New Unheard Waylon Jennings Song Emerges, Billboard Mystery Revealed

It was announced on June 15th, which happened to be Waylon’s Birthday, that not one, not two, but three full albums of unheard Waylon Jennings songs were on the way. Waylon’s son Shooter has unearthed a trove on previously-unheard Waylon Jennings recordings, and has gone through them to assemble them into albums. The recordings weren’t cohesive albums at the start. They were leftover recordings from various sessions throughout Waylon’s career.
The first installment from these albums called Songbird will be released on October 3rd, with the title track released in June. The first song was Waylon’s version of the Fleetwood Mac tune written and sung by Christine McVie. Now we get another unheard track from the upcoming album, and its another dandy.
The new song is called “The Cowboy (Small Texas Town),” and it’s taken from the same recording sessions of Waylon’s 1978 album I’ve Always Been Crazy. This is the same album that Waylon’s “Don’t You Think This Outlaw Bit’s Done Got Out of Hand” came from. That became a hit, along with the title track. Waylon produced the sessions himself with drummer Richie Albright.
“The Cowboy (Small Texas Town)” was written by fellow country legend Johnny Rodriguez, but it’s the perfect composition for Waylon, singing about humble beginnings in small town Texas (In Waylon’s case, Littlefield), along with referencing the “hippies and cowboys” scene that Waymore stumbled upon in Austin, TX after Willie Nelson convinced him to head there from Nashville.
The song also takes a stab at white collar criminals—something Waylon interfaced with regularly in the music business.
That white collar crowd may be stealing, anything that the law will allow
With a pen for a gun they can’t have no fun, ’cause they don’t fit in our crazy crowd
You can tell that the end of the song gets cut off somewhat abruptly, and is perhaps the reasons it ended up on the cutting house floor. But loose ends and all, Waylon fans won’t be looking this gift horse in the mouth.
“The Cowboy (Small Texas Town)” was released Thursday evening/Friday morning like many new tracks are. But on Friday evening, a video emerged for the song that answers the question many Waylon fans from his hometown of Littlefield and beyond have been asking: Who is behind the mysterious billboards that have appeared throughout the town of 6,000 in the Texas panhandle?
It was pretty obvious the answer was probably Shooter Jennings as part of the rollout of the new Waylon albums. But the video spills the beans as it’s made up of footage of crews installing the new Billboards, including one that reads, “I’m a cowboy who came here from Texas just to play you my music that’s all,” which is one of the lines from the new song “The Cowboy.”
A second Billboard also reads, “My long, shaggy hair and the clothes that I wear don’t fit your big fancy ball,” also taken from the song. The video also features “Waymore’s,” which is a liquor store in Littlefield operated by Waylon’s young brother James Jennings and his wife.
The upcoming album Songbird is currently available for presave/preorder.
August 16, 2025 @ 8:26 am
Very Excited for this album the new song sounds great. Shooter found his calling as a producer and I’m sure Waylon is very proud of him. On another note While Wheys new album was stellar it would be cool for Shooter to lend a hand in producing Wheys next album
August 16, 2025 @ 8:37 am
Dang, from the opening note you can tell it’s a Waylon Jennings song. The man had a distinct sound.
August 17, 2025 @ 5:36 am
Oh yes I thought exactly the same.
August 16, 2025 @ 8:56 am
I imagine this was not released in part because there is no bridge. It is always interesting to me to see why certain things might not have been released, but in this instance I don’t care at all because anything that we can get out of his unreleased catalog has the potential to be gold.
August 17, 2025 @ 6:01 pm
I find the bridge more annoying than helpful in many instances. The greats rarely used one. In Waylon’s generation, neither did Cash or Willie, and rarely did Merle. I love me some Strait, but some of those bridges in his songs are superfluous. “You can find a chisel, I can find a stone.
Folks will be reading these words long after we’re gone” is an example of this. It always seemed to be a nod to pop music.
August 16, 2025 @ 9:03 am
I was 14 years old when the Ol’ Waylon album came out. I haven’t stopped listening to him since. Shooter is doing a great job with these songs. It is like a time machine to my childhood and I am grateful.
August 16, 2025 @ 10:06 am
It is a great song.
August 17, 2025 @ 7:00 am
As steel picker Bruce Bouton said in the very interesting interview linked below;
“Those days are gone. It’s just, songwriters have been killed, they’ve been killed by the modern music business.”
https://kgnu.org/music-posts/interview-bruce-bouton/
He states some facts about the industry.
August 17, 2025 @ 1:22 pm
I was forced to listen to the FM radio last night on the way home from a gig because my bluetooth speaker went dead and modern Country on every radio station in Murfreesboro was playing the most awful clique music – it’s worse than the worse of Bro Country. The worst was Scotty McCreery’s song ‘Bottle Rockets’ – holy shit. It’s a Sam Hunt knock-off but worse and the incongruent inclusion of Hootie and The Blowfish ‘Hold My Hand’ hook. If it wasn’t produced by A-listers I would have assumed it was AI-written…maybe it was in part. All that being said, this new Waylon song is better than stuff on the radio now – and Waylon has released a good number of duds.
August 18, 2025 @ 8:12 am
I stick to classical music on the radio when I’m driving these days, or some oldies (pre-60’s).
Radio as we know it – FM/AM/DAB – will probably disappear soon. Too expencive to maintain..
August 16, 2025 @ 10:14 am
Fantastic song, I really miss Waylon.
August 16, 2025 @ 11:30 am
Great. Great. Great. Waylon and Don Willisms are my top two. This is an unmistakeable Waylon song, as they all were.
August 16, 2025 @ 11:31 am
Both of these so far have been great. Really looking forward to the whole album. Waylon is still the best to ever do it.
