The 10 Best De La Soul Songs

The 10 Best De La Soul Songs

It’s become a risible cliche to state that a recently-passed artist “taught me that it’s OK to be weird.” But what if it’s still true, not just from the perspective of an individual’s experience, but in the context of an entire culture? The reconnections people have been making with De La Soul in the last month — spurred by the near-concurrent announcement of their catalogue’s escape from sample-rights purgatory onto streaming platforms and the death of their MC Dave “Trugoy The Dove” Jolicouer at age 54 — have been more than just nostalgia trips for oldheads. They’ve actually given some perspective to where De La really stood on the precipice of hip-hop’s revered late ’80s-early ’90s Golden Era: as the geeky weirdo class clowns who skeptics struggled to take seriously until the sheer force of their creativity became impossible to deny.

A lot’s been made about De La Soul’s origins in the suburban confines of Long Island, New York, where Jolicouer (hereafter referred to as “Dave”), fellow MC Kelvin “Posdnous” Mercer, and DJ/idea man Vincent “Maseo” Mason first got together over a shared love of hip-hop. Putting aside the purported novelty of a rap group coming from that neck of the woods’ relative comfort — a rep that wasn’t as quickly thrown at, say, fellow L.I. resident Chuck D — Pos had actually relocated there with his family from hip-hop origin-point South Bronx, while Dave and Maseo had moved in from Brooklyn. They’d known about the culture since the pre-“Rapper’s Delight” days of bootleg live-party cassettes, and by the time Run-D.M.C. hit the scene they saw possibilities everywhere. “I think Run-D.M.C. exemplified the average B-Boy. We were all dressing like them. We all had on Lee’s [jeans]. We all wore Adidas. They didn’t look like Grandmaster Flash & the Furious Five, dressed in these funkateer kind of outfits. They looked like everyday average B-Boys you went to school with,” Dave told KEXP in 2016. “So it made you feel like, ‘Yo, I can be like them. They made it. This is what they’re doing. This is something that they’re doing for a job or a life hustle. I could do it, too.'”

And yet when they teamed up with Stetsasonic producer and comedically/artistically likeminded oddball Prince Paul to put their own selves out there, they had a far more difficult time getting people to accept them at face value — even if their fearlessly eclectic, stylistically innovative debut 3 Feet High And Rising became a critical darling and a modest but noteworthy commercial success. That’s because De La’s style, at least on the surface, seemed so counterintuitive to nearly every depiction of what many people expected hip-hop culture to be, both inside and outside the industry. They came across as more chill than intense, more funny than tough, and more personal than political — even if they could touch on all of those modes when the situation called for it. And by leaning into a Day-Glo, pop-art aesthetic and putting out records heavy on lighthearted-yet-complex lyricism and an almost showoffy capability of building funky breaks from the most unlikely sources and forms, they basically ensured they’d have to wind up explaining themselves to confused onlookers for at least the next few years.

This seemed so inevitable, in fact, that it became a part of their core identity in itself. The 12″ of their classic ’89 single “Me Myself And I” threw in a song-length skit as a B-side, “Brain Washed Follower,” where a kid named Jeff interrogates them over their whole deal: If they’re rappers, then where’s their gold chains, their flashy cars, their beepers? De La’s response: They’d rather spend money on video games. Jeff comes away unconvinced.

The next time anyone heard from Jeff, it was at the beginning of their second album, De La Soul Is Dead; there, he finds a copy of the album itself in the garbage and gets jacked for it by a trio of dirtbag teenagers. They don’t get it either: “What happened to the pimps? What happened to the guns? What happened to the curse words?” Even when they centered the entire concept of their sophomore album around the idea that they’d been misinterpreted, even when they provided a clear and in-depth expansion of their personae far beyond the buppie-boho-hippie rep they never asked for, even when they knew they had a whole crew of likeminded artists in the Native Tongues collective who joined them in reshaping a corner of hip-hop in their own image, they knew they were still fighting uphill.

