Cudi was relatively new to the game when he went for Jay Z’s retirement crown. In 2009, before his debut LP, Man on the Moon, had even dropped, Kid Cudi wrote a lengthy blog saying he was calling it quits. "After the release of my first LP this summer, I am not making any more solo albums,” he wrote. “The drama that comes with it is more overwhelming than [what] I was dealing with when I was piss-poor broke.” He walked it back a few weeks later, but in the wake of his sophomore LP he talked retirement again. “I think four albums will do it,” he told New York magazine last year. “Once the story is told, there's nothing else to say."