ʼ90s Indie Rap

When a genre of pop music undergoes one of those break-from-the-norm reactions, a splinter-group subgenre forming out of a sense of avant-garde opposition or a demand for aesthetic change, it’s usually a reaction to being shut out of the mainstream. But when hip-hop began its big underground movement in the ’90s, it seemed to happen in a counterintuitive reversal of all the Next Big Thing trends that caused sellout anxiety in punk and indie rock throughout the previous decade. Rather than a subterranean DIY movement that caught the attention of hip A&Rs itching to translate college-audience cachet into MTV “alternative rock” fodder for the masses, “alternative rap” only feels like it became that way after its initial golden era heyday seemed to have passed. Groups like A Tribe Called Quest, De La Soul, Arrested Development, Digable Planets, and Brand Nubian were considered stylistically bohemian and a departure from the hardcore gangsta and club-friendly pop rap that was capturing record sales and media attention, but they were still on the same labels, the same Source covers, the same blocks of Yo! MTV Raps as the likes of Naughty by Nature and UGK.

Still, something happened in the middle of the decade to put an end to all that. Sure, gangsta and pop rap moved more units, but it wasn’t just a commercial struggle: the critical and cultural battle over kayfabe versions of “street cred” and what forms of expression in hip-hop were the most supposedly true to the art form became embroiled in the idea that “alternative rap” was escapist, naive, preachy, the demonstratively wagging finger of condemnation when everyone else wanted to just throw their hands in the air. (Worst of all: it was, god help us, middle class.) So while journalists, critics, and pundits from both inside and outside the hip-hop world squabbled over the direction the increasingly eclectic and fractured art form was taking, labels started shrugging off the more ambitious artists — ones who were sometimes more artistically temperamental, and bound to a less-immediately-lucrative style that growing sample clearance costs couldn’t possibly justify. By the time the deaths of Tupac and Biggie cast the party-ending pall over the money-printing peak gangsta era of the mid ’90s, the more bohemian, more Afrocentric, and more idiosyncratic MCs and producers who’d been sidelined by that trend had broken off into an entirely different strata — one with far less exposure and fewer guarantees for stardom, but enough of a cult following to sustain careers with far more creative autonomy than any major label could even approach promising.

Pinpointing the moment this break felt most pervasive is kind of tricky. 1994 gave us Common’s “I Used to Love H.E.R.,” an early definitive expression of the “alt-rap” archetype’s disillusionment with how hip-hop lost its way in pursuit of trend-chasing and money — though Common would remain one of the few alt-rap artists of the ’90s who could go on to take his music to the majors and thrive there for at least a little while. You could also nod to shifts in label priorities — Elektra’s turn away from risky but buzzy college-audience artists after the 1994 departure of Bob Krasnow, Jive’s circa-1996 shift to teen pop, and Def Jam’s all-in investment in the Trackmasters-heavy “shiny suit” slickness that dominated 1997 all factored into the mainstream commercial downfall of alt-rap.

But the real shift — the reason this guide’s title uses the term Indie Rap — was the emergence, largely by necessity, of a new wave of independent labels that existed largely to pick up the artists the majors had discarded or ignored. In essence, these labels — typically with an additional focus on showcasing regional talents, like the Bay Area’s Solesides or Minneapolis’s Rhymesayers — pulled off a maneuver that looked simultaneously like the specialist roots of hip-hop’s first years on wax, and the devotion-cultivating subcultural branding that punk and indie rock labels enjoyed in the ’80s and ’90s. Sometimes the origins of these indies would vary — there’s a difference between, say, the idea of Robert “Bobbito” Garcia establishing Fondle ‘Em in ’95 as a way to showcase previously unsigned artists who killed it over The Stretch Armstrong and Bobbito Show’s airwaves, and the founding of Rawkus that same year as a sort of startup kept afloat with James Murdoch’s Fox Corp money — but as long as the artists were given (or gave themselves) free enough reign to do whatever they wanted, they could start building the foundations of a movement that would survive with or without corporate dollars — more frequently the latter.

As far as the attitudes and styles that were cultivated by this newfound autonomy on the margins, that’s a complicated tableau in itself. Even in its early stages, indie rap — or “backpacker rap” or even, sheesh, “undie” — could be socially conscious or flagrantly ignorant, built on murky lo-fi samples or live in-studio bands, lyrically poetic in ways that demand rewinds or heavy on the immediacy of slam-bang punchlines and mass-crowd-shoutalong hooks. Most of all, it navigated an unusual dual impulse of preserving and reviving the foundational elements of hip-hop while also clamoring for the advancement of the form, as if there could be a real reconciliation of back-to-the-real-shit and on-to-the-next shit. But in that sense, a lot of this music pulls off the strange sense of it being from its time, but not of it, a ’90s movement that was carried far enough into the next few decades to represent something more than just a brief rupture in the hip-hop audience. From here, you can hear the future — not the future in full, not even the majority of its sound, but enough of it to feel like this music’s more influential than the underground niches it was once confined to.

