Year: 1988
Sneaker: Nike Air Jordan III

Spike Lee is the perfect example of someone who made his own future. In his first feature film, She's Gotta Have It, he played the role of Mars Blackmon, a flashily dressed bike messenger from Brooklyn who wore Cazals, a huge MARS chain and Air Jordans. Someone at Nike ad agency Wieden & Kennedy saw the film, and thought Lee would be the perfect person to helm the Air Jordan campaign. Mars Blackmon returned in 1988, and nothing in sneakers would be the same.