“I Paints Pictures with Poems”

As strange as it may sound, Jay-Z is an underrated rapper. Yes, he is recognized for his swaggering self-confidence and astonishing verbal gifts. But he is not nearly as celebrated for his vivid and extremely sophisticated romp on poetry’s playground of metaphor and metonymy, simile and synecdoche. He is Robert Frost with a Brooklyn accent, Rita Dove with a Jesus piece.

Jay is a past master of American poesy. He composes in the recording studio with the tools of verse at hand. He is an architect of sound whose rhymes satisfy the ear. He is a painter of images whose visions flood the mind’s eye. He sketches verbal blueprints that map the black experience onto American rhetoric. As he makes his way to the recording booth, Jay stumbles over discarded stanzas, fumbles with multiple forms, trips on loitering tropes. He chisels away at the air until sound becomes sense and words are sculpted from mumbles. Meanwhile, Jay is ambushed by double entendres, and instead of turning them over to English authorities, he plays judge and jury and gives them long sentences.

Jay’s lyrical cleverness masks his deeper intellectual reflections on the world and on black culture itself. Jay’s claim in “Moment of Clarity,” that “I dumbed down for my audience to double my dollars,” is a misdirection of sorts. “Moment of Clarity” is one of the clearest explanations of the logic behind his approach to making commercial music with intellectual heft. Jay asks his listeners to study intently his body of work—from Reasonable Doubt to the Black Album, on which the song appears. He promises them that if they’ll “[l]isten close, you’ll hear what I’m about.”

Jay realizes that the knock on him is that he treads water at the shallow end of the pool. In order to get his audience to at least hear what he has to say, and to discover how well he can handle the deep end, he has to first get them into the water—that is, sell records. By first advertising himself as an accessible pop culture figure, and not a daunting thinker, Jay can invite his listeners into the waters of reflection as an intellectual lifeguard of sorts with the promise that they won’t get in over their heads. This is the same man, after all, who had established his trustworthiness as a well-informed guide who wouldn’t burden his listeners with obscure language and esoteric ideas. In a battle with a foe who didn’t have to be named, Jay makes it plain that his opponent, known for being an intellectual heavyweight, was outwardly impressive but lacked true substance.

And y’all buy the shit, caught up in the hype
’Cause the nigga wear a kufi, don’t mean that he bright
’Cause you don’t understand him, it don’t mean that he nice
It just means you don’t understand all the bullshit that he write

Jay argues on “Moment of Clarity” that if he took the tack of gifted rappers of conscience like Talib Kweli and Common he wouldn’t be commercially viable. Despite his admiration for them, their enormous skills haven’t created a big pay day or wide cultural influence. This isn’t the fault of the artists but a reflection of how the culture operates. Jay says that rappers must make up their minds about what their goals are and how they intend to achieve them. He makes clear that his goal is to help the poor—and his hustling history tells him that making music that sells is one way to do that. But he claims that underneath it all is a cunning intelligence that fosters strategies of wealth creation and resource sharing.

Fuck perception! Go with what makes sense
Since I know what I’m up against
We as rappers must decide what’s most important
And I can’t help the poor if I’m one of them
So I got rich and gave back, to me that’s the win/win
So next time you see the homie and his rims spin
Just know my mind is working just like them (rims, that is)

Jay’s edifying and strategic misdirection didn’t keep the depth of his gift from sounding through. His first album, Reasonable Doubt, teems with complex metaphors like these lines from “Can I Live”:

My mind is infested with sick thoughts that circle
Like a Lexus, if driven wrong it’s sure to hurt you
Dual level like duplexes, in unity
My crew and me commit atrocities like we got immunity
And his rhymes revel in intricate wordplay, like this from “D’Evils”:
She said the taste of dollars was shitty, so I fed her fifties
About his whereabouts I wasn’t convinced
I kept feedin’ her
money ’til her shit started to make sense.

The eye more easily captures the meaning on a page, or onscreen, in hindsight, after careful reading, but the ear must hear the lyrics repeatedly to get their full meaning. Such is the nature of Jay-Z’s craft. The claim to dumb things down is meant to allay the fear of depth. Jay loses none of his sophistication in his strategy to say smart things in an accessible fashion. He layers his lyrics with multiple meanings; he waxes philosophical and poetic while keeping the party lights on.

When Reasonable Doubt debuted in 1996, it wasn’t instantly hailed as a classic by critics. That designation had to wait a couple of years. In 1998, Source magazine, the hip hop Bible at the time, revised its initial rating of four out of five mics and gave the album a perfect five mics. Neither was the album eagerly snapped up by consumers. Reasonable Doubt wouldn’t garner platinum-level sales until 2002, by which time Jay-Z had become a big star. From that point forward, he left nothing to chance.

Jay learned the lesson not to wear his learning so heavily. His strategy to obscure his erudition as he spoke his piece had many aspects. It was a matter of modifying his themes. Jay made a calculated effort to disguise his intelligence by scattering his philosophical reflections on life amid lyrical nods to the good life in clubs or cars. It was also a matter of proportion. For every “Minority Report,” reflecting on Hurricane Katrina, or “Young, Gifted & Black,” a colorful indictment of white privilege, there were many more of “I Just Wanna Love U (Give it 2 Me),” a gleeful ode to bacchanalia and booty.

His approach was also a matter of placement and priority. Jay has made quite a few “B-sides,” songs not released as singles or deemed to be hits. These efforts afforded Jay greater freedom to explore his wide-ranging interests without fear that his complex wordplay or rich literacy might scare listeners away. Many of these songs contain the “eggs” he places on each album for aficionados to hunt for, for true lovers of Jay’s sophisticated poetry to seek out. A vibrant example is 1997’s “Streets Is Watching,” where Jay reflects on his divine destiny as he negotiates the treacherous code of the streets:

Was this a lesson God teaching me? Was he saying that
I was playing the game straight from Hell from which few came back?
Like bad coke, pimp or die, was my mind frame back
When niggas was thinking simplify, was turning cocaine crack

Ain’t a whole lot of brain to that, just trying to maintain a stack

On 2002’s “Don’t You Know,” Jay celebrates his embodiment of the poetic vocation by personifying his craft.

Won’t you throw in the towel? I’m better with vowels
My vocabulary murders the dictionary
Flow switches every 16, shit mean, man

…

Nigga I’m poetry
In four-part harmony, it’s like Jodeci
Check out my melody, my flow is a felony.

Jay returned on later songs to the tension between art and commerce. He said, point blank on “The Prelude,” in 2006, that “Bein’ intricate’ll get you wood, critic.” Wood, as in a disc not going platinum, or gold, but selling very few records. On 1998’s “Hard Knock Life (Ghetto Anthem),” Jay reminded his audience of its offense:

I gave you prophecy on my first joint, and y’all all lamed out
Didn’t really appreciate it ’til the second one came out.

In 2007, on “Ignorant Shit,” before he begins to rap, Jay complains about the lukewarm critical reception of his previous album, 2006’s Kingdom Come.

Y’all niggas got me really confused out there
I make “Big Pimpin” or “Give it 2 Me,” one of those
Y’all hail me as the greatest writer of the 21st century
I make some thought provokin’ shit
Y’all question whether he fallin’ off?

Jay’s one-time rival Nas said it directly on “Let There Be Light”: “I can’t sound smart, ’cause y’all will run away.”

Still, Jay’s lyric from “Moment of Clarity” has social and racial purpose: Jay can preserve the complex and coded conversations he has in his music, for instance, with folk who are still hustling or with those whose racial struggles tie them to him. And then, at his discretion, he can, as the title of his memoir suggests, decode his work, both for those who are new to his lyrics and for those who wonder just what he may have had in mind as they pore over his secular scriptures.

Perhaps we have not given him sufficient credit because our bias against hip hop artists won’t let us see that the best of them have at the ready an army of narrative techniques to tell their stories and spread their truths. Jay has proved his mettle and pedigree as a poet through the sophisticated use of literary devices and refined craft. He has proved it by arguing persuasively that intelligence is a highly desirable good. He’s shown it through the use of hyperbole and braggadocio, and by his ingenious extension of the black oral tradition. He’s also given us a glimpse of his poetic gifts, and underscored his remarkable longevity, by engaging three of the greatest artists of his time.

He had beef in the late nineties and early aughts with legendary wordsmith and Queens MC Nas. He had brotherhood and camaraderie with fellow Brooklyn icon The Notorious B.I.G. (born Christopher Wallace) before Biggie’s murder in 1997. And, on and off, over the last decade, he has had collaborations and competition with biracial Canadian rap superstar Drake. He and Drake have in particular clashed over how Jay uses poetry to spotlight visual art.

Jay not only enthusiastically embraces the visual and performance arts, but he grapples with his identity as a hustler, with racial strife and black identity, with black cultural habits and traits, and with the function of art, high and low, in the pursuit of meaningful existence. He has also used poetry to probe the relationship between rappers and superheroes.

If critics miss Jay’s literary sophistication, his high intelligence, his cosmopolitan cultural habits, his adroit readings of social life, his adept deconstructions of pop culture, his public intellectual labor, perhaps it is because, as Jay-Z says, they insist on a shallow reading of his art. They end up doing, ironically enough, the very thing they accuse him of, namely, sticking to the surface. Jay summarizes the claim and counters it on 2001’s “Renegade,” produced by Eminem:

Motherfuckers say that I’m foolish, I only talk about jewels (Bling bling)
Do you fools listen to music, or do you just skim through it?
See, I’m influenced by the ghetto you ruined
The same dude you gave nothin’, I made somethin’ doin’
What I do, through and through and
I give you the news with a twist, it’s just his ghetto point of view.

