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In 1991, Prince was at an unusual point in his career. With four Billboard Hot 100 No. 1s under his belt (of an eventual five) and a string of critically acclaimed blockbuster LPs to his name, he was one of the most successful and celebrated names in pop music. Big enough that just two years prior, he could dash off some goofy jams for a superhero flick and top both the Hot 100 and Billboard 200.

But 1990 wasn’t a kind year to the artist soon to be known as the Artist Formerly Known as Prince. The idiosyncratic trailblazer put a lot of effort into directing, starring in and composing music for Graffiti Bridge — a movie sold as a sequel to the smash film Purple Rain — only to see it collapse at the box office. And while his directorial debut, 1986’s Under the Cherry Moon, was a similar flop, he could at least save face thanks to its hit soundtrack, Parade, which produced the all-time pop jam “Kiss.”

No such luck with the Graffiti Bridge soundtrack, however: other than “Thieves in the Temple” – which went top 10 and topped Hot R&B/Hip-Hop Songs – audiences and critics responded to the movie’s songs with polite enthusiasm. What may have really stung, however, was the fact that Graffiti Bridge, as a film and album, seemed out of step with a new decade. In 1991, Prince wasn’t passé – but he certainly didn’t seem to be steering the direction of pop or R&B radio any longer.

“It’s no secret that toward the end of the ‘80s, things were getting really sort of mysterious — it was hard to tell where Prince was going,” says drummer Michael Bland, who worked with Prince from 1989-1996, with a laugh. “I know that a lot of people counted him out and said, ‘you know, well, that’s it for the hits.’”

“[Graffiti Bridge] was a pretty good, solid record,” says Michael Koppelman, who engineered that album and would go on to engineer, mix and master Prince’s following album, Diamonds and Pearls. “The movie was pretty bad and skipped over in a lot of people’s heads, so I think he wanted to prove something after Graffiti Bridge was not Purple Rain. Diamonds and Pearls was a departure into a more social thing with his band, which I think was a very positive thing for him.”

Diamonds and Pearls — which was recently given a lush re-release in several different iterations, with the Super Deluxe Edition boasting 11 never-before-released tracks – originally came out on Oct. 1, 1991, and marked the full-album debut of New Power Generation, Prince’s first backing band since the Revolution. NPG was primarily made up of players from 1990’s Nude Tour, including fresh faces from the Minneapolis music scene as well as friends Prince had known for years. “I was the youngest there – I joined Prince’s band when I was 19,” Bland informs Billboard. On the flip side, bassist Sonny T. grew up with Prince. “He played guitar and sang background on one of my first demos,” Sonny T. tells Billboard. “When we were kids, he brought [his 1978 debut For You] to my house.”

While Prince was inarguably in command of the Diamonds and Pearls sessions (“Imagine going into the military” Bland quips), the mood was noticeably lighter in the studio, according to Koppelman. “They were joking around, it was a lot more social [than Graffiti Bridge],” he says. “He really liked the musicians in New Power Generation. Like any musician, it’s fun to play with musicians you respect and like.”

“He was around people that he knew and grew up around – it’s kind of like having family around,” Sonny T. says. “It’s like Old Home Week. It was cool.”

The mixture of younger talent and familiar faces seemed to have an invigorating effect on the Purple One. While Diamonds and Pearls isn’t a masterpiece in the vein of Dirty Mind or Sign ‘O the Times, it’s an essential second-tier title in his oeuvre with an urgency and focus absent from his previous three LPs. In terms of re-establishing his commercial bona fides at the top of a new decade, the album sold 2.5 million copies in the U.S., according to Luminate — making it his best-selling album released in the 1990s. Plus, it gave him four top 40 singles on the Hot 100: the chart topper “Cream,” which came (so to speak) with a scandalous video; the lush, No. 3-peaking title track; the cool, effortless “Money Don’t Matter 2 Night”; and the hard, horny funk of “Gett Off.”

The lattermost single boasts a spotlight-stealing vocal (and scream) from NPG member Rosie Gaines, whose impact on the album extended well past what’s on wax.

