A friend recently told me about seeing Prince perform live — prefacing it, curtly, with: “Well, first he made us wait until three in the morning.” Fair enough — not everybody’s prime time is in the middle of the night the way it often was with Prince — even if, the friend attests, it was worth the wait to see the greatest musician of his generation in action. But being late wasn’t always advantageous to his music, and there will never be better evidence of it than the Prince Estate’s latest behemoth, the 75-song Diamonds and Pearls: Super Deluxe Edition.

By “late,” I mean two-three years out of date at best, and sounding every day of it. This SDE is fascinating for that reason alone. Note that I said “fascinating,” not “great” — Diamonds and Pearls has long been my least favorite Prince “classic,” for reasons we’ll get to below. But “edifying”? Absolutely.

So yes: I disliked Diamonds and Pearls from the day it came out, when my mother bought the CD. (October 1, 1991 — first of the month, payday.) What a deflation, I thought — the new band sounded clunky and the new songs sounded blatantly commercial in a way he’d always avoided or elided before. Not that Prince was unmindful of trends — far from it — but he had always either been ahead of them or operating on a parallel plane from them, in his own zone after Purple Rain gave him the world.

By Diamonds and Pearls, he was down to earth again. There was now a rapper aboard — a move that made Prince seem less like a singular genius and more like an already passé Eurodance outfit a la Snap! Even though I liked some of the songs — it was a Prince album, I always liked some of the songs — a couple felt merely cute in a solo-McCartney way, like “Walk Don’t Walk.” And the title track was so paint-by-numbers it could have been the work of a proud song-doctor hack like David Foster or Desmond Child. (That, of course, was the point.) Naturally, my mother, who adored cheesy ballads, loved it. (That was also the point.) The most thrilling ballad singer on earth, my lifelong favorite musician, reduced to this gunk? Reader, it made this overexcitable 16-year-old seethe. (This, too, was likely part of the point.)

But even then, I could credit “Diamonds and Pearls” for fitting seamlessly into the album’s larger picture — Prince as a serious contender for the pop throne again, in an arena that had changed wildly since his 1984 peak.

Purple Rain’s timing had been key — it hit at the peak of Top 40 radio’s mid-’80s resurgence, under a newer name, CHR (contemporary hits radio). Right then, many large radio markets, the Twin Cities included, had two or more CHR stations — here, it was KDWB and WLOL. But by the early ‘90s, CHRs were beginning to be bought up by large corporations moving into the radio business as part of a larger diversification strategy.

This led to higher-priced investments, in turn, by longtime radio corporations — including the one you’re reading. As 1990 turned into 1991, Minnesota Public Radio purchased WLOL for $12 million. (Today, it’s YourClassical MPR.) A KDWB executive told Radio & Records that winter: “WLOL proved that you could throw everything you had at a problem — a new staff, positioning, and logo — yet they still couldn’t make a profitable go of it.” CHR needed CPR.

What was selling in ever-larger numbers were musical styles that, in the mid-’80s, had barely creased the larger pop market and were barely on Prince’s radar anyway. There was alternative rock: Prince famously mocked Warner Bros. labelmates R.E.M. for “dressing like farmers.” There was hip-hop, whose late-’80s rise — along with metal bands like Guns N’ Roses and easily, cheaply made dance tracks — began crowding uptempo pop-rock of the Springsteen stripe, not to mention that of Prince hits such as “Little Red Corvette” and “Raspberry Beret,” off of Top 40 altogether. Many radio stations around the U.S. began using a new slogan about this time: “No rap, no hard rock.” 

Then there was country, a style Prince gets associated with mainly due to a Muppets Tonight sketch. Back in ’84, country occupied a sliver of the market — but as 1991 began, that share had swelled. Oftentimes, companies buying up two CHR stations in the same market would convert one of them to country — and clean up. “A lot of the Top 40 listeners stuck with country,” Sean Ross, a radio consultant and author of the newsletter Ross on Radio, told me a few years ago, “because that’s where the up-tempo pop music was.”