In the opening lines of “Streets Is Watching,” Jay-Z’s classic treatise on drug dealer paranoia and angst, he seizes on the question of intelligence in hustling, hip hop, and beyond, and sends it our way.

Look, if I shoot you, I’m brainless
But if you shoot me, then you’re famous
What’s a nigga to do?

Jay poses the rhetorical question like it’s an existential crisis. For those hustling on the corner, it is surely a Rubicon that, once crossed, commits them to action. Rhetoric and performance are now tied in Jay’s view; they are critical to answer the question of how one uses what one learns to set a new standard for wisdom and behavior. All of this is driven by a regard for how acute observation and tough-minded reflection can help one to navigate the perils of the underground economy and to flourish while there—that is, as long as one can stay alive while plotting one’s elevation or escape. There is the possibility that the narrator might act, or shoot, without proper forethought, without counting the cost. Thus, there is reckoning with the mortal effects of the drug dealing enterprise in toto. There is, too, grappling with the consequences of specific actions. In particular, there is the potential for brainless decisions that can turn fatal within the cutthroat capitalism of the underground drug world.

Even after many listens, one thing is clear: the opening lyrics and the song itself are smarter than they sound. The narrator urges listeners to “Smarten up, the streets is watching.” His audience includes all sorts of hustlers, and himself as well, a dealer-turned-artist who has had to make smart decisions in his transition out of the drug economy. The song presents a pitch-perfect personification of the “streets” as an urban proxy of the surveillance state. Jay’s narrator also makes multiple references to his state of mind to paint a bleak picture of the world that many critics accuse Jay-Z of mindlessly glamorizing. The lyrics come down on the side of drug dealing, finally, as a non-thinking enterprise. “Ain’t a whole lot of brain to that,” he says, concluding that the decision to leave behind the violent, communally debilitating life of the drug dealer is an easy one. “[W]hy risk myself, I just write it in rhymes.” Or more to the point: “This unstable way of living just had to stop.”

“Kingdom Come,” the title track from Jay-Z’s 2006 comeback album—he briefly retired in 2003 to become CEO of Def Jam after releasing The Black Album—offers a paradigm of intelligence as a desirable good that greatly serves an audience composed of hustlers.

And I’m so evolved I’m so involved
I’m showing growth, I’m so in charge

…

I’m so indebted, I should have been deaded
Selling blow in the park, this I know in my heart
Now I’m so enlightened I might glow in the dark.

Traditional notions of public intellectual work usually root knowledge in the ivory towers of the university. The spread of knowledge is then traced into the busy lives of everyday folk who normally can’t get to the learning the academy so viciously polices. In a way, Jay-Z has reversed this trajectory. His artistic work has done what some of our most important academic work only aspires to achieve. He speaks to those in the underground economies, and they hear him. In fact, after his retirement, he heard the chorus of pleas for him to return to form.

I hear “hurry up Hov” when I’m out in the public
Cause niggas like: “but you love it;
you be it, you’re of it
“You breathe it, we need it; bring it back to the hustlas.”

Princeton professor Imani Perry, in the Chronicle of Higher Education, has reflected on what the term “public” has to do with the phrase “public intellectual.” For Perry, thinkers like writer and former NAACP head James Weldon Johnson and author and sociologist Anna Julia Cooper set the mark for what we should expect from public thinkers who ideally “desire to contribute in diverse ways.” Perry says that there “is so much work to be done, particularly in communities of color, on a wide range of issues, including educational outcomes, imprisonment, nutrition, political representation, unemployment.” The work of public thinkers can certainly help solve many of these problems.

Jay-Z has checked marks in many of these categories: he established the Shawn Carter Scholarship for the formerly incarcerated and for disadvantaged youth who want to go to college; helped to form an organization to promote criminal justice reform; became a vocal advocate for bail reform; produced documentaries that address the tragic deaths of Kalief Browder and Trayvon Martin; visibly supported Barack Obama and Hillary Clinton at different times in their runs for the Oval Office; and used his social media platforms and other outlets to promote a healthy lifestyle to his followers, which he backed up with an investment of a million dollars in a black-owned vegan cookie company. There are, too, his New York Times opinion pieces on social and criminal justice issues, his financial contributions to 9/11 victims and Hurricane Katrina survivors, his aid to black folk in need of legal support for police brutality and free speech cases, his paying the taxes of rap superstars Lil Wayne and Meek Mill and putting up money to bail out members of the Movement for Black Lives. I will explore at length in the next chapter his ideas about social change, racial injustice, and politics. But it is clear, both on record and beyond the sound booth, that Jay has solidified his status as a thinker and artist. His ideas about the underground, education, politics, and society have been translated into practical action and have influenced millions to think about important issues.

In “Hola Hovito,” on his outstanding 2001 album The Blueprint, Jay-Z boldly claims that he “rhyme[s] sicker than every rhyme-spitter.” Literary critics would argue that that’s a clear case of hyperbole, a rhetorical means to accent the truth of his artistic superiority. Poetic principle in service of professional self-promotion. What can’t be argued is that Jay-Z’s lyrics exult in the lively and luxurious use of such poetic devices. It may be his promiscuous rendezvous with the figurative that makes him the “sickest” rhyme spitter of all time. But hyperbole is only the top layer of this particular lyric. The reconfiguration of “sick” as a metaphorical superlative has important roots in the culture. Rap music and African American Vernacular English (AAVE) are frequently spiced with ample doses of contronym, a literary mark of playful duality where a two-faced term can suggest its polar opposite in the right context. Consider Run-DMC’s great line, “Not bad meaning bad, but bad meaning good.” Within the lexical universe of hip hop, “sick” borrows its most useful double from one of the culture’s classic contronyms: “ill.” Contronymic terms in hip hop tend toward the superlative spectrum of meaning.

The relentless quest for language that adequately describes what black folk experience fuels the refiguring of the negative as the positive. Hence there is a moral meaning attached to the use of language in black life. Making it plain that speech has ethical consequences helps to filter a certain set of experiences through the prism of hip hop lyrics. A useful analogy can be made between rapping and preaching. Rappers can be conceived as evangelists who promote the idea that something can come from nothing and that negative circumstances might produce positive outcomes. Theology and sociology nicely combine. Life in the hood can be ill—that is, sick—undoubtedly in a negative way, but sick, too, in the superlative sense conjured in the contronymic figuration of the word. Jay-Z makes a compelling claim to be the sickest ever “rhyme-spitter,” even though every generation sends formidable rappers to the microphone. And even though most rhymes are more spoken than spit. But that might lead us down a literary rabbit hole where we debate whether metaphor or metonym best suits the case.

“Guns & Roses,” the song, not the iconic rock group of the same name, is one of Jay-Z’s most intriguing collaborations. “Guns & Roses” was produced in 2002 by the late, great rapper Heavy D. There are vocal and guitar contributions from Lenny Kravitz, whose rock-tinged licks underscore lyrics that wrestle with the violence and bliss that shape the ups and downs of hustling and rap music. As usual Jay proclaims his artistic greatness.

The Michael Corleone of the microphone
The Michelangelo of flow, I paint pictures with poems.

Allusions matter, like those to Italian icons of American pop culture and the High Renaissance, and I’ll get to them soon. But the punch line, “I paint pictures with poems,” is as important an analogy as Jay has ever articulated. In one line, he evokes his career-long allusions to Warhol, Picasso, and Michelangelo, his direct engagement with museum culture, and his affinity and affection for Jean-Michel Basquiat. Jay-Z does not write his rhymes in a traditional sense—and yes, more on that later, too—so it may be more accurate to argue that he crafts his images through words. This is more than poetic imagery; it harkens back to the early-twentieth-century poetic movement known as Imagism. That movement featured giants like Ezra Pound and James Joyce and a call for precise, concrete images drawn from common speech, rhythmic inventiveness, and unlimited topics of engagement, all meant to forge clear expression. It can be argued that the best rap artists embrace the Poundian and Joycean imperatives, but none more, or better, than Jay-Z.

Jay’s sublime attraction to poetic and literary devices has been fed by thousands of hours of exercising his craft. That befits his admiration for Malcolm Gladwell, who popularized the notion that mastery is achieved with at least ten thousand hours of practice. Although he told Oprah in O magazine in 2009 that English was his favorite subject in high school, and that Homer’s The Odyssey left him feeling dreamy about life partnerships and the concept of returning home, Jay has had little formal training in the craft of writing poetry. His practice, still, has almost always been intentional, a reference to another of his favorite books that explores the spiritual dimensions of intentional living, Gary Zukav’s The Seat of the Soul. That practice began on the street corners of Brooklyn, New York. In a hidden track on The Blueprint album, Jay-Z extends the analogy of lyrically working out on “Breathe Easy (Lyrical Exercise).” The track opens in medias res with an interview snippet where Jay describes his writing process. While standing on the corner, dealing crack, Jay would craft and rehearse his rhymes in his mind until he had both perfected and memorized them. “Breathe Easy” bobs and weaves seamlessly through at least three forms of exercise, including jogging, sparring, and weightlifting. There are verses but no real hook except for the extended analogy itself. Jay is rapping about the exercise of rapping using the language of exercise itself. As he brags on the track, he’s in great shape.

