4. Nike Penny Hardaway "Cent" 

Year created: 1995 

Anfernee's grandmother had a strong southern drawl and when she called him "Pretty" as a kid all his boys thought they were saying Penny — the name stuck ever since. Thanks to Nick Anderson already rocking number 25 in honor of Benji Watson, Hardaway had to switch it up from 25 to 1. Never has a marketing plan worked out so perfectly, between the Cent logo and the Chris Rock voice overs as Lil' Penny, few campaigns have been as dope as Penny's.