But far far more importantly was his approach to music. He is regarded as one of the kingpins of the outlaw movement along with his buddy Willie Nelson. Together and with others, they bucked the establishment and did music their way.
This was not a first for Jennings, who eschewed the way Nashville had done recordings in the late ‘60s. He wanted to pick his own songs and musicians to play on his albums. Such attitudes did not exactly win him plaudits in Music City. Far from it.
And he showed just how right he was with the success of the Outlaws, having commercial success to go along with an approach to how music ought to be made.
LIke many performers, Jennings’ star did not always shine so bright even though he was putting out quality music throughout his career.
But that was not his fault. When recording for a small Texas label, it was not exactly going to be easy to get much radio play at all.
Somehow Jennings’ approach seems ever so appropriate and meaningful today at a time when country music is in flux. In fact, some of the issues Jennings raised 30 years ago seem to be with us once again.
Maybe Jennings can serve as a beacon to a new generation of country singers and performers who want to do it their way instead of being told what songs to record, what they should sound like, etc., etc.
And maybe they should just ask themselves “Are You Sure Waylon Done It This Way?”
What more fitting tribute could there be to Waylon that even in death, the way he lived his musical life remains important.