Prince had lost it. That was the chatter that followed the once peerless funk-rock icon in November of 1990. Graffiti Bridge, Prince’s self-directed music film drama, was a messy critical and box office bomb. And while its underrated soundtrack boasted some inspired moments, the genius one-man-band was suddenly viewed as out of touch by critics and, more importantly, by the public. This was a startling development for an artist that led much of '80s musical zeitgeist with a string of genre-defying, landmark works.

It was the golden age of hip-hop and the 32-year-old Prince Rogers Nelson was being eclipsed by a rebellious, Black youth culture. Rap and R&B had become the new pop. Prince was listening. For a year and a half, he had been laying down tracks with a new band for his ballsy, hip-hop infused comeback album, Diamonds and Pearls.

Prince’s two-fisted ensemble—which included LoveSexy (1988) guitarists Levi Seacer, Jr. vocalist/organist Rosie Gaines, drummer Michael Bland, bassist Sonny T and keyboardist Tommy Barbarella, rapper Tony M. and his fellow Game Boyz background dancers Damon Dickson and Kirk Johnson, would serve as a catalyst for his return to glory.

“I want you to get ready because things are definitely going to change for you,” Prince told the group. “I’m getting ready to announce a new band—The New Power Generation. You guys are in the band.”

“He was getting us prepared for something big,” remembers Tony M., New Power Generation’s lead MC, who along with the Game Boyz, grew up in the same North Side section of Minneapolis, Minnesota as Prince. “Prince started calling us into the studio to jam. Sometimes we didn’t even realize that some of the stuff we were doing would end up on an album.”

Released in October 1991, Prince and the New Power Generation’s Diamonds and Pearls became the celebrated artist’s best-selling studio album since his Academy Award-winning blockbuster, Purple Rain (1984), moving nearly 6m copies worldwide. It reached #3 on the chart, #1 on R&B Albums and spawned five hit singles, including the infectious, blues-rock chart-topper “Cream.”

Not only was Diamonds and Pearls the first Prince project to share equal billing with a backing band since The Revolution, the New Power Generation was unapologetically Black in sound, presentation and swagger. The most impactful member on the NPG roster was Bay Area native Gaines, whose soul stirring vocals on took Diamonds and Pearls' self-titled, Top 3 power pop ballad to church and back.

“When Rosie came in and did her parts, Diamonds and Pearls just blossomed,” marvels record producer Michael Koppelman, who in the late '80s and early '90s worked as a studio engineer at Paisley Park, the visionary’s storied Minnesota-based complex. “Prince knew that she was great.”

Yet Diamonds and Pearls’ boldest statement was the hip-hop infused first single “Gett Off,” which featured the bandleader rapping. It was a shock to the system for longtime Prince followers, especially given his complicated history with rap.

“I told him, ‘Whether you think they did or not a lot of hip-hop fans heard you dissing rap,’” remembers Tony M., referencing the infamous Prince track “Dead On It” featured on his legendary 1987 bootleg The Black Album, on which he mocks rappers as “tone deaf.” “I always felt like during Diamonds and Pearls, I had the gloves on because I was boxing people from both sides. There were hardcore Prince fans from the ‘80s that did not want to hear no rap.”

Prince, however, remained unbowed. “Don’t write what you think other people are going to like,” he responded. “Write for yourself. Some people are going to like it or hate it. Just write what you feel.”

In the end Prince’s risky gambit paid off big time. Diamonds and Pearls’ string of artfully shot videos were all over MTV and BET. When he and the NPG delivered a shock and awe performance of “Gett Off” amid a lavish, simulated staged orgy at the 1991 MTV Video Music Awards, the provocateur appeared in a lemon yellow lace bodysuit that exposed his backside as he wailed away on guitar. Years later, it was revealed that Prince’s iconic “assless pants” were actually made with a flesh colored fabric. No matter. Prince won.

Since the untimely 2016 passing of Prince, Diamonds and Pearls’ legacy has elevated in stature. A sprawling deluxe box set, due out 10/27 via NPG/Legacy, captures not only Mr. Nelson’s unrivaled prolific zeal—the re-polished collection includes 75 audio tracks, including 47 unreleased songs, and previously shelved 1992 concert of Prince concert performing at his Glam Slam nightclub in Minneapolis—it highlights an artist who was never afraid of the big moments.

“Diamonds and Pearls was the album that showed he was still in the game, that he was still pushing himself to do different things,” says Koppelman. “We are talking about a talent who could hang with Mozart, Count Basie, everybody. The man was music.”