15. Kenny "Sky" Walker — Converse ERX-300

Year: 1989 

In the late '80s sneakers were getting bigger and bulkier but that didn't stop Kenny "Sky" Walker from bodying a 270-degree windmill dunk so bad that Clyde Drexler essentially said "fuck it" and gave up on his final dunk. The large "CONS" logo was impossible to miss even on your grainy-ass television and from there a star was born — Walker did alright for himself too. In the dunk contest, anyway.