20. Madvillain - Madvillainy

Perfectly marrying the sophisticated with the peculiar, Madvillainy is 22 disparate snapshots, completely stripped of mainstream rap's pop sensibilities and obsession with hooks and freed to be willfully obscure, off-the-cuff and hysterical. Super groups rarely succeed, let alone eclipse previous individual achievements, but pairing Madlib's capacity for regenerating the grooviest relics of jazz past and MF Doom's impossibly sophisticated, stream-of-consciousness jabberwocky was a stroke of genius, birthing a work beyond genre, song structure and conventional wisdom.

Vocalist and cover model MF Doom rhymes with a deep, stoned growl, working his tongue and lungs to capacity, all in the name of coughing up dense, symbol-laden, lyrical poetry. His verses are pop culture at its most arcane, showcasing a man obsessed with junk food, syndicated space operas and creamy clouds of marijuana smoke. His vocal ebb and flow can be rather entrancing, which slightly distracts from the complex use of simile and double entendre, demanding repeat listens and even note taking from his ever-growing army of disciples. Verbal trickery is the name of the game on "Money Folder," where he claims to have penned the rhyme after downing a few "Heines," only to reveal moments later that he was referencing warm derrieres and not cold beers. Gambits like this occur endlessly, often multiple times in a single verse, showcasing an author capable of constructing an extremely intricate narrative and demanding enough to expect listeners to keep up with his manic pace and rapier wit.

"Curls" intends to slow Doom's roll, opening on the low tinkle of steel drum, pulled back in the mix slightly as to not overshadow muted guitar strum and gently scraped hand percussion. Doom deliberately harnesses his flow, exposing the crackle in his smoke-damaged throat, but never stumbling over a syllable or gasping for air. His uncommon gift for phrasing shines radiantly, mutating banalities about money-grubbing women into an eloquent game of near-rhyme hopscotch ("reckless nekkid girls get necklaces and pearls"). It's exhilarating to hear his verbal ingenuity, particularly when classing up well-worn cliches, ranging from the joy of financial frivolity to the perilous life of the young hustler. This supposed "coming-up" story revels in absurd exaggeration, so implausible that it appears Doom's having a laugh at his peers' expense, mocking their eternal quest for authenticity. His farcical tales of toddler battle rapping and second-grade smoke-outs are accompanied by eerie Gothic organ and intermittent electro drum kick, camping up an already cartoonish anecdote.

Madlib gives the entire LP a sense of knowing mischief, rudely throwing seemingly incongruous pieces of jazz, soul and 60's ephemera at the wall, never giving a damn if any individual piece sticks. Somehow, amid the sound and fury, wavering from speaker to speaker, is a disorienting and brilliant piece of Musique concerte, constructed from thousands of lulling, symbiotic sound puzzles. Dashes of maraca and robust bass marinate with old-world accordion, book ended by superhero clips and bizarre B-movie sound effects, all corrupted and rearranged by constant breaks in tone and shifts in focus. Familiar elements are tossed in via bubbling bong rips and funk riff strut, acting as a buoy to the listener, forever drowning in a sea of details. This sense of security is temporary, washed away in a flood of half-audible cackling and faded dub scraps.

The elements are tightly packed, never showing their patchwork or revealing a formula, orchestrated with a surgical, almost inhuman, focus. Yet, this is not de rigeur studio product, but free-form experimentation, built around two friends sharing a laugh while pugnaciously stripping away two decades of perpetually-recycled genre convention. Rarely do inside jokes brim with such versatility, personality and boundless enthusiasm.

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.