Will Fenton
Rap is unflinching, unapologetic poetry.
It combines the lyrical, rhythmic conventions of literary forms with the candor and unvarnished veracity of life encountered head-on.
Rap can be delightful, rousing, vulgar, and arrestingly intimate in turn.
While the top 40 rappers and hip-hop icons usurp the attention the genre receives from the mainstream, there is a vital, gregarious, charismatic underworld to rap, undiminished by the lack of status quo accolades and media profiles.
In different creators’ hands, the genre evolves into strange, eclectic new forms.
The geographical provenance of a rapper shapes the messaging and approach of their work in a potent, uncompromising way.
Underground rap and hip-hop took shape in the early eighties and experienced something of a Precambrian explosion during the early and mid-nineties.
It was during the nineties that the underground movement began to separate more profoundly from the mainstream.
But it didn’t stop there – let’s assess the best underground rappers in music history.
1. MF Doom
Lauded in the underground circle after underground circle, MF Doom has a small coterie of obsessives who compulsively follow his musical moves.
He is as close a thing to a kingpin as the scene has, and you know a dyed-in-the-wool hip-hop lover when they list off MF Doom as a favorite.
His rhymes are head-spinning, fervent, and devilishly untamed and all of his bars are saturated with arrestingly creative metaphors, symbols, and insinuations.
His signature metal mask is unsettling, sure, but it adds a patina of mysterious gravity to his visionary, literary output.
His instrumental melodies are lush, and, daresay, transcendental.
“Doomsday”, “Coffin Nails”, and “Rapp Snitch Knishes” are three of the most chilled-out, instrumentally atmospheric, lounge-worthy rap songs in the canon.
2. Kool Keith
Kool Keith is surreal, bizarre, and fearlessly offbeat, and his lyrical offerings are uncommonly head-scratching.
He is something of a method actor, or method rapper, if you will, occasionally descending into personas like Dr. Octagon in Dr. Octagonecologyst or Dr. Dooom on First Come, First Served.
His delivery, spitting style, and theatricality can be frenetic and lend a dizzyingly disconcerting cast to his sounds.
Kool Keith is staunchly underground, rejecting the norms and conventions of mainstream rap, and as a co-founder of Ultramagnetic MCs, he is both insatiable and prolific.
“Poppa Large” and “Livin’ Astro” give a newbie a taste of his tight, well-executed mastery.
3. Mos Def
Prolific beyond belief, the charismatic and lyrically dynamic Mos Def is probably one of the most mainstream figures on this list, collaborating with legendary acts like Massie Attack.
Mos Def is ceaselessly, unflinchingly political, and his lyrics contain eloquent, piercing analyses of social and cultural issues without descending into hysteria or sanctimonious hectoring.
Mos Def has always maintained an articulate, academic aloofness and is in many ways a true artist’s artist, content to confound and challenge listeners’ expectations.
1999’s Black on Both Sides is one of the most audacious, transformative albums in the hip-hop canon.
4. El-P
Getting his start in the rap group Company Flow, El-P eventually dipped his toes into the solo world, and ultimately became one of the most salient figures in underground hip hop, cofounding the Definitive Jux record label.
It would be hard to find a rapper as forcefully eccentric as El-P, relying as he does on obscure sci-fi references and the complex futuristic work of Philip K. Dick of Do Androids Dream of Electric Sheep?
Fame.
He can be theatrical, lighthearted, and vulgar, but he never deviates from a commitment to the experimental and unexpected.
El-P is ultimately a storyteller, a rapper with an uncommonly cultivated vision and the ability to weave strange tangents into truthful expositions on life, childhood, and trauma.
5. Aesop Rock
The closest thing to a postmodern Shakespeare that we have, Aesop Rock is erudite, maddeningly literate, and voraciously articulate.
Aesop Rock was a big name in the nineties underground world and he kept listeners rapt with his deviously-executed rhymes.
The dictionary is light work in Aesop’s hands and he infuses his rhymes with complex entendres, metaphors, and intriguing allusions.
His albums are conceptual and nearly surreal in their perplexing visionary tangents – Spirit World Field Guide and Labor Days will give you a taste of his potent, well-crafted narratives.
6. Talib Kweli
You might recognize Talib from his collaborative project with Mos Def, Black Star, but his most fervent, electric output comes courtesy of his solo career.
His debut solo album, 2002’s Quality had sustained mainstream crossover success and garnered him buzz in the Billboard 100 circles.
