5. The Notorious B.I.G.
Though lacking any real social message, Biggie possessed enough pizzazz to sway audiences young and old. His effortless wit and unparalleled flow made him one of the greatest rappers of our time.
Best Album: Ready to Die
Some call him a street prophet for his poetic, conversational-style lyrics. An absolute master of lyrical extravaganza, Nas often paints vivid pictures of urban life in his rhymes.
Best Album: Illmatic
3. Big Daddy Kane
The King of Swagger, Kane entertained the rap world with his peculiar flair and flamboyant wardrobe. Latter peers like Jay-Z, Biggie, and Snoop would later adopt his player persona.
Best Album: Long Live the Kane
The Teacha transformed the violent brusque of street life into a story of uplift and self-awareness, starting with BDP's incendiary debut, Criminal Minded.
Best Album: By All Means Necessary (w/ Boogie Down Productions)
While others bragged about their guns, Rakim celebrated his swagger. A smooth, laid-back flow, intense lyricism, and positivity were his stately hallmarks.
Best Album: Paid in Full (Eric B. & Rakim)