24. Cypress Hill - Cypress Hill

Subverting hardcore hip-hop's stone-faced severity with gallows humor and inebriated indifference, Cypress Hill is more mischievous than dangerous, opting instead for a comedy of excesses, both in piercing sound wave and nihilistic subject matter. What they sacrifice in realism they gain in artistic freedom, allowing for a debut full of focused chaos, flailing wildly between exploitative killing spree, bleary-eyed parody and loose-bootied anarchy.

Acting as head agitator and primary vocalist, B-Real forces out each syllable with nasal drawl and arrogant sneer, both mimicking and embodying the tenets of a gangster rapper. Taking inspiration from the absurdist humor of Cheech & Chong and confrontational delivery of Jello Biafra, Real spins street narratives both strikingly vivid and playfully comic, nearly always ending with violent death bordering on caricature (i.e. "broomstick up your ass").

In contrast to his penchant for employing shock tactics, Real's moments of hallucinatory wordplay, usually relating to his passion for cannabis sativa, make for tightly-woven, meticulous poetry. "Light Another" finds him detailing the body's reactions to huge waves of marijuana smoke, moving from trembling lungs to scorched windpipe to cellular damage. His contemplative passages are just as striking, taking astute and informed stances on prison culture, government corruption (particularly in the police force) and environment influencing behavior.

Feeding off of B-Real's intensity, DJ Muggs constructed a sound scape of polar opposites, marrying gnarled, fun house psych loops with squeezed bass lines and woody, cavernous percussion. Further contorting the composition, his choruses are less hook than messy collage of word and instrument, comprised of sampled non-sequiters, ecstatic funk riffs and slurred record scratching. Muggs makes murder danceable and accessible, perverting chestnuts like Gene Chandler's "Duke of Earl" into brainwashed melodies, lulling the oft-stoned listener into full compliance atop a bed of bubbly static and upbeat high-hat.

"How I Could Just Kill A Man" is just as dichotomous, radically manipulating its samples into a piece somehow still firmly rooted in contemporary pop. Backed by a loop of whiny white noise, like a far off signal from a fading AM radio station, Muggs continues with his motif of coupling the shrill and the subdued, adding a layer of rich blues guitar pluck and thumping, low-end drum stomp to the mix. Jimi Hendrix's caterwauling guitar from "Are You Experienced" adds a heightened sense of menace to the proceedings, as does B-Real's postured take on the right to bear arms. Puffing out his chest and brandishing his "chrome" like a cop flashes a badge, B acts as an unsympathetic assassin, reveling in the cartoonish nihilism of his lyrics, with Muggs' grooves acting as an accessory.

Even more jarring than B-Real's moral vacuousness is the mid-track breakdown of warped flute and creepy carnival organ. As if impoliteness and anti-authoritarian attitudes didn't already align Cypress Hill to the Angelino hardcore that predated hip-hop's West Coast migration, the curious tempo shifts, horror flick atmospherics and penchant for Juvenalian satire are a direct link.

Concise and unwaveringly resolute, Cypress Hill single-handedly modified LA street rap just like they modified their shotguns, relieving it of its self-seriousness and replacing it with caustic wit and the macabre melody of a nursery rhyme.

25. Gang Starr - Daily Operation

Daily Operation is the sound of two performers (vocalist Guru and DJ Premier) merging their unique perspective with the influences of their predecessors and the history of their surroundings. Taking the melody and impact of jazz music, the “cultural awareness” of their Brooklyn homestead and a distinctly non-commercial sensibility, they fashioned an LP that expounds on the jazz platform and expands hip-hop's breadth of topic, digging deeper into what makes New York’s music culture great and castigating the violent aspects that seek to corrupt it.

Taking a conversational tone and rarely fluctuating pitch or sounding aggravated, Guru takes these corrupting elements head on, giving a singular and often controversial perspective on religion, government and record industry politics. His deliberately paced articulations act as the perfect vehicle for conveying complex ideas, particularly accusations of an anti-black sentiment in the media and governmental connection to crack cocaine distribution. His less serious diatribes even pack compelling dialogue, lending an air of gravitas to joint smoking etiquette and clingy ex-girlfriends.

