1. The "Hustler" Stage
Era of Prominence: Late 1980s
It was the 1980s and Jay-Z definitely was dressed like it. The rapper worked with Jaz-O at the time and appeared on tour with Big Daddy Kane. His look? A hi-top fade, four-finger rings, and dookie chains. This clearly isn't the same Jay we know now, but how awesome would it be if he grew a hi-top fade again?