It wasn’t just the radio changing over this period. It was also the charts. Thanks to a change of how sales were tabulated, the Billboard 200, as the album chart had been called, shifted violently in the spring of 1991 — among the effects, gangsta rap arrived in force. N.W.A, Ice-T, Geto Boys, and Ice Cube all reached Billboard album top 10 — in most cases, with no radio airplay at all. This was an era completely different from the ones Prince had lived through and mastered musically.

One net effect of hip-hop’s rise is that it changed the idea that Black musicians needed to cross over to pop audiences in order to see any really big money. It wasn’t as if white people weren’t buying N.W.A records — most of the people buying them were white. But N.W.A had accomplished this (and how) without appeasing to middle-class, middle-of-the-road taste, the way a previous generation of artists might have been pressured to by record executives. (At the end of “Jughead,” the Tony M showcase on Diamonds and Pearls, Prince included a sketch addressing this, naming Little Richard’s notoriously bad ‘50s contracts in particular.) Gangsta rappers did the exact opposite: announcing themselves proudly as street thugs who were as likely to punch you as talk to you. Whatever else it was, it was young. And whatever else he was, Prince was not getting younger.

If there’s any comparison to Diamonds and Pearls, it might be the late-’60s Frank Sinatra albums, where he tries on material from rock-generation songwriters and finds that the cuff links don’t match. That’s basically Prince and hip-hop here. Not only did he hire an untested MC for the New Power Generation — the first band credited on a Prince album in five years — he also gave MC Tony Mosely, or Tony M, ample space to, uh, do his thing.

Time hasn’t exactly deepened this music — what it’s done, instead, is draw out the music’s basic charm, in a way I was not ready to hear in my flaming youth. (I have also lightened up considerably.) Never mind the Revolution — in music right then, the revolutions were elsewhere; Prince was trying to push himself but also was getting comfortable. There’s a stagy grandeur here (cf. “Thunder” and “Live 4 Love”) that read as old hat to a teenager getting into indie rock and hip-hop and rave all at once, and starting to hear the radio that Prince wanted back onto as increasingly stale-sounding. But Diamonds and Pearls is also a lot fresher than I gave it credit for — still second-tier for Prince, but more purely enjoyable to revisit than I’d anticipated.

An open-minded re-hearing opened up songs I’d long dismissed. “Daddy Pop” is a song about how music writers just wanted to be Prince, a particularly misguided notion: writers are too busy envying other writers to bother with musicians, however fabulous, and nobody who writes wants to wear those outfits. Yes, I took this song personally even at 16. (Incidentally, I have it on inside authority that Prince hated my writing about him, which only made me freer to do it exactly the way I please. Thanks, Prince.) But the fact is, the Sly & the Family Stone-indebted arrangement is ingenious fun, and so are the group’s (and Prince’s) roundelay of voices, and the same thing goes for “Walk Don’t Walk.”

What time has truly given us regarding this music is, of course, perspective. From a modern vantage, Prince’s détente with hip-hop is of major interest — a hinge point between Black-music epochs. We know Prince had vocally detested rap early on but began to change his tune as the ‘90s turned — in 1990, he’d given MC Hammer permission to loop “When Doves Cry” for his omnipresent ’91 hit “Pray.” Diamonds and Pearls was Prince’s first extended engagement with hip-hop on, at least a little bit, hip-hop’s own terms for the first time. (He’d included brief raps on individual songs before, but they were walk-ons, not incorporated by a regularly employed MC.) Bringing on Tony M, however basic on the mic, was a major step, a public admission — and this was no small thing for Prince — that he’d been wrong.

Getting back onto Black radio was a paramount concern. So was making sure that Prince was being seen as a Black artist — with the rocking ascent of the Revolution, coming simultaneously with the increasingly militant sound of hip-hop, and then of new jack swing, Prince was meeting resistance from Black radio. He’d made similar overtures before — it was part of the idea behind the shelved Black Album, scheduled for December 1987 and Prince’s first all-funk LP in years — and Diamonds and Pearls’ hip-hop leanings were just one of the elements aimed in that direction.