Premier's best asset is an uncanny knack for picking the perfect snapshot, whether it be a staccato drumroll, pinch of organ or bent guitar string. Not only finding a funky beat, but one capable of matching Guru's unique flow, Premier doles out flirty bass lines, clunky woodblock and jaunty bursts of horn, highlighting the plain-spoken vocals without overshadowing. The dustiest jazz nuggets stick to Guru's words like glue and Premier keeps things low-tech and nocturnal, as to not take away from the stoned monotone.

Nevertheless, jams like "The Illest Brother" demand full attention, building a loop from a messy coupling of cymbal clash, vague wind instrument and barroom piano, all bleeding together like paint spilled on a canvas. Guru takes a chance by going at hyper speed on the mic, but keeps the conversation discernible, especially when elaborating on his talents as a wordsmith and man of the people. Premier also tests his agility, cycling through a handful of choice loops, the best of which pits a jazz fusion passage against playfully chopped up break beats.

"Soliloquy of Chaos" has the drama and tension of a prize fight, reflecting Guru's range of emotions through stirring strings and vocal swoon, mated with a soft xylophone stroke and faint bongo as percussion. Ever the storyteller, Guru sets an exciting nocturnal scene, abuzz with anticipation for a packed live performance. His characterization is rich, expounding on the five-car procession, extra rolls of film, "beige Tims" on his feet and adoring fans at the club. You can almost hear his heart break as gunfire rings out and police cruisers approach the venue.

Never missing the big picture in the smallest of details, Guru exposes the corruption of violence as a domino effect, not only ruining a Friday night, but damaging the art form, its supporters and the urban community as a whole. It's rare to find a lyricist so perceptive and universal, but Guru manages to boast without being solipsistic and perceive without being subjective, bringing a wisdom to Daily Operation scarcely found in the 21 years since its first pressing.

26. Peanut Butter Wolf - My Vinyl Weighs A Ton

Amidst a sea of drunken Soul, disoriented scratching and mush-mouthed vocal fragments, Chris Manak has buried a thesis statement deep in his sprawling My Vinyl Weighs A Ton, correlating the hip-hop DJ's creative process to an archaeological endeavor.

Nestled in the center of the album and a mere 24-seconds-long, "Top Illin'" takes liberties with Audio Two's seminal smash hit, distorting its drum break into a vociferous clatter and pairing it with jagged cuts of funk guitar and vocal moan. Breaking a loop down and pasting it into a new composition has been fair game since the dawn of rap music, but recycling a work that is itself a collage of previously used elements becomes "meta" exercise, revealing the producer as both artist and historian.

Dubbing himself "Peanut Butter Wolf," a name equal parts childish and sinister, Manak deals in exhuming forgotten swatches of music and placing them in a familiar context: the hip-hop head nodder. All of the routine elements have been compiled: the cinematic strings, the jazzy organ, the sharp clap of synthesized drums. Yet, an off-kilter sense of humor and precocious enthusiasm has dragged the commonplace into the Twilight Zone. Queasy kazoos and waves of distortion pervert an otherwise danceable tune. Beats sound hollow and cavernous, as if pounded out on an empty barrel in a mossy, underground bunker. Bass lines thud along in a morphine-addled haze, dragging endlessly before getting throttled by record scratching so fast that it's reminiscent of squealing tires and active smoke alarms.

"Tale of Five Cities" is an epic length ode to turntabilism as sport. Loops of soul and funk are jarringly contorted into new shapes and milked to a snail's pace, spawning an oafish and mesmerizing warble. Coupled with the propulsive scratching and constant shifts in beat and tone, the experience is not unlike psychedelia or noise music, that is, capable of evoking physical response and mood. Wolf understands the entrancing quality of his work (and hip-hop as a whole), drawing sonic parallels between the soothing voice of a hypnotist and the rowdy demands of a hype man.

