Watch Sturgill Simpson Cover Waylon Jennings’ ‘Waymore’s Blues’ Back In 2014

After his Grammy success in 2017, Sturgill Simpson became a little more well known to the general music-loving public, but to the hardcore country music fans, it’s a name that’s been in the mix for about a decade now.

Do you remember the first time you heard his voice on a song? Do you remember saying, “holy shit, this guy sounds like a modern Waylon Jennings.”

You weren’t alone… but Sturgill did not take too kindly to those comparisons.

Sturgill was compared to the man so much that he ended up just covering Waylon Jennings’ “Waymore’s Blues,” but my God, is it amazing.

Here’s a young Sturgill covering it at a bar in Texas in 2014:

“I get so fucking tired of hearing how much I sound like this guy, I just decided to start playing one of his songs.”

I know Sturgill doesn’t like the comparison, but man can he sing the hell out of some Waylon.

Seeing where he is now, and seeing the venues he was playing just eight years ago is pretty wild too… he’s come a long way.

From small venue in Georgia, to making history as the first artist to be nominated for best country album and best rock album by the Grammys some years later…

Go off, King.

And the crazy part…. he might be done with all of it.

Sturgill Simpson Confirms “Dood & Juanita” Is His Last Solo Album

After the glorious release of Sturgill Simpson’s concept record, The Ballad Of Dood & Juanita, the one thing in the back of everybody’s mind is… is this his last album?

Sturgill has said in the past that he planned on making five records and then calling it a career… but would he really?

And in a recent interview, Sturgill said he was sticking to it.

“I don’t want to say I’ll never make another record, but this five-album narrative was really clear when I moved to Nashville. My wife really helped me carve that out, in terms of how to go about the beginning, middle and end for each chapter. But then after that, I am not sure.

I love the studio. I like sleeping in my bed. I like seeing other people succeed. And I really love helping other people succeed—people like Tyler or Margo or Lucette or anybody else who would be willing to work with me.

I can’t think of any other greater way to use the knowledge or experience—or whatever you want to call it—that I’ve gained from the last seven or eight years, then by helping other people who I’m already impressed with make more music that will improve the musical landscape, as opposed to just 20 more Sturgill records.”

At the time Sturgill had pretty much finished his new album, but the future of Stu in the country music world appeared to be in more of a producer capacity.

However, now that “Dood & Juanita,” Sturgill’s 5th studio album, is out… has anything changed?

Not really… but sorta.

According to a new interview with Rolling StoneSturgill is making good on his promise that this is indeed his final Sturgill album.

“This is the last Sturgill record. I always said there would be five, and I wondered if I’d go back on that.

But it really has cemented every step of the way how much I don’t want to carry all that weight.

Going forward, I’d like to form a proper band with some people who I really love and respect musically and be a part of something truly democratic in terms of creativity.

Not having to stand up there behind my name would allow me to be even more vulnerable, in a way.” 

So while we haven’t heard the end of Sturgill Simpson the musician, it seems as though we have heard the end of Sturgill Simpson the solo recording artist. He also added that he has a few band members (and band names) in mind.

And if there was one more thing you were wondering about, he says that he’s content to never play an arena show ever again.

“I don’t care to step into an arena ever again. I don’t want to play shows where the first rows are 50 yards away.”

Of course, prior to the pandemic, Stu was just beginning a massive area tour with Tyler Childers, a show with a such a demand that some cities were offering multiple dates. Unfortunately, he was just 12 shows in when COVID hit, and the entire live music world was put on pause.

But if you were hoping to see that tour rescheduled… doesn’t look like that’s on the docket.

At the end of the day, whether it’s solo artist Stu, band member Stu, producer Stu, actor Stu…. whatever he has his hand in, you can bet your ass I’m going to be paying attention.

Even Stu going to Waffle House with Stephen Colbert:

A beer bottle on a dock



A beer bottle on a dock