21. Ice-T - O.G. Original Gangster

Ice-T always fashioned himself as a politically-astute Lothario; the kind of guy capable of getting a snobby English dame to dub him the "epitome of antidisestablismentarianism" right before she admits, in far more explicit terms, to fancying his genitalia. In contrast, the media labeled him as a threat to decency, seeing his lack of sentimentality and penchant for bleak crime narrative as a conduit between the violent realities of urban life and the ears of pristine suburban teenagers.

Detractors did manage to get one detail right, Ice's sphere of influence was expanding, but the new audience he'd won over wasn't keeping up with his growth as an artist. Friend and foe alike never saw the forest for the trees, fixating on his affinity for profanity and sexual broad-mindedness instead of his radical politics, musical diversity and incorruptible honesty. Unphased, but concerned, Ice stripped O.G. Original Gangster of hardcore rap's creature comforts: the sexcapades, empty threats and xenophobic attitudes, re-branding his street talk as both incendiary satire of political corruption and depressing portrait of urban poverty. By siphoning off the unnecessary elements, Ice-T concentrated his already potent poetic realism, constructing a work that never panders to easy shock tactics, aiming more to expose America's antiquated caste system and the complacency that keeps it in power.

Likening his mind to a lethal weapon, Ice takes aim at the endless cycle of crime caused by disparity in income between the rich and poor, expressing frustration and sympathy through blunt, oft-sardonic cautionary tales. Depending on content, he can waver between jarring bursts of spoken word or quick vocal jabs, both equally capable of illustrating his themes and flexing his verbal skill set. As for creativity, he knows the players of the drug game and can easily adopt the perspective of a 19-year-old hustler or paranoid jailbird, showing how fast money makes streetwise teens into amoral capitalists and how the prison system turns men into animals, hell bent on survival.

His turn of phrase is just as canny as his playacting, transforming a gun in pocket to a "parabellum in the leather attache" and utilizing double entendre to show how silk sheets make one lie like a politician. He also draws startling parallels between historical atrocities and injustice at home, likening ghetto indoctrination of the black community to the crimes against humanity committed by the Khmer Rouge regime and the genocide of the American Indian.

The production, helmed by Ice and fellow Rhyme Syndicate members, matched the gravity of the vocals through a skittish, churning and noisy sound profile, culled from synth blast, industrial clatter and abrasive, squealing wind instruments. Though stripped of much its pomp, this is primarily 70's funk territory, accelerated to match the rapidity of Ice's declamation and the lives of his rebellious, but doomed protagonists. When not following in Funkadelic's footsteps, Ice favors horror movie atmospherics or Black Flag style rave-ups, even handing a track over to his burgeoning hardcore band, Body Count, in an effort to broaden audience horizons. This sort of diversity can be a blessing on a 72-minute LP, particularly one with a predilection for confrontation, but Ice's gift as a linguist is best served in the shorter, less adventurous moments.

Comprising barely a minute and composed primarily of Ice's deep, commanding tone, "The House" is complex enough to demand multiple listens, initially suggesting an indictment of unfit parents, but gradually revealing something far more sinister: willful ignorance. By neglecting to acknowledge abused children and confront contemptible adults, the community is implicit in the outcome of the situation, leading, in this case, to a child's death. It's a heart wrenching moment, but Ice doesn't intend for this story to act as a singular moment of urban desperation, but as an indicator of a larger problem. He confronts this apathy, whether it be on the part of wealthy bureaucrats or members of his community, on nearly every track of Original Gangster, painting a portrait of a nation on the brink of collapse under its own cold comfort.

22. De La Soul - 3 Feet High and Rising

Framed like a novel and as madcap as the best sketch comedy, 3 Feet High and Rising churns through samples, social issues and stereotypes with a levity unbeknownst to the late 80's hip-hop landscape; a scene that had split its focus between radical politics and street-wise chicanery. Where the era's torchbearers spoke with a certain severity, rarely taking a breath or cracking a smile, Long Island's De La Soul emanated an almost rigid positivity, creating a frenetic and bouyant puree of AM radio pop and cartoonish flotsam that was equal parts heart and innovation. This contrast in values and outsider attitude not only provided the genre with an alternate viewpoint, it forced the form to broaden its horizons, championing detail and individuality and refusing to paint in broad strokes.

Capable of a complex and knotty verbal discourse, Posdnuos and Trugoy (Plugs 1 and 2, respectively) are far less concerned with rhyme and reason than most of their peers, instead dabbling in vivid imagery and subtle word games that rarely reveal themselves on the first listen. "Eye Know" focuses on love making and the female of the species, abandoning commonplace sex metaphors, instead eloquently comparing the emotional impact of a kiss to being "filled with the pleasure principle in circumference to my voice."

Accompanying the rapturous poetics is a penchant for cheeky in-joking, which rears its head in every phallic nickname and plea for good hygiene, reaching its summit in the hilariously candid "A Little Bit of Soap." They're even willing to buck songwriting convention, taking a break midway through a compelling tale of promiscuity to give a sexual competitor the chance to pound out "Chopsticks" on the piano, cheering him on as his fingers nervously fumble over the keys.

The overall lyrical impression is diverting and sunny, which may have inspired detractors to label them as hippies, but don't let whimsy overshadow intention. The prime directive is to further the medium by standing in contrast to it and no other moment does that better than "Ghetto Thang," which recognizes the endless cycle of violence and parental neglect and fingers rap's fascination with gun play as a corrupting element.

