One night in the fall or winter of 1996, JAY-Z and The Notorious B.I.G. were relaxing at Daddy’s House, the studio that Bad Boy owned in Midtown. This was almost certainly after the car accident that shattered Biggie’s left leg and forced him to use a wheelchair, and later a cane, as he worked slowly on the sophomore album that he planned to call Life After Death… Til Death Do Us Part. The rappers were friends if not exactly peers: Big’s first LP, Ready to Die, had taken on a mythic quality, where Reasonable Doubt, Jay’s debut from two years later, had been a modest success.

That night in the studio, Big played Jay some works in progress: “Hypnotize,” “My Downfall,” a handful of others. Jay was a little envious, looking at somebody who by the age of 25 had mastered virtually every popular style of rap and was slipping tangents about kidnapping plaintiffs’ daughters onto radio singles. He was, it seemed, peerless. Worse: Jay only had one new song of his own to share.

It didn’t sound like Reasonable Doubt—it had a little more gloss and bounce—but it was knotty, sarcastic, vivid. It was called “Streets Is Watching,” and it ramped up to a virtuosic, 42-bar final verse full of drug operations that teetered on state lines, looming droughts, visions of God, impaneled grand juries. Big heard it once, and then he played it again, then five more times. Finally, he stopped, and looked at Jay out the corner of his eye. “Is the whole album gonna sound like this?”

He wouldn’t live to find out. In the early morning hours of March 9, 1997, Big was shot and killed at the intersection of Wilshire Boulevard and Fairfax Avenue in Los Angeles. The case, as you probably know, is still unsolved.

After Biggie’s death, Puff Daddy, who had discovered Big and then put himself all in the videos, dancing, set out to pay tribute. He asked Jay to write verses for “I’ll Be Missing You,” a flip of the Police’s “Every Breath You Take” that would also feature Big’s wife, the singer Faith Evans. Jay declined. Instead, he drove down to Virginia Beach and channelled his grief into a song called “The City Is Mine,” which was produced by Teddy Riley, featured Blackstreet (plus saxophone by a then-unknown, pre-Neptunes Chad Hugo), and was built around a sample of Glenn Frey’s “You Belong to the City,” which sounds like an extremely sensual elevator ride. “What’s the deal, playboy?” he asks at the song’s beginning. “Just rest your soul.”

“The City Is Mine” is In My Lifetime, Vol. 1 distilled into a four-minute sample: wrought with grief and buoyed by extraordinary technical skill, packaged in (and maybe marred by) a fixation on the most commercial sounds of the moment. It captures Jay doing things he’d try more audaciously in the future: “I’m the focal point like Biggie in his prime/On the low though (shh), the city is mine” is the polite precursor to what he’d do four years later on The Blueprint: “And if I ain’t better than Big, I’m the closest one.” It’s the sound of a remarkable talent attempting the leap into superstardom and fucking up the landing just a little bit.

Big’s death had left a vacuum in rap; that Jay was in a position to dream of filling it was a minor miracle. After brokering a small deal to promote a single and then a slightly bigger one to distribute Reasonable Doubt, his label, Roc-A-Fella records, was able to leverage that album (along with Jay’s work as a ghostwriter on Foxy Brown’s Ill Na Na) into an unusually favorable arrangement with Def Jam. Jay’s appearance on Life After Death helped signal this next, presumably more lucrative era for the Roc. The song he was on, “I Love the Dough,” is a perfect little triumph, all sheen and sneer. Big washes Jay, but that’s beside the point. He was welcome in the real-cash Monopoly game.

The first way to understand Vol. 1 is as Jay’s Bad Boy album. Despite jilting Puff for “Missing You,” Jay recruited that label’s producers to handle about half of the album’s beats, and the ones they didn’t touch mostly replicate Bad Boy’s signature shine. At times, this works beautifully: the way the O’Jays are flipped into a somber suite for confession on the jarring closer “You Must Love Me,” or the way Rene & Angela, who were the basis for “I Love the Dough,” morph into something sinister for “Imaginary Players.”

But, as is characteristic of every Bad Boy release (even that skit on Ready to Die), there are lapses where the album seems to have been thrown together haphazardly. For example, it’s impossible to reconcile the fact that the unforgivably desperate “I Know What Girls Like” is made to flow right into “Player.” In the latter, you have one of the slickest, most irresistibly arrogant songs in Jay’s catalog, complete with that absurdly condescending final monologue. But you spend half of that track trying to scrub your brain of clumsy bullshit from the song before, like: “I never seen a face like yours before/And I’ve been around some cute whores before.”

Fortunately, Jay has always had a gift for giving emotional depth to his albums without cheating or showing his hand too early. The violence that’s introduced on “Rhyme No More” (“Shoot up the whole block, then the iron I toss”) and complicated on “Streets Is Watching” (“For the first time in my life, I was getting money, but it was like my conscience was eating me”) is given a second, more harrowing layer of guilt on “You Must Love Me.” That song opens with a verse to Jay’s mother, who was struggling with her own addictions just as Jay began hustling: “All you did was motivate me: ‘Don’t let ’em hold you back!’/What’d I do?/Turned around, and I sold you crack.” The next verse recounts the time that Jay, at just 12 years old, shot his brother in an effort to retrieve some stolen jewelry. His brother survived, then asked to see Jay in the hospital the following day. You must love me, he raps.

