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17. Rob Dyrdek
image via Visionary Artistry MagThough it’s easy to give Fred Durst or Lil Wayne the props on DC popularity, Rob Drydek was with the brand from the beginning. Leaving school to pursue his dreams, Dyrdek signed with Droors Clothing as a teenager. This move helped propel his entrepreneurial spirit and also launch a long line of signature shoes. Like others on this list, his ability to do great things outside of sports kept him and his kicks current.