Here’s a head-scratcher for Jay-Z fans: Why wasn’t Reasonable Doubt considered an instant classic back in 1996? After all, Jay’s debut album puts his lyrical skills on full display. And the subject matter on Reasonable Doubt, while familiar—this is a record that goes deep on the perils and spoils of the drug trade—is rendered with a density that makes it feel new. Yet for all the album’s well-deserved accolades, hit singles, and sales accomplishments, Reasonable Doubt was still viewed as a bit of an outlier upon release—as was Jay himself. Whereas Nas’ work brimmed with writerly introspection, and Biggie’s verses exuded raw charisma, Reasonable Doubt-era Jay is somewhere in-between: He depicts himself as a born hustler who embraces the high life, but who seems too preoccupied to enjoy it. Is the Jay we meet on Reasonable Doubt supposed to be a hero? (No way—he’s too cold.) A villain? (Nope—too empathic.) It’s hard to get a handle on a guy who, on Reasonable Doubt, sometimes sounds so soured on his own success. “We hustle out of a sense of hopelessness,” Jay proclaims on the intro to “Can I Live.” “Sort of a desperation/Through that desperation, we become addicted/Sort of like the fiends we accustomed to servin’.” The Jay-Z who dominates Reasonable Doubt may be rich—or at least on his way—but with beats so spare, and a delivery so quietly intense, you could easily mistake him for starving. That tension can be felt throughout the record, on which Jay lays out a grand vision—wealth, mobility, autonomy—which he executes with a scrappy attitude and a small budget. On Reasonable Doubt, Jay twists words for sport (“Two 22’s”) and flexes like a battle rapper (the Biggie-featuring “Brooklyn’s Finest”). And when he explores the moral ambiguity of his business, it isn’t for pity or forgiveness, but to externalize a reality he knows doesn’t make sense (“Regrets”). “Don't cry, it is to be,” he raps on “D’evils.” “In time I'll take away your miseries and make ’em mine.” Reasonable Doubt doesn’t just capture his ambition—it captures his PTSD. The album is an evolutionary step toward the lavish, corporate-don rap that came to define the late 1990s—and that Jay himself would help to define, in no small part through his future work with Puff Daddy. But Reasonable Doubt also captures the gritty details of urban life that had defined hip-hop—especially New York hip-hop—since “The Message,” or even The Last Poets. That Jay had to start his own label, the soon-to-be-mighty Roc-A-Fella Records, to actually get it out makes a kind of sense: For however big he became, Reasonable Doubt feels rough and underground, the sound of a self-made striver who has limitless confidence, yet who still can’t tell his fish fork from his dessert one. Jay famously once said that he’d quit rapping after Reasonable Doubt to take care of the business of running Roc-A-Fella (a move that forecasted the expanding opportunities of Black artists in pop music). But this is an album that makes his creative and commercial ambitions clear, no matter how torn Jay might feel about them. To paraphrase Oscar Wilde, we’re all in the gutter, but some of us are looking at the boardroom.