Adjusting to the lulling, narcotic quality of the grooves can be a challenge, especially when the tone can shift from placid to menacing at a moment's notice. Peanut Butter Wolf strives for this disparity, as it expands the range of sounds he can draw from, allowing him to catalog and interpret the art world en masse.

27. Black Sheep - A Wolf in Sheep's Clothing

First impressions make Black Sheep out to be chauvinistic ne'er-do-wells.

Vocalist Andres "Dres" Titus and DJ William McLean fashion themselves as city dwelling Ferris Buellers, keen on left-of-center jazz, casual sex and cold Heineken. Superficial listens only corroborate their claims, but an attentive ear will reveal a crafty team of parodists, capable of lampooning the excesses of contemporary rap, while putting a magnifying glass up to society's absurdity.

Skillfully walking the line between earnest and glib, Dres' vocal flow is a cocky, conversational spoken word, accented by cool kid nonchalance and a penchant for vivid wordplay. His inability to show frustration, even when opining about race-related corruption and feckless rapper wannabes, reflects a deeply perceptive individual beneath the surface of sex drive and materialism. That's not to say that he won't "shoot you with the joint inside [his] zipper," he just won't break a sweat doing it.

His most interesting quirk as a writer is his unorthodox use of double entendre and metonym. Breasts become Vitamin D dispensaries, Nike goes from a sneaker to the verb for motion and the SAT exam becomes "the sad ass truth." His tour de force of figurative language is the verse-long symbol occupying much of "Black with N.V. (No Vision)," which aligns a hopeless and unmotivated life to a Sisyphean nightmare of endlessly washing dishes. Dres paints a complex portrait of the black struggle to find a role in American culture and uses the dish as a physical representation of forced labor, lack of opportunity and indifference.

Rhyme schemes of such a grand scale deserve equally elaborate sonic textures and the duo manages to construct a rich sound from maxed-out organ, unremitting bursts of muffled horn and deep, playful bass guitar groove. Drums are often low in the mix, lending an atmospheric, homemade quality to the affair and tone leans more towards the bouncy, jovial strut of genre pioneers than the sharp-edged sonic collage of East Coast contemporaries. The pool of samples smartly sidesteps sacred cows, instead favoring willfully obscure passages of Canadian prog, New Orleans R&B and contemplative, loose jazz saxophone.

They're even willing to modify their routine to match the targets of their sardonic genre spoofs. "U Mean I'm Not" mimics N.W.A's wah-wah funk guitar and machine gun chatter, while pushing their brutish physicality to the nth degree. It's all pure fantasy, but Dres murdering his extended family for botching breakfast and using his toothbrush is both hilarious and shockingly curt.

"La Menage" sets its sights on the other side of the hip-hop cliché coin: the sex jam. What starts as a racy provocation slowly degenerates into an unsavory four-way, complete with detailed descriptions of engorged genitalia, ambiguously gay gestures and enough prurient behavior to shock the Marquis de Sade. By the time Q-Tip starts his guest verse, we're too gobsmacked to realize how well it subverts the male-oriented sexuality of rap culture.

Though certainly more tongue-in-cheek than austere, a songwriting team willing to take on genre and social shortcomings right out of the gate is nothing short of commendable. It's this enthusiasm and anomalous comedic sensibility that sets A Wolf in Sheep's Clothing apart from the flock.

28. Ghostface Killah - Fishscale

Authenticity in writing is not necessarily based on one's personal experience, but the willingness of an author to bring real emotion to the fictional lives they put on paper.

A common misconception of the hip-hop songwriter is that they're constantly speaking from their own perspective, cataloging their life experience in diary form, avoiding creative license and the occasional white lie. Not only does this fallacy give the impression that rappers are all egotistical materialists (though some certainly are), it paints them into a corner artistically, forcing them to "keep it real," in lieu of making it innovative.

Ghostface Killah has always put the composition before the image, treating Fishscale more like a compilation of short fictions than a commercial rap record. A willingness to indulge artistic flourishes has yielded the richest of character development, breathing life into the paranoid crack dealers, septuagenarian assassins and strung-out strippers that occupy the dark alleys of Ghost's noir-influenced street poetry. Through these minute details, Ghost has created a body of work that demands attentive listening, packed to the gills with the subtle footnotes and cultural references that beg for an annotated dictionary and scholarly attention.

