19. Air Jordan Retro IV "Cavs"

Released: May 

Poor Craig Ehlo — "The Shot" was damn near 25 years ago, and Michael Jordan just can't leave him alone. Known as the "Knicks" Air Jordan IV before the backstory was revealed, this IV is part of a long line of retros meant to assert MJ's dominance over his one-time foes. Jeez, we get it.