32. DJ Jazzy Jeff & The Fresh Prince, He's the DJ, I'm the Rapper (1988)

Art Direction: Douglas Rowell
Photographer: Douglas Rowell
Label: Jive/RCA

The He's The DJ cover might feature more frolicking than all the other albums on this list put together. Interestingly enough it also features Jeff, not Will, on the front cover, while the future megastar is resigned to the flip side of the gatefold vinyl. For all his charisma, the Prince still had to defer to the fact that he was playing second fiddle to one of the greatest DJs of his—or any—time.