Player: J.R. Rider
Year Released: 1994

J.R. Rider was one of the most high-flying dunkers of his day. Converse recognized game and laced J.R. (or was it Isaiah?) with his own signature model, the Sky Rider. With a name so cheesy awesome, it was bound to fail, but Rider's temper and run-ins with the law prevented him from really making the most of his career and subsequent sneaker deal.