Among the dozens of great stories in JAY-Z’s memoir Decoded is the one about the night The Notorious B.I.G. first heard “Streets is Watching,” a standout track from the soon-to-be-released In My Lifetime, Vol. 1. The two were hanging out at the Bad Boy Records studio, swapping new tracks and stoking the fire of friendly competition. Jay was a little jealous of “Hypnotize” and the way Biggie could make material so street sound so pop. But “Streets Is Watching” gave Biggie real pause. It was gritty and virtuosic, yet also smooth—hardcore rap with just enough polish to glide. In Jay’s memory, one given to ego if not outright hyperbole, Biggie played the song five times—or was it twenty?—before looking at Jay sideways and asking, “Is the whole album gonna be like this?” Of course, the whole album wasn’t quite like that—if anything, “Streets” is one of the few tracks on In My Lifetime, Vol. 1 that follows logically from Reasonable Doubt. At the time, rap was at the front end of a major commercial boom, transitioning from the commercially successful but culturally standoffish sound of gangsta rap to the shiny, 1980s-sampling crossovers that defined the late 1990s. It was the moment when hip-hop transformed from healthy subculture to the fulcrum of mainstream pop, which means Jay’s hiring of Puff Daddy and Bad Boy’s in-house producers The Hitmen—with their R&B hooks (“(Always Be My) Sunshine”) and slick, featherlight sound (“Lucky Me”)—wasn’t just a bid to keep pace with the times. It was also an effort to meet an investment at the ground floor. At the time, Vol. 1 was considered transitional, even awkward—an attempt to reshape JAY-Z as a household name. Jay didn’t deny it: This wasn’t just artistic growth, it was a marketing plan. But the album’s sweet-and-sour mix of pop sounds and street material sounds strangely prescient today, a blueprint not just for artists like Lil Wayne (he has a verse from “Lucky Me” tattooed on his leg, and the title on his neck), but for a generation of post-2010s rappers who think nothing of mixing bleak lyrics with cute, toylike melodies, or transfiguring their most personal material with Auto-Tune. And where Reasonable Doubt was light on the specifics of Jay’s background, In My Lifetime dives unflinchingly into his dangerous past on tracks like “You Must Love Me” and “Where I’m From”—a mark not just of his maturation, but of his debt to Biggie, who was dead by the time it came out. So when he compares selling rap to selling crack, as he does on “Rap Game / Crack Game,” you’d better believe him: Just because Jay wants to get rich doesn’t mean he won’t bleed for it.