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Diego Mallo for Vox

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How Drake won

The Canadian, biracial, Jewish, middle-class, former child actor has reshaped rap, pop, and the masculinity wars.

At Chicago’s United Center arena earlier this month, Drake perched comfortably on a couch and read aloud from his new poetry book, Titles Ruin Everything. The book may have been released by Phaidon, the well-respected arthouse publisher, but this was no typical poetry reading. It was the first night of Drake’s first tour in five years, and aside from the 25,000-strong crowd and one giant inflatable sperm, the rapper was joined that night by what appeared to be a hologram of his younger self, decked out in baggy denim and a Chicago Cubs jersey, with the superstar’s former curly hairstyle. The “hologram” turned out to be merely an uncanny lookalike, and the quasi-poetry reading a textbook example of how Drake challenges the expectations of masculinity forced upon rappers. But the message Drake was sending with the surreal, life-imitates-art-imitates-life moment was clear: He’s 36 now, worth an estimated $250 million, and has morphed himself into a superstar who has stretched the rigid boundaries and rules of hip-hop and R&B. The nerdy, eager version of himself also shaped who he is today.

Whether or not you’re a devout follower of the cult of Drake, few can look at his rise to fame and not acknowledge that a biracial boy from Toronto rose against all odds from a teen actor on Degrassi to a beefy, self-referential hip-hop demigod. Everything that makes Drake, Drake — the cryptic, emo self-deprecation, the media aversion, the desirable mirage of an image that he’s cultivated — should have set him up to fail. Instead, the rapper born Aubrey Drake Graham has gained a chokehold on popular culture.

Where Lil Wayne — considered one of rap’s GOATs — once inspired Drake, it’s now Drake who inspires the next generation of musicians, regardless of genre. Fellow streaming giants and previous collaborators including Bad Bunny, fellow Toronto native The Weeknd, and unlikely emcees such as Jack Harlow have all cited Drake as a major career influence. A co-sign from the rapper also almost instantly signifies stardom: Jorja Smith, Yebba, PartyNextDoor, the City Girls, and many other artists have benefited from associations with the rapper.

At the beginning of his career — and even after his seminal mixtape So Far Gone dropped in 2009 — outlets such as Pitchfork called him simply “not a great rapper” and described his rhymes as amateurish and prosaic. Now, seven albums in, Drake still seems determined to prove his naysayers wrong. In the meantime, he’s managed to flip an entire industry upside-down and redefined what it means to be one of the best rappers in the game.

What has helped him along the way is his uncanny ability to be relatable and unobtainable at the same time. His alternately sad and sultry lyrics resonate not just with men who want to be him but also with the women who want to be with him. His unapologetically emo demeanor attracts the I-can-fix-him types, while his playful toxicity encourages the rest of us to keep pressing play. Whatever and whoever Drake wants to be — rich and balling, or low and alone — we know him only through what he chooses to share, be it an Instagram caption, a song, or a poetry book.

“It would be next to impossible for another musician from anywhere in the world to mimic or copy what Drake has done,” says Dalton Higgins, a Toronto Metropolitan University professor and author of Far from Over: The Music and Life of Drake. “He’s the textbook definition of a ‘unicorn.’ When you tick off all the boxes — Canadian, biracial, Jewish, grew up middle-class, a former child actor, and so on — you can’t deny his inherent ability to appeal to the widest swath of humanity.”

The carefully calculated mystery

While numbers don’t fully explain the scope of Drake’s success, they certainly help put it into perspective. He’s remained one of the top-streamed artists on Spotify for years, surpassing 50 billion streams in 2021. He’s sold more than 170 million albums — a rarity for any artist these days — taken home five Grammys, and has more Billboard Hot 100 No. 1 singles than any other rapper. (He’s tied with Whitney Houston in seventh place for the most No. 1s overall.) His Summer Sixteen Tour with Future in 2016 was the highest-grossing hip-hop tour of all time, raking in $84.3 million, surpassing previous tours from industry heavyweights like Jay-Z and Kanye West.

Drake’s pop star peers tend to rake in more: Beyoncé’s current Renaissance World Tour is projected to bring in a staggering $2.1 billion; Taylor Swift’s Eras tour will earn $1.6 billion, according to Forbes, while Bad Bunny broke the record for the most profitable tour in a single calendar year in 2022, bringing in $435 million. Cash aside, Drake shows seem more interested in inspiring discourse.

