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30. The Jaz feat. Jay-Z, "The Originators" (1990)

At the age of 21, Jay-Z was mostly paying dues, whether sleeping on Big Daddy Kane's tour bus for a chance to spit a verse or two in concert, or slinging drugs in Brooklyn and Trenton, New Jersey. Luckily, his Marcy Projects friend and mentor Jonathan "The Jaz" Burks enjoyed a label deal with EMI. "When Jaz scooped me up from the projects, I was young," he told Blaze magazine in 1998. "I was just his man, and he brought me along for the whole ride." Jay-Z landed cameos on both of the Jaz's albums, including the kitschy minor hit "Hawaiian Sophie." But it's the 1990 single "The Originators," which found the two joining forces on an Afrocentric-themed fast-rap fusillade that hints at Jay-Z's future mastery of a cool, dexterous verbal style. Over a funky James Brown loop, he works a stutter-step flow to punch out rhymes like "Stop fakin ya makin' it, son/I'm breakin' a-breakin' a-breakin' ya tongue/Don't get caught perpetratin' the cool ones."