41. Schoolly D, Schoolly D (1986)

Art Direction: Schoolly D
Illustrator: Schoolly D
Label: Schoolly D

Not content to just self-produce and run his own label, Philadelphia's first gangster rapper also took design matters into his own hands with his earliest records, laying some very Philly handstyles and blockhead characters onto a simple comic strip layout on a blindingly yellow sleeve. There he boasts of victory "in his never ending battle against bitter's [sic] and squares."