Jennings

REMEMBER those big rectangular pre-digital VHS tapes?  

Well, Shooter Jennings, son of late country music great Waylon, has held on to a few of them. 

Now I’ll explain why they’re so precious to him.  

They contain episodes of a TV show almost as popular as Dallas in the early Eighties — The Dukes Of Hazzard. 

As the opening credits roll, you see “The General Lee”, a souped-up 1969 orange Dodge Charger, careering into view.  

Inside are outlaw cousins Bo and Luke Duke, on the run from crooked officials, Boss Hogg and Sheriff Rosco P Coltrane. 

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You hear the rollicking theme tune, Good Ol’ Boys, being sung in commanding, if tongue-in-cheek fashion by — you might have guessed — Waylon Jennings. 

He also serves as the show’s laidback narrator, The Balladeer, and one of his pearls of wisdom is about poster girl Daisy Duke, remembered for her skimpy denim shorts. 

“She drives like [stock car racer] Richard Petty, shoots like Annie Oakley, and knows the words to all of Dolly Parton’s songs.” 

But he doesn’t appear on screen until season seven when, after demands from fans, he is presented as an old friend of the Dukes in an ­episode titled Welcome, Waylon Jennings. 

‘A massive cultural moment’ 

“Just last night, my wife and I were watching some episodes,” Shooter tells me via Zoom from America’s West Coast as we discuss a fabulous new project involving his father’s previously unreleased music. 

“It made me think what a massive cultural moment the show was,” he continues. “Just how perfect my father’s voice was for it. 

“I think he loved doing those shows and it wasn’t a lot of work for him. He’d be on the road and just stop by a studio and do the voiceovers. 

“There’s real humility about them. He seems to be making fun of himself the whole time. It’s really funny to hear.”  

Waylon is remembered as a ­pioneer of the “Outlaw” country scene, a singer who wrestled the Nashville music-making machine and won control over his recorded output. 

Hellraiser, maverick and bearer of a rich baritone, he was an obvious choice to join fellow renegades Johnny Cash, Willie Nelson and Kris Kristofferson in Eighties supergroup The Highwaymen. 

Born in Littlefield, Texas, in 1937, he was consumed by music at an early age and, in 1958, came under the wing of Buddy Holly, who arranged his first recording ­session. 

The stuff of legend, Waylon gave up his seat on the flight that killed Holly, The Big Bopper and Ritchie Valens on February 3, 1959 — “the day the music died”. 

Shooter says: “If my dad had got on the plane, the music world would be quite different. I often think what it must have been like for him to have survived that. 

“Throughout his life, Buddy was huge to him and he used to talk about him all the time. 

“A lot of his spirit and energy came from rock and roll, from Buddy, who gave him little lessons in songwriting. 

“But he also loved country music, the beauty and sentiment of it, and his voice was just so ­vulnerable and awesome.” 

From the mid-Sixties onwards, Waylon would become a fixture at the top of the country charts but his best work appeared after he gained creative control from RCA Records in 1973.  

He delivered a string of fine unvarnished albums including Lonesome, On’ry And Mean, Honky Tonk Heroes, Dreaming My Dreams and Are You Ready For The Country. 

In 1979, he and fourth wife Jessi Colter, a fellow “Outlaw” country singer, had their only child together, Waylon Albright “Shooter” Jennings. 

The Albright comes from Richie Albright, Waylon Snr’s right- hand man and drummer in The Waylors. 

And the main reason I’m talking to Shooter is because he has unearthed a goldmine of un­released Waylon recordings, taped between 1973 and 1984. 

This has resulted in the appearance of Songbird, the first of three albums culled from the material and lovingly restored by him with the help of surviving members of his dad’s band, along with younger musicians and backing singers. 

‘Passion and soul alive today’ 

“It’s been surreal,” says Shooter, a singer in his own right and in-demand producer. “Everything has lined up for me to have this purpose. 

“This project has given me an entirely new chapter in my relationship with my father and working on this music has brought a whole new understanding about how, when and why my dad made music.  

