Jay-Z spent the summer of 1997 on Puff Daddy’s No Way Out tour, and he must’ve learned some things there. In Jay’s mind, he was already a titan. The year before, he’d given the world Reasonable Doubt, an album that he knew was a classic even if its sales didn’t reflect it. Reasonable Doubt introduced Jay’s slickly casual gun-talk and regal bearing; it’s a complete vision. But on that No Way Out tour, Jay was just one more face in the crowd. The ridiculously crowded bill for Puffy’s tour included people like Mase, Lil Kim, Usher, and Busta Rhymes. Most of the reviews of those shows don’t even mention Jay. If Jay was going to get to where he wanted to be, he was going to need to switch things up and adapt to the times. And on his sophomore album, In My Lifetime, Vol. 1, that’s exactly what he did.

Today, In My Lifetime, which turns 20 tomorrow, stands as a strange time capsule, half smooth and half awkward. It’s Jay’s great capitulation to Puffy’s jiggy era, his attempt to compete commercially in the shiny-suit landscape. Consider, for instance, “The City Is Mine,” the album’s biggest hit. The luxuriant beat comes from Teddy Riley, the new jack swing mastermind who was, at the time, doing his best to reinvent himself as Puffy-style impresario. On the hook, Riley and his R&B group Blackstreet, then riding high on their monster hit “No Diggity,” sing a Puffy-ized version of “You Belong To The City,” the 1985 hit that the former Eagle Glenn Frey contributed to the Miami Vice soundtrack. A young, pre-Neptunes Chad Hugo plays his own version of the original song’s tootling noir sax. In the video, Jay and Michael Rapaport reenact the interrogation-room scenes from The Usual Suspects, a movie that was two years old at the time. (They also spoil the ending, something that really bothered me at the time.) It’s a deeply 1997 song and video, and yet it still gives Jay room to flex his considerable charisma. It’s not a great song, let alone a classic one. It might be the album’s biggest hit, but it still topped out at #52 on the Hot 100. It showed us a version of Jay that we’re not used to seeing in 2017 — one who was still figuring things out.

In My Lifetime is full of moments like that. Jay has said that “(Always Be My) Sunshine,” with its Fearless Four “Rockin’ It” sample and its silky Babyface hook and its Foxy Brown guest-verse and its Hype Williams video with Jay in an eyeball-searing lime-green suit, “killed the album.” He figured out, after the fact, that a song like that didn’t really play into the persona that he’d built for himself, and his pop overtures were going to have to be smoother and more sui generis than that. Meanwhile, the Puffy/Lil Kim collab “I Know What Girls Like” is basically a Puff throwaway, one he must’ve known would be too irritating for his own album. (Its hook comes from the Waitresses’ playground-taunt 1982 new-wave nugget “I Know What Boys Like,” and 20 years later, I can’t believe anyone thought it would be a good idea to build a big-budget rap song out of that.) Jay got a few In My Lifetime tracks from his Reasonable Doubt producers DJ Premier and Ski Beatz, but the lion’s share of the album’s production comes from Puff’s Hitmen braintrust. This was a rational decision for Jay at the time, but it still made him sound more like a Bad Boy B-teamer than a star in his own right.

Still, the rapping on In My Lifetime was uniformly excellent. A song like the Sauce Money collab “Face Off” was vintage Jay — imperious, dismissive, deeply misogynist, almost athletic in the dexterousness of its flow. Tracks like “You Must Love Me” expanded and deepened the character that Jay established on Reasonable Doubt. And much of the album comes from that same sonic template — lush funk samples, orchestral strings, drums that stay out of Jay’s way. (Sometimes it’s too close to Reasonable Doubt; “Who You Wit 2″ doesn’t vary much from the original.) And the street hit “Where I’m From” remains one of the hardest songs in Jay’s deep catalog. It’s a panoramic, unflinching, weirdly affectionate depiction of the Marcy Projects, where Jay grew up: “I’m from where the beef is inevitable / Summertime’s unforgettable / Boosters in abundance, buy a half-price sweater new.” The minimal, ominous, hammering beat doesn’t come from Ski or Premier but from D-Dot and Amen-Ra — Puffy’s guys. And if you’ve seen Jay live at any time in the past decade or so, “Where I’m From” is probably the only In My Lifetime song that stayed in the setlist.

Even if In My Lifetime is a transitional work, all the ingredients for the superstar version of Jay are there — the transcendent arrogance, the pop instincts, the unimpressed-to-the-point-of-boredom street-talk. A year later, everything would click for Jay. Jay would release Vol. 2… Hard Knock Life, the album where Jay really became the larger-than-life figure that he’d always imagined. To listen to In My Lifetime in 2017 is to hear Jay’s process at work. It’s a fascinating exercise, and its best moments still go hard.