But what their fans got out of that uphill fight was something revelatory. Their first two albums were elaborate self-contained worlds where the interstitial skits felt as crucial as the songs and the weird referential detours and non-sequitirs all felt like an in-joke that you were invited to laugh along with. Their partnership with Prince Paul bolstered the producer’s reputation as one of hip-hop’s great sample-hunting adventurers, the kind of fuck-it-why-not approach that found funk just about everywhere — Steely Dan, sure, but also Tom Waits, Serge Gainsbourg, the B-side to the Harlem Globetrotters theme, whatever. But Paul’s role was also to cultivate and channel De La’s own sensibilities, often as the guy who was there to refine and assemble the parts that they gave him. So by the time they parted ways after 1993’s maturation-effort soul-jazz masterpiece Buhloone Mindstate they could not only land on their own two feet but elaborate on the precedent of those first three collaborative albums.

In the meantime, they thrived as both their own iconoclastic selves and as part of a bigger movement that would provide the backbone to what people call “alt-rap” now. It’s possible that we could’ve gotten to that point without De La, but not probable — even accounting for early contemporaries like their fellow Native Tongues members in Jungle Brothers and A Tribe Called Quest, simpatico wiseasses like KMD, abstractionists like Organized Konfusion, oddballs like the Pharcyde, and bohemian jazz heads like Digable Planets, it still feels like 3 Feet High And Rising was the album that proved this strain of hip-hop could even be viable in the first place.

And that’s because when you dig past the signifiers and the aesthetics and the associations and the rivalries and all the other trappings, De La Soul were absolutely diabolical on the mic. Look up the lyrics to any one of these songs and you’ll be confronted with — and rewarded by — some of the unlikeliest rhyme structures and turns of phrase to ever capture mainstream attention, all delivered by two MCs who sounded both conversationally approachable and rhythmically labyrinthine in their deliveries. Even when their spark seemed to fade a bit towards the end of their initial 15-year run, they were always good for an unpredictable twist of phrase or a shift in their flow that served to remind their indie-rap successors just how much they owed to them. So stopping at just 10 examples is a tricky undertaking — even when one limits it to top-billed songs. (Otherwise you could easily throw in Gorillaz feature “Feel Good Inc.,” Prince Paul’s A Prince Among Thieves rap-opera highlight “More Than U Know,” or even their Teenage Fanclub teamup “Fallin'” from the notorious rap-rock soundtrack to Judgment Night.)

At this point, it’d be easier (and a lot shorter) to draw up a list of De La Soul songs that don’t sound transcendent or at least fascinatingly strange in some way — and maybe now that their catalogue is finally easy to hear again, this can just be the starting point for a deeper immersion into one of the most uncompromisingly unique discographies in all of hip-hop.


"Oooh." (from Art Official Intelligence: Mosaic Thump, 2000)

It seems like a very De La bit of comedy to add a full stop to the title of this track when it practically demands an exclamation point in its place. As the lead single off 2000’s Art Official Intelligence: Mosaic Thump, their first album in four years, “Oooh.” feels like a necessary reintroduction in an uncertain time that saw hip-hop’s market-share stakes even more heightened than they were in ’96. So they drop a speaker-quivering hands-up anthem that features hooks and ad-libs from Redman in classic “world’s most energetic stoner” mode — and yet it’s on De La’s terms because it can’t work if they’re not. Some of those terms read like reconnections; in the wake of their role on A Prince Among Thieves it’s good to hear them working again with co-producer Prince Paul. (Whether it was his idea or De La’s to rearrange the Minimoog from the J.B.’s “Blow Your Head” into the melody from Lalo Schifrin’s Enter The Dragon theme, the world’s a better place for it.)

