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Air Jordan 3

Year Released: 1988
Designer: Tinker Hatfield
Most Popular Colorways: White/Cement, Black/Cement, Fire Red, True Blue
First Retroed: 1994

Michael wasn't too big on signing with Nike from the start and after two of the people who did the most to bring him to the brand (Peter Moore and Rob Strasser) left, he was considering a change of scenery as well—his initial deal was up in 1988. In the end, it was young designer Tinker Hatfield's incorporation of the elephant print and the Moore-conceived Jumpman logo on the revolutionary Air Jordan IIIs (and Michael's dad telling MJ that Nike had his best interest at heart) that convinced him to stay.

The shoe was originally named the Air Jordan Revolution and incorporated Mike's personality into the design concept. In the end, Nike decided to keep the Roman numeral system for marketing reasons and it also introduced us to Mars Blackmon after the brand decided to hire Brooklyn native Spike Lee to direct and star in the commercial. The gamble ended up being another win for the brand and 25 years later its iconic status isn't up for debate.  Another timeless moment that helped etch the sneaker in history was MJ taking flight in the IIIs from the free-throw line during Chicago's All-Star Weekend and winning the Slam Dunk Contest — earning MVP honors in the black/cement pair during the game itself didn't hurt either.