An unexpected lightness radiated through New York City’s Webster Hall on March 3, 2023. Dozens of hip-hop luminaries had gathered to celebrate both the debut of De La Soul’s first six albums on streaming services and the life of founding member David “Trugoy The Dove” Jolicoeur, who had died just 20 days earlier.

No one had expected the elaborate event to double as a memorial for a fallen friend. While the timing of Trugoy’s death felt like a cruel joke, De La Soul’s surviving members—Kelvin “Posdnuos” Mercer and Vincent “Maseo” Mason—knew they had a job to do; not only did they have to get through the evening with as much composure as they could possibly muster, but they needed to remember why they were there.

In 1989 De La Soul ushered in the D.A.I.S.Y. Age (“DA Inner Sound Y’all”) with the release of its critically acclaimed debut album, 3 Feet High & Rising, on Tommy Boy Records. Guided by the production prowess of Prince Paul, the group delivered a groundbreaking work that transcended genre with its prolific use of samples; Steely Dan, the Beastie Boys, Hall & Oats, Johnny Cash, Michael Jackson, Sly & The Family Stone and Cymande represent just a sliver of the artists seamlessly woven into that eclectic tapestry.

Thus began the journey of De La Soul, one that would produce five more stellar albums under the Tommy Boy umbrella: De La Soul Is Dead (1991), Buhloone Mindstate (1993), Stakes Is High (1996), AOI: Mosaic Thump (2000) and AOI: Bionix (2001).

Behind the scenes, communication between the trio and Tommy Boy founder/owner Tom Silverman had broken down, leading De La Soul to eventually leave the label. The arduous road to regaining its recorded catalog would prove to be the group’s biggest challenge. Contentious contract negotiations led to years of pain and suffering, ultimately resulting in De La’s inability to upload its catalog to DSPs. This was a battle the act thought it might never win. Then everything changed.

In June 2021, after a very public spat with Tommy Boy and an ensuing “TommyBoycott” championed by The Roots’ Questlove, Reservoir Media acquired the Tommy Boy catalog for $100 million. It took roughly a year to license most of the samples (those that couldn’t be cleared were interpolated, or re-played), but as 2023 dawned, the members of De La Soul finally exhaled and announced that, at last, they’d been given the green light to release their albums digitally—they had just never anticipated they’d have to bask in their hard-fought victory as a duo.

Trugoy took his last breath on February 12 following years of health issues, including diabetes and congestive heart failure. It was a jarring blow to the entire hip-hop community but especially to Posdnuos, Maseo and Prince Paul, who’d grown up with him. Still, that night at Webster Hall, something magical happened; what could’ve been a storm cloud of grief morphed into an outpouring of love, support and fun.

“That was like a wedding night, because there was so much going on that even all the great things Amazon Music did, all the details, I couldn’t fully experience,” Posdnuos admits. “What Mase and I did experience was the love from any and every person who came into our presence; they hugged us, embraced us, prayed with us, cried real quick with a laugh—that’s what we were experiencing.

“There was a genuine feeling of ‘We're together in this lossâ€•we're not just here to comfort you; we're trying to get through it ourselves.’ At the same time, it was such a beautiful moment with the music being released. So we shared all of that, really naturally and organically. For me, it was just a beautiful night.”

The support was reflected in album sales, too; as memes reading “Stream De La Soul” dominated social media, 3 Feet High & Rising returned to the Top 200 for the first time in 34 years. Pos describes it almost like an out-of-body experience: “Sometimes I don't even realize that, no, this is actually me; I'm actually in the group that this is happening to.”

It all started with a demo of the song “Plug Tunin’,” which would land on 3 Feet High & Rising. Growing up in Amityville, New York, on Long Island, Pos, Maseo and Trugoy had heard of Prince Paul, who’d made a name for himself as a member of Stetsasonic. When Paul heard the song, the creative symbiosis of the talented trio was too much for him to ignore—and so were their senses of humor.