But it’s their sheer determination to maintain their unpredictable timing and fractured, refracted rhyme schemes on the mic that give Pos and Dave the spark that makes “Oooh.” work well outside party-jam confines. They trace their lineage through referential riffs off Fearless Four’s “Rockin’ It” and Tribe’s “Can I Kick It,” emphasize their impossible-to-reproduce lyrical quirks through their metaphorical/simile-riddled tangential journeys, and give it all an enduring curiosity by making their verses so allusively dense you can find entire rabbit holes of potential meaning in a couple stray lines. That they lick shots at a shiny-suit edifice already on its way out is almost beside the point: when Pos tauntingly shrugs “It ain’t my fault your ass is on the asphalt/ Got your chin touched by my fam who though you brought harm, you see,” it’s the kind of flex that declares their legacy to be built off legions.


"Nosed Up" (from And The Anonymous Nobody..., 2016)

Kickstarted into existence after a nearly dozen-year wilderness of side projects (2012’s in-all-but-name First Serve) and corporate-patronage tie-ins (2009’s Are You In?: Nike+ Original Run), And The Anonymous Nobody… felt at the time like an all-star tribute album where the tribute was reminding everyone that De La Soul were still worth listening to — and not just their back catalogue. In retrospect, its eclecticism and the accompanying hit-or-miss genre-hopping (Justin Hawkins???) might’ve distracted from the simpler pleasures of Pos and Dave aging into reflective mode — and while their energy level might’ve flagged here and there, it’s only because they seem to have saved it for the deep-focus drive of their lyrics.

This is why one of the best tracks on the album is a non-single deep cut that plays like a grown perspective on their younger selves’ nonconformist social combativeness. The pitched-down Parliament-ary monologues and the youthful skulk of their liveliest bassline since the ’90s gets you to move your hips by elbowing you in the ribs, but it’s the 1,001 ways they scoff at oblivious coke-ego standoffishness that make it a late-career gem. It’s a tossup as to whether the coldest line here is Pos’ oh-shit simile “People can see you coming like 9/11 ash/ Toxic ’til your last days,” or Dave just scoffing, “A star is born, but who’s claimin’ that birthright?”


"Ego Trippin’, Pt. 2" (from Buhloone Mindstate, 1993)

As much as the bohemian rule-rewriting and no-gold-chains defiance made 3 Feet High And Rising feel like a challenge to some old order, De La never really wrote themselves out of the hip-hop continuum. Sure, they might’ve goofed on its so-recent-it’s-imminent past in a take that Kangol off kind of way, but they still saw their immediate predecessors as something to riff off rather than reject entirely. (They’re not hippies, but they’re no punks, either.) This is how they not only got away with writing a spiritual sequel to an Ultramagnetic MC’s classic from five years earlier, but building their own hyper-referential set of lyrics around lifts from and references to classics by Kris Kross, BDP, Big Daddy Kane, Melle Mel, Run-D.M.C., Slick Rick, Pete Rock & C.L. Smooth, Jungle Brothers, Salt-N-Pepa, and inevitably their own damn selves.

And even if the point is to goof on rap lyrics’ fundamental self-big-up tendencies — Dave just states “I’m the greatest MC in the woooooorld” at one point and it sounds like a tongue-in-cheek shrug — their encyclopedic depth and the sharp-honed ease with which they exhibit it would just wind up justifying any superlatives anyways, whether they came from De La themselves or the heads who gave Buhloone Mindstate a long-tail rep as a fan favorite. That it comes over one of Prince Paul and De La’s chillest yet head-nod-worthiest beats — a huge drum-boosted flip of an easy-listening soul jazz number by Al Hirt — is almost as integral to its vibe as the fact that they bookend the whole thing by just screaming at the top of their lungs as a goof.