Prince had always believed in God, said so from day one right on the albums, but on Diamonds and Pearls his music is more steeped in gospel than it had been up to that point — in particular the title song and “Willing and Able,“ a lithe, swinging groove also reminiscent of South African township jive. Both “Willing” and “Diamonds” feature the vocals of new keyboardist and soul belter Rosie Gaines, whose presence proved a catalyst for the band’s new amalgam. “Willing” also featured vocals from the local family gospel act the Steeles — and it came after Jimmy Jam and Terry Lewis had signed another Minneapolis gospel unit, Sounds of Blackness, and began having hits with them. Powered by a Korg T3 keyboard guitar, on “a nylon guitar patch,” played by Tommy Barbarella, “Willing and Able” is the album’s highlight, a sui generis masterpiece that jibes with prevailing trends but does so on its own unique terms. The video for “Willing and Able” was directed by Sotera Tschetter; it isn’t Prince’s most famous clip but it may be his best. Even Tony M comes off.

Let’s jump ahead in the box, from first disc to last — a live show recorded in January 1992 at Glam Slam, the downtown Minneapolis nightspot that Prince had opened in 1989. (The footage is also on the box as a DVD.) For me, this is the real prize of the set. For one thing, it’s heavy not only on Diamonds and Pearls, but also features songs from albums fore and aft: “Thieves in the Temple” from Graffiti Bridge (1990) and “The Sacrifice of Victor” and “Sexy M.F.” from the self-titled (after a fashion) from 1992. (We also get a hits medley of “1999”/“Baby I’m a Star,” but even that ends with a section of D&P’s “Push.”) That touch of chronology helps better tie this behemoth to the full fertility of that time, as well, and not just of the album in question.

We even get a preview of the battles with Warner Bros. to come at the tail end of “Thieves in the Temple,” when Prince suddenly and mysteriously asks questions of his audience: “Do you know me? Do you really? Naw, I don’t think you know me.” Then, suddenly, his voice cutting: “Do you think I’m senseless?” This must have seemed baffling to the crowd; it’s startling even now. But the sudden terseness of his tone makes it easy to imagine him repeating the word he’d recently heard used against him during a meeting with the brass.

That kind of anger blankets disc two, which houses the album’s many accompanying tracks. Prince’s B-side strategy had long been to include new or different songs than on his LPs — a good way to siphon off excess creativity, a good consumer impetus too. By the time of Diamonds and Pearls, though, having only one B-side per single was an anachronism. Prince, like many, began filling up CD5s (what singles and EPs on the format were dubbed to differentiate themselves from albums) with remixes of album tracks, and other tracks that amounted to mega-mixes of album material with new rapping, mainly by Prince, over them. 

Diamonds and Pearls was cover-billed to Prince and the New Power Generation, and Prince did solicit his bandmates’ input to the material for the first time in a while. In the box’s booklet, drummer Michael Bland calls it “this weird sort of dichotomy or mixture of loops and kind of hip-hop culture and rap with this old-school way of recording everything.” 

It’s easy to see why Prince took so readily to these players. The New Power Generation — in particular, bassist Sonny Thompson, drummer Bland, guitarist Levi Seacer Jr., and keyboardist Tommy Barbarella — could execute at his speed. Their early first-take energy still sounds rough to me on Diamonds and Pearls — a suspicion proven right for me within a year, with the 1992 album showcasing a far nimbler unit, utterly relaxed and locked in completely (check “And God Created Woman”). The NPG’s core — Thompson, Bland, Barbarella, Johnson — would become go-to players and collaborators with Prince for years to come. 

Having them around enabled Prince to — let’s imagine him rubbing his hands together here — record even more music than usual. Soon enough, all that overage would begin creating increasingly visible friction between the artist and his record company. But that’s only hinted at during the Glam Slam show. There, the material comes alive. The band is a well-oiled machine, ready to take on the world. And “Diamonds and Pearls”? They take it to church, of course. I’ll never love that song. But even I have to admit that in this setting, it soars. Because it’s true: David Foster could never.

Correction: A previous version of this piece credited Spike Lee with directing the “Willing and Able” video. Lee directed the video for “Money Don’t Matter 2 Night.”