42. Jay-Z, Reasonable Doubt (1996)

Art Direction: Cey Adams
Photographer: Jonathan Mannion
Label: Roc-A-Fella/Priority

Like Too $hort before him, Jay's debut cover wisely shifted focus from himself to a simple outline of the character he created. We didn't have to see his face. The tilted brim and half-smoked cigar told us everything we needed to know about the sophisticated hustler music within.