"A Roller Skating Jam Named 'Saturdays'" (from De La Soul Is Dead, 1991)

If De La Soul Is Dead held the conceptual weight of a group itching to seem at least a couple degrees less lighthearted, they offset it by providing even more intricate and in-joke-filled displays of their characteristic comedy — and, crucially, a radio-ready single that played up their carefree upbeat side in ways nobody else was really doing. Simultaneously nostalgic and cutting-edge, with one of Prince Paul’s (or anyone’s) greatest throwback disco-rap beats and a thematic immersion in classic roller-rink vibes, “Saturdays” pushes De La’s rep for sonic pastiche towards such a distinct snapshot of youthful high-and-flirtatious celebration that it still resonated vividly among people who were kids in 1991 instead of 1979. Q-Tip’s presence is integral — he kicks the first verse in an elaborate and funny extension of the old cliche “boy meets girl” phraseology — as is the god bless the weekend radiance of Vinia Mojica on the greatest R&B-adjacent hooks De La ever allowed themselves. Even Russell Simmons gets in on the act; that’s him as the hyped-up, reverb-soaked DJ introducing the song for fictional in-universe radio station WRMS.

And then there’s Pos and Dave’s roller boogie flows, perpetually momentum-shifting deliveries that make even James Caan’s Jonathan E. look newborn-calf wobbly by comparison. The dips and dives of their phraseology are ridiculous. Pos shines with the second-verse abstract-yet-clear barrage of “Back once more with the wallop in the score/ Must I ride and rip, should I make you rock your hip/ Reviver of a roller-boogie in a rink/ And sure to make you think about the times/ To scope fun instead of fights.” And Dave is amazing gliding through the emphatic intricacy in “Out comes the bodies following the one idea/ It’s clear, rattle to the roll/ Hold back up the track, grab your rollerskates y’all/ And let’s zip on by.” They so defiantly disassemble traditional A/B rhyme schemes in favor of dizzying internal-rhyme assonance that you’re free to focus on how their voices also wind up boosting an already momentous rhythm.


"Me Myself And I" (from 3 Feet High And Rising, 1989)

Before they recorded this song, De La Soul were confident enough in the complete-package scope of 3 Feet High And Rising that they took Tommy Boy’s “yeah but can we get a little something more for the radio” nudge as a nuisance. After they cut this song, they made a thing — ironic or otherwise — of being sick of it, to the point where they’d integrate the phrase “we hate this song” in place of some of its other verses during live shows. But it was a deeply necessary component of their repertoire for a whole lot of reasons, especially its role in attempting to get ahead of some other outside party’s narrative. They saw the potential for their individualistic, colorful aesthetic to be misinterpreted — a potential that was met later on tour, when local goons tended to conflate their bohemian style for an inability to throw down and were frequently proven wrong the hard way. So they asserted their individuality, even as they offered the possibility for a whole lot of others to find out they were in the same stylistic ballpark: they weren’t hippies, they hadn’t carefully manufactured their look for some broader pop-crossover appeal, this was just who they were.

There’s a level of irony there in that this declaration of uniqueness was based on the way their Native Tongues collaborators the Jungle Brothers flowed on “Black Is Black” (which Q-Tip shows up and drops the line just to confirm); there’s another in the fact that their Prince Paul-fueled P-Funkateering — not too far off from Digital Underground’s own contemporaneous vibe on the opposite coast — would wind up at least partially anticipating the favored sound of the gangsta rappers De La positioned themselves in striking contrast to. But as their biggest hit — a #1 on Billboard’s Dance Club and R&B/Hip-Hop charts — you couldn’t ask for a better introduction, both the presentation of the question “who are these guys” and an answer open-ended enough to encourage plenty of follow-ups.