Black Star cover

One of the underheralded aspects of the first — and, for 24 years, only — full-length collab between Mos Def and Talib Kweli is that it not just embodied but reconciled the contrasts of the indie rap world. Aside from the wildly different yet complementary styles both MCs provided — Mos as the savvily bemused voice of observational wisdom, Kweli providing the nagging-conscience urgency of a lifelong campaigner — there’s other fascinating backpacker dualities at work. They’re retro preservationists who homage the old school (an Adidas-on-cardboard throwback “B Boys Will B Boys”) and found contemporary mainstream rappers wanting in the face of Slick Rick-ian golden era mores (using the ironic move of rewriting “Children’s Story” to mock derivative style-jackers). But they also wrote a potential alternate future where ’92-style jazz-laced boom bap could sound as hi-fi and Tunnel-ready and hooky as anything on ’98 Bad Boy (Da Beatminerz-produced “Astronomy (8th Light)” especially), while Hi-Tek’s beats hit on a reflectively meditative yet hard-bumping sense of motion that a lot of indie rap record production would resemble five years down the line. And their lyrical themes, delivered with a complexity that never foregoes clarity, refuse easy-target didacticism: alongside the conflicted moods of their “Definition”/"RE:DEFinition” diptych, there’s also the acknowledgement of self (“K.O.S. (Determination)”) as a means to turn individualistic pride outwards to a communally uplifting teaching effort, even as cuts like “Hater Players” drop ruthless condemnation on anyone who’d doubt the pride these MCs actually possess for their own talents. It all peaks with Common collab “Respiration” — the greatest rap track ever recorded about the struggle to love a city that may not love you back.

Dr. Octagonecologyst cover

One of the weirder developments to come out of the mid-late ’90s indie hip-hop scene was Kool Keith, one of the most hardcore-head-acclaimed rapper’s-rappers of the Golden Era, becoming a college-radio crossover favorite thanks to a morbid new guise and a teamup with Dan the Automator in his nascent, bizarre something-to-prove mode. That they did it on their own terms is secondary to the fact that those terms involved a Cronenberg-goes-Blowfly atmosphere of porno, horror, comedy, and various intersections thereof, where even the standard-since-’73 drum breaks took on a giallo-tinted unreality.

Soundbombing, Vol. 2 cover

Soundbombing II, the Beat Junkies-hosted sequel to the ’97 Rawkus mixtape that set the stage for Mos Def and Talib Kweli’s imminent underground stardom, is as definitive a snapshot you can get of the indie-rap canon as it existed on the cusp of Y2K. It might be a solid hunch to deduce that it sold a bit extra thanks to an appearance by Eminem at the next-big-thing dawn of his career, whose young-and-hungry “Any Man” still hits because he raps like controversy’s more a side effect than a motivating force. And there’s further doses of the Black Star alumni’s continued excellence (Mos Def’s intense-to-the-point-of-joy shit-talk session “Next Universe”; Kweli flowing like he’s pulling off blindfolded brain surgery on Reflection Eternal’s “On Mission”) to capitalize on the lingering glow of their ’98 teamup. But its breadth is impressive amidst the underground claim-staking — this is an underground with enough room for R.A. the Rugged Man as gravelly dirtbag beat poet from your nightmares (“Stanley Kubrick”), Common and Sadat X coming across like resilient conscious-rap scholars-turned-teachers (“1999”), and Bahamadia’s hushed cool glimmering icily in Reflection Eternal teamup “Chaos.” And some of it’s aged so well — like Pharoahe Monch masterfully concoting the scenario of a certain unnamed NYC politico’s downfall (“Mayor”) and El-P’s furious embodiment of America’s sadistic cruelty on the fresh-for-202X “Patriotism” — that it makes Soundbombing II less a time capsule than a time-release.