Besides the poetic interlude, that first Chicago date for the It’s All a Blur Tour featured a towering likeness of the late Virgil Abloh and UFOs in between a 48-track setlist. The tour is his first in the US since 2018’s joint show with Migos. Starting this week, he will perform seven back-to-back dates in New York City alone, at Barclays Center and Madison Square Garden.

Drake is a classic product of the times: a child of the internet generation who’s savvily used Instagram, the press, and his lyrics to create his image. Drake circa 2006, at the time of his musical debut, and Drake in 2023 are almost two different people — with two completely different backstories. Both iterations of the rapper have carefully paid attention to the ebbs and flows of internet culture to craft a sound that many critics now claim will define a generation. (Did a Drake album even drop if it doesn’t immediately inspire a million Instagram captions?)

Old Drake was overly earnest, determined, and a little bit awkward. “That early era, where he kind of pivoted from just relying on R&B sonics, is when you could really tell he was studying the craft of rapping,” says Robyn Mowatt, a music and culture writer and former Okayplayer editor. “He was actually starting to embrace what was happening in hip-hop at that time and morphing himself into the kind of artist that he needed to be to be taken seriously.”

“I watch other artists from the past in awe — in awe of the preparation it must have taken to, like, be that individual — the grandiose production of [it],” the rapper told the Fader in 2015. “And I’ve sort of gotten by just being myself. I just want to be remembered as somebody who was himself.”

Drake today is more closed off, more jaded, and keener to control the narrative. The rapper’s mainstream success has always hit a nerve within the hip-hop industry. A history of his publicized beefs with fellow rappers (Meek Mill, Pusha T, Kanye West, and more) could be a separate story in itself. The core debate always seems to be that because he found a formula of rap that appeals to so many, he can’t possibly be a real rapper.

It’s true that Drake has defied the notions of what more typical rappers say and do. (Take the music video for the hit “Hotline Bling,” which was inspired by the work of contemporary artist James Turrell, of all people.) Drake has seemingly never aimed to push himself solely for the approval of his peers, though. It’s almost as if the only person he’s had to prove anything to is himself.

As his fame erupted, so did Drake’s complicated relationship with the press and media as a whole. The world’s most popular rapper stopped doing press in 2017. His last true music profile was the one in the Fader, while a story for the Hollywood Reporter two years later centered around his work producing TV and films (he would go on to executive-produce the HBO megahit teen drama Euphoria). After being “disgusted” with a 2014 Rolling Stone story, he tweeted that he would never do traditional magazine press again — and he largely hasn’t.

By his own design, the only way to learn anything about Drake is through Drake himself — a media tactic that stars such as Prince, Sade, and Beyoncé have all adopted at pivotal points of their careers. His albums, his Instagram, and even his videos poke fun at or redirect the cultural narrative surrounding him, and you can’t say the approach doesn’t keep the public interested.

“We’ve seen him reinvent himself sometimes even on the same album. He’s always evolving, even as a current project rolls on,” says journalist and former Essence features editor Brooklyn White. ”It’s easy to become stale and complacent as a creative, and he hasn’t done that.”

The “Beyoncé-ification of Drake,” as White describes it, has helped create more allure around everything Drake says and does and ultimately creates.

“He’s a masterful curator and he always has been,” says White. “He definitely has a finger on the pulse of what young people want to consume and what they’re already consuming.”

A complex relationship with Black women

Vulnerability is a core trait of Drake’s music, even if songs have evolved from waxing poetic about ex-girlfriends in Toronto to supermodel flings and buying Birkins. Through his music, Drake manifested the type of artist — and maybe, on a personal level, also the type of man — he aimed to be. His aggressive pursuit of success attracted the ears of eager young men who also long for a life of luxury and publicly perceived greatness. Generation Drake, countless Billboard hits aside, is for better or worse associated with fuckboy culture. His Certified Lover Boy album cover, featuring a blank white background dotted with emoji of belly-holding, pregnant women in every skin tone, is a prime example of how he’s further embraced and turned into the caricature some of his fans imagine him to be.

