Sneaker: Air Jordan XIV
Year: 1998

By 1998, Michael Jordan could do pretty much whatever he wanted. And on the verge of his sixth NBA title (and sixth Finals MVP), he decided to stage his own product unveil on national TV. Having worn the Air Jordan XIII through the playoffs (including some PE lows), he switched into the upcoming Air Jordan XIV for part of the Finals, including the penultimate Game Six. The sneaker wouldn't release until the following year, but the shot over Bryon Russell was more effective than any commercial could have ever been. Sorry, Mars.