His brutal, political anthem “Get By” was produced by Kanye West and reached a mass audience with its unvarnished veracity.
He is a master of a smooth, intentional technique but his softer delivery never detracts from his politically charged message, which focuses incisively on the struggles of black people and on persistent cultural oppression.
The delicate piano and melodic political lyrics of “2000 Season” is proof of a legend in the making at work.
7. Joey Bada$$
Joey Bada$$ is a YouTube success story, and his freestyle beats eventually garnered him critical success and a turn with Cinematic Music Group.
His voice is smooth, with an alluring sensuality that comes through in soft, textured rhymes and downtempo, unruffled choruses.
His instrumentals take a heady cue from classic smooth R&B, refined and elegant lounge, and dreamy-jazz tempos.
His 2012 debut was featured on Complex Magazine’s list of the best albums of the year and his chilled-out “Love Is Only a Feeling” and “Show Me” are lush, relax-rap at their very finest.
8. CunninLynguists
Kentucky-based CunninLynguists consist of Kno, Deacon the Villain, and Natti and single-handedly raise the profile of Southern rap, in a genre dominated by California and New York.
As their name would suggest they are mischievous pen-wielders, producing mordant, labyrinthine, creatively variegated lyrics that could easily land them a Pulitzer.
They are fearlessly offbeat and eclectic as evidenced by groundbreaking concept albums like Oneirology, which is all about dreams.
Surreal, abstract instrumentals lend a quirky veneer to their confounding, delightful lyrics while unexpectedly gorgeous classical arrangements in songs like “Linguistics” and “Urutora Kaiju” show a commitment to the entrancing and uncommon.
9. Blu
Blue is a meticulous craftsman, a purveyor of well-rounded, fully fleshed-out musical experiences with his blend of West Coast attitude and elegant references to mid-century masters.
He infuses his melodies with a distinct jazz ethos, perfect for contemplative evenings or thoughtful forays into the world of words, allusions, and cultural analysis.
A born wordsmith, Blu tackles dense, problematic aspects of society and culture with a deft, unlabored hand.
The Colour Blu(e) is a revelatory ode to the color blue while Below the Heavens is a thematically cohesive masterpiece, an album-length achievement that eschews snarky cheek and focuses on the meaning lingering behind the surface of every word.
10. J Dilla
During the nineties, the name J Dilla was valuable currency in the thriving, unapologetic Detroit hip-hop underground.
Though tragically deceased, J Dilla’s legacy lives on in his fervently experimental, wackily juxtaposed musical arrangements.
Anthems like “U-Love” are a moving feast of sounds, a sonic tapestry dense with complexity, magic, and warmth.
His tracks are soulful and satisfying, drawing on the smooth R&B of the eighties and the funk-flecked dynamism of the late seventies.
11. Inspectah Deck
You may recognize Inspectah Deck from the rap supergroup Wu-Tang Clan but you need to do yourself a favor and spin his solo work, which is decidedly more laidback and less hostile than his Clan peer’s solo work.
Content to swim under the radar of the main current, Inspectah has a distinctly street-level, nineties sound and a curiously animated voice with a biting edge.
“Execute Them” retains the ferocity and audacity of any Wu-Tang hit with a calmer, less frenzied cadence while the seductive, tawdry beat of “Elevation” is the perfect medley of evocative instrumentals and unbound, in-your-face bars.
12. Roc Marciano
Marciano has a sound that is distinct and inimitable: dedicated to decentering percussions, his melodies, and rhymes sound visceral, crisp, and forceful.
He is something of an intimidating figure, dishing out flippant, arrogant one-liners and witty one-two punches that leave the listener dazzled and unmoored.
Marciano is cooler than the rest of us, and almost aloof in cocksure, ominous tracks like “Quantum Leap”.
There is a stoic coldness to Marciano, and his unfazed style lends itself intriguingly to the occasionally industrial instrumentals that serve as his backdrops.
13. WestSide Gunn
With a high-pitch and an unorthodox commitment to fiercely independent output, WestSide Gunn is relentless, forceful, and deserves the comparisons to Wu-Tang Clan that he frequently gets from critics and observers.
His lyrical style has been referred to as absurdist and over-wrought, leading to a curiously engaging and delightful listening experience.
His melodies are gritty, grimy, and densely textured, assaulting the ear in a compelling, unsettling way.
His preternatural fluency with the language of beats is a rare and special gift and can be encountered in songs like “BDP.”
