42. Playa Fly
From: Memphis, TN
Signature Song: Playa Fly "Nobody Needs Nobody" (1998)
Memphis legend Playa Fly has been rapping in the city's underground scene for going on two decades. He made a name for himself in the early '90s but his career seemingly took off when he got with Three 6 Mafia. Unfortunately, after recording one album with the group, he had a falling out with them because...well it's Three 6 Mafia, and they always have a falling out with new members. (Crunchy Black, anyone?) Despite that, Fly went on to record more material and release a series of albums (he also had a memorable diss record called "Triple Bitch Mafia"), but he remained an underground sensation and never got national exposure on the level of Juicy J and DJ Paul.