Braggadocio is the pervasive ethos of Jay-Z’s music. If the repetition of a statement or a concept makes it a perceived reality, then Jay has consistently reminded us of how real his greatness is. Given the accumulation of lyrical repetition at work in Jay-Z’s boasting about his gifts, the simplest lines at times deliver the most powerful figurative effects. Take his line “flyer than a piece of paper bearin’ my name” from “Public Service Announcement.” Paper fliers are paper advertisements that are widely distributed by mail, posted in public places, or passed on to individuals. They have an important place in the history of hip hop. In fact, hip hop fliers are enshrined in the Harvard Hiphop Archive and Research Institute, the Cornell University Hip Hop Collection, and the National Museum of African American History and Culture. They are concrete, well, metaphorically at least, and if not concrete, then material representations of the culture.

The concept of the flier in hip hop flies effortlessly in and through this one line. The flier is an example of an image carefully stamped in a lyric that represents Jay-Z’s artistic signature. A throwaway line becomes a classic, much the same way that a flier to be thrown away becomes a hip hop staple. (Of course most fliers were single-page advertisements without need of a staple, except to pin them to a tree or billboard, just as Jay’s line helped to pin down the performance of “Public Service Announcement.”)

But there is more. Flight in African American culture has deep conceptual resonance. There are historical aspirations to flee bondage and to imagine being able to fly away from captivity. The modern notion of being or looking “fly” is all about style and sartorial excellence. Of course, when Jay suggests that he is flyer than a flier, a nifty homophone where the words sound the same but have different meanings, he breaks and enters into their homophonic connection to gain figurative access to the wealth of their suggestive meanings. (He also plays on the multiple meanings of the term on 2006’s “Beach Chair,” where he says, “Son said: ‘Hov’, how you get so fly?’ / I said: ‘From not being afraid to fall out the sky.’”) It is at least a triple entendre embedded in braggadocio that is committed to the poetic principles of Imagism while paying homage to a key artifact of hip hop’s material culture.

As a writer, I find it astonishing that Jay-Z does not write down his lyrics. He does not impress paper with ink in order to impress his hearers with his complex rhymes. He does not so much as scribble his thoughts on paper or type them on any surface or screen. Given the huge quantity and high quality of his oeuvre, his work is all the more remarkable. Orality is a defining feature of black culture. The oral tradition of crafting and transmitting African American folktales was inherited by enslaved Africans from their continental forebearers. These oral stories were designed to make sense of the brutal conditions foisted on black souls in the New World during the long siege of transatlantic slavery. Folktales from the African oral tradition seeped into the fabric of black expression and performance. One popular example, “The People Who Could Fly,” captures the incredible story of mass suicide by Africans in bondage. The story is transformed into a celebration of resistance and liberation in the face of racial violence and chattel slavery. There is little doubt that hip hop culture creatively extends the moral instincts of the oral tradition. As a hip hop writer, Jay-Z epitomizes black orality in the twenty-first century.

But Jay doesn’t primarily rap about slavery. His most profound contributions to the African American oral tradition are more like hustler turned author Iceberg Slim than novelist Charles Chesnutt. (“Where’s Iceberg Slim he was the coldest cat?” say those asking Jay-Z to come out of retirement on “Kingdom Come.”) Instead Jay has made high art of low culture. Some of his most salient contributions to the African American oral tradition are gritty and at times violent narratives that portray underground economies in the waning years of the twentieth century. “Friend or Foe,” from 1996’s Reasonable Doubt, and 1998’s “Friend or Foe ’98,” from In My Lifetime, Volume 1, are two classic examples of this form.

Neither of these are best described as songs. “Friend or Foe” has a run time of about 1:50 and “Friend or Foe ’98” clocks in at just over two minutes. Neither track has any semblance of a hook. Both performances in tandem complete the story of how Jay’s narrator first warns and then disposes of his would-be competition in the drug game. The style of the lyrics is conversational and flippant, downplaying the sort of cutthroat approaches to the turf wars that plague illegal drug dealing. The setting is “out-of-state,” and in “Friend or Foe,” with piercing staccato horns blowing away, Jay’s narrator advises his opponent to never “ever-ever-ever-ever-ever-ever come around here no mo’.”

In “Friend or Foe ’98,” fretful guitars dominate the soundscape as his competition returns with schemes to murder Jay’s narrator. His opponent is foiled, and Jay’s narrator kills him, and in the process of pulling the trigger, sends salutations and “ice cubes” to his recently departed friend, Biggie Smalls. The “Friend or Foe” tag team was not designed for radio airplay. The songs don’t have, nor do they require, music videos. Each is its own cinematic glimpse into the life of a New York drug dealer hustling in Virginia, or elsewhere in the South, only to find that some other Northeastern hustler has the same idea of making easy money where the demand is high, law enforcement is soft, and competition is limited.

Jay’s vocal performance, particularly on the original “Friend or Foe,” sounds effortless. The recording plays more like a freestyle than a premeditated “written” set of rhymes. This is both intentional and a consequence of Jay’s artistic process. The lyrical work sounds unrehearsed and therefore more authentic and, in this sense, more easily absorbed into an established African American oral tradition. But the unrehearsed free-flowing aesthetic of the “Friend or Foe” verses also reflects Jay-Z’s non-writing “writing” process. That process in turn helps to bolster the aesthetic and epic nature of the “Friend or Foe” conflict. The aesthetic requires a demeanor in the narrator that is effortlessly cool but ultimately calculating given the stakes of this illegal “game.” Revisiting the “Friend or Foe” narratives reminds listeners of the prelude to Jay-Z’s “Breathe Easy (Lyrical Exercise),” where he talks specifically about committing lyrics to memory as he navigates urban corners, hustling his illegal product.

Jay-Z’s lyrical process itself feels a tad illegal, as if his gifts violate some unwritten law, as if not writing words down and using mnemonic tricks should not lead to artistic dominance. Jay-Z’s artistic process forces us to rethink exactly what it means to write, which should be reimagined, at least in his case, as an operation exclusively using the mind.

We often consider metaphor to be the figurative tool of choice for MCs and rappers. That is a subtle allusion to the fact that aficionados make a distinction between kinds of rhetorical creativity. MCs master the mic with technical skills and verbal dexterity. Rappers command the mic with political passion or personal zeal. But the art of allusion has quietly become a major component of all great hip hop songs. Allusions thrive as implied references and have always been near the top of Jay’s creative chamber. Much of Jay’s artistic swagger relies on the implications of his proven ability to survive the pitfalls of hustling in America. Thus his body of work regularly alludes to his life as a hustler. This “macro” allusion to his life experiences requires him to tap into the underground world of drug dealing in the belief that his audience shares some measure of the experience with him. And yet from the time of his first release, 1996’s Reasonable Doubt, most of Jay’s audience wasn’t standing on urban corners “slinging” crack rocks. But something artistically transformative occurred. Jay’s allusions to hustling assumed an audience that understood the experiences he detailed in his lyrics. There was an allusive connection between an ex-hustler rapping about hustling and his audience of hustlers. That allusive connection in turn provided all of Jay’s listeners an authentic sense of the experiences he alluded to in order to create the music in the first place.

Allusions often require a lyrical leap of faith that the person, figure, text, art, or piece of literature the poet suggests can be easily discerned by her audience. That discernment is driven by the shared experiences that underwrite the figurative force of allusions. After Biggie’s untimely death, Jay repeatedly cited his fallen friend on record. Each citation of Biggie is a self-contained allusion to him. These allusions—and Jay’s recurring citation of Biggie’s lyrics or references to them in various ways—form an ongoing tribute to his comrade and permit Jay’s audience to share the experience with him. In this case it is the experience of loss and the mourning that attends the brutal public murder of an iconic hip hop figure.

These and other poetic concerns are at play in Jay-Z’s richly allusive “Meet the Parents,” from his 2002 The Blueprint 2 album. In his memoir Decoded, Jay writes that he “never intended ‘Meet the Parents’ to be subtle,” and yet the subtleties of this track abound. “Meet the Parents” has a powerful effect for first-time listeners that will be ruined by my exposition. The title “Meet the Parents” alludes to the great Ben Stiller movies of the same name. (As a sixty-year-old black man, I harken back as well to the film Guess Who’s Coming to Dinner, in which a black physician, played by acting idol Sidney Poitier, meets for the first time his white fiancée’s liberal parents, played by screen legends Spencer Tracy and Katharine Hepburn, who have no idea in advance of his race.) Stiller’s 2000 film Meet the Parents, directed by Jay Roach, and also starring Robert De Niro and Blythe Danner, was a remake of a 1992 film of the same name directed by Greg Glienna. Stiller’s Meet the Parents was popular enough to inspire two sequels, Meet the Fockers and Little Fockers, and two television shows, the situation comedy In-Laws and the reality-television show Meet My Folks, both of which debuted in 2002. There’s no doubt that Stiller’s Meet the Parents was an apt allusion that easily worked in the collective consciousness of Jay-Z’s listeners. The film humorously details a time-honored tradition of life partners meeting each other’s families. Stiller’s version of this tradition stews in the anxiety that these situations often provoke. It is pure comedy. Jay’s “Meet the Parents” is decidedly darker, an epic tragedy.

Jay-Z’s “Meet the Parents” exposes without effort the unspoken white and class privileges that fuel Meet the Parents. In the film, two upper-middle-class families come together before the upcoming nuptials of Greg Focker (played by Ben Stiller) and Pam Byrnes (played by Teri Polo). The film highlights the cultural differences between the Byrneses, a white Anglo-Saxon Protestant family, and the Fockers, a white American Jewish family. “Meet the Parents” is about a monumental inner-city one-night stand between two characters named Isis and Mike. Their brief union produced the unnamed protagonist of Jay-Z’s tale. Isis loves Mike for all the wrong reasons.