“I’m one of the few people that point out that Prince could be a dick,” Koppelman says, smiling. “I don’t think it was necessarily trying to be a dick… but I think he made people nervous purposely to keep people on edge. Rosie broke all of that up. She and Prince had a very friendly relationship that was just infectious. She was so f—king good. When he brought her in to do something, he was just blown away. She was just absolutely lovable and this ray of sunshine.”

Their chemistry is abundantly clear from watching Live at Glam Slam, a concert filmed at Prince’s Minneapolis club Glam Slam on Jan. 11, 1992, which is newly available on the Diamonds and Pearls box set. The concert documentary finds Prince and Gaines trading vocals on an incendiary version of “Nothing Compares 2 U”; not only does Gaines push him vocally, but she teases out his impish sense of humor, particularly during a hilarious moment that finds him batting his eyelashes at her with a Chaplin-esque charm.

Live at Glam Slam also reveals how ridiculously well-rehearsed NPG was – six minutes into a 14-minute “Gett Off,” Prince cries out “double time!” and the outfit shifts gears into maximum overdrive without missing a beat.

Of course, Prince was just as demanding of his band off stage. Koppelman, Bland and Sonny T. all talk about the long hours spent recording Diamonds and Pearls over the course of a year. “He was he was a disciplinarian. He knew what he wanted to hear,” Sonny T. says, sharing that rehearsal might run from lunchtime to 9 at night, followed by hours of studio time until “three or four” in the morning. “Sometimes I just didn’t go home – I’d sleep at Paisley Park, go upstairs, take a shower and then start rehearsal again.”

Plenty of the songs took shape over the course of months, with NPG band members learning what songs made the album – and in what shape — along with the wider public. “Unless he felt the desire to show you what he’d been working on, you were just in the dark until he turned the light on,” Bland notes, which he says was the case with “Push,” “Strollin’” and “Willing and Able” to varying degrees. Other tracks – like “Money Don’t Matter 2 Night” (which Bland worked on in Tokyo while fighting a stomach bug) and “Cream” were faster. “[‘Cream’] just came out, just kaboom,” says Koppelman. “I told Prince immediately, ‘Prince, you need to release this song, it’s gong to be a hit,” Sonny T. recalls of “Cream.” “First, he gave me that look – you know, the Prince look? Then he’s like, ‘okay.’ Then it was a hit – he couldn’t say nothing after that.”

Sonny T. remembers Tony M.’s rapped verses on Diamonds and Pearls coming out with similar alacrity. Tony M., who began working with Prince as a breakdancer on the Purple Rain film, eventually graduated to on-mic talent, with his verses factoring heavily into Diamonds and Pearls. “He’s just such a great lyricist. He would just write lyrics, right on the spot, just boom, boom, boom, boom,” says Sonny T.

“There was a whole other idea for how Diamonds and Pearls might’ve been, but I think it leaned a little too hard on the hip-hop of the day,” Bland opines. Thanks to the expanded reissue, we can sample some of the hip-hop-influenced tracks Prince left on the cutting room floor, such as “Something Funky (This House Comes)” and “Glam Slam ’91.” “I’m not sure what made him change gears or what informed his creative process to turn to a more commercial direction,” Bland says. “Diamonds and Pearls is a very positive, bright record. It’s friendly. But there’s some serious playing on that record.”

“I tend to think of, you know, Controversy and Purple Rain as the best of his career,” says Koppeman. “But it’s super gratifying [to have worked on songs that are] an important part of Prince’s career.”

“When we got on stage together, that was one of my favorite things that’s ever happened to me in my life,” says Sonny T. “We really moved as a unit – it’s just clean, cool. And that’s a fun thing.”

“I like that I was one of the tools he used to get back on top. We all take pride in that – he chose mostly young, local musicians to reinvigorate his creative process,” Bland says. “Creatively, he kind of had been dwindling in a dark place. And I feel like we helped chase the clouds away a bit.”