One of the few rappers on this list you should already probably be aware of on this list, Andre 3000, rapper from the critically acclaimed and incredibly popular Hip-Hop Duo, “OutKast,” is one of the most well liked and respected rappers in the industry from non-fans. And for good reason too; while his slang-heavy southern dialect may turn some listeners away, he has expressed untold ability to use language to paint beautiful pictures and make poignant statements, and he remains a wonderful story-teller. As his group progressed with its music, Andre 3000 became increasingly cerebral in his raps, often dipping into abstract lyricism and existentialism, and his unconventional use of language began to become more metaphorical than ever, making the average listener listen twice before continuing to groove out and have fun. Indeed, Andre’s penchant for funk and “prince-esque” musical production led many to know him for his catchy and funky, non-rap single, “Hey Ya!” however he will always be remembered by those original fans as a master emcee and powerful poet. Check him out on the first verse in this link.
Slug, from his Producer and Emcee duo Atmosphere, has become, over the years, the poster boy for Underground Hip Hop. He blends spoken word poetry with good ol’ fashioned rapping to create something that, in its early years, was an unusual but powerful combination of straight-forward honesty and abstract expression. In his later years he has moved on to telling sad, everyday life stories from a universal perspective in his continual journey to explore the human psyche. However, I found his raps most unpredictable and artistic back in the days when he was simply just trying to explore his own psyche. Slug takes us on a painful, cathartic, and often times humorous journey through the caverns of his own mind, just trying to find out who he is, justifying it, apologizing for it, and eventually accepting himself.
Kool Keith paved the way for a lot of oddball rappers succeeding him. His lyrics were strange, oddly literate, always vulgar, and occasionally his free associative style dipped into the just plain nonsensical. And yet, he was always captivating, and he was unique and still is. Often times when listening to his tracks you could just imagine the grin on Kool Keith’s face; the man *loved* to play with language, and occasionally you would catch the obscure pun in rhymes and at others his frustratingly abstract yet crude style managed to be beautiful before resuming repulsive once again. Certainly Hip-Hop’s most peculiar export, Kool Keith also proved, from his lyricism, to be the most intelligent. *NOTE: Kook Keith rapped under many other pseudonyms, in the below link he went under the name of Dr. Octagon.
Probably the last entry on this list that the average reader will have heard of, Lupe Fiasco is an extremely popular artist despite having some of the most deeply multi-layered lyrics the genre has ever seen. Normally I would see this as a positive thing for the industry, however his last album was a terrible, pandering piece of work thanks to people working at the label (I’m not a guy who rails against mainstream evil hampering artistic integrity or even like other people who spew such things, but in this case I was very angered). That last tidbit aside, however, his previous work was glorious. He always had a socially responsible message in his agenda, but his rhymes were more than that. He would paint beautiful, detailed pictures, often times listening to him provided an experience akin to lucid dreaming, the way he delivered his fantastical lines in his trademark laid back manner. Yet, his lyrics were not just free-associative “mush,” he always rapped with substance, often times just one couplet would offer three different meaning simultaneously, and yet his command of language never allowed the listener to be overwhelmed or frustrated. Even if you did not always know what he meant you always felt it. And damn… the man had a way with words.
From Eyedea & Abilities
It is one of my great regrets in life is that I never saw this man perform live before he passed away, just recently. Eyedea was a formidable wordsmith, whose notoriously witty freestyling abilities made him the most feared opponent to be opposite of in a battle rap. And yet, it was in his actual songs where his true achievements lay. Collaborating with DJ Abilities (who, by the way, would easily make any top ten DJ’s list) he rapped about philosophical themes such as existentialism and social economics, and he was able to maintain a narrative through the use of extremely clever use of words. Indeed his style of rapping caught many of the uninitiated off guard but attracted a committed following from those who dedicated their time to truly listening. While he may tragically no longer be with us, his words will remain immortalized.
Back in the mid nineties El-P formed the group, Company Flow, which would introduce to the world his self-coined “independent as fuck” music which would single-handedly reform the underground Hip-Hop movement with its sparse, dangerously witty, intelligent rhymes and production, which was all coated with an attitude so fierce it would outmatch early nineties “gangsta rap” in terms of intensity. Not that the two were ever compared before, nor did they ever detail excessively graphic violence in his rhymes (which would not make them any worse if it did, I am not biased against violent rap) but he always spoke with such defiance and pride, as well as with cynicism that would freeze the heart of a divine angel. Even far into his solo career, long after he founded one of the most well respected underground Hip-Hop labels, Definitive Jux (which is only matched by Atmosphere’s Rhymesayers), El-P would never bother making his music the slightest bit accessible. His lyricism was always abstract and intense, and he always rapped in a manner which would make one think he was aware of some vague, impending apocalypse, however science fiction buffs would appreciate his references and those willing to dig deeper might be surprised by the preconceived nature of his symbolism. Sometimes it seemed El-P was more interested in attacking the listener than anything else, but to his benefit, after several listens, El-P would provide an extremely deep listening experience to those who took the time to give him the time of day.
