151 Jay-Z Jay-Z Although the late Biggie Smalls used to joke about going from "ashy to classy," his Brooklyn partner-in-rhyme, Jay-Z, would best embody that shift in style and station. Jay's recording debut, however, was anything but auspicious, spitting a well-constructed yet unremarkable verse on 1993's " Can I Get Open? " by Original Flavor, a group that featured Big Jaz, Jay's mentor in rhyme. At the time, Jay was a small-time hustler trying to make ends meet; "Open" gave him the boost he needed to begin working on his debut album, Reasonable Doubt . After shopping it to every major label record company with no success, Jay and his business partner, Damon Dash, decided to form their own label, Rec-A-Fella Record s, a move that would eventually make them very rich men. To this day, Reasonable stands as one of rap music's essential albums, not to mention one of the greatest debuts. Like Biggie's Ready to Die , released two years ...