In John Ashbery’s poetry, pronouns rarely serve as signifiers for specific people but as ambiguous subjects that shift throughout the course of a collection, even a single poem. “The personal pronouns of my work very often seem to be like variables in an equation,” Ashbery once said in an interview. “ ‘You’ can be myself or it can be another person, someone whom I’m addressing, and so can ‘he’ and ‘she’ for that matter.” By obscuring the second person pronoun the possibilities for address become endless; with each use Ashbery could be addressing me or you or some fictive other co-created in the consumption of the text.

While it’s hard to imagine Drake as an avid reader of John Ashbery, he nonetheless obfuscates pronouns with Ashberian flair on his 2011 album Take Care. On a record obsessed with identity and self-mythology, loneliness and social overextension, Drake uses the direct address to fill many needs. Sometimes he pleads with a “you” for emotional reciprocity, while other times he’s begging for forgiveness. Or sometimes, like Ashbery, the “you” appears to be Drake himself. Take the following lyrics from the album’s titular track: “You hate being alone / You’re not the only one / You hate the fact that you bought the dream and they sold you one.” The “you” addressed here seems detached from any cogent point-of-view, alternating between Drake and his audience, even between Drake and himself. This, of course, is a space in which Drake thrives—warring between selves, haplessly soul-searching. At one moment he’s the bicep-slapping rapper who “killed everybody in the game last year” (“Over My Dead Body”), the other an emotional masochist who experiences a loneliness so demanding that after several glasses of rosé he calls an ex to ask if she still thinks about him the same way he thinks about her (“Marvins Room”).

As if to affirm the split between bipartite selves, Take Care finds Drake fluctuating between pride and misery, sometimes even within the same verse. “Bitch, I’m the man,” he sings on synth-pad ballad “Shot For Me,” telling a past lover that he’s doing just fine without her. But then, on a whim, his confidence wavers and the song becomes a wounded confessional: “Okay, look, I’m honest: girl, I can’t lie, I miss you / You and the music were the only things that I’d commit to.” Such flip-flopping embodies the gospel of Drake: a continuous conflation of self-confidence and self-loathing, future ambitions and recurring nostalgia, fame and chronic isolation. And while Drake’s more recent work is less adept at balancing these incongruities, Take Care wrestles with them in a tonally linked coming-of-age narrative that declines to moralize or offer much in the way of resolution. Like our own minds, the album is a landscape of repetitive, circuitous ideas that, in the aggregate, lead nowhere.

What makes this significant is that before Take Care few hip-hop albums (save Kanye West’s foundational 808 & Heartbreaks) had expressed vulnerability and psychological anguish with such self-conscious precision. Hip-hop is built on a bedrock of historical suffering and cultural trauma, and rap albums have long been a venue for harrowing introspection. But Drake’s brand of self-reflection is unique in descending so willfully into melodrama. Released on the heels of Kid Cudi’s Man on the Moon I and II and The Weeknd’s House of Balloons, albums that floated in a haze of drugged-out depression, Take Care immediately stood out as a magnum opus of male vulnerability. It is one of the first mainstream rap records to make emotional transparency something that actually sold records. And hip-hop’s current glut of SoundCloud rappers—teens who make depressive, emo-bending trap songs—would likely not enjoy the same level of profitability without Drake’s initial willingness to be sad.

Still, it is easy to overlook Drake’s contributions to contemporary hip-hop since he has seemingly lost the ability to make emotionally affecting art. And indeed Drake is much more than an artist in 2019. He has evolved into a hundred-million-dollar institution unto himself, a corporate avatar who crafts radio-smashing singles intended to eviscerate streaming records. Occasionally, though, he tries to turn back the clock and espouse the same vulnerability he did on Take Care. “I want to let you know there’s more of me,” he sings half-convincingly on “After Dark,” a deep-cut from last summer’s Scorpion. The “you” here could be a prospective lover, or it could be us, the audience, who have endured every angle of Drake’s fame since 2009 when he rocketed into the mainstream with “Best I Ever Had.” Either way, Drake’s newer music has sounded increasingly removed from a relevant social reality, making it difficult to digest his continued quest for reciprocity, for someone to understand exactly what he’s feeling.

It’s hard to remember, but Drake was not always the meme-generating mega-narcissist notorious for appropriating Caribbean flavor and London grime and lesser known rappers’ styles for unfettered personal profit. There was a time when he was still a self-afflicted up-and-comer, a demure pop music polymath perfecting a sound that would fundamentally transform his career and hip-hop alike. Back then, he was not only singing to you but for you, his music capturing an inclusive internal dichotomy that a million different selves could believably project themselves onto.