The album’s masterpiece, though, is “Where I’m From.” The scaffolding is an Yvonne Fair sample that sounds like a steel city grinding its inhabitants into dust. Jay raps vividly about the Marcy Houses, describing himself and his neighbors as “foul” all while taunting outsiders: Prodigy, the Mobb Deep MC who feuded with Jay for years, took the line about Marcy being where “you and your mans hung in every verse in your rhyme” as a direct shot. It’s also the most acrobatic rapping Jay had done to this point in his career: There are times when he’s deep in the beat’s pocket, and others when he’s rapping as if the beat is a mere suggestion. In the middle of the second verse, there’s an absolutely breathtaking passage:

I'm a block away from hell, not enough shots away from stray shells

An ounce away from a triple-beam, still using a hand-held weight scale

You're laughing—you know the place well

Where the liquor stores and the base dwell

This sort of free, cascading run, where every line is extraordinarily technical but sounds as if it was ripped from casual conversation, is something he’d continue to perfect over the next several years but would mostly abandon by The Blueprint, opting instead for digestible midtempos. With hindsight, Vol. 1 is more gripping as a show of raw skill than it is as an act of myth-making: The way he floats over the beat on “A Million & One Questions” and burrows into it on its twin song, “Rhyme No More,” or that extended, staccato climax to “Streets Is Watching,” is the element of his post-9/11 catalog that’s most sorely missed.

The softer songs are tougher to grapple with. “Lucky Me” has its own cult following (Lil Wayne has its title tattooed on his neck and a verse from it tattooed on his leg) but is stiff and overproduced; its complaints about fame are more exhausting than insightful. And then, of course, there’s “(Always Be My) Sunshine.” “Sunshine” shares a Kraftwerk sample with a Whodini song; it’s the sort of thing that can be rehabilitated with time, but would have seemed painfully out of date in the moment. And then there’s its video, where dancers run through fierce choreography in what looks like the stomach of a Rubik’s cube while Jay mugs in a lime-green suit. It’s awful. “Sunshine” has mostly been relegated to the footnotes in Jay’s career—it wasn’t a big enough success or spectacular enough a failure to seem, today, like a turning point—and that’s fortunate, given how close it flew to an extremely fluorescent sun.

Eight years before Vol. 1 came out, Jay-Z was living in London. His mentor, a fellow Marcy Houses native who went by Jaz and who, for a time, had a reputation as one of the best unsigned rappers in Brooklyn, had been advanced nearly a half-million dollars by the record label EMI. He brought Jay across the Atlantic, to the flat in Notting Hill, to soak up whatever he could while the album got made.

At first, the label guys seemed nice enough. Jaz’s finished records were sounding close enough in spirit to their demo versions. But at some point, EMI insisted Jaz record a gimmicky, ukelele-driven song called “Hawaiian Sophie.” It was an utter disaster. The video was full of hula dancers gyrating in front of green screens and palm trees painted on large tarps that were hoisted clumsily toward a soundstage “sky.” Imagine the Lost pilot staged by kids at a summer camp. Jay, who appears in the video behind giant sunglasses, draped in a lei, would later say it was “nearly career suicide.”

“Hawaiian Sophie” was supposed to turn Jaz into a star. But when it inevitably bricked, the label stopped returning his phone calls. The album dropped in May 1989 as little more than a tax write-off. That’s when executives at EMI finally picked up the phone—to call Jay, wondering if he was interested in a record deal of his own.

This turned Jay’s stomach. He buried whatever rap dreams he had, skulked back to the States, and moved his crack trade from East Trenton, New Jersey down to Maryland. This was a good idea until it wasn’t: There were shootouts in nightclubs and rumors of sweeping police investigations.

When Jay returned to music, he was wary of and wearied by the EMI experience. The “Sophie” debacle seemed to shape his approach to the industry for the years to come: It confirmed his distrust of record companies; it urged him to hone the double- and triple-time skills he’d been developing, then shed them for something more communicative. The impeccably dressed kingpin from the Reasonable Doubt cover could never be seen in Bermuda shorts. He even references “Sophie” on the opening song of Vol. 1—both the fact that it exists, and the fact that it made him disappear. And yet it’s impossible to see the “Sunshine” video without thinking, for a second, about all those plastic palm trees.

There’s this incredible trick that Big pulls at the beginning of Life After Death. It opens with a narrative song called “Somebody’s Gotta Die”; the broad strokes are that one of Big’s old friends knocks on his door in the middle of the night with blood on his shoes, saying that their mutual friend had been shot. A revenge plot whirs to life—and ends with a tragic mistake. Straightforward. But in the first verse, as he’s talking himself into a frenzy, Big shatters the implied divide between these crime tales and real life: “‘Cause I’m a criminal,” he raps,

Way before the rap shit

Bust a gat, shit—Puff won’t even know what happened

On an album that is primarily about the experience of being a rap star, Big is staring into the camera and smirking, as if to say: For all you know, I could be in the streets right now. The times when Big shows you the seams of this stardom add to the effect—the barbs at New York rappers on “Kick in the Door,” the tongue-in-cheek ode to the other coast on “Going Back to Cali.”

By comparison, Vol. 1 labors to achieve the same feeling. Its plays for radio feel deliberate, as if they were pulled from a totally different set of sessions than the “Where I’m From”s and the “Streets Is Watching”s. Big blurred those lines between pop and pure instinct (“Playa Hater”) or reveled in just how arbitrary they were (he has those threats to kidnap daughters on “Hypnotize,” he raps about phone taps on “Mo Money Mo Problems”); the only time Jay comes close to this fourth wall-fracturing magic is on “Friend Or Foe ’98,” when he’s about to kill a rival hustler in a “two-hotel town,” and leaves him with a message to send Big in heaven. The songs on Vol. 1 are almost uniformly excellent. But the greater the commercial and mythic stakes Jay tried to attach to the set as a whole, the more the vacuum threatened to swallow them all at once.