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.

33. Boogie Down Productions - Criminal Minded

To call Criminal Minded trendsetting would be a grave understatement. Not only did it bring street crime into the conversation, it merged the bass-heavy tones of Jamaican dub with New York City hip-hop, made disrespecting your contemporaries a sport and provided a frame of reference for the socially conscious rap to come.

Though the debate over hip-hop's birthplace is far from an underlying theme, Bronx's own Boogie Down Productions endlessly lobby for the title of rap's first and finest. Focusing his energy on besmirching the clumsy writing and stale production of the en vogue Queens figureheads, sole vocalist KRS-One brilliantly illuminates the power of creative thinking and socio-political brainstorming. Often affecting a playful growl or menacing patois, KRS stresses the importance of acquiring knowledge at his most serious and goofs on crackheads and DJ Scott La Rock's promiscuity at his most whimsical. His style focuses on a potent conveyance of rhyming words. That's not to say that his songwriting is basic, he's just perfected simplicity, which is much harder than hiding flaws in forced complexity.

The production follows suit, concentrating on high-pitched funk breaks, fragmented bits of James Brown's vocal wail and Scott La Rock's accelerated turntable work. Though uncomplicated by modern standards, it's suitable for the commanding thrust of KRS' voice, adding an authoritative drum blast on diss tracks and a bassy synthesizer to their reggae-leaning crime anecdotes. It's a sound that packs confidence far beyond their years, reflected in the effortless genre hopping and tonal shifts. Additional studio work provided by Ced Gee (of Ultramagnetic MCs) may be responsible for some of the manic energy, but the duo's ability to play off each other is the record's strongest virtue.

This partnership is well advertised on the title track, which opens with a jovial "Hey Jude" interpolation, followed in striking contrast by one of the most ferocious displays of linguistic power ever put on record. "Criminal Minded, you've been blinded, lookin' for a style like mine, you can't find it" is the crushing opening statement; so simple in its delivery, but so profoundly expressed. KRS' rhythmic verbal composition is backed by a powerful synth thud, high-stepping drum beat, disembodied moans and spastically disassembled horn samples.

What could have been a chaotic mash of opposing sonic elements and themes is reigned in by the scholarly intonation of KRS-One, a dauntless MC capable of verbal malevolence to his subordinates without sacrificing positivity or the desire to elucidate the power of poetry. His pairing with Scott La Rock is at once effortless and boundlessly exciting, marred only by the fact that Scott's untimely death would make it their only collaboration.
 

49. Big Daddy Kane - Long Live The Kane

Big Daddy Kane's voice is deep without being gruff. He's always in command of his prose, never stumbling over words or pausing for a deep breath. He's capable of being funny, suave and serious all in the same verse, never overstuffing his bars with an unnecessary syllable. His 1988 debut, Long Live The Kane, is a superb documentation of his ability as an MC.

Super-producer Marley Marl recognized Kane's speed and precision and matched it sonically. Whiplash James Brown samples, cymbal-heavy drum loops and lightning-fast turntable work compliment Kane at every turn. They even accompany him on the R&B loverman oddity, "The Day You're Mine," which feels out of place in '88, but would saturate BDK's later releases.

The pinnacle of this collaboration is "Ain't No Half Steppin'," a contender for the best single display of rhyming ever recorded. It's an endlessly quotable paean to Kane's ability to demolish the competition, layered over smooth piano and a Billy Squire drum beat. BDK effortlessly moves from slow, molasses smooth vocals to a syncopated, choppy fast flow. Despite shifts in speed and tone, he always goes out of his way to annunciate, even noting that he speaks "clearly so you can understand."

Rappers understood all right. It's hard to pick out an important MC of the past 25 years who hasn't stolen a page from Kane's rhyme book, whether that be emulating his flow or heavily sampling his archetypal lyrics.