5. Nike Air Jordan IX PE 

Year released: 1994 (Penny only)

Back in the '90s, things were different. You didn't just play in Jordans, you had to be chosen. And Penny Hardaway, even early on, was one of those chosen. His "Dark Charcoal" IXs done up with royal blue trim and his No. 1 on the heels were proof positive that the kid was going places.