Waylon Jennings Billboard Promises More New Music in 2026
The 2025 archive album from Waylon Jennings called Songbird was so well-received, some named it their Album of the Year. It also ended up charting on Billboard’s Country Albums chart at #17—quite a remarkable feat for a new album of old music.
Usually when you get a posthumous “previously unheard” release, it’s full of odds and sods, what was left on the cutting house floor, and unfinished business. In truth, that’s not an entirely unfair characterization of the songs Songbird. It just happens to be that Waylon Jennings was such a musical beast back in the day, his seconds and scratch tracks are better than most artists’ featured singles. Son Shooter Jennings also did a great job curating and finishing the selections.
When Shooter first announced he’d stumbled upon releasable, unheard tracks from his father, he didn’t promise just one album, but three of them coming from the vault. Well it looks like #2 will be on the way some time in 2026.
A couple of weeks ago, a billboard appeared along Interstate 10 in Southern California just outside of Palm Springs with the visage of Waylon, the word “Diamonds,” and the year 2026. This was around the time the Stagecoach Festival happened in Indio. It’s probably a safe bet this is the first sign of the second release from the Waylon Jennings vault.
At this point we don’t know much more than “Diamonds” is likely the title of the album or the first single from it (or both), and that it will likely arrive in 2026. But according to Dillon Weldon who spoke to Waylon grandson Struggle Jennings about it, Struggle said to expect the album to be a little rowdier, and a little more Outlaw than Songbird was.
Since Songbird came out in October of 2025, perhaps the Fall of 2026 would be a good time for the second release. Either way, it appears we’ll be getting more new old Waylon Jennings music sooner than later.
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May 16, 2026 @ 10:16 am
It’s interesting that for a performer to have this much interest some 20 plus years after their death speaks
Volumes to the state of modern country in that mothballed material is more anticipated than anything out of the latest mainstream releases. Of course, Jim Reeves has songs chart into the early 80s and he died in 1964. Waylon Joins a very small group of performers that were successful even after their deaths (the aforementioned Jim Reeves, Hank Sr,, Patsy Cline, Elvis, Johnny Cash and Keith Whitley to name a few).
I’m looking forward to see what gems had been unearthed on this album.
May 16, 2026 @ 6:55 pm
Johnny Cash had two posthumous #1 Country albums–“American Recordings V” in 2006 and in “Out Among the Stars” in 2014. Those CDs also hit #1 and #3, respectively on the all-album Billboard Top 200 chart. There had to be some hall-of-fame level marketing behind that.
As far as scoring a posthumous #1 single–or even just a top 10–it seems that’s highly unlikely for an artist unless the artist died while they were an active “major league” radio singles artist–definitely not a good trade-off. In addition to Hank Sr., Reeves, Patsy Cline, and Whitley, you could add Johnny Horton with “North to Alaska” in 1960, and on the pop chart, Joplin with “Me and Bobby McGee” in 1971 and Jim Croce with “Time in a Bottle” in 1973.
Jim Reeves, btw, had SIX posthumous #1 country singles. That’s a respectable total career tally for a H-o-F caliber country artist
May 17, 2026 @ 3:52 am
Well, frankly, Waylon never reached the status of Cash and Reeves.
Few outside of the US knows the name (and few inside the US), something that got on his nerves during the Highwaymen years. People from New York to Orlando and from Finland to Greece knew Johnny, Willie and Kris, but stared blankly at Waylon.
That’s why he demanded to be the emcee of the shows; to get a little focus on himself.
I guess Haggard did the wise thing after all when he turned down the offer to be a part of the Highwaymen. According to him it would be a hell of a tour, each of them with a huge ego and then the trouble of splitting the pay between the artists and the high-profile musicians. To Haggard, it wasn’t worth it.
May 17, 2026 @ 8:06 am
I’m sorry but this information is totally wrong on all fronts. Haggard never was offered any part of it and Waylon was not “stared at blankly”. Waylon was huge overseas. There was also no MC role.
May 17, 2026 @ 8:14 am
Sofus was right that at one point, there was talk of Haggard being in the Highwaymen. But both Sofus and Luckyoldsun are significantly downplaying Waylon’s role and legacy. Waylon might be one of the most popular deceased country artists in history. During The Highwaymen, he was much more commercially relevant that Johnny Cash. If there was anyone who didn’t fit, it was Kristofferson, but what was cool about all of them is they fit together so well with intertwined legacies.
The reason Waylon’s music still resonates today is because he never gave up on his integrity. He might have not had as many #1s as Del Reeves or Conway Twitty. But there are a lot more folks listening to Waylon’s music these days and walking around with the Flying W on their shirt than there are Twitty birds.
May 17, 2026 @ 9:25 am
When did Twitty dump his integrity? He repaid all his donators after the Twitty Burger fiasco and left rock & roll over his displeasure with fan behavior. He risked a lot by suing to escape his contract.
Twitty’s legacy, as you wrote in several good articles, was drastically impacted by dying at 59 and squabbles between his heirs. Cash and Waylon are extremely fortunate that their sons are dedicated to releasing archival material and properly ensuring their fathers are known.
Meanwhile, the Twitty clan fights over Franklins and Haggard’s vast vault remains locked.
Let’s also acknowledge that much of Waylon’s legacy, like Cash’s, originates around their cool, rebellious aesthetic. The 70s Outlaw movement is regularly hyped as the Alpha and Omega of country music and Burns revolved his court history documentary on the Man in Black, while barely mentioning Twitty. And every hack writer in Nashville name-drops the duo to show how country they are. Granted, many independent writers are prone to the same exercise.
