JAY-Z’s 1996 debut wasn’t an instant classic. In retrospect, it's hard to understand why: His skills are obvious, and the subject matter, while familiar—the perils and spoils of the drug trade—is rendered with a density that makes it feel new. The hitch, such as it is, may have been persona: Where Nas represented writerly introspection and Biggie raw charisma, Jay was somewhere in between: a born hustler who touted the high life but seemed too preoccupied to enjoy it. If you admire him, it isn’t for his friendliness but his discipline. If you envy him, it’s not for what he has, but for how methodically he came by it. Is he a hero? Too cold. A villain? Too empathic. “We hustle out of a sense of hopelessness,” he says 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’.” He may be rich—or at least on his way—but with beats so spare and a delivery so quietly intense, you could mistake him for starving. The vision is big—wealth, mobility, autonomy—but the budget is small and the attitude scrappy. He can twist words for sport (“22 Two’s”) and flex 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/In time I'll take away your miseries and make ’em mine,” he says on “D’evils.” Reasonable Doubt doesn’t just capture his ambition, but past traumas. The album is an evolutionary step toward the lavish corporate-don rap that came to define the late 1990s—in no small part through Jay’s own work with Puff Daddy on Vol. 1, and just about everything he made between then and The Blueprint. But it also captures the gritty detail of urban life that had defined hip-hop—especially New York hip-hop—since “The Message,” or even the Last Poets. That he had to start his own label—Roc-A-Fella—just to 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 with limitless confidence who doesn’t yet know his salad fork from his dinner fork. He’d famously said that he’d quit rapping after its release, to take care of the business of running Roc-A-Fella—a move that forecasted the expanding opportunities of Black artists in pop music. To paraphrase Oscar Wilde: We’re all in the gutter, but some of us are looking at the boardroom.