19. Puff Daddy
Why He Made The Cut: Can't stop won't stop stylin' on 'em.
Say what you will about his personal rap cred: Sean "Puffy," "P.Diddy" or "whatever-the-hell-we're-calling-him-now" Combs is first and foremost a businessman. The man signed Biggie for God's sake. (He also produced some of the decade's biggest albums, too.) So it's no surprise he did it all with a calculated sartorial mission--whether it be silk Versace shirts or monochromatic, futuristic track suits--to go along.