40. Too Short, Born to Mack (1987)
Label: Dangerous, Jive, RCA
We can't think of a better way to describe Short Dog's entire career than the name of his first full-length and first major-label release. Short was already keenly aware of his specialty: first-person tales of pimpery, sex and street life. 30 years deep into his legendary career, he's still at it-although he did promise to tone down earlier this year after a ill-advised interview in which he gave underage boys some racy advice for seducing the opposite sex. We'll believe it when we see it.