De La Soul on carrying on, honoring Trugoy the Dove's legacy: 'Every member has to actually die before this thing can be over'

De La Soul’s Vincent “Maseo” Mason is chatting with Yahoo Entertainment ahead of this weekend’s Blue Note Jazz Festival in Napa, Calif., where his famously boundary- and envelope-pushing hip-hop group will perform a special set with the festival’s artist-in-residence, progressive R&B pianist Robert Glasper. The gig takes place during a bittersweet time in De La Soul’s career. Their music finally became available on streaming services on March 3, after a protracted legal battle with their former record label, Tommy Boy. But on Feb. 12, Dave “Trugoy the Dove” Jolicoeur, with whom Maseo and Kelvin “Posdnuos” Mercer formed De La Soul in 1988, died at age 54 after suffering from congestive heart failure since 2017.

Trugoy’s presence will definitely be felt at this weekend’s Blue Note fest, just as it was felt at March 2’s “The DA.I.S.Y. Experience,” De La Soul’s all-star concert at New York’s Webster Hall that served as both a celebration of the pioneering trio’s newly streamable catalog and their late bandmate’s legacy. “That was already planned to be the [digital] release date, and it ended up turning into a memorial service,” says Maseo.

“That word, ‘bittersweet,’ has been somewhat cliché in this situation. You know, it's been hard to celebrate,” Maseo continues. “It's awkward. It's weird. It's empty. I'm mustering up energy at times. I can choke up a lot. Every now and again it's like, crying is sporadic. It's like it comes out of nowhere — and laughing, as well. I think the most therapeutic thing for me is facing it, showing up and facing it, confronting it, instead of just running and hiding, because it does hurt really bad. So, to be honest with you, yeah, ‘bittersweet’ is the term to use. [The DA.I.S.Y. Experience] was a joyous occasion. It's extremely sad when [Dave] is not here in the physical to celebrate with us. He's not here in the physical to enjoy it. Everything that we talked about 48 hours before he passed… granted, we always knew he wasn't quite really all that healthy, but we didn't ever expect death, really. We was just pretty much making our adjustments so we can actually get out [to New York] and do what we need to do, without him overly working himself.”

After Trugoy died, three weeks before the DA.I.S.Y. Experience, Maseo admits that he and Posdnuos were “on the fence” regarding whether to proceed with the Amazon Music-sponsored celebration. “I was really upset. I was in a dark space,” he says. But in this year marking the 50th anniversary of hip-hop, a landmark film of the genre inspired Maseo and Posdnuos to continue.

“So, Pos came to my house and grabbed me out my little hole that I was in, and we spent days together,” Maseo reveals. “And he came up with the greatest idea that I thought was perfect. We always had made a lot references to the movie Beat Street. … There was a scene in the movie where Ramon, the graffiti artist of the movie, was obviously murdered, and then the New Year's Eve celebration that they were supposed to have ends up turning into a memorial service for Ramon. [Posdnuos] was like, ‘Yo, Dave is our Ramon, man. He's our Ramon. He was our Ramon.’ And by calling him Ramon, I got the picture so clear. It was like, ‘Yeah, we need to celebrate this, like that New Year's Eve party in Beat Street, and let it be about Dave — the release, but Dave and his legacy, and our legacy.

“And it ended up working out perfect. It turned out perfect. It was a perfect storm, I guess you would say. All our friends came out, everybody we grew up with,” says Maseo, choking up a bit, as he reminisces about the Webster Hall event that was attended by comedian Dave Chappelle (who is MCing this weekend’s Blue Note Jazz Festival), Busta Rhymes, Jungle Brothers, Queen Latifah, Monie Love, Talib Kweli, Black Thought, Chuck D, Beat Street icon Grandmaster Flash, and many more. “The performance was incredible. The love in the room — yeah, it was good.”

Maseo doesn’t divulge much about that private final conversation that took place 48 hours before Trugoy’s death, but the fact that he died knowing that De La Soul’s music had finally been cleared for streaming and would soon find a whole new listenership gives Maseo some peace. “Put it like this: It was a lot of love. It was a lot of 'I love you's,'” he says. “It was a lot of ‘thank you, Mace.’ And ‘thank you,’ to me, meant everything.”

