Bridget Kelly

Out of these musicians/businessmen (they've all done an endorsement deal or two, and can certainly sell music)--only one has leapfrogged the demographic boundaries of rap to become, in one cross-cultural, multi-categorical swoop, a living brand. That would be Shawn Carter, known to all--including those fans who've bought 50 million of his recordings--as Jay-Z. His estimated worth: $450 million.