40. Del the Funky Homosapien - I Wish My Brother George Was Here

Teren Delvon Jones defies categorization.

He's not a gangster rapper, despite his zip code and family ties. He's too contrary and antagonistic to fit in with the Native Tongues Posse. His affection for George Clinton makes for ass-shaking grooves, but don't dare ask him to dance. He'll point fingers at mainstream, derivative rappers ("crumbsnatchers"), but will never revert to violence or jealousy. If only one thing is certain on I Wish My Brother George Was Here, it's that Del the Funky Homosapien is completely content being himself.

Despite barely being out of high school, Del's storytelling flows organically, stressing his passion for authenticity and capacity for internal rhyme and playful alliteration. Words roll off of his tongue in an eloquent, nonchalant Californian sway, with punch lines delivered through delicate shifts in vocal tone.

Much like his cousin and production partner, Ice Cube, Del is a laconic orator, explicating complex ideas in an economical fashion. He's even capable of allowing counterpoints to his more controversial opinions, particularly on "Dark Skin Girls," where he chides light-skinned women for their superficiality, despite Cube's call for impartiality.

That isn't the only moment Ice Cube makes his opinion heard. With the help of DJ Pooh, he immerses every track in subwoofer-destroying bass, synthed-out organ and flirtatious female choruses, birthing a sound that wasn't chic in 1991, but would become the establishment by 1993. The result is a pacifist's G-funk album, free of the hedonistically violent dialogue that would eventually swallow up the sub-genre.

"Sunny Meadows" is the antithesis of G-funk to come, providing Del with a base of smoked-out saxophone and gently-strummed guitar to wax poetic about while scrawling in his notebook at the park and languishing for a more pastoral life. His thoughtful discourse seems better suited for the genre than most of those who followed, but we can't expect them to have such a singular vision. His is a stridently particular viewpoint that can't be strapped down to a genre, crowd or status quo.

41. Company Flow - Funcrusher Plus

Company Flow's labyrinthine lyrical content is so rich, listening closely and at high volume is a necessity.

Polysyllabic words are thrown out at high speeds, referencing everything from obscure sci-fi literature to outsider politics to popular music's lack of integrity. El-P and Bigg Jus stand firmly as opposition to the superficial, playing contrarian to the sacred cows of radio rap by packing every verse with as much abstruse substance as possible. Hell, even when they say nothing, "it's a beautiful use of negative space."

Musically, El-P's multi-layered, low-tech soundscapes are just as mysterious, evoking dense, static-laden field recordings. Eerie, distant piano, horn and sitar are juxtaposed by glitchy and skittish digital blips, disconcerting film clips and water-logged echo. A tone of paranoia cloaks every track like a veil, making for an unsettling, but unified sonic experience.

The culmination of lyrical and musical ingenuity is also the most personal. "Last Good Sleep" is El-P's harrowing portrait of domestic hell, depicting a frightened child whose adulthood is haunted by an abusive stepfather. Film noir horn, jarring tonal loops and ominous "'til the day I die" choral snippets speak volumes about the haunting terror that is the human memory.

The lasting impact of a violent household may seem like serious subject matter for self-financed musicians, but Funcrusher Plus is no tempest in a teacup. This is a full-fledged masterpiece, responsible for expanding hip-hop's umbrella to allow high-concept, introspective and esoteric work.

42. Prince Paul - A Prince Among Thieves

As the unofficial fourth member of De La Soul, production wizard and pioneering sampler Prince Paul invented the hip-hop sketch, cracking wise in carefully placed 20-second blasts of childish glee. Paul and De La's skits were delightful confections, fitting perfectly between songs and rarely overstaying their welcome. Sadly, their passion for play acting would inspire every half-wit to fill their lackluster LP with lame boasts and absurd sexual escapades.

Despite the over-saturation of rap record fluff, Paul would try to reinvigorate the concept with a 70-minute skit about an up-and-coming MC who enters the world of crime in order to finance his demo. It's a brilliant story that holds a mirror up to the current state of hip-hop, impolitely skewering late 90's clichés.