14. Conway The Machine
Conway The Machine processes his trauma and struggles through rap and his music is raw, disarming, and fearlessly, unblinkingly enraged.
One of the founders of the peerless underground record company, Griselda Records, Conway’s entire life is steeped in hip-hop culture, storytelling, and the craft of beat-making.
He is clever, subversive, and hard to pin down, dishing out dark asides atop grimy, unsettling beats and gritty, unflinching industrial instrumentals.
The G.O.A.T. is a seminal album in underground circles and powerful, disconcerting tracks like “Scatter Brain” will stun you into silence.
15. Immortal Technique
East Coast cult icon Immortal Technique is unapologetically, unabashedly political and his rhymes are a veritable manifesto against oppression, systemic violence, and war.
Partially disguised in palatable, catchy beats, his music is unbridled and electric with a fully-formed rage and fury at the miserable status quo.
If you are brave enough to hear a voice against injustice give his Revolutionary, Vol. 1 a spin and get fully engaged in the veracity of his message.
16. R.A. the Rugged Man
Confident, charismatic, and intriguingly detached, R.A. has long been a kingpin of the underground, blending self-assured showmanship with hard-hitting, forceful lyrics.
His voice is gravelly, rough, and intimidating but replete with unparalleled passion and potency.
“Uncommon Valor: A Vietnam Story” is a hip-hop elegy of the terrors and human despair of the Vietnam War, and is an arrestingly innovative approach to exposing the truth behind the historical record.
“Definition Of a Rap Flow” is animated and engaging beyond reason, with a calm cadence and a funk-infused chorus.
His 2020 release All My Heroes Are Dead is frank, abrasive, and stubbornly defiant.
17. Benny The Butcher
One of Griselda Record’s mainstays, along with previous entries, WestSide Gunn and Conway The Machine, Benny lacerates traditions and niceties with his brusque, hostile lyrical style.
His beats are cold, disconcerting, and domineering, allowing no space for tender poetics or sweet asides.
This is your rapper of choice for dark nights of the souls when you feel uncontained and hateful and ready to take revenge.
18. J-Live
J-Live embodies the DIY, street-level roots of hip-hop with manically vital lyrics and untamed pacing that keeps you, quite literally, rapt.
The playful, charismatic arrangements on “Them That’s Not” will have you thinking back to the glory days of early hip hop, and the subtle, vibe-heavy instrumentals make for inviting listening.
The luminous instrumentals and vibrancy of “Beyond The Sun” and the intellectual prowess of “Satisfied?” belies J-Live’s former identity as an English teacher.
It is rare to find a musician who times his drops so curiously and immaculately with the tempo and beat, but J-Live makes light work of this technical wizardry.
19. Atmosphere
Surreal, abstract, and charmingly mercurial, Atmosphere is composed of the rapper Slug and the producer Ant.
Lo-fi, trippy, cheerful anthems like “Sunshine” and the upbeat, heartening “The Best Day” are generous, effusively optimistic, and ideal for a cozy night in.
Their songs are veritable storyboards, saturated with linear narratives and quirky characters, not unlike themselves.
20. Elzhi
Vibrant, energetic, incorrigible Detroit rapper Elzhi blends jazz with high-impact boom box beats for a raw, fiery sound that demands full attention.
Elzhi has been at it since the nineties and his creative verve and enthusiastic demeanor haven’t diminished since.
Tracks like “Light One Write One” are infused with a casual serenity, warmth, and soul that is uncommon in any genre while rough and tumble “Halftime” is insatiable and assertive.
21. Billy Woods
The ever-unhinged, chaotic rapper Billy Woods is like a bolt out of the blue, a wily and turbulent idol who dishes out some manic, feral beats.
He is something of a willfully misunderstood poet laureate, a lyricist who catches the listener off-guard with off-beat delivery and unexpected tonal choices.
2012’s History Will Absolve Me is a masterwork of dissonant beats and anti-colonialism while his most recent release, 2023’s Maps is surly, creatively invigorating, and disarmingly candid.
Woods is radical and intellectually frantic, restoring a carnal aspect to 2020’s rap.
22. Company Flow
Brooklyn-born Company Flow consists of a trio of rappers: El-P, Bigg Jus, and DJ Mr. Len.
They dominated the underground currents of the late nineties with futuristic and unsettling stylistic choices.
Their sound can be distant, even abrasive, but is also possessed of a tender poignancy and emotive momentum.
Funcrusher Plus, released in 1997, is wildly refreshing and unlike the more stylized rap that was coming out in advance of the millennium.