"Rock Co.Kane Flow" (from The Grind Date, 2004)

The phrase “De La Soul featuring MF DOOM” is maybe one of the most self-evident definitions of rap-nerd joy there is. And while the bulk of 2004’s The Grind Date was remarkably strong for an album rescued from the ashes of their aborted-trilogy Art Official Intelligence concept — a concise yet broad-scope dozen-track length, great beats from Dilla and Madlib and 9th Wonder and Supa Dave West, memorable guest spots from Common and Ghostface — there’s a reason this one is the closer that slams the door on the record. Jake One’s beat, a piano-sledgehammering boom-bap superchop of Space’s ’77 Franco-disco classic “Deliverance,” pulls off a similar time-dilation trick as DOOM’s own “Tick, Tick” five years earlier, slowing the tempo to a stuttering crawl at the end of each verse and pushing each MCs to find new emphases in their flows. Everyone steps up, natch — DOOM’s in top form with his idiom-rhyme shit-talk aimed at weak-hearted wannabe usurpers (“He eat rappers like part of a complete breakfast/ Their rhymes ain’t worth the weight of they cheap necklace”), Pos weaves through his own rhythmically counterintuitive lyrics like Thelonious Monk on the mic, and Dave fulfills the role he’s often met of letting his defiant streak add some hard and emphatic toughness to the mix — not aggression, necessarily, but resilience.

The far-too-soon passing of two of those MCs has cast a retroactive pall over what should be an eternal crowdpleaser: Pos’ line “They say the good die young, so I added some/ Badass to my flavor to prolong my life over the drum” hits even harder to the heart considering the losses of DOOM and especially Dave, who closes it all out with the downpitched conclusion “The birthdate’s September 2-1, 1-9, 6-8/ Too old to rhyme, too bad, too late.” Since this is his way of declaring himself a lifer — that while people think he’s not supposed to be rapping in midlife, De La built a career off ignoring “supposed to” — it’s a now-bittersweet yet triumphant conclusion for a remarkably strong 15-year, seven-album initial run few of their peers (and fewer of their detractors) could reach.


"Millie Pulled A Pistol On Santa" (from De La Soul Is Dead, 1991)

Dr. Dre got a lot of the credit for hip-hop’s engagement with P-Funk, but consider how De La and Prince Paul approached them as source material. First they drew on their comedic, trippy side for “Potholes In My Lawn” (which sampled the twangy yodelling of Parliament’s psychedelic-era 1970 country-and-western goof “Little Ole Country Boy”), then the dance-party boogie-funk inventiveness of late ’70s Warner Bros.-era Funkadelic for “Me Myself And I” (“Not Just Knee Deep” refracted through a beat-collage prism). And then, for the bleakest track on De La Soul Is Dead and in their entire catalogue, they masterfully incorporated the mournful soul-versus-the-void excursions Funkadelic would explore during their early ’70s Westbound years. It’s one way of putting De La in the context of the visionary Afrofuturists they were — it’s just that they approached their themes as though they were already in a future that they had to continue making.

But the droning acid-ballad ruminations of “I’ll Stay” are just a suitably unsettling backdrop for the most stunning revelations here: That De La Soul were not only capable of storytelling raps that could rival anything precursors like Slick Rick and successors like Ghostface could concoct, but that they were able to use their supposedly lighthearted literary voices to address the most dead-serious topic possible.

Inspired by Pos’ real-world experience with a friend who survived familial abuse, “Millie Pulled A Pistol On Santa” channels his emotions over that situation into a sprawling tale of a titular semi-fictionalized schoolmate whose beloved social-worker father Dillon has been secretly molesting her. And while Pos plays the role of the facts-on-the-ground narrator with a carefully deployed sense of both disgusted bitterness and sympathy for the victim, it’s Dave who brutally embodies the denialist perspective of someone — one of many someones, really — who just can’t believe anyone as respected by his community as Dillon would do that. (When Millie calls Dave up to see if he can score her a gun, and tells him exactly who she’d use it on and why, Dave spits back: “You’re just mad he’s your overseer at school/No need to play him out like he’s someone cruel.”) Then it all concludes with the song title’s promise, where Millie enacts her revenge on her father while he’s out in Macy’s playing Santa to a group of kids, and the only closure we really get is in that last standalone line without a couplet: “Millie bucked him and with the quickness it was over.”