Leading the ensemble cast is Breezly Brewin', a deft vocalist and likeable narrator capable of showing a range of emotions while effortlessly rolling out the lyrical tongue twisters. His counterpart, Big Sha, takes on a grimier, baritone flow, which allows for two distinct opposing viewpoints. Guest appearances range from the bizarre (Kool Keith) to the menacing (Everlast), with each reflecting a specific hip-hop persona amplified to a point between sincerity and parody. It's no small feat that Paul's sonic composition also delicately walks this line.

At its most serious, the production takes on a cinematic air of suspense, layered with strings, subtle guitar loops and heavy-duty bass, particularly effective on "Other Line" and the bitingly ironic title track. Yet, a certain playful whimsy permeates "Steady Slobbin'," which repurposes Ice Cube's ode to gang violence as a snickering dirty joke, basking in its own degeneracy. These moments of levity make a potentially self-indulgent project feel complex and imperative.

Ultimately, A Prince Among Thieves is both loving tribute and discerning satire, so spirited in its execution and earnest in its delivery that one can forget every bloated concept album released before it. Its enthusiasm and narrative drive are infectious, particularly due to the collage of quirky, danceable beats that have cemented Prince Paul as one of contemporary music's finest producers.

43. N.W.A - Straight Outta Compton

"Life ain't nothin' but bitches and money."

With that fateful line, Ice Cube and his partners in crime (Dr. Dre, DJ Yella, Eazy-E and MC Ren) beget 1,000 impostors. Their crime-obsessed, profanity fueled, lyrical Molotov cocktails would enrage parents, provoke the government and influence the masses, so much so that the sub-genre of hip-hop they actualized would become status quo.

Yet, they've still managed to separate themselves from their offspring nearly 25 years since the release of their seminal debut. It's not that the subject matter or production style is any different or more complex, but that the creators were more inspired. Beneath their front as provocateurs, they were actually diligent craftsman, capable of building narrative and diversifying their sound to broaden influence. They also wisely never hid from a little bad press, wearing their troublemaker persona as a badge of honor.

Cube was the most outspoken of this group of agitators; brazen, hostile and chauvinistic. He'd be easy to pass off as brutish enfant terrible, if he wasn't skillfully crafting compelling characters. With Eazy-E, he constructed a devilish anti-hero, both comedic and carnal, packing a drunken bravado that matched his high-pitched vocal wail. "8 Ball (Remix)" is their collaborative apex, bringing the smart-ass rebelliousness of Licensed to Ill and Van Halen to the streets of South Central.

These incendiary voices are backed by low-tech 808 clash and bass line thump, buoyed by skittish horn and guitar that wouldn't be out of place in a Blaxploitation montage. Despite the relatively primitive construction, the conceptual aspects of Dre and Yella's production are quite brilliant. Each track is built to fit a certain niche, whether that be rallying cry ("Gangsta Gangsta"), club jam ("Something 2 Dance 2") or, dare I say, sanitized inspirational anthem ("Express Yourself"). They're casting a wide net in hopes of attracting multiple demographics, possibly to counter any controversy inspired by aberrant and anti-social lyrics.

Ultimately, Straight Outta Compton benefits more from this pop sensibility than its sensationalism. Emotionless violence is a hard pill to swallow, but N.W.A manage to temper it with enough smirking and song craft to make us forget... if just for a moment.

44. Black Star - Mos Def & Talib Kweli Are Black Star

Mos Def and Talib Kweli want to advance hip-hop. They've seen what the genre can be, taken the pieces worth saving and left the materialism and violence behind. Their mission is to promote black culture without leaning on hypocrisy or stereotype. As Black Star, they attempt to redefine the genre they love before it fades from glory into a tired cliche.

Sonically, Black Star traffics in the jazz and hip-hop of New York's past, deeply inspired by Gil Scott Heron's soulful spoken word and KRS-One's outspoken politics. Thankfully, they temper their austere influences with a spirited verbal interplay that can be unbelievably quick-witted, meticulous and jocular.

