Lifespan: 1990-2005
Reminds us of: An ill-fated Cabbage Patch kid

Taking a more theatrical approach than his rap competitors of the early '90s, Busta Rhymes somehow made flamboyant costumes, humorous characters and lots of fish-eye lenses seem totally legit. And he couldn't have done it in a Caesar cut. Sure, he looked like an utter fool, but you gotta hand it to him for originality.