Let’s start with a bridge — one between the insurgent wave of early ’90s West Coast indie and all the potential dynamism, insight, and creativity that underground hip-hop would cultivate by the decade’s end. The Pharcyde were already a known quantity bordering on cult stardom when Labcabincalifornia, their ’95 followup to their ’92 debut Bizarre Ride II The Pharcyde, added a more reflective and downcast air to their previously comedic repertoire. And while the album would take years to shake off its divisively downcast sound — provided in part by an emerging Detroit producer going by the name Jay Dee — lead single “Runnin'” was quickly recognized as a high point of the album (and the year).

Like a moodier sequel to unrequited-young-love anthem “Passin’ Me By,” “Runnin'” is fueled by an almost painful amount of self-conscious recollection. And Jay’s Stan Getz samba-jazz loop amplifies the air of deceptively mellow but deeply propulsive reflection that would be one of indie rap’s calling cards for the rest of the decade and onwards.

One of the other calling cards, it should be noted, is rapping about rapping — the recentering and arms-race showoff of skills. And if many of the “scientifical lyrical miracle” cliches about backpacker lyricism are both kinda true and kinda unfair, it’s because of tracks like J-Live’s “Braggin’ Writes” that we’ve got something to measure those lyrics against and find them wanting. “For underground metaphors/ You can scrape an inch below the turf, for what it’s worth/ My style’s been developed in the core of the Earth” — that opening line from the NYC rapper’s mission statement served as a challenge to surface level MCs, and a warning as to why that challenge would be a bad idea.

Punchline similes and metaphors that range from med-student (“The penetration’s exact, like amniocentesis“) to chess grandmaster (“I know you wanna make moves but son you best to take a second look/ Before my knight takes your rook”) to rap historian (“You belong in Special Ed if you think you got it made”) equally sting from a flow that never lets up but always hits clearly. His label-purgatory deal meant he’d go more than five years between his November ’95 “Unsigned Hype” status in The Source to the actual-on-shelves release of his 2001 debut The Best Part — at which point “Braggin’ Writes” earned a revisit, but that just made it more obvious how ahead of the curve he was. Oh: That’s him scratching on the decks, too, in case you thought being a tight MC wasn’t enough.

Kool Keith’s always been a crazy bastard, if by “crazy” you mean “can sound fly even rapping complete nonsense” and “bastard” you mean “stylistically fathered by immaculate conception.” He’s the closest hip-hop’s ever come to a genuine Lou Reed analogue: relentlessly evocative of pre-Giuliani dirty old New York, with the Ultramagnetic MCs as his endlessly influential-if-undersold Velvet Underground, and his teamup with Dan “The Automator” Nakamura as his surprise-hit Transformer — though Dan wasn’t Bowie-famous and still a few years away from getting his own goon squad (beep, beep).

Dr. Octagonecologyst was where producer and MC and everyone in their orbit let their most morbid ideas run haywire, from the guest turntablist DJ Qbert slathering Skratch Piklz brine everywhere to Brian “Pushead” Schroeder bringing a crossover-thrash aesthetic to the instantly-recognizable album cover. First released as a Mo’ Wax import in ’96 before it got Dreamworked over to the States the following year, Dr. Octagonecologyst is best taken as an album-length immersive audio nightmare, but the Bartok-meets-Kraftwerk wooze of “Blue Flowers” is the crash-course in VHS splatter hauntology, the disorienting American health care system taken to its logical anxious conclusion: Your insurance is high, but my price is cheap. Now look at the lamp, turn the bright on, and combine the supersonic waves.

When street rap mourns, it’s the strongest case there is for hip-hop not as the detractors’ “inspiration for violence,” but as something inspired by violence — of something that has to be paid attention to, made sense of, after-the-fact justified, but not so much celebrated as chronicled in ways that at least try to find the resilience of artistic expression in the midst of a grim scenario. Des, née Ron Smith, is the rapper who made the titular refrain “I’d rather be tried by 12 than carried by six” feel so central to the ’90s-and-onward American street-justice vernacular.

And his verses cut to the core, too — “beef starts with the shove then ends with the shovel.” It’s almost unfair that the beat from East Flatbush Project mastermind Spencer Bellamy is that nuts — a koto-plucked melody from Odetta In Japan married to some Al Jackson Jr. drums circa Al Green ’72, ironclad enough to persist well into later decades. It’s a thin line between sounding like a funeral and a wake, but even if “Tried By 12” bumps like the latter, it’s the kind of rumination that desperately wants to put off any of that being-laid-to-rest shit, celebratory or otherwise.

