50. Wilson Pro Staff
Year Released: 1980s
If you ever actually played tennis in the 1980s, then you may have had a coach who claimed to have been a pro [entered one tournament and went out like a sucker]. For whatever reason [coke problem], he never reached his [minimal] potential. But you were lucky to have a coach with that kind of experience [because he always had weed]. If you ever knew a guy like that, chances are he was wearing the Wilson Pro Staff. The Pro Staff was a clean, basic shoe featuring that sexy W logo in the saddle (ladies, back off. . . I just want to play tennis and nothing more). Wearing this shoe enabled you to clearly signal your allegiance to 1977 by virtue of the slap-happy San Diego Padres font reading "PRO STAFF" on the midsole. Somewhere there is an old tennis coach in a Steely Dan cover band wearing these, and hoping for just one groupie. FYI, if you feel like the preceding paragraph accurately sums up your steez, the Pro Staff is still in production today.