Mike was the hard head from around the way
That she wanted all her life, shit, she wanted all the hype.

Mike immediately denies his paternity and absolves himself of any fatherly responsibility. “If that was my son, he would look much different,” he says. Mike disconnects from his son and from Isis. The decision by the father to not claim or care for his son is one with which Jay-Z personally identifies, since his father left home when Jay was eleven years old. It was a tragic and defining moment for the young Shawn Carter. As an internationally renowned artist, Jay takes a moment to allude to his pain and to underscore the pain of black fathers who abandon their kids.

But “Meet the Parents” functions lyrically as a composite of interlocking allusions. More tragedy looms for Isis, Mike, and their unnamed son. Fourteen years go by in “Meet the Parents” without Mike and Isis speaking and without Mike talking to his son. In a Shakespearean twist of events, Mike confronts a young hustler on the urban strip where he normally hustles. He tells the younger man to move along, and the younger man bristles. They face off and draw weapons on each other, each armed with a snub-nose thirty-eight pistol. The younger man hesitates because he sees a glimmer of himself in the older man’s face. That bit of hesitation proves to be deadly as the older man fires six shots, killing the younger man. Jay’s narrator provides the costly moral lesson as the song concludes.

Six shots into his kin out of the gun
Niggas, be a father, you killin’ your sons

Jay repeats the lines for emphasis and chilling effect.

Black fatherlessness has often been prompted by draconian public policies like unjust prison sentencing and counterproductive housing rules. It has also been overblown by media coverage and made political fodder for right-wing and liberal interests. But the allusion to Meet the Parents is a powerful reminder that the challenges of parenting and absenteeism in African American communities are real. “Meet the Parents” may not be so subtle in its jarring contrast of black fatherlessness and the easy paternal privilege of the film it alludes to. But the figure of Isis demands a deeper reading as we grapple with black rituals of mourning. After seeing her son’s dead body in the morgue, Isis’s

addiction grew, prescription drugs, sippin’ brew
Angel dust, dipped in WOO!

She is as tragic a figure as either of the men who draw on each other in the song. In too many painful ways, Isis embodies the modern black mother in mourning. We know these mothers, Sybrina Fulton, Leslie McSpadden, and Lucy McBath among them. They are women who are forced into a sorority of suffering to publicly mourn children lost to senseless violence by the police or by black folk. It is telling that Isis is the name of the Egyptian goddess of mourning. When her husband Osiris is killed by her brother Seth, her mourning becomes mythic and divine. With her divine magical prowess, she reassembles her husband’s body and brings him briefly back to life. But ultimately Osiris cannot remain among the living and becomes the king of the dead. This establishes Isis as the goddess of mourning and the queen of the dead. The myth of Isis is a family affair in Egyptian lore, and Jay-Z taps into that timeless mythology, connecting it to the challenges that we face in contemporary urban and black communities. “Meet the Parents” is a mythic tribute of its own. It is a warning to its listeners of the perilous outcomes of forsaken parenting, and an indelible paean to those who struggle to survive the neighbor-to-neighbor, father-to-son, and brother-to-brother violence that plagues our communities.

It is ironic that Jay’s conscientious rebuke to intramural black violence came in the recent aftermath of his epic row with Nas. By every measure the lyrical war on and off record between Shawn Carter and Nasir Jones was the best “beef” in hip hop history. Their government names are interchangeable with their rap monikers here—and only here—given the personal nature of aspects of their pugilistic exchange. By the time most of us started to pay attention to the Nas and Jay conflict, there was already a greater war unfolding. Shots had already been fired when Jay-Z took the stage at Summer Jam 2001 and teased the world with the first bars of “Takeover.” Summer Jam is the annual hip hop summer festival sponsored since 1994 by New York–based radio station Hot 97. That year it took place in Long Island’s Nassau Coliseum.

Many followers of the New York rhyme scene had been paying attention since Nas bragged that a Lexus with television sets in it was the “minimum” luxury car one should enjoy, a direct jab at Jay-Z’s vehicle choice in 1996. Some say the beef predated this slight, to when Nas failed to show up for the “Dead Presidents II” studio session for Jay-Z’s debut album, Reasonable Doubt. (To outsiders these jabs and offenses feel light; their heaviness is determined by how they signify in a syntax of insult and a grammar of grievance driven by turf, tone, and testosterone.) Ironically Nas’s physical absence from the recording session turned into his sampled presence on the song. Producer Ski Beatz interpolated Nas’s vocals from “The World Is Yours” into “Dead Presidents II.” That song in turn became one of Jay-Z’s signature recordings.

Jay-Z’s opening salvo in this battle was a boast of membership in rap’s pantheon. On 1997’s “Where I’m From,” he contends that hip hop partisans

argue all day about
Who’s the best MCs—Biggie, Jay-Z, or Nas.

Jay was then a young upstart with only one record to his credit. Claiming comparable status to Nas and Biggie may have seemed premature. But these lines rang true. True enough, Reasonable Doubt only got its just due after Jay-Z gained prominence, even if some fans spotted its lyrical pedigree from the start. But discussions about Jay-Z’s capabilities as an MC were already drawing “G.O.A.T.” (Greatest Of All Time) comparisons.

Jay began this beef in earnest at Summer Jam when he declared, “Ask Nas, he don’t want it with Hov. NO!” That line got tongues wagging all over the hip hop universe. Consider the context. The first thirty bars or so of the “Takeover” are directed at Queens hip hop duo Mobb Deep, composed of rappers Havoc and Prodigy.

I don’t care if you Mobb Deep, I hold triggers to crews
You little fuck, I got money stacks bigger than you
When I was pushin’ weight back in ’88
You was a ballerina, I got the pictures, I seen ya
Then you dropped “Shook Ones,” switched your demeanor
Well, we don’t believe you, you need more people.

It was a spot-on verbal tirade that challenged the group’s hood bona fides because of Jay’s withering disbelief in their claims of toughness. It left the authors of “Shook Ones” a bit shaken themselves. Although Jay claimed, “I got the pictures, I seen ya,” the actual photos that Jay flashed on the screen at Summer Jam showed Prodigy in a Thriller-era Michael Jackson outfit, with a multiple-zippered jacket, white socks, and black loafers. The photos were snapped by Prodigy’s grandmother as he performed as a boy for her dance studio’s annual recital at a New York concert hall. Interestingly, at the same Summer Jam concert where he dissed Prodigy and Nas, Jay brought out Michael Jackson in a spectacular cameo appearance, thus undercutting his diss of Prodigy and signifying that he actually embraced Jackson.

The diss of Prodigy was an instance of Jay playing the dozens, a game with long roots in black culture where insults are exchanged in a ritual verbal battle between contestants. Prodigy thought the display of the photos was funny and took no offense. He told me as much when we had a public conversation about his autobiography, My Infamous Life, six years before his death in 2017. He also said he had encountered Jay outside a New York restaurant a few months after the Summer Jam incident. Jay extended a brotherly handshake and claimed they had no beef and that it was just music. As we will see below, that is consistent with Jay’s views about most rap beefs.

For Jay to tag Nas at the end of that blistering attack was the equivalent of laying down the gauntlet and then stomping it into the ground. Or, to shift metaphors, the beef between them had been fileted and seasoned and now it was ready to be sautéed.

Hot 97’s Summer Jam has been a perennial platform for the hottest hip hop artists and the most salacious hip hop conflicts. But after that 2001 moment, I could not, in good conscience, join those who breathlessly awaited the next entry in what would be hip hop’s greatest battle. I was at the time contemplating the lyrical life of Tupac. I was still in deep mourning for both Tupac and Biggie, two lyrical souls locked in mortal conflict. How could hip hop audiences gear up for another battle between hip hop legends? I knew that when titans battle, their minions go to war as well. Unless you have been to the Queensbridge Houses or the Marcy Projects, you might not be able to fully understand the grip of desperation that residential poverty has on its victims. You might not grasp how the lyrics from a champion of your hood might galvanize forces against his opponent’s hood in ways that lead to unreported collateral damage. These rap battles are too often ratcheted up by media frenzy.

And so, for the “Takeover,” and later, with Nas’s response “Ether,” I couldn’t actually enjoy the artistry. I was unable to think of these exchanges as two verbal virtuosos trading well-organized modern versions of the dozens. For me, these were two mythological brothers at war with each other and hip hop culture hung in the balance. Hip hop could not survive a war between Jay-Z and Nas that moved off the records and into the streets. It was simply too soon.

My dark fears of the war between Jay-Z and Nas lightened in the aftermath of September 11, 2001. The world of hip hop seemed smaller in the face of the destruction, terror, and loss of human life that 9/11 projected across our television screens and seared into our imaginations. Like 9/11, the war between Jay-Z and Nas was ignited by actions and paradigm shifts that we didn’t quite understand at that moment. When writers and thinkers return to the beef between Jay-Z and Nas now, they rarely fully engage the fear that cast a pall over the entire proceedings. Even for those who lauded the lyrical revival of Nas, or for those who eagerly chose their side in the bitter battle, it was fear of bloodshed that really underwrote hip hop’s greatest war. It was clear then, even if it isn’t now, that it wouldn’t take much for the beef to turn into bullets.

