Year: 1989
Sneaker: Nike Air Jordan IV

It's been nearly 25 years, and it's a testimony to Spike Lee that no better tribute to the importance of sneakers to urban culture has ever been set to film. Nike products run all through 1989's Do The Right Thing, but Buggin' Out's anguish over the scuffing of his brand-new $100 Air Jordans ($108 with tax!) still resonates.