40. Jean Grae
From: Cape Town, South Africa
Signature Song: Jean Grae "My Story (Please Forgive Me)" (2008)
Enter: Jean Grae. A modern day female rapper who actually raps about the plight of being a woman. Formerly known as What? What?, Jean's career has mostly been defined by false starts. She hit the underground scene in the late '90s, dropped a well-received debut album in 2002, Attack of the Attacking Things, which started building her buzz and getting attention.
Then she teamed up with 9th Wonder and crafted the wonderful, underrated Jeanius. The album leaked on the Internet in 2004 and for whatever reason, Grae went into a hiatus for a few years until the album was officially released in 2008. Her career hasn't improved much since then.
It's too bad because Grae is such a rare talent, armed with an off-kilter flow that always keeps you guessing and the vocal tenacity to shove unbelievable amounts of syllables into a sentence. Plus, she's great at baring her soul. For proof, peep the dark and twisted, "My Story," where she details an abortion, a miscarriage, and a failed suicide attempt.