Buddy Slim and Breeze Brewin’, the original pair (later joined by Queen Herawin) behind NYC’s Juggaknots, put their first indelible mark on hip-hop’s underground with a ’96 LP that snuck in one of rap’s great conceptual gambits in the tracklisting’s second-to-last slot. “Clear Blue Skies” is, plainly put, one Black man rapping in the guise of both a white father and son arguing about the latter’s mixed-race relationship. That escalates into an examination of false-friendly-face quasi-liberal racism, one that’s barely sublimated until a family situation makes it burst out like bile.

That “Clear Blue Skies” sounds like a conversation at the same time it’s clearly a rap performance is a remarkable balancing act, Brewin’s natural (if slightly manipulated) voice keeping it from veering into a mayonnaise-accent joke and laying all the cruelties and arguments bare. The nausea is tempered by a son who chooses to rebel against his father instead of submit to him, and the production feat of making a guitar-driven loop of the Meters’ “Stormy” sound like it could’ve come from some of the alt-rock the son’s demographic was bumping at the time. When the debut was packaged with some new material for 2002’s Re:Release — three years after Breeze Brewin’ took on the role of a lifetime as a lead MC on Prince Paul’s rap opera A Prince Among Thieves — “Clear Blue Skies” took the closer slot. By then they knew it was the exclamation point.

Hip-hop hit the upper Midwest like it hit a lot of other places, just in its own form: punk-adjacent, railway-car-tagging, indie-or-death grassroots bolstered by a scene that could be remarkably eclectic even when it was locally cordoned off. And if any rap group embodied the phenomenon of how Minnesota did things, it was (and remains) Atmosphere. Rapper Sean “Slug” Daley and producer Anthony “Ant” Davis have been constants in the city’s music scene just a hair short of a quarter century, with the former’s stress-rap introspection and the latter’s well-selected soul-break itinerary providing a constant presence throughout the Twin Cities-based Rhymesayers label/collective.

Their 1997 release Overcast! was the second full-length non-mixtape album the label ever released, and “Scapegoat” is one of the moments that will stick with you the most afterwards, a basic concept delivered with intense bravado. As Slug’s voice builds from dazed reflection to simmering annoyance to an agonized panic attack, he pinpoints every single reason everything’s so fucked up around him — from an unchanged litter box to the very structures of capitalism itself — while defiantly declaring, with the intensity that only those who know they’re kidding themselves can deliver, that at least the problem isn’t with him.

The most famous alumni of the San Francisco Bay Area’s label Solesides isn’t even a rapper, but a producer — namely DJ Shadow, whose solo work from the early ’90s onwards made him one of the most meticulous, innovative MPC-slayers to ever dig through a record store’s basement. But while 1996’s completely instrumental Endtroducing…… was the victory lap after a half decade of sweating ideas out in the lab, it was Shadow’s beats for his labelmates’ rap tracks that kept him closely connected to hip-hop’s collaborative lifeblood. And none of those tracks bumped as directly as the ones he did with the Lyrics Born/Lateef The Truthspeaker superduo Latyrx. Forget losing yourself in trying to spot obscure samples or getting dazzled by “Napalm Brain/Scatter Brain” explosions of drum breaks — Shadow settles for a cosmic-funk groove that just so happens to be 10 miles deep bass-wise, which is what you want when Lateef and Lyrics Born rap like the mics owe them four figures.

Rapper/producer Jay Dee had already gotten a hot rep by late ’96 after making beats for The Pharcyde’s “Runnin’,” De La Soul’s “Stakes Is High,” and A Tribe Called Quest’s “Stressed Out,” among others. But he was still committed to his city and his crew, and when they emerged with Fan-Tas-Tic it became the stuff of legends. A demo tape that eventually became one of the most bootlegged records in hip-hop history before its Vol. 2 revamp three years later, Slum Village’s Fan-Tas-Tic Vol 1. earned the Detroit group Native Tongues comparisons that went beyond the Dilla gigs. (Never mind that their lyrics were a little more sex-guns-and-money than anything Tribe or De La put out; a well-placed dragged snare and a super-dense bass tone can mollify even the most ardent antimaterialist backpacker.) Rappers T3 and Baatin are more than up to feint, parry, and smack around the already slippery beat with aqueous flows, finding every possible way to counterpoint the bass hits while still keeping it grimy.