“The hard work is there on the tapes and the passion and the soul within is as alive today as it was the day it was recorded.” 

I guess the reason The Dukes Of Hazzard cropped up in our chat is because much of the Songbird album’s music was recorded around the same time as the show aired. 

Then I just kept finding these hidden albums,” he says. “It didn’t feel like stuff that was not meant to be released and there were songs I never knew he’d attempted.

Shooter Jennings

Shooter became aware of Waylon’s buried treasure in 2008, “about six years after he died” aged 64 from complications of diabetes.  

But the project only began in earnest last summer when he started sorting through hundreds of high-resolution multitrack transfers of his father’s personal studio recordings.  

What Shooter discovered blew his mind.  

Listening to his dad performing with his ace band became “a wild adventure”. When Shooter heard their cover of Fleetwood Mac’s Rumours track Songbird, written by Christine McVie, he realised he was on to something “really exciting”. 

“Then I just kept finding these hidden albums,” he says. “It didn’t feel like stuff that was not meant to be released and there were songs I never knew he’d attempted.” 

Shooter says that much of the material was “professional cuts with a lot of attention to detail, much more than sketches”. 

“My mom told me that my dad always said that every song he recorded should be good enough to be a single when it was done. He had a great work ethic.” 

Shooter settled on Songbird as the opening track and album title because he realised that Waylon “was a kind of songbird”. 

“I wanted to hit home how good a song interpreter he was and how he could make a song his own,” he says. “And I wanted to bring him back with an emotional song, one that’s going to make you cry. 

“Every time I play it for anyone, they tear up at the bit which goes, ‘And I feel that when I’m with you, it’s all right’. 

“It’s such a beautiful take that people are shocked they haven’t heard it before.” 

In order to take Songbird to even greater heights, Shooter enlisted contemporary country singers Ashley Monroe and Elizabeth Cook to provide backing vocals. 

‘Obsessed with Hank Williams’ 

“They’re the funniest people, like a duo, and they’re hill­billies like me,” he says. 

“Elizabeth and I have been really good friends for 15 years plus and she brought Ashley to my studio around the time I was going through this. 

“And they were so moved by Songbird. I realised their airy, birdlike voices could elevate it to some fantasy realm. 

“So I asked them to come back and do some background vocals and they really killed it.” 

Also adding finishing flourishes to the album’s ten tracks are some surviving Waylors including guitarist Gordon Payne, bassist Jerry Bridges, keyboardist Barny Robertson, and backing vocalist Carter Robertson. 

The second song The Cowboy (Small Texas Town) is credited to Johnny Rodriguez but Shooter suspects his father had a hand in writing it. 

These telling lines back up that theory: “My long shaggy hair, and the clothes that I wear/Ain’t fit for no big fancy ball.” 

The song fits with Waylon’s image of staying true to his humble origins — a quality Shooter sees in today’s stars such as Charley Crockett, Tyler Childers and Benjamin Tod. 

He credits his father with blazing a trail for these independent spirits thanks to his battle with RCA Records. “My dad really opened it up. And even though Nashville got their grip back on it for a little while, they’ve been blown apart now.

“They’re just scrambling to find anyone who’s like one of these guys.” 

I ask Shooter what Waylon used to tell him about growing up in Littlefield, Texas. 

“He would tell me how poor they were, for sure, that they had dirt floors, that his mom would put him in places the rats wouldn’t get to.”  

When Waylon became famous, the town would hold a Waylon Jennings Day and their favourite son “would go back there and do a show”. 

Shooter adds: “I loved my dad’s family, his brothers and his mom. I got to know all of them and his brother James is still around and runs this little gas station there.” 

Unbeknown to the residents of Littlefield in 2025, Shooter decided to put up billboards around town featuring lyrics to some of the Songbird songs.

He and Johnny [Cash] came from the exact same background. They both picked cotton. They both listened to Hank Williams on the radio and both journeyed to Mecca [Nashville] to make music.

