10. Lupe Fiasco
If I’m introducing a reluctant friend to hip-hop, Lupe Fiasco is my go-to. The man has so many styles while remaining accessible and has a razor-sharp flow that never slips out of pocket. He can switch up cadences like no other, and his catalogue shines because of it. Lu can make bangers, conscious ballads, tracks about skating and everything in between. His angles on life and society combined with his insane writing ability make his catalogue a trip to dive into.
Lupe’s 2006 debut album Lupe Fiasco’s Food & Liquor took a look at his hometown of Chicago in a way that explored new territory. He examined the thrills and ills of his city as a sort of prophetic fly on the wall. His calculated schemes and crazy wordplay are smooth on the surface but take many listens to get into. A real MC’s MC, Lupe takes spot number 12.
9. Talib Kweli
Talib Kweli embodies the underground. Although he’s stayed out of the spotlight for the most part, Talib has been quietly killing it outside of the mainstream, paving the way for many conscious rappers to get shine.
The Brooklyn MC has a quick, steady flow; a waterfall of ideas and articulate imagery that feeds into a deep pool of low-key classics from over the years. His collaboration with Mos Def for their 1998 love letter to hip-hop Black Star is an absolute must-listen for anyone getting into underground rap. The two feed off of each other’s flows for an unstoppable lyrical force.
When Talib hops on tracks with more mainstream artists he always brings it. Talib’s feature on Kanye West’s song “Get ‘Em High” brought Kanye fans from the underground before he was known, and Talib still arguably killed ‘Ye on his own track.