"Buddy (Native Tongue Decision)" (from "Buddy" 12", 1989)

Consider the canon of hip-hop remixes that eclipse the original — Pete Rock’s army-of-horns reconstruction of Public Enemy’s “Shut ‘Em Down,” Coldcut’s Ofra Haza-sampling psychedelicized rework of Eric B. & Rakim’s “Paid In Full,” that ridiculous run of mid ’90s Bad Boy expansions-slash-refinements of hits from Craig Mack’s “Flava In Ya Ear” to “All About The Benjamins.” Now consider just how drastically this version of 3 Feet High And Rising single “Buddy” outpaces its origin point, to the extent that this all-star posse-cut reinvention deserves its own hallowed place in that pantheon.

In its original form, as a mellow-grooving take on casual horniness (“buddy” being in-joke slang for a sexual partner), it felt like a lighthearted goof on libido-rap that brought a couple friends along. And since those friends were Q-Tip and the Jungle Brothers, you can see where this is going: Above everything else, the remix is where the original’s loose concept of a Native Tongues collective actually coalesced as an actual presence, a unit where De La Soul, Jungle Brothers, A Tribe Called Quest, Queen Latifah, and Monie Love could embody their own artistic braintrust that could emphasize both their collective vision and each individual voice. (One of those voices belonged to new-kid Phife Dawg, who took the original track’s in-joke slang to its bluntest relationship-goals conclusion — “A brown skin buddy with shoulder length hair/ Nice firm breasts and a round derrierre” — in what amounted to a brief but successful on-wax audition. He was cut from the music video, but you need the 7-minute 12″ mix regardless.)

A fun verse from the ever-underrated Monie Love and a cameo/co-sign from the legendary Queen Latifah mix things up gender-wise and make the buddy-appreciation-society vibe feel a lot more mutually inclusive, even if the source material generally skewed more playful than macho anyways. And the idea to rework the beat with a nod to the other end of the ’80s was inspired: In clumsier hands, a sample of Taana Gardner’s b-boy-beloved ’81 R&B classic “Heartbeat” might’ve felt like an old-school premature-nostalgia move, but the Prince Paul/De La partnership concocted a perfectly ’89 vibe out of it, a celebratory creative freedom that feeds off the collective energy of a movement of artists who saw the upcoming decade as theirs for the taking — if only because it felt like there was plenty to go around for everybody.


"Stakes Is High" (from Stakes Is High, 1996)

You could be excused for coming away from De La Soul’s fourth album with a bitter aftertaste in your ears — the sense that, even through the more upbeat and tongue-in-cheek moments on the album, the good times were getting harder to come by. Part of that came from the circumstances around the album’s creation, where De La were still feeling stung by the aftermath of Buhloone Mindstate’s commercial underperformance (and underpromotion). That led them into a deeper state of self-consciousness, that mode of true-to-self autonomy that had clashed with the supposedly prevailing trends in hip-hop since their first overtures in ’88 and only seemed more stark in the wake of their decreasing pull on the mainstream charts. So it makes sense in retrospect that they were feeling embattled on multiple fronts — a disillusionment that would be impossible to fully conceal because it wouldn’t be honest of them to do so.

But it really all was just perfectly embodied the most in this one track, the penultimate title cut that only the warmth of closer “Sunshine” could even start to dispel. The Jay Dee beat on its own is epochally iconic enough to move a million Dilla Changed My Life t-shirts, a loping ascent towards enlightenment in the form of a masterful Ahmad Jamal revamp that sounds melancholy and motivating all at once. That’s only heightened by the sheer frustration in Pos and Dave’s voices — the kind you get when the don’t try to be cool, just be yourself messages of childhood empowerment have proven to be insufficient in the real-world conflicts of hip-hop artistry, and the only thing more frustrating than seeing the malaise take you over is seeing what it does to everyone else.