De La Soul’s music always managed to reach new, younger fans over the years, despite it being so digitally unavailable. Maseo credits that to the group’s tireless touring, which he adamantly believes is “still something every artist supposed to do,” as well as to their various cross-genre collaborations. He refers to Gorillaz’s Damon Albarn, with whom De La have worked multiple times over the past two decades, as a “brother” and a “fifth member” of De La Soul (after producer Prince Paul), and De La’s most recent studio album and final album with Trugoy, 2016’s Kickstarter-funded And the Anonymous Nobody..., featured Albarn, 2 Chainz, David Byrne, Estelle, Snoop Dogg, Jill Scott, the Darkness’s Justin Hawkins, Pete Rock and others.

The fact that De La Soul have such a wide range of collaborators and fans, and can play a Wine Country jazz festival in 2023, shows just how groundbreaking they have been since the release of their landmark debut, the sampledelic 3 Feet High and Rising, in 1989. But Maseo — who says he always found labels like “backpack rap” and “hippies” to be “disrespectful” and “derogatory” — humbly insists, “I have to honestly say I didn't know I was the new trend. I just knew I was doing something for my heart and soul, with my friends. That just came from a very organic place. Because it wasn't about money. It was about making great art. … The ‘hippie’ concept wasn't something we identified ourselves with. [I think that was due to] the music that we chose to sample, whether it was like Steely Dan or Hall & Oates — or even the Turtles, for that matter.”

The Turtles sample Maseo is referring to, or more specifically the legal battle surrounding it, played a “significant role” in the issues that De La Soul would later face regarding streaming, when that ‘60s folk-pop group successfully sued De La for $1.7 million in 1991 over the use of the Turtles’ “You Showed Me” on the 3 Feet High and Rising track “Transmitting Live From Mars.” The rules of sampling were still being written when De La Soul burst onto the scene, and the many samples they used back then had only been cleared for physical media distribution, since the internet obviously didn’t exist in the late ‘80s/early ‘90s Wild West the way it does now.

“At that time, nobody knew how big the music, the genre, was going to be, let alone the way we even created music,” Maseo explains. “Who would've thought that [“Transmitting Live From Mars”] would have turned into a pop-culture phenomenon that started a new business around lawsuits for copyright infringement? We were all new artists at the time. We all were just embarking upon this art form called sampling, especially deriving from DJing and DJ culture. We were just trying to advance our art. But the business got developed around it in a harsh manner.

“I still sample. I have no regrets about anything. It's all lessons learned. Granted, it's a helluva college education, well-paid for!” Maseo continues with a wry chuckle. “But there was things that we've learned as a band, and that even the label has learned. I don't think anybody was even prepared for the internet and what it became. It was a different era. There was no real business model around this thing called hip-hop. I think we adopted a lot of ideas from punk rock, and as [hip-hop] began to grow, I think nobody expected the internet to be what it is today. I think our story happened to be one of the biggest stories because it was horrendous and the label was just being completely unfair, but there have been other artists who've been through this situation, because no one could anticipate the growth.”

But De La Soul survived, and Maseo attributes that tenacity to him and his bandmates always “sticking together. And three Black men sticking together. I have to emphasize: three Black men. … I think sticking together actually says a lot, as simple as that may seem. It says a lot to our genre. It says a lot to our culture. And it says a lot to the music business in general, for bands who couldn't really hold it together. I think that speaks volumes.”

And while Trugoy is no longer here, Maseo and Posdnuos are sticking together, with plans to keep making new music. Their next release will be a long-overdue and much-anticipated third installment in their Art Official Intelligence series, which was “always supposed to happen” after 2001’s AOI: Bionix, before their legal disputes got in the way.

“I have to,” Maseo answers matter-of-factly, when asked if De La Soul will continue to release new records. “I have a responsibility, not only to what we've created, but to Dave and his legacy. That is necessary. He just transitioned, but he's still here with us. His energy is widely spread. I think anybody who's been touched by this music can feel his presence every time a song comes on. I feel his presence a lot, you know? Based on the conversations that we've had amongst one another, amongst family and friends and let alone his immediate family, we have a responsibility to do it the way we actually said we was gonna do it: till we die or until we break up. And obviously, we never broke up. So, every member has to actually die before this thing can be over.”

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