The 30 Worst Fall-Offs in Rap History

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.

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