Year: 1989
Sneaker: Nike Air Jordan IV

It took Michael Jordan and his Chicago Bulls four seasons to win a playoff series, but when they finally did break through they did it in brilliantly dramatic fashion. With the best-of-five opening series against the Cleveland Cavaliers tied at two games apiece, they returned to Ohio for the deciding game. With the Bulls trailing late, Jordan-already with 42 points-received an inbounds pass, elevated over Cavs defensive specialist Craig Ehlo, and buried the game-winning jumper. It would be another two years before the Bulls won their first title, but The Shot even resonated after the rings started to stack up.