Shooter Jennings

“I didn’t even tell them. But when we put out that song, The Cowboy, I really wanted to put the focus on Littlefield.” 

We’ve heard about Buddy Holly but I’m keen to find out from Shooter who else was his father’s music hero. He instantly mentions country music’s first superstar — Hank Williams, who lived fast and died young. 

“My father was obsessed with Hank Williams. He was similar in a way because of the vision he had for his songs.” 

As for Waylon’s reputation as a hellraiser, Shooter has this to say: “It’s funny, he didn’t drink. People always get that wrong. 

“He only did the uppers but we had an empty alcohol cabinet in our house because he just didn’t get any.” 

And what does Waylon’s recently remarried widow Jessi Colter, Shooter’s mother, think of the Songbird project? 

“She has helped us,” he replies. “I had to borrow money from her to do it because I didn’t want to get a label involved. 

“She was also a great emotional support to me, even if she wasn’t emotionally tied up in the project.” 

Hearing Waylon sing “didn’t make her sad but she loved it. She’d say something like, ‘They sound like they were having a good time that day.’ ”  

Before we go our separate ways, Shooter opens up about Waylon’s famous friends, notably his Highwaymen buddies Johnny Cash, Kris Kristofferson and Willie Nelson, still touring and making records at 94.

Waylon and Cash shared an apartment in Nashville in the mid-Sixties and had a strong, if sometimes tempestuous bond. 

“They loved each other,” says Shooter. “Just like anybody else, they would have little bicker fights and not talk for a couple of weeks here or there.  

“But he had a great relationship with Johnny and June [Carter Cash].  

“He and Johnny came from the exact same background. They both picked cotton. They both listened to Hank Williams on the radio and both journeyed to Mecca [Nashville] to make music.” 

Shooter continues: “And I loved Cash. We used to go to his house when I was little. He was always very nice to me.” 

He also remembers hanging out with Nelson’s daughters Amy and Paula. “We were all around the same age and together on the road during the Waylon and Willie tours.  

“And then The Highwaymen happened and I was around Kristofferson’s kids because they lived in Tennessee. 

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“Life’s weird, man,” decides Shooter. “I got dealt a really good hand being born to who I was. So I don’t take it lightly.” 

Hence a son’s labour of love to bring Waylon’s music to a whole new audience. 

WAYLON JENNINGS 

Songbird 

★★★★☆

Ken Jennings wants you to know he didn’t name his trivia game “Kennections.”

“It’s really an unpleasant name,” the “Jeopardy!” champion turned host says of the quizzes now published weekly by Mental Floss. “We have to lead with that. It was suggested by an editor at Parade Magazine, but it doesn’t look good or sound good.”

But Jennings loves the quizzes themselves, which are now collected (kellected?) in “The Complete Kennections.” The Simon & Schuster release, on shelves July 29, follows earlier Jennings books that included more writing. Those include: “Brainiac: Adventures in the Curious, Competitive, Compulsive World of Trivia Buffs,” “Maphead: Charting the Wide, Weird World of Geography Wonks,” “Because I Said So!: The Truth Behind the Myths, Tales, and Warnings Every Generation Passes Down to Its Kids” and “100 Places to See After You Die: A Travel Guide to the Afterlife.”

Jennings recently spoke about his books, AI and why trivia matters. This interview has been edited for length and clarity.

Was writing books always a goal?

I was an English major in college. I wanted to write and to teach, but writing didn’t seem like a practical choice. I was also doing a double major in computer science, and in 2000 it was absurdly easy to get a job at a friend’s startup, even if you were a terrible programmer, which I was.

Writing about geography and myths and fabled places of the afterlife all seem to make sense coming from the brain of a “Jeopardy!” champion.

It’s easy to imagine the same kid in an elementary school library, reading about these things in the World Book encyclopedia during a rainy recess. That’s my origin story. I was just a sponge for weird information. That’s my origin story right there.