The second verse has Dave riffing off the term sick of like he’s been exposed to toxins he can’t escape, rattling off a list of entities that he resents because he feels both alienated for not participating in a zeitgeist he doesn’t fit (“I’m sick of talkin’ ’bout blunts, sick of Versace glasses”) and horrified by the consequential problems that trendiness glosses over (“cocaine and crack, which bring sickness to Blacks”). Pos offsets that by radiating the kind of fuming confidence you need just to survive through the down times — “Every word I say should be a Hip-Hop Quotable,” he demands of The Source — and addresses the feeling of struggle through a grown-folks maturity that approaches tough love (“Man, life can get all up in your ass/ Baby, you better work it out”), but only because it’s better than “love for the fact of no longer lovin’ yourself, kid.”


"I Am I Be" (from Buhloone Mindstate, 1993)

Buhloone Mindstate is as good a candidate as any for the best album of De La’s discography, but part of its strength is that it comes from a very particular place in their self-directed narrative: If 3 Feet High And Rising hinged a lot of its initial outsider appeal on “we’re not like everyone else” and De La Soul Is Dead on the defiant corrective of “we’re not who people assumed we are,” their third album was “this is what we’ve been trying to tell you about ourselves the whole time.” That they go about doing this by diving even deeper into their own idiosyncrasies and abstractions is just the artistic coup de grace — “fuck being hard, Posdnous is complicated,” he brags/admits/warns on “In The Woods” — and it’s almost too fitting that the best example of this is on a track that simultaneously clarifies and obscures their identities (and personae) as artists.

“I Am I Be” shows up deep in the album’s second half, an elaborated-upon reprise of an instrumental track sequenced earlier in the album — “I Be Blowin’,” which was basically just a well-justified excuse to let J.B.’s sax legend Maceo Parker sink into an amazing vamp. Parker is joined by fellow J.B.’s horn section alumni Pee Wee Ellis and Fred Wesley here, and their harmonizing with the majestic-repose sounds of a beat built significantly around a piano melody from Lou Rawls’ David Axelrod-produced version of “You’ve Made Me So Very Happy” feels like a culmination of everything that Golden Era sampling did to revive and recontextualize the previous generation’s soul and jazz heritage.

As a paired set of statements from De La’s two MCs, it reveals the complementary dichotomy beneath their creative partnership. Pos is openly if allusively autobiographical: jabbing back at the industry by calling himself “the new generation of slaves,” namedropping both the mother who passed before he became a star and the daughter he pledges to support, and invoking the internecine drama that had caused his once-tight-knit Native Tongues family to grow distant (“I guess we got our own life to live/ Or is it because we want our own kingdom to rule?”). And Dave, well, he goes the other way entirely, hitting a level of tangled poetic intricacy that still sounds confoundingly impressionistic and full of revelatory wordplay three decades later. There are still armies of alt-rap verb-twisters trying to catch up to lines like “I bring the element H with the 2/ So ya owe me what’s coming when I’m raining on your new parade/ It’s just mind over matter/ And what matters is that the mind isn’t guided by the punished shade.”

Even when they seemed to appear on the precipice of winding up alone in their own rarefied artistic stratum that the industry or the mainstream might not fully comprehend — “It might blow up, but it won’t go pop,” as the album’s intro stated — they emphasized the truth that they still had people looking out for them somewhere. That came in the form of a whole cross-talking, song-bookending chorus of them, ranging from briefly-incandescent rapper Shortie No Mass (whose mid-’90s-recorded, 2021-released Here Goes Nothing gave closure to what her Buhloone Mindstate emergence promised) to an on-the-cusp Busta Rhymes (just a month or so before Leaders Of The New School practically broke up live on Yo! MTV Raps and sent him towards his solo-megastar destiny). De La had brought forth a change in speak and kept the faith throughout all the doubt — this was them confirming they’d earned the right to live in that world they’d built, and knowing that the right people would join them.

Below, stream all 10 tracks in playlist form.

We rely on reader subscriptions to deliver articles like the one you’re reading. Become a member and help support independent media!

more from 10 Best Songs

Please disable your adblocker or subscribe to ad-free membership to view this article.

Already a VIP? Sign in.