29. Snoop Doggy Dogg, Doggystyle (1993)

Art Direction: Kimberly Holt
Illustrator: Joe Cool
Label: Death Row/Interscope/Atlantic

Rather than bring in the professionals, Snoop called on his cousin Joe Cool for this hilarious cover that did a perfect job of depicting what one would imagine his life to be like if he was indeed a cartoon. Of course, casually passing the art duties of hip-hop's most anticipated debut album to his cousin seems all too appropriate considering Snoop's ideology. Because it truly ain't no fun if the homies can't have none.