12. Penny Hardaway

Who And Why: All-NBA first teamer, Lil Penny's big bro

Penny may never reach the halls of Naismith, but in the sneaker world, he is a first-ballot Hall of Famer. Today, Penny is more relevant than ever with the sneaker market and youth. He stays active in the promotion of his line and can hang his hat on being the only guy to have a signature shoe made for him more than a decade after the prior model dropped.