What was ultimately at stake in this war of words was the lasting legacy of Notorious B.I.G., known even more colloquially as B.I.G. or Biggie Smalls. Biggie was murdered in a drive-by shooting in 1997 in Los Angeles on the eve of releasing his second and final album, Life After Death. Biggie and 2Pac had been caught in an ugly, tragic war of words. Their epic talent, and the hostilities encouraged by other figures, especially in Tupac’s camp, framed their beef as a war between the East and West coasts. Sadly, careless coverage of the so-called coastal beef by segments of the hip hop media exacerbated the tense climate in which both Biggie and Tupac were brutally murdered.

Both Nas and Jay were close to Christopher Wallace. Biggie influenced and competed with them both. And when he was alive there was little question that Biggie was the king of New York rap. It was great sport for fans to debate who was better, supplying the name of whoever else may have been top of mind at the moment. But in the mid-nineties Wallace was so clearly the lyrical monarch of New York City rap that even Nas and Jay could agree on it. Vying for B.I.G.’s legacy was the natural trajectory for both men. Each had legitimate claim to it. Each had the requisite skills and borough bona fides to prosecute their claims effectively. After all, to be the king of New York rap is not only to inherit B.I.G.’s substantial crown, but to lay claim to ruling the broader cultural kingdom where hip hop began. At a certain point, things got ugly, super ugly in fact.

It is neither necessary nor helpful to rehash the drama of the “Super Ugly” phase of the Jay-Z–Nas rap war. “Super Ugly” was the second, more personal, more lethal installment of Jay’s diss of Nas. It included the claim that Jay seduced Nas’s baby’s mother in their luxury car and left condoms on the infant seat. That fracas has sold enough magazines, funded enough radio ads, and generated enough clicks online for those who want to revisit that moment on their own. What makes “Super Ugly” the most important phase in this hip hop war was the singular intervention of Jay-Z’s mother, Gloria Carter. A maternal touch transformed the tone and tenor of it all. She scolded her son for going too far in a rap battle that could have taken a far uglier turn than it did. Her scolding, and Jay’s responsiveness to it, made hip hop better and, in fact, made Jay-Z a better man too. It didn’t end the battle, but it reduced it to a respectable scuffle that ultimately ended in resolution, reconciliation, and collaboration. People talk about restorative justice and don’t always know what it means. Gloria Carter restored justice to hip hop at one of its most critical junctures. And, most important, her son didn’t lose his life in a senseless act of violence like his dear friend Christopher Wallace.

In “Moment of Clarity,” from 2003’s The Black Album, his first retirement record, Jay summarizes his legacy connection to the Notorious B.I.G. this way:

I’m strong enough to carry Biggie Smalls on my back
And the whole BK, nigga, holla back.

I use the term legacy here as an adjective, referring to software or hardware that is outdated but stays in use because it is pervasive and valuable. This is one of the best ways to appreciate Jay-Z’s profound personal and professional ties to Biggie Smalls. But it is also a more effective way of wrestling with the notion that Jay-Z the artist, including his performances, music videos, books, tours, and lyrical acumen, is better than B.I.G. was. This is a tough pill to swallow for hip hop heads, and even for Jay-Z. You will never hear him in song or in an interview claim that he is better than his “brother” Biggie.

Sure, he laments lyrically from time to time that his biggest competition is the unvanquished specter of two MCs whose legacies haunt him. In “Grammy Family Freestyle,” in 2006, and then later on “Most Kingz,” in 2010, Jay characterizes how he’s viewed as an MC in comparison to his late friend, and his friend’s rival, only to lament his own impossible dilemma.

Hov got flow though he’s no Big and Pac, but he’s close
How I’m ’posed to win? They got me fightin’ ghosts.

The closest he has ever come to a claim of superiority is in a line from “Hola Hovito,” where he opines, “And if I ain’t better than Big, I’m the closest one.”

That might have been the case at the time of The Blueprint’s release in 2001. But since then, Jay has expanded his lyrical and artistic corpus, adding eight more albums, including Watch the Throne with Kanye West. He has become a figure that in many ways transcends the culture of hip hop, amassing along the way a fan base and fortune that exponentially exceed that of his beloved brother from Brooklyn. Hip hop’s reverence for Biggie Smalls is well placed, but nostalgia often clouds proper judgment. It is a legacy assessment to place Biggie over Jay on your Top Five list. We should acknowledge B.I.G.’s enduring place in the history of hip hop culture, his tragic and premature death, and his exceptionally canny approach to storytelling and narrative, the one area where he remains unrivaled. But in almost any other aspect of rhyming, and in every other aspect of performance, artistry, and industry success, Jay simply and categorically tops one of his best friends.

Twenty-two shots are fired on 1996’s “Brooklyn’s Finest,” Jay and Biggie’s first collaboration on record. The shots are blasted off before any lyrics are fired by these verbal impresarios from this storied borough of New York. There are at least a half dozen assaults with deadly weapons, retributive shootings, and robberies referenced in the song. Like Jay-Z’s more recent urge to aggressive action on 2009’s “D.O.A. (Death of Auto-Tune),” “Brooklyn’s Finest” indeed, as Jay says on the former, “get[s] violent.” The gunshots and the random referencing of clap backs, robberies, and kidnappings are more remarkable now than they were late in the last century. Gun violence on rap records in 1996 was more conventional than gun violence on rap records now. This is especially true for Jay-Z, who has evolved from his Reasonable Doubt days as a hungry MC with much to prove in an East Coast arena that still featured Nas, Wu-Tang Clan, and Biggie Smalls at their heights. You can hear hints of the competitive spirit between Biggie and Jay on “Brooklyn’s Finest.” They were both reformed hustlers, and the competition is about how ghoulish each MC can make their past seem in the rhetorical milieu.

The lyrical blueprint that Biggie lays down in his verses is instructive. “Brooklyn’s Finest” isn’t Jay and Big’s only collaboration, but it is the most telling, because so much of what will happen to B.I.G., and how Jay-Z will eventually align himself as B.I.G.’s heir apparent, is built into these lyrics. Consider the following references in B.I.G.’s verses: “Frank White,” the character in the 1990 cult flick King of New York; the phrase “Cristal forever”; the line “who shot ya?”; the word “warning”; and the line, “If Fay had twins, she probably have two Pacs (uh!) / Get it? Tu … Pac’s.”

The allusion to the film King of New York is the basis for the eventual contention that will erupt between Jay and Nas. Cristal definitely wasn’t forever for hip hop culture, and it was Jay-Z, emerging from the shadow of B.I.G.’s legacy, who led the charge against Cristal for their racism in 2006. Hip hop frequently mentioned the high-end champagne in its songs for years. It often featured its trademark gold-labeled bottles in its music videos. But hip hoppers got a rude awakening when Frédéric Rouzaud, the managing director of the company that produces the bubbly, said that he viewed hip hop’s affection for his brand with “curiosity and serenity.” He said that while he couldn’t “forbid people from buying it,” he was “sure Dom Perignon or Krug would be delighted to have their business.” Jay led the boycott of the company and eventually bought the champagne company Armand de Brignac, dubbed “Ace of Spades.” Jay captured perfectly how social change often flows from personal experience on “Kingdom Come”:

Fuck Cristal, so they ask me what we drinking
I thought dude’s remark was rude okay
So I moved on to Dom, Krug Rosé
And it’s much bigger issues in the world, I know
But I first had to take care of the world I know.

“Who Shot Ya?” and “Warning” are both breakout tracks on Biggie’s 1994 classic debut, Ready to Die. But the phrase and word, along with the acerbically ironic reference to Tupac, are also eerily intermingled with the intangible yet volatile exchanges that fueled the so-called bicoastal rap feud. It is tragic and telling that both men’s murders, one on a Las Vegas strip after a Mike Tyson fight, and the other on a popular Los Angeles nightlife strip after a Vibe magazine party, remain unsolved.

And yet for all the gunshots and threats that ring through this energetic collaboration between Jay and B.I.G., the lines that ultimately carry the most weight, the words that have the most potential to haunt listeners even now, are the lyrics directed at Biggie’s wife, the R&B singer Faith Evans. Tupac claimed on record that he had a sexual encounter with Faith, a claim she vehemently denied. Given the tensions of the time, I believe Faith without question; I did then, I do now. But the fact that Faith became the instrument through which the beef between Biggie and Tupac was deepened is one of the saddest and most misogynistic moments of this dark phase in hip hop’s short history. The most vicious exchanges between these two men came at the expense of an innocent woman. Referencing rumors of a relationship between his wife and Tupac, Biggie let loose on “Brooklyn’s Finest”: “If Fay had twins, she’d probably have two Pacs (uh!) / Get it? Tu … Pac’s?” Two weeks later, Pac responded with a vile onslaught on his song “Hit ’Em Up,” saying in the spoken intro to the song: “I ain’t got no motherfuckin’ friends / That’s why I fucked yo’ bitch, you fat motherfucker!” Then he spoke venom in verse:

First off, fuck yo’ bitch and the clique you claim
Westside when we ride, come equipped with game
You claim to be a player, but I fucked your wife
We bust on Bad Boys, niggas fucked for life.

The words ring shamefully in our ears now even if they did not do so then. It is especially tragic that Christopher Wallace and Tupac Shakur didn’t get the opportunity to mature as men and find their way past the abhorrent visions of masculinity that imprisoned them both as young men. Thank God that Shawn Carter was given more time and space to work through his own views of women and relationships in a way denied these other two lyrical legends. Jay also would have many more beefs, mostly inconsequential skirmishes, but they were instructive both for their lack of violence and for showing how one can disagree, and be quite disagreeable, at first, before finding one’s way to peace.

