Born: In 1976 in Cape Town, South Africa (before relocating to New York as a child)

Sounds like: A female version of Talib Kweli or Masta Ace—but funnier than either of them. 

For fans of: Little Brother, Blackstar…sample-based underground hip-hop. 

Latest release: Cookies or Comas, a DJ Drama-assisted mixtape full of brag raps and thought-provoking concept tracks that serves as the predecessor to her forthcoming full-length. 

Why you care: Because Jean Grae has had a rough go in the music biz. Every time she seems poised to make a dent, kryptonite hinders the superwoman MC from saving the world. Album leaks, label politics and disenchantment with the industry—Grae has been through it all. She even said goodbye to her fans in 2008, retiring only to come back a few months later. The road has been long and full of detours for Grae—who has held her own alongside acclaimed hip-hop heavyweights like Atmosphere and Mos Def—and even more difficult for her fans, who have watched her tiptoe the fine line between hip-hop prominence and obscurity for over a decade now. But Grae's still a captivating talent on the microphone—from hard-hitting bravado raps to witty and playful jabs at others, and even heartfelt, brutally honest love songs. The world-savvy MC has persuaded some to brand her not only as the best female rapper of her era, but as one of the most talented MCs in the history of underground hip-hop. 

SEE IT: Jean Grae plays the Crown Room on Saturday, Sept. 10, with Mr. Len, Philly's Phunkestra and DJ Zimmie. 9:30 pm. $5. 21+.