The storytelling is evocative, utilizing vivid imagery that seems more at place on the page than the turntable. Tongue twisters abound, as both MCs strive to fill each bar with as much meaning as possible, yet they never sound winded or over stuff their verses. These vocal calisthenics are admirable, particularly when expressing complex themes like martyrdom, record label tyranny, inferiority complexes and social stratification.

"Thieves in the Night" takes on these matters brilliantly, chiding pity and striving for individualism, despite the fact that "captors own the masters" to everything Black Star writes. They understand that, as musicians, they'll have to cooperate with the record industry, but that doesn't impede their goal, which is to go beyond music as entertainment and expose society's hypocrisy. It's a noble and thoughtful effort that would sound highfalutin if its spokesmen weren't so ardent and astute. 

45. Ultramagnetic MCs - Critical Beatdown

As described in Paul Edwards' How to Rap, rapping, in its simplest terms, is a blend of content, flow and delivery. Basically, a musician would construct a rhyming poem detailing their emotions, which would then be conveyed through their vocal cadences.

Ultramagnetic MCs, led by chief lyricist, Kool Keith and part-time rapper/full-time producer, Ced-Gee, intentionally disrupted their content, flow and delivery, much like free jazz disrupted chord changes and tempo. What came from this break with conformity was both danceable and droll, a fully unique creation born from the deconstructed elements of hip-hop.

Kool Keith's odd delivery is like an off-kilter game of word association. As he barrels through verses at breakneck speed, he defames opposing MCs like a vivisectionist, chopping heads and dissecting bodies. He fashions himself a mad scientist, and he might be right, since his syncopated delivery and schlocky lyrical content may have given life to the gory absurdity of horrorcore and the abstract spaciness that would shape rappers like Del the Funky Homosapien and El-P.

Keith's partner-in-crime, Ced-Gee, produces the record with a similarly skewed vision. As chaotic as the Bomb Squad, Gee layers each track with tinnitus-inducing vocal squeals, hyper-kinetic samples and skittish record scratching. His take on funk has more in common with the "chopped and screwed" mixtape movement than Sly Stone, since an organ blip or random synth beat can explode out of nowhere and repeat endlessly, giving the LP an almost nervous energy.

It's this verve and sense of adventure that have made Critical Beatdown so timeless. Kool Keith and Ced-Gee purposely tried to subvert hip-hop cliché and reconstruct its language and sound. What they actualized was made of hip-hop's puzzle pieces, but alien in its construct and presentation.

46. The Pharcyde - Bizarre Ride II the Pharcyde

A Bizarre Ride indeed.

The Pharcyde's debut is a cartoonish collage of mischief, unabashed libido and comically high-pitched vocal delivery. Interested more in making their audience smirk than inflating their egos, Fat Lip and company playfully walk the line between funny and over-the-top obscene, never to be taken to seriously, unless they're ridiculing your mother or hawking your girlfriend.

Sonically, J-Swift's lively production is forward thinking, while still digging deeply into the hip-hop and jazz that came before. Piano samples and celebratory horn point towards John Coltrane and ATCQ as reference points, but those boisterously shouted group choruses make me think Black Flag might have snuck onto the tape deck during group smoke sessions. Luckily, a little weed didn't distract from the goal, which was to gently rib sell outs and make dirty jokes.

Their most successful joke is "Officer," a hysterical take on Public Enemy's "Black Steel in the Hour of Chaos," transferring indignation concerning the American military and penal system to the palpable West Coast equivalent, the Department of Motor Vehicles. I know, it's rather irreverent, but civil unrest needed to be reflected through their unified voice, even if it is in relation to parking tickets.

Bizarre Ride's greatest feat is its depiction of that singular viewpoint. The Pharcyde are secure enough with themselves to be goofballs, skewering the cliché that rappers are infallible supermen. They smoke too much weed, get their licenses suspended and can't seem to pull the cutest girl in school. It's this relatability that makes them so compelling.