2. Nike Air Max Penny

When: 1996

Who: Ray Allen 

Name a player that didn't have Penny in their top five in the mid-90s — his game was sick, the commercials were dope, and most importantly Nike hooked him up with some crack kicks that they wanted to rock on the court. Penny's first signature shoe was easily his greatest shoe in the I-IV series. The sneaker featured the visible heel Air Unit with the "1 Cent" logo right above it, a pinstriped tongue and a PU support panel, and its great design and black/white/varsity-royal colorway made these just as appealing for hoopin' in or rockin' to class.