23. Open Eagle Mike
Open Mike Eagle is a comedian and rapper, and he cross-pollinates his lyrics with potent tales, humorous asides, and conceptual narratives.
He is heartfelt and possesses a certain earnest quality that makes his songs feel almost confessional in nature.
His gift for story structure and his open-veined approach will have any listener rooting for Mike as the protagonist of his own story.
He is playful, but also unceasingly articulate, and occasionally jaded, and his gift as a wordsmith weaves its way through powerful albums like Brick Body Kids Still Daydream.
24. KOTA The Friend
Eternal optimist that he is, KOTA The Friend is a spacey, minimalist indie rapper who looks on the bright side with his open-hearted lyrics and way-chilled-out approach.
You are probably already familiar with his beats, and his 2020 album Everything gets consistent playtime on thrifty shop playlists, patio session background beats, and your effortlessly trendy neighbor’s stereo.
Plush piano blends seamlessly with his honeyed voice and unharried pace to create a soundscape that inspires, uplifts, and provides solace in a dark world.
25. Brother Ali
Brother Ali lives and breathes his work, and walks the walk when it comes to fearless activism against racism, oppression, and human rights violations.
He confronts injustice head-on with unrestrained political messages, but he couches them in an amicable, almost open-hearted way with a smooth, refined delivery.
The result is potent, impactful poetry that feels inviting and optimistic while also fostering worldliness and empathy in listeners.
His 2000 Rites of Passage is powerful magic and feels as relevant and tectonic twenty-three years later.
26. Boldy James
Detroit-bred Boldy is laidback, and relaxed, and offers a rap experience shorn of the more aggressive lyricism and emboldened emotions of his peers.
While his name may not ring a bell, he is quietly prolific and has released nine albums during his tenure, gaining a committed following who appreciate the amicable authenticity of his output.
The stress levels are turned all the way down with lightly ska-infused “Great Adventures” and the spacey, buoyant “Level Tipping Scales.”
Boldy will be the soundtrack to your long, speculative walks or your afternoons getting into a creative, unconfined creative flow.
27. Ka
A Ka track is heavy on dense, sultry atmospherics and smooth and luxuriant vocal range.
Unlike his peers, his songs are usually drum-free, and rather than feeling like a glaring omission, it creates a sharp emphasis on the depth of his vocals and the insightful, academically challenging lyrics.
His cadence is intentional and restrained, with a certain arthouse refinement that provokes thought and reflection, helped along by his conniving double entendres.
“I Wish (Death Poem)” has one of the most lush, entrancing soundscapes in hip-hop history, and “Conflicted” is almost intoxicatingly sculptural.
28. Necro
Call it Death Rap, call it horrorcore, but whatever denomination you choose, one thing is unmistakable: Necro is gory, obscene, and grotesque – and proud of it.
He is kind of like rap’s Glenn Danzig, singing explicitly about gruesome murder scenarios and disturbing death fantasies.
He is unapologetically crude and commits wholeheartedly to his dark, depraved vision, adding death metal instrumentals and violent beats to truly bring the message home.
While the mainstream couldn’t stomach him, he has a loyal and unbridled cult following who worship his brand the way some might worship a football team.
29. Vinnie Paz
Producing music at the razor edge of horrorcore, Philadelphia-based Vinnie Paz is not for the weak-stomached, as his lyrics often descend into some truly debased, gory places, filled with violent fantasies and murderous revenge plots.
With a hoarse delivery and a volatile, belligerent tone, this is not the music for your family reunion, but Vinnie knows his vision and maintains an enviable fidelity to it.
Grimy and gritty, with bold, audacious instrumentals, Vinnie Paz has carved out a niche for himself that is hard to duplicate.
30. Armani White
Philadelphia-bred Armani White is one of the newer additions, released his debut album in 2019 but according to his own estimation he has been at it a long time, beginning his rap journey at age seven.
His single “BILLIE EILISH” broke through into the mainstream and garnered him commercial success and at 25, chances are high he’ll have many more singles under his belt.
Armani is plucky, insolent, and cheeky, with a Gen Z flair and an unflappable fluency with postmodernist internet culture.
Best Underground Rappers – Final Thoughts
The underground current of rap and hip hop is populated with an almost dizzying cast of characters – from arthouse lyricists to social justice poets to unfettered rage-mongers, it is all here in spades.
You’ll quickly be leaving the mainstream repetitions and tired conventions behind for a terrain rich with magic, experimentalism, and vigor.
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