42. Nike Air Penny I

Year released: 1995

Complex says: 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/varisty-royal colorway made these just as appealing for hoopin' in or rockin' to school. The Nike ad campaign is still one of the most memorable to date starring "Lil' Penny," a puppet voiced by Chris Rock, and Tyra Banks at the height of her fineness.