3. A Tribe Called Quest - The Low End Theory

Not content to recycle or reinterpret, The Low End Theory is an extension of the jazz that came before, merging the fluidity of hip-hop vocal with airy, open spaces and curt instrumentation. Abrupt stops and starts allow each word to hang over an abyss of negative space, contributing to the composition as much as an instrument and stoking the narcotic aura of jazz's profligacy. The mood set by the intimacy of the environment and propelled by the rumbling undercurrent of bass is warm and nostalgic, placid enough to strike a demeanor mirroring A Tribe Called Quest's silken, phonetic flow. The coherence in sound and vocal composure has inspired an expansion of lyrical scope, capturing the playfulness of the debut with a new found ardor for sexual politics and major label maneuvering.

Introspective and sneakily political, Q-Tip's brilliance lies in his ability to unveil obscured truths, whether they be as profound as a lyrical exploration of art's seasonality or as trivial as a comprehensive list of backstage snack requests. His mastery of the form lies in this alternation between serious and frivolous, respecting even the most foolish of his conceits enough to take it beyond the two-bar minimum. Vocally, he's deeper than his counterpart, but no less agile, managing to strike a balance with the beat much like the one he's struck between disparate thematic material.

Crucial concerns find his words spit out at a quick clip, adding a needed tension to arguments against racial discord, vanity and the wiles of record-industry "shing-dings" (his word for phonies). Breakneck speeds find him concise and crystal-clear, as he's never one to fumble over an unneeded syllable, but relaxation and comfort only truly shine through when he "fluctuates the diction," ruminating over his sexual prowess in the most floral and frequent manner. These dirty dalliances are buried in the knottiest of stanzas, peeking out in feline metaphors that smack of chauvinism, even if his tongue is planted firmly in cheek. Measuring his capacity for copulation as a stockpile of "Tender Vittles" is amusing for its Chaucerian bawdiness, but assuming any female rejection happens around the 28th day of the month sounds positively primitive in the 21st century.

Phife Dawg doesn't fare much better on "The Infamous Date Rape," but he earns all other moments, maturing into a splendid storyteller and uproarious comedic writer. "Butter" finds him as a high-school Casanova, conquering every female opponent in sight and whimsically harmonizing their first names, until "Flo" serves him an unexpected dose of teenage heartbreak. Thankfully, this two-timer only gave him the life experience needed to shuffle on to a new partner, which most certainly won't be a lady with a weave ("I asked who did your hair and you tell me Diane made it.") or one of the snobs that dissed him before his royalty checks cleared.

Vocal sounds are as pronounced as the lyricists and at the fore of the production, with omnipresent bass and the thrum of snare drum gently resting behind, coaxing out a seductive, organic rhythm. Libidinous urges are as fleshed out sonically as they are in the minds of the vocalists, resulting in grooves that shake the pelvis and demand a complicit head nod. The bed of samples selected is fertile and lively, alternating between boisterous horn and subtle, dulcet organ tone, tranquil enough to go unnoticed next to the speaker-rupturing low end. One particularly muted passage finds Tribe leaning towards ambient atmospherics, flipping a sumptuous Grant Green guitar improvisation into a floating, spacy psych segue, replete with trails of heavy echo and sustained keys. Morphing quotations from other artists into parts of a bigger puzzle has allowed Tribe to define their own style, instead of linking their legacy to one artist or movement in particular.

Sidestepping avant-garde jazz in favor of a more fundamental sound, Tribe refurbished a lumbering Mike Richmond bass line into chunky, melodic gold. The resulting track ("Buggin' Out") is gloriously groove-oriented and fixated on its sonorous, obsidian low-end, varying only for bits of contrasting, crisp drum clash and sharply struck high-hat. Stripped of studio-imparted formality and artificiality, the composition pares down the sound to a trinity of words, bass and percussion, striking a distinctly unrestrained space suited for lyrical exploration. Phife thrives in this environment, dishing out scrappy, nuanced banter from the first-person perspective, phrased as punchline or retaliatory exclamation, often in relation to his diminutive stature. Q-Tip is eminently more confident and effortlessly poetic, effusive in his applause of musical expression, black introspection and uplifting positivity. His words are beautifully strung and rife with meaning, likening the catharsis of emotion in his writing to the release of seminal fluid, proliferating a thoughtfulness and imagination in hip-hop that wouldn't succumb to the emptiness of intellectualism or gangster rap nihilism.

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.

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.

48. Mobb Deep - The Infamous

Mobb Deep makes urgent, desperate music. Rarely do they relish the spoils of a life of crime, focusing more on the need to make money at any cost and the danger of getting caught doing it. Their world is a paranoid one, full of snitches copping pleas, police on the prowl and competition lurking in every alley.

They may paint a bleak picture, but Havoc and Prodigy are exceptional storytellers, layering each track with real characters, believable stories and even traces of self-doubt. One of their finest moments is "Up North Trip," an often sad depiction of how jail time affects the inmate and the family they left behind. It's these details that separate Mobb Deep from the bevy of faceless mid-90s "gangsta" rappers.

Their sound even strays from the status quo. Havoc handles the production brilliantly, maintaining a sonic continuity birthed from classic New York jazz and merged with menacing piano loops and a feverish sense of dread. It's to his credit that he crafted a focused piece with so many collaborators (i.e. Q-Tip's guest production, Nas, Ghostface and Raekwon verses), but with a crushing drum track in the forefront on nearly every song, most contributors are forced to coalesce with the beat.

The end result is an authentic slice of Queens crime "fiction." The Infamous is free of cheesy party tracks, pop hooks or moralistic backpedaling. It's completely honest about its intentions and depicts street crime at its most dehumanizing.