9. Lupe Fiasco – The Cool
Once upon a time Lupe Fiasco was the Next Big Thing in "conscious" hip-hop. Immediately after The Cool dropped, an air of excitement just followed the man around -- much like the one that surrounded Kanye West after the release of The College Dropout. Except Lupe's lyrics were smarter, his attitude was more nuanced, his rhymes were both quicker and wittier. And for one album, he bested his colleague's theatricality.
There's no shortage of Faust retellings in pop culture (in fact there's another in this list), but Lupe's interpretation mixes in equal parts allegory and autobiography. Lupe's characters in The Cool all strive for greatness, and face a choice between different sorts of good and evil. Lupe becomes every aspiring rapper that has ever been or will be, and along the way writes some of his most heartfelt numbers; "Hip Hop Saved My Life" is so earnest that any lesser emcee would make it laughable. But the finest moments on The Cool come when Lupe goes bad. His stint as a mafioso cheeseburger in "Gotta Eat" stands out, as does his ice-cold Mephistopheles in "Put You On Game."
A staged version of The Cool could be as past-meets-present as its premise. Its multifaceted exploration of urban culture is reminiscent of Rent and Moving Out. Lupe's large cadre of male and female guest singers opens up diverse cast options. Many arrangements on The Cool sport lush string sections as well as big electric beats. This adaptation could even be a smart career option for Lupe if Food And Liquor II fails as a return to form.