Jay followed very closely by 50 cent and Master P.I'll chose Jay though.
Jay,because even if you ignore the first 26 years of his life and forget that he's from Marcy and a former drug dealer, and you set the cut off mark as 1995, he went from being Big L's sidekick in a freestyle in 95 to co-starring in an hour long business interview with Warren Bufett. He has basically lived 2 different lifetimes in his music career alone: 1995-2003 and then everything after that.
50 cent, because this nikka was almost (literally) dead and buried, if he had stayed in the streets for another year or two he might have been killed. Eminem and Dre literally saved dude's life and what's more, he was able to make a couple of 100 million after all that.
Master P a close third, a nikka from the south that built his empire from one record store he setup in an era where music was still heavily dominated by the east and west.
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