In a 2002 interview with radio personality Angie Martinez, while still embroiled in a very public war of words with Nas, Jay-Z explained the rationale behind most benign rap beefs. “People clash at the top,” Jay said, echoing Nas’s line on his 1999 song “We Will Survive,” where, speaking directly to the late 2Pac, Nas confessed they “had words ’cause the best supposed to clash at the top.” Jay continued: “I’m number one, you wanna be number one. You feel you number one, I wanna be number one. Let’s do it.” Jay implored the audience not to “believe these guys when they be talking tough.” Jay summed up hip hop conflict in two words. “It’s wrestling.”

He drew on his own experience for an example. In 1999, then unsigned rapper 50 Cent had a radio hit, “How to Rob,” where he boasted he would perpetrate thievery on Jay. Jay retorted with a caustic couplet on “It’s Hot (Some Like It Hot)” in 1999 at that year’s Summer Jam.

Go against Jigga your ass is dense
I’m about a dollar, what the fuck is 50 Cents?

Jay told Martinez that before his performance, backstage, he said to 50 that “I respect the record, yeah I liked that record, it was hot. But you know I gotta spank you dog.” “No doubt, do your thing,” 50 told Jay. “Then it was peace,” Jay says. “History.” Although they’ve traded barbs since, their minor conflict never threatened to bleed into the streets. WWE for certain.

Jay referenced the tiff on 2009’s “A Star Is Born,” a song at once praising gifted newcomers and applauding those who left their mark on the rap game since Jay started, many of whom had fallen off, proving Jay’s staying power as he bragged,

I am one of one
Can’t you see just how long my run?

Jay said of the newest rap phenom, “Drake’s up next, see what he do with it.” Jay realizes that rap is “a young man’s sport,” as he told New York Times executive editor Dean Baquet, that the “white hot space” of artistic creativity belongs to those who are hungry to exult in clever cadence and mesmerizing meter, a spot he occupied for a long spell. But Jay knows that there is something greater, something deeper than immense popularity: staying power that trumps musical trends. He is enormously wealthy and influential today because he has been for a long time a cultural giant who divines the zeitgeist through a microphone. Several decades later he remains in utter command of his craft.

Yet, at times, he has been willing to acknowledge gifted heirs to the throne. His generosity, it must be noted, grew from supreme confidence. Jay’s unquenchable competitive fire is matched only by his unshakable belief that he holds the most revered spot in the pantheon of hip hop greats. If you’re the G.O.A.T., no need to be worried about the B.U.C.K., Best Undisputed Current King. Jay put in a stirring guest appearance on New Orleans–bred rapper Lil Wayne’s “Mr. Carter,” playing on both their surnames, on the younger rapper’s most celebrated album, 2008’s Tha Carter III. Lil Wayne was then in the white hot space of acclaim as the next greatest rapper alive, and Jay encouraged him to take, without apology, his rightful place at the top, which he had earned through electrifying elocution. The point, after all, is to be the best.

I’m right here in my chair with my crown and my dear
Queen B, as I share, mic time with my heir
Young Carter, go farther, go further, go harder
Is that not why we came? And if not, then why bother?

Lil Wayne was a verbal savant whose eccentric intellection and idiosyncratic Weltanschauung burned brightly in mixtapes and albums, but then flamed out a bit, or at least got doused, in an extended battle with his record label.

In the meantime, Wayne’s protégé Drake dominated the marketplace and proved to have epic cultural reach, in large measure because he reinvigorated the emotional register of rap. Jay’s relationship with Drake has been more complicated than that with Wayne. That is partly because Drake rose higher and has stayed longer than Wayne. It is also because Drake, despite calling Jay on Hot 97 in 2013 “an incredible mentor,” has taken louder shots at the throne than Wayne, mostly about Jay (and Kanye) falling off, or Jay’s increasing reference to art in his lyrics. “It’s like Hov can’t drop bars these days without at least four art references! I would love to collect at some point, but I think the whole rap/art world thing is getting kind of corny,” Drake told Rolling Stone in February 2014. Jay fired back a month later on rapper Jay Electronica’s remix to “We Made It”:

Sorry Mrs. Drizzy for so much art talk
Silly me rappin’ ’bout shit that I really bought
While these rappers rap about guns they ain’t shot
And a bunch of other silly shit that they ain’t got.

Drake hit back a week later on the song “Draft Day”: “I’m focused on making records and gettin’ bigger / Just hits, no misses, that
’s for the married folk,” cleverly parrying Jay’s feminization of him, a classic dozens, and sexist, gesture in hip hop. Not to be outdone, Jay fired back on DJ Khaled’s “They Don’t Love You No More”:

Niggas talking down on the crown
Watch them niggas you ’round got you wound
Haters wanna ball, let me tighten up my drawstring
Wrong sport, boy, you know you as soft as a lacrosse team.

Back and forth they went a few more times, never producing anything vicious, never anything that appeared to be more than sparring between two heavyweights, and along the way Jay even recorded two more songs with Drake, including one on Drake’s 2018 album, Scorpion.

Jay retained his respect and admiration for Drake despite their benign conflicts. But Jay’s crack on Drake’s “softness” reflected a charge made since the start of the younger artist’s career. Ironically, Drake, a figure known for his emotional intensity—and for his fearlessness in embracing his “female” energy while avoiding the relentless misogyny that plagues the genre—has also drawn derision and scorn, including from female fans of hip hop. It’s no surprise that Drake has been tagged as “soft” by zealots of hardcore hip hop. The genre is famously combative and thrives on Oedipal conflicts and stylish fratricide. Drake “hate”—of course not all criticism is hate, but a lot of the grousing about Drake certainly qualifies—is stoked by flawed ideas of ghetto authenticity and manhood. The prisoners of racial claustrophobia see Drake as a goofy black man who isn’t “real” because he’s a biracial ex–teen television star from Toronto. But those who entertain a broader view of blackness welcome Drake as a fellow traveler.

Even ardent fans are weary of hardcore artists flashing receipts for a cartoonish masculinity that few can afford to buy. Such flagrantly archaic views of manhood beg a fundamental question: Can that many “bitches” have riled that many “niggas” in the Maybach on the way to the club to pop collars and bottles before having empty sex and killing foes who offend their honor? It’s easy to lose count, and accountability, of the bodies. Drake deserves high praise for breaking the thug logjam in hip hop and pushing past brute machismo to embrace masculine vulnerability. That may be the shining core of Drake hate: he amplifies his emotions as eloquently as he speaks his mind. Too many rap artists carry their feelings like a concealed weapon while Drake shoots from the left side of his chest right into the nearest microphone.

“The game needed life, I put my heart in it,” Drake raps on “The Resistance,” lamenting on the song’s hook how the success he pined for now keeps him from loved ones: “What am I afraid of? This is supposed to be what dreams are made of.” On “Own It,” Drake reverses gender roles and pleads for intimacy: instead of sex, he wants to “make love / Next time we talk, I don’t wanna just talk, I wanna trust.” On the infectious mid-tempo stepper “Hold On, We’re Going Home,” rumored to be about on-again, off-again flame Rihanna, Drake confesses, “I can’t get over you / You left your mark on me.” Drake in these songs and in much of his oeuvre violates a cardinal rule in hip hop: when it comes to women, never let them see you fret.

Drake’s emotional transparency isn’t all that has sparked ire; his rhymes are often awash in melodies that cascade from a pleasant tenor singing voice, a feat that supposedly angers rap gods, who frown on the mingling of hip hop and rhythm and blues. Other great artists like Lauryn Hill and CeeLo Green have brilliantly rapped and sung on their respective releases. But no one in rap has ever done so as effectively as Drake, giving fresh definition to b-boy, or break-boy. He not only sings his own hooks, and sings his own songs, but breaks into song in the middle of a rap, and vice versa. Or he alternates between rapping and singing in the same line, or sometimes in the same phrase, thus breaking down the barrier between acts of speech and song and making quite nervous those intent on keeping them discrete enterprises. Drake’s sonic hybridity, his fusion of speech and song, mirrors his hybridity of race and place as an artist with a white mother from Canada and a black father from the United States.

The alienation from Drake by emotionally immature men has been matched by a surprisingly negative female reaction to the crooner-rapper. To be sure, this isn’t a scientific survey, but one drawn from anecdotes, and my evidence was collected in an informal poll of women across the country (clearly not the thousands of screaming ladies I see at Drake’s concerts) who are stumped by my affection for the self-described “light-skinned Keith Sweat,” and who find Drake intolerably self-reflective, melancholy, and emotional. It is difficult to hear such critiques when the urban version of the strong, silent type offers little comfort or support to women. That type often appears to be Hercules in sagging pants with low emotional intelligence.

The effort of many women to awaken men to the emotional currents around them suggests that such “sensitivity” is a quality they find desirable. The catty memes of Drake posted by women in social media gibing the artist for his emotional makeup amplify the distorted romantic images and expectations that engulf a generation of women inured to poor treatment by their men. The shame isn’t Drake’s; the shame is that we can’t endorse a black man who isn’t a thug and who wears his heart on his sleeve. On his masterly 4:44 Jay embraced an even more honest and redemptive emotional vulnerability than what has been touted by Drake.

Although it appears that Drake and Jay are far apart when it comes to visual art, there are signs the fine arts ice between them is melting. There is Drake’s heavy reference to light-magic visual artist James Turrell on his massive 2015 hit “Hotline Bling.” And on Drake’s turn at the mic on rapper Meek Mill’s 2018 “Going Bad” (the result of them resolving their beef to record together), he says, “Yeah, lot of Murakami in the hallway (What?).” (Takashi Murakami is a Japanese contemporary fine arts and commercial media artist who has designed album covers for Kanye West, and who has collaborated with Drake on designer jackets and other fashion items.) While Drake appears to be dipping his toes in the fine arts waters, Jay has clearly been baptized in its healing streams.