May 17, 2026 @ 9:33 am
All I’m saying is that Conway Twitty has more #1s than anyone but George Strait, yet Waylon’s legacy looms much larger that Conway’s in the present tense, and I think that is unquestionable. So citing numerous and posthumous #1s just doesn’t matter. Blame “edginess” and “coolness” on that all you want. It’s the reality. And I’d say the same for Merle Haggard.
May 17, 2026 @ 11:01 am
The Highwaymen did not start out as a group. It was just an album that was first going to be a Cash and Willie duet album that morphed into a four-way album. But the album was called “Highwayman”–in the singular–after the song and the artists were the four individuals. The song “Highwayman” became a surprise #1 hit, as did the album, and that led to a second album several years later and then a third and some tours. There was never a thought that Kristofferson was out of place. All of the other three had been singing hs songs for years. Eventually, they embraced the name “Highwymen,” though that led to some trouble and prompted a lawsuit because there was already a group with that name–a ’60s folk group famous for the song “Michael, Row the Boad Ashore.”
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Waylon was a huge country star and had about as many #1 hits as Cash–maybe more–and five times as many as Del Reeves. (How did Del Reeves get into this?).
What IS true is that Waylon was relatively unknown outside the U.S. Cash and Willie were of course know in Europe and Kristofferson was, too. Kris was a movie star (and sex symbol, for a while). Waylon was reportedly irked when they did an international tour and the European reporters were going gaga over the other and didn’t know who he was.
I actually went to two Highwaymen shows in the ’90s–Nassau Coliseum and Central Park– and Waylon was the most animated and entertaining of the group and the one that held the show together.
BTW, the lawsuit from the original Highwaymen group was settled and the “Michael” Higwaymen reconstituted and opened a show for the later Higwaymen in California. That wa in the pre-smart-phone age, of course, when people didn’t walk around with video cameras in their pockets, so there seems to be no footage of that event.
May 17, 2026 @ 8:37 am
I saw the Highwaymen perform in Charlotte NC in 1996. Everyone got big cheers that night but Johnny Cash got the biggest. You have to remember in 1996 Cash had released two albums on American Records which brought him much acclaim and put him back in the spotlight.
And in the 1970s early 80s Waylon was a certified rock star. First million album seller on music row.
May 17, 2026 @ 9:19 am
To Trigger – Waylon is the one that more current and upcoming artists claim as an influence than the other three Highwaymen. I think that’s due to his being seen as cool at a time when country wasn’t and also the way he fought for the rights of artists.
May 17, 2026 @ 10:19 pm
The Highwaymen started out on a holiday trip to Switzerland that the four friends took with their families. They commiserated over how none of them were getting radio play anymore and started talking about doing something together. They realized that four legends together could have more appeal than four fifty- ish artists performing individually.
I saw them in concert three times in 85, 90 and 95 and it was truly like seeing living history. I’m especially glad I saw them in 95 because all four were in good shape but within a couple of years both Cash and Waylon would begin to have health problems.
May 17, 2026 @ 9:10 am
Waylon certainly sought the spotlight – he didn’t narrate the Dukes of the Hazzard for the sake of art – and grew bitter when his career hit the rocks in the 1990s.
Unfortunately, his 90s albums, which were more original and country than Cash’s American Recordings, never found a market.
May 17, 2026 @ 9:48 am
Waylon narrated Dukes because he had taken a similar role in Moonrunners, the 1975 film that inspired Dukes. Gy Waldron made his low budget action movie based on Thunder Road, a favorite of his as a child, and based the characters loosely on his friends and relatives back in Kentucky. The actor boyfriend of Paula Batson, a publicist in RCA’s LA office and major booster of Waylon, recruited him to play the narrator and provide music for the film. After the huge success of Smokey and the Bandit a couple of years later, Waldron was approached by Warner Brothers to create a series that would appeal to the same audience. Since he already knew Waylon and Waylon was a big star by then, Waldron asked him to play the Balladeer and write the theme song. Waylon was connected to the series before it was even created.
May 16, 2026 @ 10:31 am
“They’d rather give you a song than diamonds or gold.” Songbird was a little softer than I would have liked and was hoping for some rowdier Waylon the next time so I’m looking forward to this one.
May 16, 2026 @ 12:40 pm
Written by Ed and Patsy Bruce. Ed had a great voice.
May 16, 2026 @ 8:24 pm
Yep. I was listening to Ed’s Evil Angel last night.
May 16, 2026 @ 4:06 pm
Watch it be disco.
May 16, 2026 @ 6:09 pm
We can only wish.
May 16, 2026 @ 7:36 pm
It appears I must have rocked the SCM boat one way or another or my comments fall off between AU and the US. Let me know if I’ve done or upset the apple cart. Meantime I’m excited with the Waylon news you bring. Pete.
May 17, 2026 @ 9:26 am
To Trigger – Waylon is the one that more current and upcoming artists claim as an influence than the other three Highwaymen. I think that’s due to his being seen as cool at a time when country wasn’t and also the way he fought for the rights of artists.
May 17, 2026 @ 7:38 pm
Waylon is my all-time favorite, I will certainly buy it! Love Songbird and I am sure I will love this!
May 18, 2026 @ 10:43 am
Just enjoy the great music