22. KRS-One
KRS-One was a pioneer of multiple sub-genres within the overarching genre of rap. The Bronx native was beyond ‘woke’ when factoring in the generation he came from. A poet with words and a brilliant guy when it came to comprehending the pulse of the nation, KRS-One often rapped intelligently. His breadth as a performer was quite impressive, and thus there’s no doubt he’s an all-timer.
Image Source: Village Voice