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Go Sell It on the Mountain

On Jay-Z, ‘Reasonable Doubt,’ and how hip-hop’s greatest mythmaker had to get some things off his chest before he could get started

Richard A. Chance

No year in hip-hop history sticks out quite like 1996: It marked the height of the East Coast–West Coast feud, the debut of several artists who would rule the next few decades, and the last moment before battle lines between “mainstream” and “underground” were fully drawn. The 1996 Rap Yearbook, a recurring series from The Ringer, will explore the landmark releases and moments from a quarter-century ago that redefined how we think of the genre. Today, we’re looking at one of the most heralded debuts in hip-hop history, Reasonable Doubt.


Rule no. 1 of hustling (the new testament, not the original commandments) is don’t tip your hand, but Jay-Z seems unable to help himself when it comes to Reasonable Doubt. The man’s still in love with his debut and can’t bear to quit flirting. It started around the album’s release, when reporters or talk show hosts or DJs would ask him what his plans were for the next project. The answer was that he didn’t have any, at least not on the mic. “It was my intention to make it my last,” Jay later wrote in his autobiography Decoded, meaning the album was designed to be his one and only opus, upon which the then-26-year-old would transition to the throne of label management and tastemaker. Of course, that’s not what would happen, but that kind of intent with a project must, at some level, breed an indomitable attachment to it—one that only making something that may or may not be your only creation can.

The love affair continued into the mid-2000s. In ’04, after a fruitful but increasingly tense partnership with his two other Roc-A-Fella Records cofounders, Damon Dash and Kareem “Biggs” Burke, Hov sought an even higher perch as CEO and president of Def Jam Recordings. As the epic goes, he offered to turn down the Def Jam position and tack on the rights to all his other previous releases in exchange for his Reasonable Doubt masters. “It meant everything to me because it was my baby,” was how Jigga described his rationale to XXL months later. They couldn’t come to a deal, so Jay went on, scorned, but also (conveniently) richer. In ’06 he went so far as holding an anniversary show for the LP; even in recent years he’s been known to make a point of performing early material. There’s also the RD20 documentary he commissioned at Tidal in 2016, a nifty bit of S. Carter Enterprises–sponsored propaganda masquerading as nostalgia. Just a few days ago, a judge ruled in Hov’s favor after he sued Damon Dash for attempting to sell the copyright to the album as a non-fungible token.

All of which is a long-winded way of saying that Jay-Z has spent the better part of three decades protecting and mythologizing Reasonable Doubt in a fashion that oozes both doting and Machiavellian concern, each of which are antithetical to the defining feature of his unequalled public persona: total and supreme nonchalance. When has he been bothered? Even his moments of vulnerability that have helped oil the increasingly corporate machine are always placed at a distance. (See: “I can’t see them coming down my eyes / So I got to make the song cry.”) And yet for a rapper who has triple-entendre’d his way to the top (and then out) of rap’s food chain, there is something about this album that he refuses to be anything but attached to. The question of why invariably gives the game away.

Reasonable Doubt, which was released 25 years ago Friday, serves as a kind of codex to understanding the birth and rise of the most dominant character in the history of rap music. He may have first imagined it as an ending, but only that project could have ignited the series of flares that have come since. It is the one thing that Jay-Z had to make if he was going to make anything at all.

“I did the same thing to Big,” DJ Premier told me over the phone in late May, as if numb to the splendor of name-dropping Christopher Wallace while describing a pact with Jay-Z. “I charged him 5 grand. At that time I was getting $25K, $30K a cut. That was a big deal back then. And I think I told [Jay] $4,000 a pop per song. I remember I told Big the same thing. I said, ‘Yo man, blow up and go platinum I’m charging you double of what I charge.’ And he said, ‘No problem.’ And when we started working on Life After Death, he gave me what I wanted. When Jay-Z and them went to Def Jam and got them big checks, he paid me what I wanted [too]. No hesitation.”

Premier, who produced three tracks on Reasonable Doubt, has known Jay since the late ’80s, when Big Daddy Kane would invite the young MC to open his shows and accompany him on tour. Hov was merely the understudy of Brooklyn rapper Jaz-O, trying to burst through the scene with the double-time cadence made popular by groups like Das EFX and Fu-Schnickens. Preemo could see that he was a different breed, dexterous enough to master any style, with a mind ahead of his years. “Even though he was younger, he was really there absorbing the same music the same way all of us DJs did: MCs, graffiti art, writers, and B-boys and B-girls,” says Premier.


Jay’s double life—between stage and street corner, cypher and trafficking—is well-trodden ground, reflected not only in his music but at the core of his image. The extent to which he incubated and developed his craft in a world prepped to ensnare him is often ignored in deference to the crime-hungry gaze of popular culture. There is a well-known tale that Jay likes to recount about the ribbing he received from his fellow dealers when word first spread that he was plotting a move to the music industry. Nobody understood why he’d forgo a higher income on the corner for the chance at a life behind the mic. “I couldn’t really explain to them how much I loved it,” he told NPR in 2010. (The fundamental trick to everything Jay-Z is that there are 99 layers of bullshit wrapped around every statement of truth, so when Jay tells you that he “couldn’t really explain to” his crew how much he cared for rap, it’s a bit like a game of polygraphic Russian roulette in that he really could be telling the truth but it would be a fool’s errand to actually believe so.)

