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.

47. OutKast - Aquemini

Big Boi and Andre 3000 were dying to expand hip-hop's palette. They saw an opening for a distinctly Southern voice, one that loved Delta blues as much as it loved Detroit soul. A voice that wasn't afraid to show the cowardice of violent crime in an era when most rappers fashioned themselves as Tony Montana wannabes. Most importantly, a voice that was capable of making you think, laugh and shake your ass all at the same time.

Lyrically, both men are capable of nostalgia, whether it be remembering their humble roots or well wishing for a drug-addled childhood pal. This sentimentality seeps into their production, which has the scope of great 70's funk and the lush body that only live instrumentation can provide. George Clinton's influence is obvious, even beyond his readymade guest appearance. It'd be hard to imagine  "SpottieOttieDopaliscious" and its big horns and opening falsetto vocals without Funkadelic's musical thumbprint.

Yet, Aquemini is distinctly OutKast, down to the trademarked speedy, but fluent, vocal delivery and oft-hilarious turn of phrase. Whether comparing the cash game to the culinary arts or giving you a minute to marinate on their double entendres, Big Boi and Dre demand full attention from their audience and a willingness to see beyond the trappings of genre. Luckily, we wouldn't have it any other way.