Hank the Grifter said:
Without even reading your list my answer is Buddy Holly. He was so far ahead of his time. He would have been an absolute legend.
And no offense to The Big Bopper or his family but thank God Waylon lost that coin flip.
The coin flip was between Ritchie Valens and Tommy Allsup. Jennings gave up his seat on the plane because the Big Bopper had the flu.