Jay-Z

Jay-Z is the businessman-rapper who turned street hustling into a blueprint for longevity, but his technical skills never quite matched Biggie or Em—still, albums like 'Reasonable Doubt' and 'The Blueprint' are untouchable. His cultural dominance and knack for clever one-liners ('I'm not a businessman, I'm a business, man') justify top 5, but the sheer volume of weaker late-era albums drops him here.