Shoe: Fila The Hill
As the Will Smith of hoops, Grant Hill was kind of a tough sell coming into the League. He could jump out of the gym, sure, and his Duke pedigree was pristine. Plus, he wasn't Christian Laettner or Bobby Hurley. But at the same time he didn't have the sneaker-selling street cred of a Chris Webber or Jason Kidd. Fila took the no-nonsense route, acknowledging his quasi-dorky roots while still lacing him with a signature shoe as soon as possible. Respect.