Rhymefest

After cutting his teeth in the freestyle battle rap circuit—he famously put Eminem to shame in 1997—Rhymefest has built a career around intelligent and witty rhymes without being condescending. Unfortunately, his career appears to have a stalled a bit: His 2006 major-label debut, Blue Collar, was a critical favorite, but commercially it was a non-starter. Rhymefest, to his credit, has lived up to the title of that record in the aftermath of Blue Collar’s lack of success, performing pretty much anywhere that will have him. Last year, Rhymefest, or rather Che Smith, ran for alderman of Chicago’s 20th ward, but lost to incumbent Willie Cochran.

Updated 01/25/2012