Art has been historically viewed as too highbrow for the black masses. Art galleries, art exhibitions, and most art museums have largely ignored or refused to cater to black communities starved of images and art that reflect their culture and their spiritual and moral yearnings. Tina Knowles-Lawson, Beyoncé’s mother, saw the value in art as a young woman and filled her home with images of black folk. “When my kids were growing up, it was really important to me that they saw images of African-Americans,” Lawson told Vanity Fair magazine in 2018. “I’m so happy that I did, because both of them are really aware of their culture, and I think a lot of that had to do with looking at those images every day, those strong images.” It is clearly a lesson that her son-in-law Jay has absorbed over the years.

In fact, the failure of the art world to accommodate black identity and to affirm norms and standards of black beauty inspired Jay-Z in 2011 to conjure a gallery of black and brown female icons worthy of curation:

I mean Marilyn Monroe, she’s quite nice
But why all the pretty icons always all white?
Put some colored girls in the MoMA
Half these broads ain’t got nothing on Willona
Don’t make me bring Thelma in it
Bring Halle, bring Penélope and Salma in it
Back to my Beyoncés
You deserve three stacks, word to André
Call Larry Gagosian, you belong in museums

To be sure it wasn’t just black females who deserved a place on the museum wall. Jay-Z found a way to insert his black body into the conversation. Officially listed as “A Performance Art Film,” the nearly eleven-minute video for Jay-Z’s 2013 song “Picasso Baby” is an ode to New York’s multicultural landscape. In it, he cites artists and also offers a verbal rebuff to persistent racism and the relentless scrutiny of his iconic status. The song’s video was given cinematic treatment when it debuted on the cable television channel HBO in August 2013. The video was filmed in July 2013 at New York’s Pace Gallery.

“Picasso Baby” is a visual gallery of Jay’s understanding of how he became the artist he is today. In the last third of the song, and midway through the film, the ebullient production of “Picasso Baby” breaks down to a grittier affair with guitar riffs and a throwback backbeat. Here the song, and Jay-Z’s performance of it before a live audience, shifts into its hardest “self.” Up until this point, “Picasso Baby” is the usual aspirational and materialistic fare with artistic shout-outs and clever references to “fine” art and artists: Picasso, Mona Lisa, marble floors, gold ceilings, MoMA, Warhol, Art Basel, Leonardo da Vinci, and the Met. And of course there is a reference to Jean-Michel Basquiat, the gifted black neo-expressionist artist whose work inspired Jay-Z as it probed “suggestive dichotomies” like wealth versus poverty, integration versus segregation, inner perception versus outer experience. But once the break intervenes, both the song and the film assume a more intense, and purposeful, tone.

Now Jay motions the surrounding crowd closer to him. The invitation suggests that proximity might enhance the experience as the artist delves into a deeper form of expression. In the earlier portion of the performance Jay is cordoned off in the center of the gallery, as if he is a work of art himself. His performance art film pays direct homage to the legendary Marina Abramović, the Serbian-born sensation who has shaken and shaped the art world with her fearless, and at times violent, performance art pieces. Abramović’s 2010 “The Artist Is Present” is a masterly show of endurance and artistic exploration built on Abramović’s commitment to sit silently for over 700 hours and look into the ey
es of those who gaze upon her performance. Abramović’s body of work quite literally, limb by limb, her flesh as the canvas, forms an improbable bridge between her status in the art world, and Jay-Z’s extraordinary journey from the Marcy Projects to the heights of the world of art. It all culminated, in a way, with Jay-Z’s six-hour performance art piece in the Chelsea Pace Gallery in July 2013, which was distilled to his eleven-minute video. Abramović’s willingness to put her body on the line is not something with which Jay-Z was unfamiliar. He did so himself, repeatedly, willingly, hustling on the dangerous streets in pursuit of material gain. But that was Jay-Z the blight hustler. Jay-Z the bright hustler, the artist, now uses those experiences to enjoy a measure of success he could scarcely have begun to imagine when he was dealing drugs on the block.

But the break in the film, and in the song, is a cue to take us back to that Jay-Z, and to situate this performance art film in the annals of the fine art forms that embrace and embody sacrifice. Attacks from the media, disgruntled fans, annoying paparazzi, and run-ins with the law form the underside of success and fame. It is a theme that regularly recurs in Jay’s body of work. In frustration Jay-Z glares into the camera for full effect. “I put down the cans and they ran amok,” he nearly screams—and here cans are at least a triple entendre of spray paint cans for graffiti, pistols, and headphones—as he pantomimes shooting his enemies with a gun in each hand. His next lines gesture toward the visceral damage that bullets cause the human body, linking him to the film’s Serbian muse and to his not-so-distant past as a drug dealer. There’s more shooting before this verse concludes as Jay recalls his “cans” metaphor to slip in another allusion to Basquiat, claiming that he will “spray everything like SAMO”—the graffiti duo Basquiat was a part of that scrawled esoteric epigrams all over Lower East Side Manhattan buildings in the late seventies. Although it is not the final line, Jay’s reminder, “Don’t forget, America, this how you made me,” punctuates the song and the performance in a way that only an underprivileged son of urban America could. It puts a period on a performance art piece in one of the most elite artistic spaces in the world.

The “Picasso Baby” performance art film reflects Jay-Z’s sustained engagement with fine art. In his “Blue Magic” video from 2007, Jay raps in front of a painting by Takashi Murakami (yes, the same artist Drake has teamed with) and spin-art skull paintings by British artist, collector, and entrepreneur Damien Hirst. In his 2008 Glastonbury music festival performance, Jay rapped before a visual backdrop that featured Hirst’s diamond-encrusted skull entitled “For the Love of God.” A couple of years later a replica of the skull was made and can be seen throughout Jay’s 2010 video for his song “On to the Next One.” (Although controversy has dogged Hirst’s art since 1999 with charges of plagiarism, his preoccupation with death resonates with elements of hip hop culture that address carnage, suffering, and mortality.) In his verse on Rick Ross’s 2008 song “Maybach Music,” Jay shows how his artistic register has expanded.

The curtains are drawn perfectly like a Picasso, Rembrandts and Rothkos
I’m a major player, 40/40’s in Vegas at the Palazzo.

It’s the same year he was spotted with Beyoncé attending the international contemporary art fair Art Basel Miami Beach, and a year before he told the Mirror that he owned pieces by Hirst and Richard Prince. In 2009, Jay also compared himself to a Warhol painting on “Already Home”:

I’m in The Hall already, on the wall already
I’m a work of art, I’m a Warhol already.

It’s the same year he bragged on “Off That” that he was “In my TriBeCa loft / With my highbrow art and my high yellow broad.”

In 2011, on “Who Gon Stop Me,” a duet with Kanye, Jay added the Museum of Modern Art to his list of artistic allusions.

Pablo Picasso, Rothkos, Rilkes
Graduated to the MoMA
And I did all of this without a diploma.

The cover art for his 2011 memoir, Decoded, was designed by graphic artist Rodrigo Corral and features a gold-embossed version of Andy Warhol’s “Rorschach.” In his classic 2006 collaboration with Lupe Fiasco, “Pressure,” on Fiasco’s debut album, Jay name-checks Warhol.

If the war calls for Warhols
Hope you got enough space on your hall’s walls.

On “Ain’t I,” a track that was likely recorded as early as 2006 but wasn’t released until 2008 on DJ Clue?’s Desert Storm Radio Volume 8 mixtape, Jay raps that

I got Warhols on my hall’s wall I got Basquiats in the lobby of my spot

His affinity for Warhol is understandable: Warhol reshaped the gateways to the fine arts world by unapologetically embracing a pop art aesthetic and relentlessly sampling and remaking popular culture as fine art, aesthetic features that made him interesting and inspiring for the young Jean-Michel Basquiat.

While the fine arts captured Jay’s attention, he was also captivated by popular art in elite settings. If we had to choose one single that catapulted Jay-Z from stardom to superstardom it would have to be “Hard Knock Life (Ghetto Anthem),” from his third album, Vol. 2, released in 1998. That album sold over five million copies in the United States. The single was instrumental in propelling that record to five-times-platinum status back when fans still purchased CDs from actual brick-and-mortar music stores. “Hard Knock Life” interpolates a refrain from the song “It’s the Hard Knock Life,” featured in the Broadway musical Annie. A Broadway musical, if not quite fine art, was nevertheless viewed as finer art than hip hop by many of Broadway’s patrons. The sampling of the song was also a nod to Jay’s openness to a variety of art forms and his understanding that common themes of existential struggle unite disparate genres of music. Thus one of his most successful songs, at a critical point in his career, features a sample from a Broadway musical that highlights the plight of poor, socially invisible children. Vol. 2 won the Grammy for Best Rap Album that year. Jay’s song, the sample of the original, the themes of the musical in which the original song was performed, and the acknowledgment from the Recording Academy all form a Warholian narrative, a pastiche of key pop cultural moments.

