He gets assailed all the time. But he does increasingly feel like less a person than, for lack of a better word, a brand.
I don’t mean that to be as dismissive as it sounds. I’m quite happy all of his vulnerability now is performative and contained. I, for one, believe his music has only gotten better as it’s gotten chillier and chillier. And I have a lot of love for him still. Not the same unexamined love I had for him that one endearingly goofy night in Toronto. But a whole lot of love still.