Fantastic, Vol. 1 cover

One of the greatest hip-hop debuts of the ’90s that roughly 90% of its audience didn’t get to hear until the 2000s, the first full-length from Detroit’s revered Slum Village existed mostly as an oft-copied and bootlegged DIY release/demo before finally getting the deluxe reissue treatment in 2006. By then, rapper/producer Jay Dee had become life-changing MPC maestro J Dilla, but his earliest work with Baatin and T3 was already above and beyond most of what was coming out of the Midwest, with the familiar off-beat rhythms and incandescent bass frequencies of cuts like “This Beat (Keep It On),” “The Look of Love,” and “Forth & Back (Rock Music)” rounding out an already-impressive circa-’96 beat portfolio alongside De La Soul’s “Stakes is High” and A Tribe Called Quest’s “Get a Hold.” (And the James Brown sample adlibs on “I Don’t Know” alone, even in its early-draft minute-long form, are ingenious.) But that’s just one facet of what makes Fan-Tas-Tic such a rarity in its class — the other is the fact that for all its proto-Soulquarian sonics, the lyrics are a lot closer to street-rap anthems than bohemian lyrical poetry. So the end result is an uncanny atmosphere of smooth-gliding shit-talk where the threats to open-hand smack rival crews for wackness (“Players”), the gigolo overtures and unapologetic horniness (“The Look of Love”), and the dick-swinging earned arrogance that fuses them both (“5 Ela Remix”) all have this tension between mellowness and rawness that the rhythmically unpredictable musicality of their flows navigates with ease.

3rd Eye Vision cover

Oakland collective Hieroglyphics made for a strong example of what indie autonomy could do for a crew in the late ’90s. Just five years before their first group album 3rd Eye Vision, most of their members were signed to majors — Souls of Mischief and Casual on Jive, Del the Funky Homosapien on Elektra, producer Domino and rapper Pep Love collabing with all of them — who then unceremoniously dropped them when the alt-rap movement failed to rake in the big bucks. This makes 3rd Eye Vision a strong DIY riposte to all that, though it’s nowhere near as bitter as you might think from a whole squad of industry-screwed battle rappers. For one thing, it’s playing to a crowd that already knows about Rule 4,080, so the thematic emphasis on Being A Better Rapper Than You is driven more by the thrill of competition and a conflict-hones-art philosophy than any sour-grapes rejection of popularity. For another, it’s as good at establishing each individual member’s bonafides — every MC in the group gets a brief but stylistically definitive solo showcase — as it is making them all seem like hyperlyrical hydras on mic-passing centerpieces like “Off the Record,” “The Who,” and the all-hands-on-deck showcase single “You Never Knew.” And even though their lyrical approach is peak backpacker, heavy on metaphor-driven punchlines and geek-culture namedrops and Afrocentric politics, it’s all delivered with a high-energy rock-the-crowd force over beats that turn underexplored regions of funk and soul-jazz into unapologetic speaker-throbbing bangers.

Overcast! cover

Rapper Slug and producer Ant have become such a long-running institution in indie rap that it can be kind of startling to hear what they were up to when they were still a largely unknown quantity. With their first album Overcast!, they sound well on their way to establishing the distinctly introspective and moody sound driven by Slug’s compelling frustration — “emo rap,” as it would eventually be dubbed-slash-cursed, though it still played a lot more like a product of working-class Twin Cities grown folks than third-ring teen suburbia. The presence of brief member Spawn hints at a dynamic that the short-term rapper’s presence might’ve shaken up considerably — a slyly self-assured counterpart to Slug’s verge-of-panic edge, but with his own emotional heft to work with (like the devastating remembrance of his father’s passing, “Caved In”). All the other pieces are already in place: Ant’s ability to whip up a zero-bullshit DITC-caliber hardcore headnod beat like “Brief Description” or “Multiples” is evenly matched by Slug’s persona-complicating bursts of good-natured arrogance, while their soufully ruminative, often-unnerving dramatic turns over suspenseful cinematic productions like the paranoid blame-flinging denials of “Scapegoat” and the interpersonal struggles of “Adjust” provide the identity-shaping nuances that began a long career of self-interrogating lyrics.

Funcrusher Plus cover

While it sounded powerfully at-odds with mainstream hip-hop at the time, Company Flow’s abstract-rap watershed feels more like a link between the free-spirited, Stretch & Bobbito-cultivated East Coast battle lyricism of the early-mid ’90s and the underground renaissance that the indies would build in its wake. El-P in young-and-hungry mode sounds like a maniacal cadence-warping death preacher on the mic and behind the boards, while the intense listen, goddammit directness of co-rapper Bigg Jus set the agenda for decades-later heirs like billy woods and Elucid.