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Take Care didn’t come out of nowhere. In the years before its release Drake was locating his sound, developing his confidence as a singer and writer, and trying to transcend the limitations of radio rap. These explorations led to an experimentation with downtempo electro-soul, a species of low-slung R&B scattered throughout Drake’s early work. Yet while his first forays into singing were intriguing, even successful, he too often sounded like a less interesting version of The-Dream. But on Take Care Drake finally arrives into his own as a vocalist, demonstrating an improved dexterity between singing and rapping. His voice is doubly complimented by producer Noah “40” Shebib’s muted, minor-chord production style, awash with aural synth pads, organ sustains, sparse drum loops, and wobbly 808s. And, as such, Take Care sounds like the album Drake and 40 had been trying to make since 2009, a sinuous blend of hip-hop and R&B subverted with the sensibilities of James Blake and Jamie xx, all while maintaining a bounce indebted to UGK and early Cash Money records.

Fittingly, Take Care’s matured musical composition is met with matured thematic concerns. Although Drake’s calling-card has always been his navel-gazing, here he expresses his deep-seated emotions with an exacting clarity. On “Marvins Room,” for instance, one of the best downbeat pop songs of the decade, Drake drunk dials an old girlfriend, goading, “I know you still think about the times we had.” It’s a facetious accusation; he’s the one in search of something real, while this anonymous “you” has moved on with her life. On “Good Ones Go Interlude,” Drake is no longer drunk but sober and crestfallen, desperately begging for a second chance: “Don’t you go getting married, don’t you go get engaged / I know you’re getting older, don’t have no time to waste / I shouldn’t be much longer, but you shouldn’t have to wait / Can’t lose you, can’t help it, I’m so sorry, I’m so selfish.” Although Drake claims he “avoids commitment” and is “scared to let somebody in” (“Girls Love Beyoncé”), he sings the former lyrics with an arresting intensity that, for a moment, makes you think he may abandon rap fame for domestic stability.

It’s hard to tell if Drake’s heartbreak is real or imagined. His focus is less on lost love than the lost opportunity to fall in love. And since fame handicaps his ability to forge genuine romantic connection, Drake tries instead to remember people from the past, those who knew him before he was famous. So when he sings to an ambiguous “you,” it seldom seems to be directed at a particular individual, but to a composite feeling of anxiety and loneliness that serves as the simulacrum of a real person, a character that could feasibly contain anyone. “You’ll say you love me and I’ll end up lying and say I love you too,” he sings on “Doing it Wrong.” What makes this strategy effective is that the “you” feels both specific and inclusive, general enough to apply to a storm of crying fans, yet intimate enough to beget an authentic emotional response from you, the individual listener, a discursive consciousness who has probably experienced a heartbreak similar to the type Drake describes here.

And so unlike almost any rap album before it, the internal conflicts on Take Care are rendered with grueling self-awareness, even tenderness. Nowhere is this more apparent than on “Look What You’ve Done,” a Static Major-sampled song about Drake’s mother and uncle, which features some of the best writing of Drake’s career. “You tell me I’m just like my father, my one button, you push it / Now it’s ‘Fuck you, I hate you, I’ll move out in a heartbeat’ / And I leave out and you call me, and you tell me that you’re sorry / You love me, and I love you, and your heart hurts, mine does too.” For once Drake has stopped brooding and bragging and has paused long enough to express genuine gratitude to those who matter more than himself. His “you” is concrete. It’s a touching moment of empathy on an otherwise solipsistic record.

While Drake has certainly made important music since Take Care, his recent work shows the wear of an atomized ego. He has grown bitter and brash and less emotionally specific. More than anything, though, he seems artistically stagnant. When he’s not making philanthropical anthems (“God’s Plan”) or female empowerment songs (“Nice For What”) or piano-house singles even your parents can hum along to (“One Dance”), he’s reverting back to his trademark brand of the wounded hero. Except Drake is no longer young enough to pull off the role; he’s thirty-two. Ideally his music would document some form of personal growth, not regression. He can’t live in the Take Care realm forever, because a central charm of Take Care is how it documents Drake in the process of maturing, articulating the interpersonal struggles one experiences while growing up under bright lights. In the eight years since the album’s release, however, Drake still seems to be grappling with the same insecurities he was when he was twenty-four. With each new release, there is more of the same: bemoaning exes, berating rivals, etc. Except now his solipsism no longer feels transgressive. It feels helpless.

Other than 2013’s Nothing Was the Same, Take Care is the album that will continue to cut through the corrosive noise surrounding Drake’s outsized persona. Through it all—his perpetual presence in the celebrity-news-cycle and corporate affiliations and questionable romantic history—Take Care remains a genre- and legacy-defining masterwork, an album consumed with loss and redemption and overwhelming loneliness through which a contemporary Western identity emerges, one that takes its own subjectivity as purveyor of the universe. We feel with Drake rather than for him—a distinction that gives Take Care that elusive Ashberian quality, the first- and second-person pronouns working “like variables in an equation.” And although Drake has a lot more music left in him, I would be shocked if any new material matched the emotional, cultural, and musical import of Take Care, or was ever as inclusive. Anything new will feel hollow, abstracted, every “you” a luxury suite we are no longer allowed to inhabit.