August 16, 2025 @ 12:33 pm
So this is completely unrelated to the song but have you guys heard the “radio play” The Boar’s Nest? It’s about the birth of the outlaw country movement just before many of the big players broke out. It’s kind of a podcast Radio play sort of thing that’s on Audible and they have different actors playing the voices of all the famous country stars. It’s really well written, supposedly from the perspective of shel silverstein of all people. Waylon and Kris Kristofferson are major characters.
August 16, 2025 @ 3:10 pm
HOLY CRAP !!! More Waylon 23 years after his death? (Elvis passed 48 years ago today Aug.16,1977 at age 42). No wonder it’s a GREAT DAY for his fans such as Yours Truly!!!!
August 16, 2025 @ 4:28 pm
New Waylon.
I’ll take it.
Johhny Rod’s lyric about white collar criminals called to mind Woody Guthrie’s ode to “Pretty Boy Floyd”, and with whom his sympthies lay:
Yes, as through this world I’ve wandered
I’ve seen lots of funny men;
Some will rob you with a six-gun,
And some with a fountain pen.
And as through your life you travel,
Yes, as through your life you roam,
You won’t never see an outlaw
Drive a family from their home.
August 16, 2025 @ 4:42 pm
Waylon was too woke.
August 17, 2025 @ 7:04 am
From his song “America”, 1984;
“And the red man is right, to expect a little from you”
He was in favor of repatriations, in other words.
August 17, 2025 @ 9:56 am
He never said anything about reparations. He was just saying they should be treated with the respect they deserve.
August 18, 2025 @ 7:59 am
Gee, learn to take a joke, buddy.
August 17, 2025 @ 12:25 pm
Waylon caught wokeness from Willie.
August 17, 2025 @ 12:29 pm
No more comments on this thread.
See, this is why I ask people to steer clear of politics in these comments sections. Even one comment which may or may not have meant to be sarcastic can veer the discussion off topic. People come here to get away from politics. This topic has nothing to do with politics. If you can’t respect this request, don’t comment. Because your comments are going to get deleted.
August 18, 2025 @ 7:30 am
agreed, the last thing I want to read is politics on this site, I thought at first too that maybe he was joking but why do that, especially in an article about Waylon, if you have negative things to say about Waylon then maybe you are the furthest from a country music fan.
August 17, 2025 @ 11:46 am
Waylon was a true legend, it’s so sad that uneducated people have to throw some word that they have no clue what woke means. I don’t care what Waylon’s politics were, he is still a legend.
August 18, 2025 @ 6:37 am
EXPLAIN
August 17, 2025 @ 5:42 am
Pick it Moon !!! Damn, I miss Waylon!!!
August 17, 2025 @ 6:13 am
Wasn’t sure what to expect, but if there are more gems like this one I’m going to be happy.
August 17, 2025 @ 7:18 am
I’ve said Waylon sang my kind of songs and music. No doubt in my mind he was the best. Glad Shooter has uncovered and redone these songs for us.
August 17, 2025 @ 1:07 pm
I noticed the line “law will allow” was reused in a much better song of his from that same time period that became the greatest theme song for any TV show, IMO.
August 18, 2025 @ 8:08 am
What? You mean that “Good Ole Boys” are better than the theme song for “Alvin & The Chipmunks”?
I agree.
August 17, 2025 @ 2:56 pm
Generations ago,Woody Guthrie observed that some men will rob you with a six-gun and some with a fountain pen,and it’s even truer today than in ol’ Woody’s era,LuckyOldSun.(Guess why,pardner?)
August 17, 2025 @ 4:04 pm
It sounds to me like they recorded the song with the intention of doing a fade out and Shooter just decided to keep everything they had. Great song.
August 17, 2025 @ 9:11 pm
Great song! As a huge Waylon fan and someone who is happiest in small town Kansas this song is great! Looking forward to the whole album. I will certainly be adding it to my collection.
August 18, 2025 @ 6:57 pm
Another great song by Ralph Mooney featuring Waylon Jennings on guest vocals!
August 19, 2025 @ 5:55 am
Haha! Good one. Yes Mooney was terrific. But let’s go back in time to say 1978 or so, or even the 80s and conduct a hypothetical experiment. Put the following name on the marquee of your favorite venue: Ralph Mooney Band. How many seats would you sell? Same with a record, how many copies would a Ralph Mooney solo album sell?
Now, repeat the exercise, but put the name Waylon Jennings on the marquee. How many seats would you sell?
Im sure any reasonable person gets the point. Mooney was a side- man, that is what he did. Waylon was an entertainer on an epic scale. Big difference.
Funny comment though.
August 19, 2025 @ 6:42 am
This!
August 19, 2025 @ 12:37 am
…if it wasn’t for the prominent texas background, some younger music fan might think: good one from sturgill. on a good day top sounds like jackson, worthington like chesnutt, king like strait – some of country’s up and comers enjoy playing back to the future. sounds good, yet not all that imaginatively. funny, but today’s spurned aldean was a lot more innovative at the outset.
whatever, it’s just so amazingly comforting and rewarding to hear waylon again – even after all this time.
August 19, 2025 @ 7:24 am
Christmas came early! How incredible would it be if these albums charted? Never a better time for Waylon sounding revival than now.
August 19, 2025 @ 3:06 pm
Its def a good one. Looking forward to the first album. I have questions for anyone particularly trigger though i may be showing my ignorance. Since this was a johnny rodriguez song, did shooter have to get permission to release this cover and secondly would johnnys estate receive any money off of it.
August 19, 2025 @ 6:57 pm
Whoever wrote the song would receive songwriting royalties from it. Spotify pays songwriters 3/1000 of a penny per stream, so they won’t be getting rich on it.
Anyone can record a song without permission once the initial license has been issued, as long as the proper royalties are paid.