Year Released: 1970s

Arthur Ashe had a number of brands on his dilznoid over the course of his career. And why not? Equal parts athlete and humanitarian, he was an ideal endorser. After a number of years with Adidas, Ashe signed up with Le Coq Sportif. I'm sure the good people at Le Coq thought the Ashe Pro Cup was a very understated shoe. Very sleek, very European, with triangular perforations on the tongue. And it was. But something funny was going on around the toe box. If your middle toe was four inches long, the Ashe Pro Cup would have fit just right. Le Coq Sportif had a lot more fun reviving the Ashe brand this year, than the company must have had launching it back in the day. Ashe was a little bit of a nerdy looking guy, and his product range could have used a little Noahfication to make it crack. The Ashe Cup is on this list because Arthur Ashe was just a dope name to have on foot. He was an incredible athlete and a civil rights activist. He purposefully brought attention to hereditary heart disease after having a heart attack in his prime, then to the inadequacy of urban health care as he fought AIDS in 1982. In the Oh Twelve, athletes don't really take their time and talent to places like that. They take them to South Beach.