If you think ’95 is too late a starting point for underground hip-hop, it’s probably a justified gripe if you’re basing your criteria on, say, Freestyle Fellowship. If their first two records, 1991’s To Whom It May Concern… and 1993’s Innercity Griots, didn’t singlehandedly invent the West Coast underground, it’s only because their homebase at the Good Life Cafe’s open mics cultivated a big enough community of artists to make the scene’s authorship a collective effort.

But FF member Aceyalone did have his share of indie-rap-fixture milestones when he went solo, too, including a co-founding role with Abstract Rude in the next-phase collective/label Project Blowed — as well as the perennial experience with creating a classic major label album, 1995’s Capitol-released All Balls Don’t Bounce, that said label didn’t do enough to promote or keep in print. His 1998 Mumbles-produced collection A Book Of Human Language provided a no-steps-lost return to an indie (his own, aforementioned Project Blowed), an album dense with existential questioning and philosophical ruminations. And noir-funk immersion “The Walls & Windows” is one of the more intricate ones, weaving together an extended metaphor of buildings and cities as silent witnesses and remnants of the people who live in them.

Back on the East Coast, here’s another conceptually-sharp rapper who released a slept-on ’95 major-label classic (Lifestyles Ov Da Poor & Dangerous, Columbia), got dropped, and managed to burn even brighter as an ascendant lyricist’s lyricist on his own indie. Big L, though, he’s different — a key component of the legendary Diggin’ In The Crates crew, the Harlem MC was grimy and diabolical enough in his style and bleak enough in his subject matter that he outdid pre-superstar status Jay-Z and Cam’ron on Lifestyles-era posse cuts.

And so when he picks a theme, he barrages you with it, like he did with “Ebonics” — an AAVE lesson that hasn’t aged as cornily as most decades-old slang roundups because when he says what something means you believe him because he’s seen some shit. The Ron Browz “BOMP BOMP BOMP” brass hits make this and not “Ether” the producer’s finest moment, though it’s also his most bittersweet one: After Big L’s murder at the hands of a former longtime friend, “Ebonics” became the last single cut in his lifetime, a massive loss of unfulfilled Roc-A-Fella-bound potential that robbed hip-hop of one of its most bare-knuckle intense storytellers.

Calling Hieroglyphics the “West Coast Native Tongues” might be a little too pat, but if there’s a crew that could carry the De La/Tribe/Jungle Brothers/Latifah vibe through to the late ’90s indie rap boom, it’s the Oakland collective with the instantly recognizable logo. Souls of Mischief, Del The Funky Homosapien, Casual, Pep Love, DJ Toure, and Domino fulfilled nearly a decade’s worth of promise with 3rd Eye Vision, but it’s a remix of the album’s second single that gets the nod here. No slight to A-Plus’s Sunday-afternoon Patrice Rushen/George Duke soul-jazz vibes in the original, but Domino’s twitchy, cello-in-a-straitjacket bassline and dopamine-faucet drums take an already fiery mic-pass posse cut and make it sound like a hazard to your sound system’s structural integrity. That the track was already an exhibition of six MCs at their most quotable makes it foundational in any form.

Speaking of third eyes. LA’s Dilated Peoples dropped four albums on Capitol Records in the early-mid ’00s, but they always came across as an uncompromising underground group throughout. An early indie 12″ that included the KutMasta Kurt-produced “Work The Angles,” Alchemist-beat-featuring “The Main Event,” and in-house job “Triple Optics” — all later snapped up for their major-label debut The Platform — drives home just how and why. It’s that latter track that feels the most characteristic, and not just because Rakaa Iriscience’s mixture of science-jargon verbiage, spiritual warfare, and next-level boasting could finesse headnods out of phrases like “triple optometrist” or “harmony imbalance.” Evidence’s piano-soul skulk of a beat vies with DJ Babu’s scratch routines as to whether your main reaction’s a rhythmic head-nod or a turntablist-awed gawk, but either way it embodies everything about indie rap’s spirit-of-’88 contingent that makes it feel progressive instead of a throwback.

Even before Madlib was a patron saint to cratediggers, back when his crew did local Toyota dealership ads and were releasing records out of his home address, he was on some other shit. As a producer/rapper he was a pivotal component of Oxnard group Lootpack for nearly the entire decade — their first singles for Stones Throw arrived five years after their first collaboration with Tha Alkaholiks in ’93.