Premier, for his part, remembers a young man who cared as much as anyone he’d ever seen about getting better, as he soaked up knowledge, styles, and craft. He watched him process all that information and combine it with the events of his life to create something grander than anyone could have expected. It took time; Reasonable Doubt dropped eight years after they met. Jay bounced off one record label and created his own. He did a lot of living. But by the time he was ready to show his full form he had mastered something wholly distinct.

“When he came out with Reasonable Doubt he knew how to speak in code. It was really for the streets to understand, it wasn’t really made for anybody else,” says Premier. “It was like if you speak Spanish, you understand what they’re saying is Spanish. He spoke code to the streets.”

Reasonable Doubt is an incredibly dark album, but furtively so. By the mid ’90s, the era of the foot soldier in gangster rap had fallen mostly by the wayside, replaced by the gleaming idol of the kingpin, occupied first by Kool G Rap and later by the Notorious B.I.G. To flex one’s bona fides as a low-level participant in the drug game was no longer enough. If you were going to incorporate dealing into your identity, coat your public persona with your proximity to the streets, then you had to have “run the show,” as Jay so aptly put it. The album was not rapturously received. The Source famously gave the record a good-but-not-great four mics, and it peaked at no. 23 on the Billboard 200. On Reasonable Doubt the trappings of the boss ethos and lifestyle shroud a pervading gloom in plain sight. It is a boastful record, but also one that cannot escape its own guilt. And like all things Hov, separating fact from fiction becomes a tedious impossibility.

He has more than enough cash on hand to bail out “a big Willie” in the Mary J.–infused album opener “Can’t Knock the Hustle,” but money won’t fill the hole in his heart a track later on the absolutely silky “Politics As Usual,” as introspection hemorrhages into self-disgust and resentment. (“They built me to be filthy / On some I-do-or-die shit.”) Jigga doesn’t just shine, he illuminates the whole show on “Dead Presidents II,” but there is no light bright enough to expunge the image of a brother’s bullet-riddled torso, his eyes unable to emit anything but a pained and begging “pray for me.” In “D’Evils,” perhaps the darkest run of words ever uttered by the rapper on wax, Jay becomes a literal grief eater (“In time I’ll take away your miseries and make it mine’’) in order to snuff out a rival. Trips to Vegas in “Can I Live”—even a bit of revelry at one of those tables that “starts a G up”—won’t numb the pain festering in his soul. It is no accident that the album’s final track is titled (and attempts to conquer his own) “Regrets.”

A bit unrelated but also a bit identical: When the writer James Baldwin would speak of his first novel, the unparalleled and semi-autobiographical Go Tell It on the Mountain, he would often refer to it as “the book I had to write if I was ever going to write anything else.” His reasoning was simple. The contents of his debut were particularly personal; it emanated from his own lived experiences, his family, his history. To write Go Tell It on the Mountain, “I had to deal with what hurt me most,” Baldwin told The New York Times. Besides their childhoods in New York, spent among a timeless striving and peddling, there are but a few things that, I believe, link Jay and Jimmy more than this knowledge: that there would be no them, no creation, if they did not first exorcise a part of themselves, the jagged remnants of their history. Reasonable Doubt is, thematically, a rumination on the life of Shawn Carter, albeit furnished with a layer of baroque Scarface-esque fantasies—one that grapples with what hurt him most. It is an album that is, in this way, growth embodied.

This reckoning is not merely limited to the thematic; it bleeds into the very language of the work itself. He’s never, truly, been more deft: how he blends his vowels and consonants into a thick stew of homophones on “Can I Live,” breathlessly stacking “My confederation, dead a nation” with “explode on detonation.” How he occasionally sidesteps the entire convention of rhyming on “Friend or Foe”—because what couplet could outrank “Let me guess, they said it was money ’round here / And the rest is me stoppin’ you from gettin’ it, correct?” How he manages to hit “I cream” and “I diamond gleam” and “high-post like Hakeem” in all the right places in “Bring It On.” It is a type of rapping that unlocked the rest of his oeuvre—a type of rapping that could be mistaken for something holy. The culmination of almost a decade’s worth of growth.

Jay’s greatest bit of mythologizing is that he’s made this all seem preordained. That he didn’t spend years grinding before emerging on Reasonable Doubt, and that he didn’t use his performance on the record to become something else entirely, both in a stylistic and ideological sense. The truth is the opposite. He spent years crafting. Nas was 20 when Illmatic dropped; Biggie was 22 for Ready to Die. Jay was older than both and had the benefit of learning from them.

He’s never equaled the language on Reasonable Doubt because he’s never needed to. (It’s his most attentive work because he had to be attentive.) The themes on the album have never really been the same since because he’s never needed to revisit them. He has tried, on occasion, to recapture what once was. Where “22 Two’s” first stood was soon “44 Fours.” In the place of “Dead Presidents II” sat “Dead Presidents III.” They never worked as they had. The climate had changed. And because of all that Reasonable Doubt stands as both disproof of Jay-Z the character—effortlessly cool, mogul, GOAT—and the starting point for it. The project allowed him to become a mythmaker, showed him the path he’d have to follow, while at the same time revealing how disillusioned and painfully human he had been.

It was to be his one and only, you see. In all of Shawn Carter’s oracular forethought and salesmanship he’d never conceived of himself as the primary product. So Reasonable Doubt became the takeoff point and also, at least in the rearview, the site that proves he was not always capable of leaving the earth behind. Once bound to the ground, he discovered a new line of business, a fresh hustle: himself.

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