Reebok Pump Vertical 

Year (of Sneaker): 1992 

Boogs may have looked like a 14-carat Urkel on the playground but we have to dap him for a quick flip and breaking out one of Reebok's hottest new models just days after getting out of jail. Either you slangin' crack-rock or you got a wicked jump shot—Boogs jumper isn't that nice.