I thought of “Jeopardy!” as a fun, crazy summer and did not think it would be my life, so I tried making each book less about “Jeopardy!” and trivia than the one before it.

Is the information in your books trivial, or do you think it’s important to get readers to understand geography and the way our culture passes down myths and tales?

I’m a believer that trivia is not just a bar pastime, or even a way for little Lisa Simpsons to get told they’re smart into adulthood. I always felt trivia was kind of a universal social good, a way to enjoy cultural literacy.

I feel I’m part of the last generation that had to justify having nerdy interests. It was kind of shameful and made you the punchline of jokes in movie comedies and stand-up. Today, it seems self-evident to everyone younger than us that, well, of course you would just be obsessive about lunchboxes or about “Battlestar Galactica” or fossils. That’s totally normalized, and it’s actually good.

But I’ve also been mourning the loss of generalists, people who knew a little bit about everything, which is what “Jeopardy!” celebrates, but it’s not fashionable. We live in a siloed society of specialists. And I really think we’d be better off if everybody knew a little bit about everything.

I do think it’s good to know trivia is not something that makes you better than other people. It doesn’t exist to show off or even to make you feel smarter about yourself. Ideally, it should bring people together and make the world more interesting and make you a more sparkling conversationalist.

“Jeopardy!” and your books strive to make learning facts fun. Is there a lesson there for educators?

I think that’s the beauty of trivia. I wrote a series of books for kids with amazing facts because I liked that kind of book when I was a kid. And you can see it in a classroom, when you see kids’ eyes light up about information and about serious subjects and about knowledge when it’s presented in a fun way, especially with narrative.

Narrative is the secret sauce. It just makes kids think the world is an amazing adventure and you just have to be curious and dig into it. But that gets beaten out of us, and then a lot of us at some point just specialize in one thing. You need to remind people that learning is not a chore. If it’s not fun, you’re doing it wrong. And trivia is very good at that.

Every good “Jeopardy!” clue tells a story in some way, saying, here’s why you should want to know this or here’s what this might have to do with life and the reason why this is not random minutia, which I think is a lot of people’s stereotype of trivia nerds. A trivia question can help you connect it to other things. Trivia is just an art of connections.

That’s certainly true in your “Kennections” book.

I grew up doing crosswords, riddles and rebuses. I’ve always liked trivia that rewards not just the recall of the right fact but has a little more mental clockwork involved so you have to solve some puzzles. You have to analyze the clue and figure out why it exists and what it’s asking or what it’s not asking, what was included, what was omitted. There’s a lot of analysis that can kind of lead you to the right answer by deduction, even if you don’t know the right fact off the top of your head. One half of your brain is just trying to recall these five facts, but you’ve got this other half that’s trying to figure it out and step back and take the big picture. And it might be something outside the box.

The art of it is finding five things that fit in the category but that can have double meanings: Commodore is both a computer and a member of a Lionel Richie combo.

You write that “Kennections” consumes your life — you go into a bagel store and wonder if you can build five questions out of the flavors. Is the problem that in your day-to-day life, you’re constantly seeing things and thinking things this way? Or is the problem that you can’t say this out loud because you’ll make your family crazy?

That’s something I learned early — that being this trivia-loving kid has the potential to be annoying. But my kids know what they’re getting from me at this point. And they both have the gene themselves. One is obsessed with Major League Baseball, and one is obsessed with the history of Disney theme parks, and they have encyclopedic knowledge every bit as awe-inspiring and freakish as I had as a kid. And I’m proud of that.

Do you worry about living in a culture that’s so polarized that facts aren’t even universally received and where AI takes over people’s need to be curious, allowing students to take shortcuts in learning?

I think an oligarch class is going to deliver us a combination of both, where the AI will not only create reliance on it but give us bad, counterfactual information about important issues. And it’s really something I take seriously. It’s really something we need to be pushing back on now.

You don’t want to trust an AI summary of a subject or AI’s take on an issue without understanding who controls that algorithm and why they want you to hear that information.