Internal Affairs cover

Organized Konfusion always contained multitudes — complex abstractionists who were also master storytellers, capable of devising both impossibly intricate flows and the kinds of instant-grab hooks that demanded to be shouted en masse — and the solo debut of member Pharoahe Monch maintains that multifaceted unpredictability and adds a bit more edge to it. While there’s a moment or two where he oversteps into late ’90s edgelording (“Rape” as a gritty reboot of Common’s “I Used to Love H.E.R.” earns winces at best), he also sounds even more free to explore past his boundaries in ways that make a total mockery of the underground/mainstream divide. “Simon Says” is the epitome of this, one of the hardest rap singles recorded by anyone anywhere ever, as infamous for its hilariously base get-the-fuck-up rowdiness (“Girls, rub on your titties / yeeeeeah / Yeah I said it, rub on your titties”) as it is underrated for Monch’s ability to bring out the most preposterous qualities of every syllable he speaks (“New York City gritty committee pity the fool/That act shitty in the midst of the calm, the witty”). That song got Monch and Rawkus into hot water with the Toho film company for the uncleared Godzilla theme sample that made it sound like a 50-story flame-spitter of a track, but delete it from the tracklist and you’ve still got a ton of depth past the big single: he’s equally at home artfully promising violence alongside the Brownsville bruisers in M.O.P. (the orchestral maelstrom of “No Mercy”), pulling off the rare-from-anyone-else feat of eclipsing Busta Rhymes’ manic energy level (pasodoble freakout “The Next Shit”), and unfurling linguistically complex but emotionally direct introspective philosophy alongside Common and Talib Kweli (the astral travel of Diamond D-produced “The Truth”). And since Organized Konfusion’s breakup was an amicable one, the brief reunion with Prince Po on “God Send” puts a stunning exclamation point on the end of their legacy with one of their bleakest, angriest state-of-the-world overviews in a decade-long stretch of greatness.

Black on Both Sides cover

The dust had barely settled from the impact of Mos Def & Talib Kweli Are Black Star before the group’s elder half dropped his solo debut full-length just over a year later. And he proved to be capable of some of the most dynamic, genre-warping, expansively thoughtful hip-hop the end of the ’90s had to offer with Black on Both Sides — a title that, if anything, understates how many facets he actually had by this still-early point in his career. From a perspective that fused ’80s old-school epiphanies, early ’90s jazz-rap expansions, and a polygot style that anticipated hip-hop’s 21st century status as an ever-broadening overgenre, Mos approached underground hip-hop as if it was the basis of the culture rather than an alternative break from it. And even as this meant he’d treat what appeared to be genre detours (screaming over a Bad Brains outburst on “Rock N Roll”; unshowily singing over cosmic soul-jazz on “Umi Says”) like foundational elements, his mic presence is a lot more direct and blunt in its delivery and messaging — he feels more accessible than most of his peers because his wordplay and his depth, while crucial to his art, are secondary to the fact that he sounds attention-demanding even when he’s being plainspoken. There’s nothing convoluted or overly abstract about the lovestruck way he wrestles his heart between romance and libido (“Ms. Fat Booty”), the perception behind his fears for an uncertain environmental future that spirals out from third world suffering to first world oppression (“New World Water”), or the clear-eyed frustration as laments how no amount of money or style can insulate Black people from the double-standard judgments and success-breeds-suspicion anxieties of racism (“Mr. N—-a”). And since that directness is paired with a remarkable sense of beat-jousting timing — he’ll sink into a rhythm so fluidly that it makes each emphatic shift or detour in his flow feel like a perfectly-placed joy-buzzer shock — he can inhabit a beat by DJ Premier (“Mathematics”) or Ali Shaheed Muhammad (“Got”) or his own self (“Fear Not of Man”) like he’s already known it for years.

The Juggaknots cover

The Juggaknots’ self-titled debut on Fondle ‘Em was the second entry in the cult label’s short, hard-to-find, but massively influential catalog. And even before a 2002 Re:Release expansion that rescued it from vinyl-only scarcity, it felt more substantial as a nine-track, 36-minute EP/LP midpoint than a lot of the skit-bloated, filler-crammed 70-minute rap offerings to hit shelves during the peak-CD late ’90s. You can credit that in part to Breeze Brewin’s ability to be as devastating with a message track as he is in pure-battler form. Of course he’s nice with the bitter punchlines and the interrogative delivery in that latter state; there’s plenty of it in “Jivetalk,” “Epiphany,” “I’m Gonna Kill U,” and especially the imposingly agile-flowing “Troubleman” — that last one a rare moment where Breeze’s brother/beatmaker Buddy Slim gets to obliterate the mic alongside him (and over a loop from Coltrane’s version of “My Favorite Things,” just to complete the audacity of the thing). But the conceptual storytelling that made Breeze such a good fit for Prince Paul’s rap opera A Prince Among Thieves three years later is what pushes Juggaknots over the line from underground collector gem to true lost classic. “Clear Blue Skies” became such a standout off its depiction of white intergenerational familial panic over mixed-race relationships — a masterpiece in the rapper-dual-role so convincingly inhabited by Breeze that some people still mistake it for a Breeze/Slim back-and-forth —  that bootlegs turned it into the EP’s new de facto title track. But the crack-wave horror stories of “Loosifa” and the next-gen youth violence warnings of “Romper Room” are no less deeply felt, inhabited with lines containing whole social panoramas that toe the line between traumatized anger and intensely sorrowful empathy.

