Movie: She's Gotta Have It
Sneaker: Nike Air Jordan 1

Spike's cinematic dedication to the Jordan line was evident from his 1986 breakthrough. The director's depiction of the childish but enduring Nola suitor who takes being dumped badly created a pop culture figure who'd take the Air Jordan franchise to the next level. While the film's black and white, those Jordans are blue and black. This film sows the seeds for too much to list in a solitary paragraph.