I know that Cash and Nelson are somewhat deeper and might not deserve the label, but I associate them with "country" music. I'm not a country music fan and have never considered myself a fan of either of these artists. However, I did appreciate some of Johnny Cash's later work. I also have fond memories of songs like "Ring Of Fire" that were played by various members of my family as I was growing-up. So my vote goes to Johnny Cash.
This was a good one I love Johnny, but Willie rules! Hell for longevity alone Willie wins. They were both born in the early 30's (32 and 33) and their music carrers started in the middle 50's. Johnny was more popular in the 50's and 60's but then faded for a long time (Although he did finish strong, the last few recordings were wonderful). Willie has never been as popular as Johnny at his peak, but Willie has managed to stay somewhat relevant for just about the entire time. so I give the nod to Willie.
Now I'm gonna go and find me a girl that can suck the chrome off of a trailor hitch.