What makes these words so worthy of dissection and different from the work of contemporaries is the ambiguity of the narrator. Moving from a gritty tale about an agitator getting fitted for false teeth to an unflinching look at memories of childhood abuse, Ghost is capable of playing the audiences' emotions like a master manipulator, particularly by giving the impression that he may have doled out or received the aforementioned beatings. The actuality is besides the point, especially in relation to his talents as an author. What does matter is his ability to envelop us in the mood and setting of a story and shade in enough detail to make each lick of the belt sting as much for us as it does for the protagonist.

His production team wisely saw the vivid, filmic quality of his prose and backed it with the heavy bass lines, blaring horns and squealing guitar solos synonymous with 70's Blaxploitation cinema. Despite a legion of producers on hand, there's a water-tight continuity to the piece as a whole and the sound never deviates from the theme, despite mild tonal shifts and the occasional surreal passage. High-profile beat conductors like MF Doom, Pete Rock and J Dilla all step up with multiple entries, but politely give Ghost most of the spotlight, backing him with a combative drum kick when he's aggressive or the angst-ridden wail of female vocals when he's feeling introspective.

One such moment is "Beauty Jackson," which finds Ghost pouring over the female form, while Dilla repeats and repositions keys elements of Philly Soul by way of The Three Degrees "Maybe." As swirling strings and a quick snippet of downtrodden bass fidget and repeat endlessly, Ghost reminisces about a bus stop belle, capable of turning heads with just the puff of a cigarette or the downwind scent of her perfume. Every aspect of her look and personality are fetishized, rolled up in an eloquent stream of superlatives that note a cute birth mark, name check the Cover Girl lipstick and express genuine surprise when she actually listens to the petty advances. He daydreams of every jealous passerby, disappointed by their inattentive spouse and dated fashion sense. He even briefly lets his guard down, only to accidentally drop his handgun from his waist, sending his object of affection running for the bus.

If this story is pure fiction, Ghostface may be subconsciously exhibiting embarrassment about his early dalliances with a life of crime and depicting the common public perception of criminal offenders. Showing vulnerability and regret is beyond rare for songwriters, but unprecedented for a rapper. On Fishscale, Ghost broadens the scope of what it means to be a storyteller and MC, birthing an expansive fictional world constructed from bits of his real life, further shaded in by a versatile wordsmith far too talented to be sequestered to the ghetto of "real" MCs.

29. Quasimoto - The Unseen

Under a plume of smoke and fogged by a head full of mushrooms, avant-garde producer, Madlib, took his passion for exhuming jazz obscurities and married it to the social consciousness and surreal wordplay of Melvin Van Peebles. The resulting tapestry of beats (The Unseen) built an army of sound from hundreds of samples, each overlapping the other to the point of frazzled disorientation. Unfortunately, the deep timbre of Madlib's voice didn't match the frenetic pace of his ideas or their accompanying noise. As a replacement, he sped up his most arcane rhymes to a chipmunky squeak, creating a Frankenstein's Monster (aka Quasimoto) as vibrant and radical as his symphonic collage.

Where most rappers turn alter-ego into artifice, Madlib uses Quasimoto as a counterbalance, both sonically and lyrically. Childish wordplay about javelin tossing and the violent disposal of antagonists better suits the helium-voiced Quas, allowing the actual Madlib to step in as the responsible and thoughtful alternative. The high-pitch even adds annunciation to peculiarities like "Droppin' shit like some horses," which can be seen as sophomoric or a wonderful moment of the figurative meeting the literal.

Socially pertinent topics like black-on-black crime and police corruption make appearances, but most of the content leans toward tribute, boasting many a reinterpretation of or knowing nod to past musical masters. Well over 50 jazz cats and MCs are called out by name, often coupled with a snippet of their work or muffled echo of their voice. This fandom goes beyond hero worship, stubbornly residing in a world of pure nostalgia, occupied by dusty record bins, analog sound and hydroponic marijuana.