So people hearing the first Lootpack full-length were already greeted with a record that felt like an ambitious stylistic gambit, from its loop-warping production style to Madlib and Wildchild’s recursively referential battle rhymes. This highlight of a cut has got Madlib sticking to production duties; he was always ambivalent about his “sleepy-sounding” voice, especially early on, hence the whole helium-voiced workaround that became alter-ego Quasimoto. And the beat he speaks with instead is a funny sort of coup, taking the relatively-recent KRS-One joint “Return Of The Boom-Bap” and muddling its bassline until it’s easy to doubt that’s where it came from in the first place. Meanwhile, Wildchild goes Oxnard Guru, a supposedly affectless voice that draws you in by dealing in an endless litany of ways to shame lesser MCs in classic battle style.

As late ’90s NYC was being Giuliani’d and gentrified into something ostensibly safer but clearly harder to recognize, the character that informed so many evocative East Coast classics was starting to slip away, too — the hardcore street rap that found its expression during the crack era started feeling pro forma and past tense amidst all the bottle-popping, and the shiny-suit celebration that replaced it didn’t always lend itself well to the sort of depth that hardcore hip-hop heads were seeking out.

So when Brooklynites Mos Def and Talib Kweli cut a track about New York’s character, with Common providing an aching Chicago funeral homecoming coda, it had an air of resignation as well as recognition. You’re not going to get Style Wars “CRIME IN THE CITY” graffiti burners on subway trains anymore, but the city’s still broken — “Can’t tell between the cops and the robbers/ They both partners, they all heartless, with no conscience,” Mos memorably laments, and Kweli’s verse, maybe the best of his career, finds tragedy and disillusionment hard to shake while still finding the words to describe what it feels like to need to overcome them. And Kweli’s Reflection Eternal production partner Hi-Tek makes the pathos bump hard — hard enough that it’ll make you breathe deep, just like the city itself.

Anyone who walked out from Sorry To Bother You surprised that Boots Riley could tell a wild story likely hasn’t heard anything by the Coup. The Oakland Marxist hip-hop group — at the end of the decade, a duo consisting of Riley and the late DJ Pam The Funkstress — built a rep over the ’90s that started with ’93’s acerbic Kill My Landlord, coalesced with the following year’s Genocide & Juice, and finally hit the first of many long strides with 1998’s Steal This Album. And while there’s theory in the margins, the main thrust of the Coup as a leftist institution is that it’s best laid out in personal everyday class-struggle terms, a life of shitty transportation and repo men and sneaking into shows you can’t afford tickets to. And where other conscious rappers might just barrage the listener with info about how much damage the sex trade can do, Boots crafts an elaborate, vivid, detail-rich story of revenge on the pimp who both fathered him and killed his mother, en route to realizing just how much all that toxic masculinity fucked him up as a kid in the process. The fact that it’s set to the kind of West Coast slow-ride funk that DJ Quik would approve of only heightens the contradictions; it’s one of the most sorrowful trunk-rattlers ever cut.

The Herbaliser’s world of acid-jazz-adjacent UK hip-hop — and the whole extended Ninja Tune label universe, with its own nods to the Stateside underground — is its own beast entirely. But Jake and Ollie made invaluable contributions to American hip-hop in their own right by being one of the highest-profile outlets for a young rapper who’d eventually rename herself Jean Grae. Jean became a regular fixture on Herbaliser albums starting with 1997’s Blow Your Headphones, way back when she was part of the Brooklyn group Natural Resource and went by the alias What What.

And while this is one of her last appearances under that name, on the mic she’s already the Jean Grae that indie heads have known for more than two decades. She’s a master storyteller who raps about intricate concepts — like, for instance, being Shanghaied into a secret ops mission for the United States Government — like they’re her everyday experiences. And few rappers this side of Slick Rick have done it with the wiseass panache and acerbic detail that Jean’s pulled off on the regular.

One of the more combatively independent-as-fuck groups to emerge in the mid-late ’90s indie rap renaissance was Company Flow, the crew that future Run the Jewels half El-P operated with alongside rapper Bigg Jus and DJ Mr. Len. The 1995 Funcrusher EP and its 1997 expansion Funcrusher Plus are still-revelatory listens that show a young, hungry squad creating the kind of gnarled, lo-fi/hi-bass confrontational experimentation that the Wu-Tang Clan sparked earlier in the decade.

