50. Neil Patrick Harris — Air Jordan IV "Cement"

When: 1994

Where: "Doogie Howser, M.D." Promo Shoot

Become a doctor as a teenager and you can wear whatever you want. And Doogie Howser wasn't gonna wear no all-white nurse's shoes. Maybe things would have been different if the series debuted after "Pure Money" Jordans had released, but it didn't.