“I was in and out of Long Island when I was with Stetsasonic,” Prince Paul says. Stetsasonic was based in Brooklyn, but Paul grew up in Amityville. “There were new people moving in and I didn't know them because I wasn't home that often. But there was this one kid that everyone was talking about—Mase. He was just a popular kid that everybody knew. It started out with him. When he introduced me to De La and played ‘Plug Tunin’,’ I was like, ‘Yo! This is the vibe, and how they think is how I think.’ That didn’t apply to Stetsasonic. I was a teenager. I was silly and Stetsasonic was grown. So having these guys, as creative as they were, coupled with their ‘I don’t care’ attitude, I was, like, ‘This is it.’ We complemented each other.”

Posdnuos, who created “Plug Tunin’” using his father’s old 45s, adds, “I constructed it and arranged it to go with existing rhymes. Maseo and Trugoy loved it. We tweaked it a bit and Paul said, ‘This is so creative.’ He added another loop beat to it and a piano sound and really made it better than it wasâ€•we came with a seed and he turned it into this amazing daisy. We felt this kinship; how we thought matched how he thought, and that's why it was so easy from that point to keep making records.”

Seven years into their kaleidoscopic collaboration, however, De La Soul and Prince Paul came to an impasse. Work had begun on the group’s fourth album, Stakes Is High, and the pressure from the label to deliver a hit was mounting. Creative differences arose, and it was eventually decided it would be best to complete the album without Paul. Talk of bad blood and a nasty breakup were perpetuated by the rumor mill.

“A lot of people assume that just because you don't work with somebody anymore, there’s a beef. That's been a big misconception,” Paul says. “The ironic part is that years later, Pos asks me, ‘Are we cool?’ I said, ‘Of course we’re cool!’ Everybody was talking, and it made us think, ‘Are we OK?’ It was so strange, because it didn’t end that way; we just weren’t hearing things the same way anymore.

“I give them a lot of credit because they were under so much pressure. The records we were making were, one by one, less popular. And I was really supposed to be out a long time before. I gave them the multitracks we’d started at my house and was, like, ‘It would be better if you finished the record on your own.’ I wanted to keep our friendship. That was way more important than an ego thing. I love those guys. I had my run with them, and Stakes Is High is brilliant. It’s probably my favorite De La record.”

The album hit #13 on the Pop chart and #4 on the Hip-Hop chart but did not enjoy the commercial success of previous releases. Even so, it was hailed by critics and helped introduce Mos Def to the masses. The title track, produced by the late, great J Dilla, is a bona fide hip-hop classic.

Still grappling with Trugoy’s death, Posdnuos and Maseo have nonetheless been compelled to promote their long-awaited digital catalog. In March they were joined by The Roots’ Black Thought and Questlove for a performance of “Stakes Is High” on The Tonight Show Starring Jimmy Fallon. Pos bravely stepped into the spotlight and rapped his verses as if Trugoy was right beside him.

“When we got to soundcheck, I didn’t even see the giant photo of Trugoy behind me,” Pos says. “I was on a mission to get it done. People were crying; it was touching to a lot of people—and this was just soundcheck. My videographer couldn’t even look my manager in the eye because they didn’t want to cry. It was magical, a real moment. Every bit of love that anyone later told me they felt from the TV broadcast, it was 100 times that. It turned out to be a beautiful performance.”

De La Soul’s future is uncertain, but it’s not beyond the realm of possibility that Prince Paul will re-enter the fold. It’s an idea they’ve been toying with for years but one that didn’t feel plausible until they reconvened to touch up the albums for DSPs.

“At the end of the day, we love each other,” Pos says. “Sometimes your personal life takes precedence, and it takes you where you need to go, but there's never any love lost. The love and respect between us is very genuine. It’s easy to fall back into a familiar place and solve a piece of the puzzle with Paul. I actually just got off the phone with him, but we're still figuring it out.

“Music from all of us? We want to see it happen. How? Not 100% sure. We just know that we 100% want to do it. Maseo has said, ‘Hey, man, we should work on the third AOI.’ [The final installment of a planned Art Official Intelligence trilogy never materialized.] We definitely want to do something with Paul. DJ Drama still wants to do a De La Soul Gangsta Grillz project. I'm just happy we want to do music and people want to see us do music. So is new music coming? Yes.”