425. Bobby Brown
Although he is a punch line for how to screw up a career (and Whitney Houston’s for that matter) Bobby Brown was the master of the New Jack Swing movement and for a time he was easily the biggest R&B star on the planet. Bobby Brown’s slick produced sound was copycatted across radio station across America. He attracted the women without alienating the men and he could move from danceable R&B to crooning ballads to thuggish Rap with ease. Bobby Brown’s career unraveled in the mid 90’s with weaker music and constant problems with the law where he would become a reality show joke (on a good day) in the decade that followed.