3. David Letterman — Air Jordan 1

When: 1986

Where: Late Show with David Letterman

Michael Jordan isn't a god, but he was a savior. Nike needed a boost in the worst way in the mid-80s, and they put all their chips on the kid with the wagging tongue from North Carolina. Which, as it turned out, was only the best bet they ever made. The NBA immediately raised objections to the red and black sneaker, which led to an amazing commercial as well as a classic Letterman moment.