2. Jim Kelly
Jim Kelly might be tied for third place in most Super Bowl appearances by an NFL quarterback, and he might be one of only seven quarterbacks in NFL history to make it to the Super Bowl five times, but no quarterback in the history of the game has led his team to the Super Bowl four straight years. None, that is, except Jim Kelly. The maestro of the Buffalo Bills’ “K-Gun” offense terrorized opposing defenses from 1989 and 1992, perennially leading the Bills to the highest offensive ranks each year. He finished his career with over 35,000 passing yards, currently sitting in 25th place all time. But for all those Super Bowl appearances and all those passing yards, Kelly will never have a ring to show for them.