Project Blowed cover

While Freestyle Fellowship went on hiatus after the imprisonment of Self Jupiter in 1993, their legacy as Los Angeles’s most fearless catalysts for underground hip-hop innovation found an enduring next chapter. With the rap-battle epicenter Good Life Cafe providing a scene big enough for a flag-planting, cafe regular Abstract Rude and FF alumni Aceyalone established a rap open mic that spurred a compilation — which spurred a whole crew and a movement that would shape the L.A. underground for decades. Project Blowed the comp has a fascinating duality to it, both as an overview of a nascent scene and a continuation of its hosts’ creative progression. Aceyalone rounds out a stunning ’95 — All Balls Don’t Bounce dropped that year, too — with some rapport-heavy Abstract Rude collabs that make the pair out like wildly contrasting but equally free-flowing shapeshifters. (The conceptual rap-subterfuge story of “Maskaraid Parts 1 & 2” is their hilariously hyperelaborate peak here.) But the cast of characters at the margins, the ones whose more localized renown would grow into reverence off this comp, paint a broader picture. This is a space which has enough room for both Figures of Speech — a feminist rap/neo-soul hybrid featuring a young Ava Duvernay — and a playalistic, “Juicy”-jacking g-funk sex jam like Tray Loc’s “Once Upon a Freak.” And there’s like ten different rapidfire styles being innovated just in the cast-of-thousands posse cut “Heavyweights Round 2” alone.

Operation: Doomsday cover

Daniel Dumile started the ’90s on the verge of golden era greatness with his group KMD, and ended a heartbreaking and frustrating decade with one of hip-hop’s most bitterly funny and quietly mournful reinventions ever conceived. After the death of his brother Subroc and a ruinous relationship with Elektra dissolved KMD in ’94, the reemergence of DOOM as the Fondle ‘Em label’s rawest-sounding punchline genius proved to be a powerful spark for the disillusioned artist. And while the Fantastic Four imagery and samples of Operation: Doomsday's Marvel-mutating origin stories seem like familiar referential geek-culture fandom on the surface, it hits on a blend of emotional directness and fantastical strangeness that captured the comics’ graf-artist-inspiring halftone pop-art surrealism and heightened reality better than any Kevin Feige gameplan ever could. Beneath that surface is the defiance of a wronged man who sees his alienation as a good excuse to fuck up the works on all kinds of fronts. Sample the Beatles as a pretext to upend the entire concept of consistent meter and flow on the timewarping “Tick, Tick…” (featuring once-close, eventually-estranged partner MF Grimm)? Invoke the Saturday morning silliness of Scooby-Doo on “Hey!” while delivering the kinds of idiomatic subversions that super-serious hardcore heads would sell their left nut to grimace into existence? Rock mics harder over upbeat Quincy Jones fusion (“Rhymes Like Dimes”) and glossy big-Deele ’80s cosmopolitan R&B (“Red and Gold”) than any of his peers could over the most rough-rugged-n-raw boom-bap NYC could provide? He’ll do all that with the kind of ease that feels like a card-pulling challenge in itself. Who’ll even try to tell him no when the threat of absolute annihilation for all who oppose him is always within his metal-fingered grasp?

Nia cover

He might be an outlier character-wise in a Bay Area holy trinity with E-40 and Too $hort, but Gift of Gab boasted the former’s facility with language and the latter’s knack for storytelling, so why wouldn’t he belong there? Turning assonance and alliteration into his own personal playthings won him plenty of unsuspecting converts, and with the backing of deep-digging soul-savvy producer Chief Xcel (and excellent walk-ons from Solesides/Quannum alumni Lyrics Born and DJ Shadow), his amiable voice breathes vivid life into any words he wants, whether celebratory or cautionary.