5. The Notorious B.I.G.
Lacking any real social message, Biggie possessed enough pizzazz to sway audiences young and old. Not to mention his seemingly effortless wit and ear-grabbing delivery.
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 a picture of urban life in his rhymes.
Best Album: Illmatic
3. Big Daddy Kane
The King of Swagger, Kane dazzled the rap world with his peculiar flair and flamboyant wardrobe. Countless others (including Jay-Z, Biggie, and Snoop) would later adopt his player persona.
Best Album: Long Live the Kane
The Teacha transformed the violent brusque of ghetto 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)