Sage Francis is an asshole, there is little doubt about that, which is why so many people have taken to hating him. However there is also little doubt that Sage Francis could go for the rest of his life winning every poetry slam he damn well pleases, making people sound like idiots because he has the intelligence and cruel wit to do so, and overall feeding his ego with delusions of being the self-tortured artist. But he doesn’t. Sage Francis instead chooses to continue make music in a genre where he will never have an audience, and yet still attracts fans, and makes records that are so deep, so haunting, and so achingly nihilistic that his music forms a deep connection with anyone who dares listen to it. And the man is so witty, he makes plays with language, takes popular phrases and abuses them, twists them and reveals them to be nothing in the first place. There is a deep rooted respect I have for the man, as big of a self-proclaimed “asshole” as he may be.
To be fair, Saul Williams was a noted and well-decorated poet before he went into Hip-Hop. However, his output as a “rapper” has given the genre some of its most thought provoking material yet. He always had an agenda far more political and ambitious than just personal poetry could provide, but his artful use of words and the sheer force he could muster provided a cathartic listening experience. Ever since allowing himself to become a part of Hip-Hop, he had forever changed how people percieved it and blurred the lines between poetry and rap to the point where people can honestly argue that rap has the potential to be true poetry without having to put up too much of a battle.
Hip-Hop’s true intellectual, one wishes that he wasn’t as damn obscure as he currently is and (unfortunately) probably always will be. I suppose some would write him off as pretentious, but I only have two friends who actually know of him and we all love him. His language is so detailed and precise, yet unusual. It takes a true master of the language to use words in the manner that he does, and his diction is (nearly) unparalleled. Not that using big words automatically makes you an intelligent rapper, but if you can make a rhyme sound as pretty as he does you would automatically go down in history. He can rap about something so simple and mundane and yet find deep meaning from within it, he can tackle topics so broad, ask questions so big, it is nearly frightening in the ways he provides answers. He references everything from Shakespeare to religious doctrine to famous scientific proceedings. I do not have the vocabulary that Illogic has, so I will use this adjective once again, his lyrics are so god damn pretty. Like on online commenter said better than I could ever, “It’s like HDTV to the ears.” Illogic one of those ever rare, ever valuable gems that you will occasionally stumble across in music.
This artist rides the line of you either heard of him or you know all about him just as much as he draws between those who passionately love him and those who passionately hate him. Meet Aesop Rock, the most intelligent rapper to have ever lived. Well, first meet the large amount of dismissive people and confounded critics who will tell you he is nonsensical and sounds like he is reading a dictionary because -obviously- anything they don’t understand must not make any sense. Actually, the most frustrating thing about Aesop Rock is that he is rarely ever, probably never, nonsensical. His lyrics are so intricately detailed that after the first line is spit it is not uncommon to be completely lost. And his abstract use of language doesn’t help either, he alway does away with placing words in linear order, and often times uses words as he intends for them to mean, not how it was originally intended to be heard. And it would take all of the internet’s resources to follow each one of his references, whether it be an ancient Greek tragedy or an episode of Dragon Ball Z.
Overwhelmed? Don’t be. He is not as intimidating as I may be describing him to be, oftentimes I have no idea what he is talking about and yet the images that he paints and the way in which says them still leave a strong emotional response. He adopts an abstract (I fear I have been abusing that word much too much over the course of this list) and fractured manner of phrasing, that all contributes to one general theme which can range from a grounded examination of twenty first century Americans or can be more off the edge like an existential contemplation on the nature of human’s disillusionment with the imagined forces that be. Do not try to decipher all the lyrics in one of his songs at once as that can be as frustrating as wading through Joyce’s “Ulysses” or as futile as attempting read “Finnegans Wake” cover to cover. But whenever something clicks, and the meaning to one of his lines unlocks its meaning it can be the most satisfying experiences possible to reap from any art form.
And yet somehow, even with all of this, he can still manage to make his lyrics sound natural and unpretentious. It is hard for listeners to convince themselves that his work is not somehow genuine, which is possibly his greatest achievement of all. Aesop Rock will probably be remembered in a more significant stature than the genre itself when it is all said and done, even if for now he will only play to a smaller, niche market. In honor of his stature at number one, I’m providing three examples, however the first one is probably the most definitive of his body of work and best starting point for new listeners, check the other two out afterwards if still interested.