When the world's most famous sneaker debuted in 1985, it was met not with celebration but censure. The dramatic red-and-black Air Jordan I crossed swords with the NBA's uniform police, who banned the shoe from the league for its "non-regulation" colors. Michael Jordan, then a Chicago Bulls rookie, b ...ucked league brass by wearing his signature kicks, a decision which cost him $5,000 in fines every time he set foot on the court. You can't put a price on fashion. Or winning.

Since its launch, the Air Jordan has become a global sports and style phenomenon, unquestionably the most famous icon of one of the world's most famous brands. Every year since 1985, even after Jordan retired for good, a new pair of Air Jordans has been released, along with a countless number of colorways and models. In honor of the legendary sneaker, we asked Matt Halfhill, a preeminent Nike expert and collector from Austin, Texas, to rank the top 23 Air Jordans of all time.

Indeed, every pair of Air Jordans in our top 23 list has its own privileged place in sneaker history. Back in the late 90s, MJ’s friends used to call him “Black Cat” for his feline quickness and agility. Nike ran with the concept, designing a sneaker inspired by a panther’s paw that eventually became the Air Jordan XIII, number 16 on our rankings. When Jordan elevated over the Cleveland Cavaliers’s Craig Ehlo to hit “The Shot,” one of the classic clutch baskets in NBA history, Jordan was wearing the Air Jordan IV. Fittingly, the IV ranks number four. See the complete rankings illustrated by nine pinup Playmates, helped along by illustrator Nigel Evan Denis.

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