Mysterious Waylon Jennings Billboards Pop Up In His Hometown Of Littlefield, Texas

A Waylon Jennings billboard in 2025? You love to see it – but what does it mean?

Of course we lost the country music legend back in 2003, but his legacy and influence on country music is as strong – or stronger – than it’s ever been. And recently, Waylon’s son, legendary artist and producer Shooter Jennings, announced that there would be new Waylon Jennings music on the way soon.

It all started last year when Shooter announced that he was in possession of some never-before-heard Waylon Jennings recordings. Not unfinished demo tapes, but unreleased music that just needed to be mixed and mastered before being released to the public.

So that’s what Shooter set out to do. Last month, he announced that there would be THREE new Waylon Jennings albums on the way, and that he had even brought in his dad’s original band members to help with the songs that weren’t totally finished:

“I’ve been waiting so long to share this with you. It hasn’t been an easy road to get here, but it’s been one that has given me a new purpose in life. I dug through my dad’s old tapes and found a plethora of music by Waylon and the band at the peak of their abilities. For the stuff that wasn’t totally finished, I brought out four of the remaining original members of his band to put the finishing touches on it.

I was able to make three albums out of it and ‘Songbird’ is the first one. It’s coming out on October 3rd and you can pre-order all kinds of versions of it now… I have lots more in store for you, but for now, here is ‘Songbird,’ the beautiful Fleetwood Mac song written by Christine McVie and featuring Waylon, Richie Albright, Ralph Mooney, Jerry Bridges, Barny Robertson Gordon Payne, Ashley Monroe and Elizabeth Cook.

This video shows a compilation of videos recorded during the completion of the tracks across the three albums. Elizabeth Cook and Ashley Monroe were brought in to sing on “Songbird” and take it to new heavenly heights. Waylon Jennings is STILL THE KING!”

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While the first album, Songbird, isn’t set to be released until October 3, the title track from the album dropped last month featuring Elizabeth Cook and Ashley Monroe on background vocals, along with a video showing never-before-seen footage of Waylon.

Well with all the exciting news surrounding Waylon and the new music, a Whiskey Riff reader recently sent us some pictures of some interesting billboards that have recently gone up in Texas.

The billboards have been spotted in Littlefield, Texas, where the country music legend was born, and feature Waylon’s iconic logo, as well as a couple of different phrases from the Johnny Rodriguez deep cut “The Cowboy.”

“My long, shaggy hair and the clothes that I wear ain’t fit for no big fancy ball.”

“I’m a cowboy who came here from Texas just to play you my music, that’s all.”

At this point there hasn’t been any word on the billboards from Shooter or his team, so it’s not clear if they’re behind them or if they were just put up by a Waylon fan in his hometown. There hasn’t been any indication that more singles are coming ahead of the album release on October 3, so I guess we’ll just have to wait and see what the billboards mean.

In the meantime, if you see any more pop up, shoot us a picture over on social media…and let us know what you think they mean.The post Mysterious Waylon Jennings Billboards Pop Up In His Hometown Of Littlefield, Texas first appeared on Whiskey Riff.