Year: 1987
Sneaker: Nike Air Jordan

When the first Air Jordan sold through almost immediately on its release in April of 1985, retailers and consumers alike clamored for more, more, more. Nike gleefully obliged, but the second run was too much of a good thing. Pairs languished on shelves literally for years, reduced to rock-bottom prices. And while basketball players had moved on to the next big thing, skateboarders did their best to take care of the Air Jordan overstock. Cheap and durable, Air Jordans were better than anything being produced by skate companies. The high-water mark was in 1987's Search For Animal Chin, when nearly the whole Bones Brigade was outfitted in Jordans of all colors. Watch it and cringe.