It’s worth noting that sometimes a fuckboy is exactly what women want. Drake’s candor on love and relationships resonates with women. His verses tend to double as pickup lines that some women would maybe only openly accept from someone of Drake’s stature. If there were such a thing as a lovable fuckboy, Drake would fit the bill.

“He’s never been the typical masculine rapper, and with that, the lyricism is something that a lot of women may resonate with more,” says Mowatt. “I hate the stereotype that women are more emotional. But I think he taps in with a lot of his feminine side in the music, and that attracts his huge fan base of Black women.”

“If you look at his dating patterns, he almost singularly and exclusively dates Black women,” including Rihanna and Serena Williams, says Higgins. “If you do forensic audits of all of these women he’s name-dropping who he’s dated, who he’s had flings with — it’s all Black women. There’s something to be said about that. Black women to a point probably take in his music as if he’s singing directly to and about them.”

Being a swole and tatted internet-deified daddy also tends to help. But with his physical transformation has come a cultural one, too, say those who follow Drake closely.

“Drake eventually just had to lean into some of those masculine tropes that hip-hop kind of thrives in. Once he started embracing that more, of course his image started changing as well,” says Mowatt. “In a way, it’s almost as if he’s become a caricature … He really just started leaving those bits and pieces of the former Drake behind.”

Even with culture-defining turns such as the music video for “Nice for What” (a pseudo-anthem for the modern independent woman) and songs like “Best I Ever Had,” which celebrates a loyal girlfriend as the one that got away, misogyny has seeped further into his songs, critics say. In a lyric in 2022’s “Circo Loco,” off of 2022’s Her Loss, he raps, “This bitch lie ’bout getting shots, but she still a stallion / She don’t even get the joke, but she still smiling” — which many have read as a reference to Megan Thee Stallion’s highly publicized trial against rapper Tory Lanez. (Lanez was eventually found guilty of shooting the star.)

Of course, there’s no defining Drake moment more discussed than when his son, Adonis, was introduced to the world via a diss track from rapper Pusha T. The track essentially cornered the secretive rapper into confirming the existence of his son — and his French artist mother — to the public. The star who entered the world clean-cut and coy was quickly becoming messier, altering the way his female fan base viewed him, and it was all his own doing.

“The relationship that Black women have with Drake is the same relationship that Black women have with hip-hop. You can’t 100 percent love it,” says White. “There’s always going to be that one part that’s cringe or in poor taste or just flat-out unacceptable. That’s not every Black woman — some are going to say music is music. But some of us can’t let go of the idea of marketed toxic masculinity.”

Drake’s desire to control the narrative has also landed him in trouble in other ways. Take the faux Vogue cover produced to promote last year’s collaborative album with British rapper 21 Savage — a confusing PR move, considering Drake has the pull to land any cover he wants, whenever he wants. It led to a lawsuit from Vogue publisher Condé Nast. (The lawsuit was settled.)

“You have to talk about Drake”

Drake, an artist so associated with youth — the parties, the mistakes, the messiness, and the love that exists between it all — is now in his mid-30s, and it raises the question of where he goes from here.

“I hear paranoia in his music, at least way more than I used to hear. There was always a kind of guardedness to his work, but now it’s amped up,” says White. “Drake is that guy in the club, looking over his shoulder, not really knowing who to trust or creeping down his own street at 2 o’clock in the morning. He has a hyper-awareness of who he is. He flipped an Aaliyah lyric actually —‘I gotta watch my back cause I’m not just anybody.’ That mindset has just become a little more prevalent in his work.”

In that way, Drake has managed to expand past the social boundaries of rap and has created a genre and entity all his own. Sad boys, sex, and success have all become synonymous with the star, and it’s clear the world isn’t sick of it yet.

“When we talk about the globalization of R&B and rap, you have to talk about Drake. When you talk about cult followings and hardcore music enthusiasts, it’s all become a euphemism for Drake,” Higgins says. “That’s what makes him different from the rest.”

Bianca Betancourt is the digital culture editor for Harper’s Bazaar, where she covers music, film, television, and pop culture at large. She’s previously written for the Washington Post, Rolling Stone, Teen Vogue, i-D, Remezcla, and more.


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