Jay-Z, Reasonable Doubt (1996)

Label: Roc-A-Fella, Priority

Although his subsequent work is best noted for its commercial appeal, Jay-Z's debut is a mafioso rap classic. Laced with intricate rhymes, street tales, and Jay's relentless cool, RD is an unforgettable listening experience. While other rappers sounded excited by the violence of street life, Jigga was concern with the high life and the dark side of the game weights heavily on his mind on cuts like "D'Evils" and "Regrets."