Year: 1985
Sneaker: Air Jordan I

Back before the days of colorful PEs and special-makeup sneakers for every achievement and holiday under the sun, the NBA had rather strict uniform rules than ran all the way to players' feet. A team wearing white sneakers meant the WHOLE team wearing white sneakers - primarily white, anyway. So when Nike introduced the original Air Jordan-all red and black-and Michael Jordan wore them, he was in violation of the rules. The NBA responded with a $5,000 fine, and Nike in turn responded with a brilliant commercial. Marketing at its best.