1. Kenneth "Supreme" McGriff
Nas: "I fell in love with all that poetry, I mastered that/Cutting school with Preme team" (" The Don")
50: "When you hear talk of the Southside, you hear talk of the Team/See, niggas feared Prince and respected Preme"
McGriff, the head of the powerful Supreme Team drug gang (his nephew Gerald "Prince" Miller was also a high-up), was so ballerific that, in his late-1980's heyday, his team was making $200,000 a day. After being in and out of jail during the late 1980's and 1990's, he managed to get back into trouble for a 2001 murder and is now serving a life sentence. It is also rumored that he was involved in the shooting of 50 Cent (over the very song we're quoting in this piece!) and the murder of Run-DMC's Jam Master Jay, who was mentoring 50 at the time.