Year: 1999
Sneaker: And1 Tai Chi

What started as a line of trash-talking t-shirts that everyone seemed to order from the back of Slam magazine, eventually become one of the hottest sneaker brands of the turn of the century. In fact, you may even be able to argue that for a brief moment in the late '90s, And1 was THE hottest sneaker brand around. Queue the Vince Carter dunk contest highlight reel.