And yet, while Warhol is undeniably an artistic touchstone, Jay-Z identifies far more intensely with the Brooklyn-born fine artist Jean-Michel Basquiat. In Decoded and elsewhere Jay discusses how Basquiat’s 1982 painting “Charles the First”—featuring the artist’s rendering of jazz saxophonist Charlie Parker with textual inscriptions about the god Thor that elevate Parker to mythical stature—inspired his 2010 song “Most Kingz,” produced by DJ Green Lantern and featuring Coldplay front man Chris Martin. For Jay, Basquiat’s “Charles the First” is a visual treatise on the perils and pitfalls of success. “Success is like suicide,” he claims on the track. The track where Martin sings the hook functions as the auditory leitmotif, the spoken complement to Basquiat’s raw textual interventions in the painting: “Most kings get their heads cut off.” Basquiat was likely alluding to the late great Charlie Parker, who, like Basquiat himself, died early from a drug overdose. Like Basquiat, and Jay, Parker contended with a white world that eventually embraced his art even as he continued to face racism. It was tough to survive in such a world, one that drove both Basquiat and Parker to taking drugs, and Jay earlier to selling them.

Jay doesn’t take his survival lightly. “Most Kingz” gives a litany of those, like Martin Luther King, Jr., Malcolm X, and even Pac and Biggie, who achieved fame and died well before their time. His purchase of art, besides its aesthetic, financial, and political value, may possess a compelling existential one, too: it is a way of keeping alive the legacy of black men who blazed the path before him. In 2013, Jay paid $4.5 million to acquire Basquiat’s “Mecca” at Sotheby’s in Manhattan. With the exception of B.I.G., Jay alludes to Basquiat more than any other artist. In a standout line in “Picasso Baby,” he claims:

It ain’t hard to tell
I’m the new Jean Michel

And in some ways, he is a new, longer-living version of the legendary Basquiat: born nearly a decade apart, both are black prodigies, both became global icons, both fought to have their art taken seriously by the world.

But the first line, usually overlooked when this verse is cited, is similarly allusive and just as powerful. It’s a quote from the 1994 song “It Ain’t Hard to Tell,” from Illmatic, the classic debut album of Nas, another rap genius. It shows how Jay-Z continues to appreciate the art forms that nurtured his own gift. But it shows, too, how Jay reconciles artistically what he has reconciled personally, and that by alluding to one of Nas’s most famous songs, he has found peace and brotherhood with a former rival. And it means something even more important: that, at least rhetorically, perhaps even literally, he kept at least two kings’ heads, Nas’s and his own, from being cut off. That may be one of Jay’s most generous if greatly unappreciated gestures.

If Jay has tangled in verse with icons like Nas and Drake, and if he has cited the lives of fallen icons like Basquiat and Parker, King and Malcolm, he has also occasionally explored the appeal and relevance of another iconic figure: the comic book superhero. Indeed, hip hop has a long-standing love affair with superheroes, in part because of their similar quest for social justice. The relationship is also fed by the belief that rappers and superheroes both overcome enormous odds to represent their communities on the largest platforms possible. It wouldn’t be an exaggeration to say that rappers are superheroes for many of the folk in the communities they come from. It makes sense that hip hop artists often turn to comics and superhero genres to make important points about love, the hood, crime, poverty, and, in the case of Jay-Z on Kingdom Come, the music industry itself.

Kingdom Come takes its title from a popular comic book miniseries of the same name. In DC’s 1996 version of Kingdom Come, traditional superheroes like Superman and Wonder Woman have receded from public life and left the work of world-saving and fighting bad guys to a new breed of hero. In this world, traditional superheroes are out of touch with reality and disconnected from the goings-on in the streets. Therefore, just as Jay-Z did in the music industry, these heroes retire. In their place rises a new hero, named Magog. He is of an utterly different ethical order. For Magog the ends always justify the means; he kills and destroys to save, serve, and protect. The results are disastrous, and the traditional superheroes, especially Wonder Woman, plead for Superman to come out of retirement. Superman finally agrees and comes back to better the dystopic world that Magog has created.

Jay’s microphone went silent, symbolically, in 2003 after the release of The Black Album, one of the top three records of his career. In the three years of his retirement, the music, production, and lyrical aesthetics of hip hop shifted regions, altered themes, and, too often, dipped in artistic skills. 2006 saw artists like Chingy (“Pullin’ Me Back”), Young Dro (“Shoulder Lean”), Yung Joc (“It’s Goin’ Down”), T.I. (“What You Know”), and Dem Franchize Boyz (“Lean Wit It, Rock Wit It”) take center stage in hip hop. Between 2003 and 2006 the mainstream rap music industry took a turn toward trap musical production—which is bass heavy and features rapid-fire high hats, glowing in Southern drug dealer chic—and what some critics cynically refer to as “mumble rap,” a trend so dominant that it thrives in the present moment.

In this sense, Kingdom Come is a comeback album that plays as an extended superhero comic book analogy. Jay represents those traditional heroes who have receded in retirement only to see the culture that they spent their careers cultivating squandered in the hands of a new crop of rappers and heroes with a different set of artistic and moral standards. If we push this comparison further, we can understand the monumental significance of Jay’s collaboration with former N.W.A (Niggaz Wit Attitudes) member and seminal producer Dr. Dre on this record. Dre produced “Lost One,” “30 Something,” “Trouble,” and “Minority Report.” A mere decade earlier such an extensive collaboration was unimaginable. (Although Jay had in 1999 supplied the words for Dre’s influential hit “Still D.R.E.”) And much like Jay, Dre was coming to terms with the changing paradigms of the culture. In Dre’s case it was musical production shifting away from the aesthetic conventions and musical vocabulary he was familiar with, especially the G-funk sound of throbbing bass, melodic synthesizers, live instrumentation, dense harmonies, and sprightly chord progressions that reigned on the West Coast during the “golden era” of hip hop from 1988 to 1998.

“Kingdom Come,” the title track, features a variety of iconic and superhero allusions, including Superman and Clark Kent, Spiderman and Peter Parker, Iceberg Slim, Underdog, and Flash Gordon.

Just when they thought it was all over
I put the whole world on my back and broad shoulders
The boy HOVA, who you know talk all over tracks like that?
Guess what New York, New York—we back!

Themes of retirement, heroics, and the savior’s return in “Kingdom Come” are emblematic of the moment. They resonate throughout the rest of the record, putting each track in the context of rap music’s paradigmatic shifts and the angst felt by aging hip hop impresarios as the reins of the culture seemed to be slipping from their grasp.

Kingdom Come is widely considered, even by the artist himself, to be Jay-Z’s weakest album. Jay and the critics couldn’t be more wrong. Kingdom Come is one of his most accomplished and mature albums—4:44’s prelude in some ways. Jay seriously considered releasing Kingdom Come under his “government name.” And maybe history will categorize this record and 4:44 as the Shawn Carter albums within Jay-Z’s full body of work. If Kingdom Come is his worst effort, then how do we account for the palpable pain expressed at losing his nephew Colleek in an automobile accident, and feeling partly responsible for his death, on “Lost One”?

My nephew died in the car I bought
So I’m under the belief it’s partly my fault
Close my eyes and squeeze, try to block that thought
Place any burden on me but please, not that, Lord
But time don’t go back, it goes forward
Can’t run from the pain, go towards it
Some things can’t be explained, what caused it?
Such a beautiful soul, so pure, shit!

How does one account for the dreamy existential reflections on destiny, his nephew in heaven, karma, and the consequences to his unborn daughters in “Beach Chair”:

Colleek, are you praying for me?
See I got demons in my past, so I got daughters on the way
If the prophecy’s correct, then the child should have to pay
For the sins of a father
So I barter my tomorrows against my yesterdays
In hope that she’ll be okay

What of his unsparing self-examination and advocacy for social justice on “Minority Report,” which I’ll explore at length in the next chapter? And “The Prelude” is likely the best opening of any hip hop album of that era, where Jay gets back at rival rappers, does an autopsy on the hip hop game, and announces that at thirty-seven, and coming out of retirement, he is still king of the hill:

Woo! Guess who’s back?
Since this is a New Era, got a fresh new hat
Ten year veteran, I’ve been set
I’ve been through with this bullshit game but I never can
I used to think rappin’ at 38 was ill
Well last year alone I grossed 38 mill’
I know I ain’t quite 38 but still
The flow so Special got a .38 feel
The real is back.

Kingdom Come is a decidedly adult album with mature themes. If hip hop is becoming “lil,” and “young,” Kingdom Come is all grown up. It does many of the things that make Jay a powerful poet and influential intellectual: it alludes to pop cultural moments and figures, reflects on aging, rampages through metaphors, tropes, and double entendres, fights the powers that be, addresses urban crises, beefs a bit, mourns loss in elegiac gestures, proclaims his greatness in eloquent verse, embraces his mother’s love, thinks out loud about fame’s costs, and probes the ethereal, transcendent nature of human identity and destiny.

The album was panned by critics, at least in part because Jay wasn’t exclusively, or primarily, rapping about hustling. (Maybe the critics skimmed through the hustler’s itinerary performed con brio as Jay’s narrator brags he “brought that crack back like a yo-yo” and lamented “all these rival dealers trying to do me in” on “Oh My God.”) That said, Jay-Z did follow Kingdom Come with American Gangster, considered a return to form by critics and his core fan base alike. It is a great record, but so is Kingdom Come. In fact, what Here, My Dear was to Marvin Gaye, Kingdom Come is to Jay: an underappreciated record that was far greater than its critical reception suggested at the time. But to match the naked self-revelation and brutal honesty that Gaye managed on Here, My Dear, Jay would have to dig deeper into his life and look deeper into his soul. Jay would soon discover, more than ever before, the wisdom of the feminist credo: the personal is political.