31. Flavor Flav
Height of Style: "911 Is a Joke" video
Signature Look: Kitchen clock as medallion, dark glasses, top hats and tuxes, gold grills
One of the most endlessly creative figures in hip-hop—bar none, Flav is also the greatest hype man of all time, and a reality TV superstar. He could pull off tuxes and Viking Hats with equal vigor. He once rocked a Mohawk shaped like a backward F, and was one of the first to sport his name on his gold grills. His signature kitchen clock hung around the neck —“You know what time it is!”—makes this strangely charismatic man one of the most distinctive figures in all of American pop culture.