The sound is equally as stubborn, building steam from legions of samples that fade in and out perpetually. Drum beats shuffle between thudding, low-tech drone and soft, spacey water droplets. Xylophone samples add a psychedelic ambiance, especially when juxtaposed with choppy jazz organ and hyperactive turntable gymnastics. A familiar beat or vocal sample will drop in, mid-thought, only to fade into the distance, moments before you can pinpoint the source material.

"Goodmorning Sunshine" capitalizes on this dizzy blend of wonder and befuddlement. Moving from the calming tone of Augustus Pablo's melodica to the wavering nausea of hissing dub resonance, the track never settles on one sound, throwing in drum stutters and vocal samples to further elaborate on its lack of structure. Quasimoto and Madlib rhyme in unison, allowing their vocals to blend together and co-exist with the samples, rolling endlessly over themselves like an aural Mobius strip. It's incredibly chaotic, particularly when coupled with the hypnagogic street poetry of Melvin Van Peebles, whose words act as guide, referencing everything from religious hypocrisy to untimely death to Swedish erotic cinema.

For all of its anarchic, purposely messy abandon, The Unseen is anything but a failure. The end result is a massive, complex quilt of influences, channeling 70s urban America and record store culture through the mindset of an oft-stoned, but undeniably brilliant, curator. Hearing Madlib rip the art from the museum walls, dissect it and implant his own ideas is an exhausting and transformative experience.

30. A Tribe Called Quest - Midnight Marauders

Everything about Midnight Marauders, from lyrics to beats to album art, is about community. Building steam from the massive praise showered upon The Low End Theory, A Tribe Called Quest expanded on concepts that record only glazed over, taking a closer look at the urban social climate and adding complex layers of samples to their previously stripped-down sound. Experimenting with a sure thing was risky business, but, like the jazz players that preceded them, Tribe refused to cement themselves to one approach. Marauders is the product of this growing confidence, reflecting artistic maturity and positioning them as spokespersons for the party of rappers that adorn the liner notes.

Lyrical content has taken a "day in the life" approach the third time around, putting the superficial and the severe into perspective. Q-Tip and Phife Dawg postulate about everything from violence to sex to Knicks basketball, taking a progressive, thoughtful approach to hot button issues (racial epithets, HIV), while still maintaining a light tone and avoiding the sophistry of rhetoric. Q-Tip plays both of these parts well, alternating between college professor and smart aleck, as dictated by tone. Vocally, he swoons like a poet or doo wop singer, flowing like water over a jazzy note, stopping only to pose a question or pass the mic to his wily counterpart.

No longer playing second fiddle, Phife has fully developed into a witty comedic author, throwing out playful boasts and hysterical similes with high frequency. Riffing on Barney and comparing inferior MCs to "cheese grits" is only scratching the surface. Repeat listens reveal a perceptive storyteller capable of exposing how day-to-day disappointments can lead to an attitude of blind complacency.

The vocal duo and DJ Ali Shaheed Muhammad handled the bulk of production, creating a dense layer cake of unearthed jazz elements, ranging from the standard to the obscure. Big brass bands and groovy organ lie in a bed of atmospheric and warm static, jaunty bass and driving drum beats. Inorganic sound effects and dark, cinematic keys lend a nocturnal feel to the piece, draining the manic energy of previous releases and leaving behind the molasses-sticky, sonic personification of hot asphalt.

"Electric Relaxation" drips with softly-strummed guitar and spacey electro bleeps, acquiring body and texture via a liberal dose of stand-up bass and the clip of a snare drum. Words unfurl as calm poetic exercises, stressing the female physique and the healthy libidos of our narrators. They collectively preach discreet sexuality, halting these chivalrous advances only for the occasional off-color joke or passage of patois riffage. The most pleasing aspect of their gambit is the effortless integration of two distinct voices, illustrating similar ideas through different inflections. In essence, this shared viewpoint and collaborative spirit reflects the very idea of community.