8. Big Daddy Kane
Thanks to songs like "Raw" and "Ain't No Half Steppin", Big Daddy Kane emerged in the late 1980s as one of the leaders of the hip-hop pack, showing off his fast-rapping and his unique fashion style. In the early 90s, Kane was gracious enough to bring Jay-Z on tour and let him show off on stage during costume changes. And while Kane won a Grammy Award in 1991, he was already on a commercial downswing by the time he showed off his "skills" in Playgirl Magazine and Madonna's Sex book; he never got it up again, so to speak.