Confidence is an important thing when one is creating something new. To (metaphorically) birth something into the world requires strength and a sense of assuredness that what you’re bringing deserves to be there. But how one achieves confidence can be a touch-and-go situation. And confidence itself is precarious; it’s easily broken. Any artist will tell you that. But one who can also speak eloquently about the idea from myriad vantage points is the 42-year-old Nashville, Tennessee-born Shooter Jennings.
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If you ask the Grammy Award-winning artist about when he began feeling proud about the songs he’s written, he’ll hesitate. “It’s a learning process,” he’ll say. But that’s the funny thing about confidence. If you express too much of it or believe too much of it regarding yourself, you can be crushed. Instead, it’s best to leave it up to others to talk about your great work. Like Jennings’ latest single, “Gene’s Song,” which Americans Songwriter is premiering today (December 15).
“I’m really hard on myself,” Jennings tells American Songwriter. “To me, of all the songs I’ve ever written, there’s only a handful that I’m proud of, to be honest… The older I get, the harder I am on myself.”
Jennings talks about other songs he’s written, some of which have earned hundreds of thousands (or even millions) of streams. But when he hears them, if he still listens to them at all, he’ll notice lines or licks that he’d change. There are other creative people who share this feeling, like actor Adam Driver who famously never watches any of his performances, from indie films early on to Star Wars sequels of today. Driver is forward-looking. In this way, art is more like the wake from a boat, rippling through.
“You just commit to turn your back and keep walking,” Jennings says. “You just hope you didn’t do something damaging in the long run. But you learn from things, what to keep in an arsenal.”
Many might not know, but Jennings has, over the years, invented a few video games, to go along with his songs and albums. They are dialogue-based, discovery games. He says he remembers being so excited to complete the first one; now he can’t really play it. He’s less embarrassed by the second version and now he thinks version three is good. (Perhaps until the new and improved version 4.0 drops.) But he’s the same way with his music. Of course, the closer one is to something, the easier it is to see the flaws. Jennings also likens it to the idea of a chef.
“You start to have more refined taste,” he says. “When you first start, your palate is pretty bland but the older you get, the more refined it becomes.”
No matter what Jennings will say about his work, personally, there are many who love it. From his solo efforts to his more recent production work on albums like Brandi Carlile’s LP, By the Way, I Forgive You, and others from artists like Jason Boland and Billy Ray Cyrus. Jennings has his hands in all aspects of the business, from lyric writing to singing to arrangement and instrumentation to working behind the boards and promotion. It’s different than those who just have to sing the words put in front of them.
“When you’re writing on your own, you can be your own worst critic,” Jennings says. “You’re tapping one well for the most part. But to be able to do five or six or 10 projects a year with other people, personally, the creativity level is so much higher than, say, one record a year.”
But here’s where the latest bit of magic happened: in his recent role as a producer, Jennings has been able to turn the tables a bit on his psyche. Whereas he once saw all the holes in his own efforts, he now has the instinct to plug those holes in other artists’ work. He can use all the tools he’s honed in his career to buoy and buttress performers who need his help—his confidence building. It’s a brilliant evolution and one he’s been now recognized for in big ways (including award nominations and receipts).
“With production,” he says, “and working with another artist, I didn’t realize how much it was going to fulfill me. All of a sudden, that feeling of pressure, that criticism thing goes away. The artist is carrying the brunt of that on themselves. My job is to relieve that to some degree, to fortify their confidence in themselves.”
It’s funny; those things we wanted to do as young people are often the things we wish we could be as adults. Growing up, Jennings remembers that he wanted to work in production. The electronic ‘90s band Nine Inch Nails was the group that first inspired him to make his own songs. He bought some computer software and began dabbling. Jennings, who is the son of the famous country artist, Waylon Jennings, had music all around him as a kid. But it was NIN that made him dive in. He still sometimes uses the $100 bass he bought back then in 1999. One of the first albums he produced was by the country artist Jason Boland, and more recently, Jennings ran the boards on Carlile’s 2021 Grammy-nominated, In These Silent Days.
“When I was young,” Jennings says, “I had a studio setup in my dad’s house. The first band I got into was Nine Inch Nails. They made me want to play music. I was a little computer nerd.”
But just because Jennings has become a sought-after producer, doesn’t mean his own songs have taken a total back seat—for instance, Jennings released the new song, “Leave Those Memories Alone” in November. In fact, there are some that remain integral and crucially important to both his story and catalog—and that of the larger Americana catalog, as a result. Take, for example, “Gene’s Song.”
When Jennings’ father died nearly 20 years ago, he remembers telling himself that he was a tough guy and his father’s passing wouldn’t bother him. But of course, it did leave an absence in his life. Jennings’ friend and former high school art teacher, Gene, helped fill that void. Gene has since passed away, but before doing so he drew Jennings a card.
“I remained friends with Gene,” Jennings says. “He quit teaching and opened an art supply store in Nashville. I’d smoke cigarettes with him and listen to John Lee Hooker and talk about music.”
Gene showed Jennings pictures of when he used to be in a band and one in which Gene was dressed like a proto-Kurt Cobain in a dress. Jennings would visit Gene when he came back to Nashville from Los Angeles where he lives and works. And when Gene died, his daughter sent Jennings the card he’d drawn, a cartoon pistol. For Jennings, who is now a father himself and who understands the need to keep that wondrous creative spirit alive, the note with the little handmade drawing and Gene’s signature was immeasurably moving.
“I got it and it touched me,” Jennings says. “It meant a lot that he in the last moments of his life remembered me. Because I always loved him. He had a huge impact on my life. Especially after my dad had passed away. At times, I didn’t know what I was missing. But having these figures in my life made me the person I am today.”
Photo courtesy Big Hassle