Sturgill Simpson Covering Waylon Jennings’ Iconic “Waymore’s Blues” Will Never Get Old

Sturgill Simpson country music
Dennis Tudor

“Waymore’s Blues” is up there on my list of all-time great country songs.

While many, many artists have laid down killer covers of the Waylon Jennings classic… something about Sturgill Simpson’s versions just hits different.

Maybe because Sturgill Simpson recently returned to the stage during Healing Appalachia, that is making me dive back into his older video. And man, I forgot how damn good his cover of “Waymore’s Blues” is.

Simpson has taken this cover to the stage many times over the years, but one of my all-time favorite videos hails from 2014 during an Atlanta, Georgia, show. The video and audio quality from this video is truly a chef’s kiss.

“I get so f*cking tired of hearing I sound like this guy, so I just decided to start playing one of his songs. All right.” 

Simpson says into the mic as he kicks off the intro guitar riff.

While I don’t think Sturgill sounds like Jennings, they do share the same grit and outlaw spirit that makes them so loved by their fans. Real country music is what these two do. Sturgill Simpson’s smooth baritone twangs and full-band arrangement give the track a rockin’ beat that makes you want to get up and stomp your feet.

As most Waylon fans know every word to this track, I always find myself singing along.

“If you wanna get to heaven, gotta D-I-EYou gotta put on your coat and T-I-EWanna get the rabbit out of the L-O-GYou gotta make a commotion like a D-O-GLike D-O-G…”

There is genuinely nothing to not love about this cover. Still holding out hope that one day, he might cut this 1975 classic in the studio.

Simpson is one of those artists I could listen to sing a phone book, and I’d still be dialed into every second of it…

Check it out.

A beer bottle on a dock



A beer bottle on a dock