Year: 2001
Sneaker: Converse Chuck Taylor

How does the company that produces the most popular sneaker in the world end up filing for bankruptcy? Dennis Rodman and Master P's No Limit were left wondering the same. We're not sure either but we do know that Nike sure was quick to swoop up on the ailing Converse brand when they seemingly hit rock bottom in 2001. Over a decade later, Converse has revived retro line and a flourishing skate line, amongst other successes. Nike knows.