#7 - Lupe Fiasco
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.