Album: Reasonable Doubt

After the success of his street single "Dead Presidents," Jay proved he could make a radio hit with "Ain't No Nigga." While navigating the underground under the wings of Jaz-O and Big Daddy Kane, Jigga and friends were funneling drug money into a record label, paying producers and contributors with sneaker boxes full of cash to get their indie label off the ground. They eventually made a partnership with Def Jam. With a powerhouse label now behind him, Jay started sowing the seeds to his empire. His new label pushed the single by placing it on Eddie Murphey's Nutty Professor soundtrack. This helped Jay's second single take over video channels and the radio, and introduced the world to an 18-year-old rapper named Foxy Brown. Both blew up after this track and was the start of beautiful musical relationship; Jay and Fox were Def Jam's answer to Bad Boy's Biggie and Lil Kim. —Angel Diaz