24. Grand Daddy IU, Smooth Assassin (1990)
Label: Cold Chllin'/Reprise/Warner Brothers
Golden Era rap label Cold Chillin’ Records was generally associated with Queens and the Juice Crew but Tyrone “Fly Ty” Williams’ imprint had other acts, too. A product of gritty Hempstead (hometown of Prodigy, and the birthplace of Method Man), the dapper, baritone-voiced Grand Daddy I.U. had a pair of minor, R&B-flavored hits with “Something New” and “Sugar Free" but Smooth Assassin tracks like "Nobody Move" and "Behind Bars" showed that Strong Island MCs could get just as gully as their city peers. And to think, this project almost never happened! When album producer Biz Markie initially called I.U., the rapper thought he was bluffing and brought baseball bats to their meeting before wising up.