5. Too $hort, Born to Mack (1987)

Art Direction: Mark Wholey
Photographer: Ann Flanagan Typography
Label: Dangerous/Jive/RCA

Easily winning the award for the best use of negative space on any hip-hop cover, the Born To Mack design places Todd and his Caddy dead center in a sea of white. This technique aimed to pull the focus back from $hort, instead drawing attention to the player lifestyle—his car, his swag—but never his face. $hort's original plan was to maintain this relative anonymity throughout his career, but label brass persuaded him otherwise and he was front and center on the cover of subsequent releases.