But it’s one of the last tracks to be credited to CoFlow that serves as the best entry point to their world, even if it plays a little more like a preview of El-P’s solo career than a collective effort. (Bigg Jus’s solo stuff wouldn’t take off until the following decade; it’s absolutely worth bumping, as is Mr. Len’s.) It’s not too far a stretch from this horrifying Y2K-era portrait of the American experiment’s Mengele tendencies to the kill-your-masters cleansing fire of recent RTJ — “This is where the pain grows like poppies/ In a Field Of Dreams I paid for, I’ll burn it down if operated sloppily” is some foresight-is-2020 shit — but sometimes being prescient just means you’ve been paying attention.

In 1997, the Solesides label had been disbanded for less than a year before it re-emerged as Quannum Projects, a nearly seamless continuation that carried over the big names from the original entity and saw the release of some of their greatest successes. And if Latyrx’s The Album was the last great Solesides release, Blackalicious’s A2G EP — which dropped two months before the label-showcasing reintroduction Spectrum — was the first great Quannum release. Rapper Gift Of Gab and producer Chief Xcel capped off a productive ’90s and the run-up to their long-awaited full-length debut NIA with an EP that showed Gab at full strength in all his modes.

There’s the conceptual enthusiast (alliteration exhibition “A To G”), tongue-twisting flow machine (the motormouthed “Alphabet Aerobics”), and the conscious-minded storyteller — most memorably on this super-hooky cut that turns an obscure Elvis cover into the kind of sellout warning that could really sting back when there was industry money to sell out for. Of course nowadays it’s a bit less cut-and-dry just how letting money change you can bring you down (modern rewrite option: “don’t let streaming jerk you“), but Gab’s rubbery, mocking-yet-sympathetic delivery and Xcel’s slick beatmaking (dig how he switches up the bassline in the second verse) at least show a style worth staying true to.

Fondle ‘Em was made out of necessity, but if the label that Bobbito Garcia formed to help showcase more unconventional unsigned rappers was relatively short-lived — it folded in late 2001 after just under six years in business — it made sure to release at least one legendary album before the doors closed. And it makes all the sense in the world for that album to be by MF DOOM: 10 years after he debuted as KMD’s Zev Love X on 3rd Bass’s “The Gas Face,” Operation: Doomsday capped off a career that could have been abandoned to the vagaries of major-label cold feet if it weren’t for Garcia’s label. Fondle ‘Em went all-in on DOOM in the late ’90s; his first singles as the supervillain, including a ’97 12″ that featured an early version of this track, were concurrent with the label’s efforts to unearth KMD’s shelved-classic sophomore album Black Bastards from Elekta purgatory.

You could hardly ask for a better indie-level advance campaign, or a better full-length to lead up to. DOOM’s ability to mutate any truism and find the perfect rhyme scheme for just about any phrase culminated in one of the most entertainingly weird hip-hop records of the entire spoiled-for-choice decade en route to doing the same for the 2000s. “Gas Drawls” gets the nod for a bunch of reasons — a slick Steely Dan sample (that DOOM beat-boxes along with), a performance that feels like it should be lit by a Tesla coil, and some of his finest lines (“The supervillain cooler than a million, I be chillin/ Still quick to slice squares like Sicilians”) in an album crammed with them. The funniest thing is that it was kicking around for five years, and there’s a nascent form of the song he premiered on Stretch and Bobbito’s radio show that reveals just how long it was in his back pocket — and how far he’s gone under the mask since then.

Backpacker club bangers? Why the hell not. Organized Konfusion were second to none when it came to envisioning a workable fusion of lyrical intricacy and throw-your-hands-in-the-sky anthemic potential. This is the group that put lines like “When I’m in a renovative state of mind I’m innovative” in the verses and massed shouts of “bring it on, motherfucker, bring it on” in the hook. In going solo, Pharoahe Monch took those two supposedly distant poles and made them clang together until it was the biggest, most undeniable thing to come out of the Rawkus catalog. A better Godzilla tribute than Puffy and Jimmy Page could ever dream of — though Toho Studios sadly hit Monch with a lawsuit over it — “Simon Says” is one of those tracks where every line could be a hook if it was easy to shout along with. Then again, it’s Monch, meaning that half of his lines only sound easy to shout along with, so maybe it’s best to just let the subwoofers do the harmonizing. And if you’re really all in, there’s a monster battle of a remix with Redman, Method Man, Busta Rhymes, Lady Luck, and Shaabam Shadeeq out there that’ll strip the gloss from your paint job.