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3. Air Jordan 5 and 6 featuring Mars Blackmon (1990 & 1991)
The Mars Blackmon series within the Air Jordan lineage propelled perhaps the greatest sneaker character of all time. With his persistent nature and inquisitive personality, Mars would always be featured in iconic commercials. While that remained true for the Air Jordan 5 spot, Jordan and company elicited the help of a notable musician in order to help prop-up the Air Jordan 6.