Keeping with the theme of disparity, Prince Paul recycled old elements to fabricate a new style, favoring thrift-store eclecticism over studio sheen. The product of this strident anti-conformity was more puzzle than composition, marrying breezy guitar, infectious bass lines and the fuzziest and most esoteric of vocal loops, often culled from instructional records or dated curios. Though random upon on first glance, Paul's brilliant melding of flavors provided context to the songs they accompany, particularly effective when stealing Daryl Hall's vocals from "I Can't Go for That (No Can Do)" and re-purposing them as an anti-drug screed. He further rebels against structure and copyright law on "Cool Breeze on the Rocks," scotch-taping a variety of songs prominently featuring the word "rock" into an ungainly sonic prank, aligning himself more with Dadaism and tape-loop experimentation than his soul and funk-obsessed contemporaries.

Yet, his most passionate endeavor is merging these so-called "serious" artistic conceits with whimsy and guile. His finest union is "The Magic Number," which bursts with more color than a box of crayons, brims with zeal and floats on a wave of xylophone, cymbal clash and deep groove. This one is more dance than discourse, kept afloat by Paul's need to cram every moment with a unique noise or peculiar discovery. Case in point, the track's denouement is jammed with bursts of James Brown and Johnny Cash, reckless scratching, snippets of Mayor La Guardia reading comic books, multiplication lessons from Schoolhouse Rock!, Eddie Murphy asking his audience if they've ever been hit by a car...

It's a disorienting and exhausting clash of differing elements, as if three TVs playing different commercials at full blast were all vying for your attention. The passage of time hasn't minimized this maddening euphoria, nor has it provided an act capable of reproducing it. Though the cut-and-paste technique has been carbon copied and the attitude has been adopted, none are as recklessly creative, wistful or seamlessly synergistic.

23. Dr. Dre - The Chronic

The Chronic is a paradox.

It was a mainstream pop success cobbled from the pieces of an underground sound. It paired the grooves of a dance party with the brutality and hate of a street fight. It emulated the meticulous design and studio proficiency of ambient composers, but was best heard as the passing thud of a low rider’s sub-woofer.

Yet, its wealth of contradictions only made its influence more profound. Never before had hip-hop sounded this grandiose, taking on the emotional heft and depth of a motion picture soundtrack, replete with cinema’s storied anti-heroes and penchant for glorified violence.

At the center of this story of revenge was West-Coast production wunderkind, Dr. Dre, rising from the ashes of N.W.A to dole out slanderous tongue lashings to his critics, contemporaries and ex-bandmates. His ideas unfurl as a tough guy shtick, spoken in choppy half sentences, but convincingly scowled and backed by an army of like-minded agitators, some of which are considerably more proficient on the microphone.

Dre’s best verbal passages come when he avoids keeping up with his teammates, instead relaxing and opining over his lustrous Chevy Impala and penile hubris. Honest about his lack of pretensions, Dre claims “No medallions, dreadlocks or black fists” here, just gangster rap, which lies somewhere between admirable and willfully ignorant. Despite this apolitical stance, many tracks do carry valid arguments for uprising against social injustice, specifically in relation to the Rodney King beatings and the living conditions of South Central Los Angeles. Even the melancholy “Lil’ Ghetto Boy” has a contemplative nature that seems to contradict Dre’s occasionally bleak posturing.

Accompanying Dre on a staggering 11 of 16 tracks is Snoop Doggy Dogg, a gifted and skillful rookie capable of picking up where Dre’s rhyming abilities leave off. Funneling each sentence through his fast and limber voice box, Snoop traffics in “sing-songy” inflection shifts, nonsensical slang and stoned indifference, vocally falling somewhere between reggae patois and schoolyard joshing. If it wasn’t for his diverse portfolio, his flow would come off as a gimmick, but his storytelling is strikingly authentic and one-liners indelible, exceeding the influence of a song and permanently infecting popular culture. 

Just as culturally significant was Dre’s pioneering production work, which more than makes up for any inconsistencies in his oratory abilities. Riding on a constant wave of a neon, squealing synthesizer, Dre weaves eerie and menacing tones from otherwise benign elements. His bass lines are tense and husky, reminiscent of the captured din of a boxing match, but slowed to a leisurely, drifting pace. As a contrasting element, exotic and suggestive flute floats into the mix, almost subconsciously, paralleling vintage sex jams from the bedrooms and massage parlors of exploitation cinema. As a binding element, piano pleasantly swirls from speaker-to-speaker, hammering the nail into vinyl’s coffin and solidifying CD’s stereophonic sound.

Taking advantage of these advances in high fidelity, Dre pushes his gassy, self-congratulatory bass lines to the forefront on “Fuck wit Dre Day…,” backing them with jovial organ tinkle and plucked guitar string. Posing as an electronic answer to Parliament’s big-bootied funk, Dre adds heavy doses of synthetic horn and orchestral atmospherics, which give the track a celebratory vibe, contrasting the decidedly spiteful and homophobic lyrical content.

This inclination to ridicule the competition into submission may be the only misstep of an otherwise brilliant effort, but where the message fails, the performers succeed. Dre and Snoop exude chemistry while excoriating their enemies and those willing to see past their childish bigotry will find a tremendous confidence in the power of the chosen sonic elements and the overall listening experience. The resulting hybrid of dark, delicate atmospherics and hyperactive soul bounce was jarring enough in its originality to forever alter the face of American music, heightening our expectation for ambitious and daring soundscapes.

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.