Lupe Fiasco

Back in 2005, Kanye West asked Chicago rapper Lupe Fiasco to contribute a guest spot on his album, Late Registration. That song was called “Touch The Sky,” and it gave Fiasco a chance to do just that: to succeed commercially while flexing his creative muscles in some pretty unusual ways. A 2007 concept album called The Cool was as tangled and opaque as they come—it had something to do with characters called The Cool, The Game, and The Streets, and it didn’t really make sense—but it furthered Fiasco’s reputation as a sharp-tongued and deeply thoughtful MC, capable of taking an outsider’s stance on his scene while remaining a consummate insider. The 30-year-old mentioned a couple of years ago that he would be retiring after his third album, Lasers; it dropped in March 2011, though, and a sequel to Fiasco’s debut, Food And Liquor, is reportedly due later this year, so take that as you will.

Updated 05/10/2012