To the casual observer, Darden Smith’s approach to art and life looks like cliff diving. Over the course of his 35-year musical career, the 59-year-old Brenham native has thrown himself headfirst into a lot of unusual projects without being entirely sure how he’ll land. Fortunately, most of those leaps of blind faith have turned out beautifully, earning Smith a reputation for stretching boundaries and defining his career on his own terms.

It’s worth noting, though, that Smith doesn’t always land on his feet. But that’s a big part of what keeps him going, too. His willingness to constantly explore new challenges comes not just from being curious and creative, but also from crashing, burning and yet thriving. Which is why when Smith chooses guests for “Who Said You Could Do That?,” his new live interview series at Austin’s Stateside Theatre, he has but one rule: He only interviews people who’ve crashed and burned.

“The artists I love, the ones I admire as they age, all of them have crashed,” he says. “They’ve crashed and they’ve rebuilt in a truer way.”

For Smith, rebuilding truer has meant stepping out of the spotlight and helping other people — kids, soldiers and now frontline workers — experience how deeply transformative songwriting can be. Of course, that work has transformed him as well, giving him the wide-open vision that’s behind his new multipart, multimedia album, Western Skies.

A Boy and a $22 Guitar

Smith’s childhood on the outskirts of Brenham gave him ample room to develop an artist’s sensibility. After taking care of cattle and chickens after school each day, he’d get lost in 500 acres of woods and pastures, making up stories in his head before finding his way home for dinner.

He first picked up a guitar — in his brother Dugan’s room — when he was 9 years old. When Dugan found out, he declared the guitar “ruined” and made Darden pay $22 for it.

But Darden got the better end of that deal. He loved guitar and got serious about learning to play. He took lessons from the daughter of his church choir teacher, discovered Neil Young, and learned every song in the Harvest and After the Goldrush songbooks. Soon the sounds of Willie Nelson, Jerry Jeff Walker and Leon Russell seeped into his bones, too.

When he was in eighth grade, Smith’s family moved to Humble, which was quite different from Brenham at the time: urban, chiefly Anglo and, for a transplanted country kid, alienating. So he retreated into his room and started writing songs. “I was a suburban boy,” he says, “but music was my superpower.”

During his freshman year of high school, he bribed his way into his brother’s band. He knew they needed a microphone and guitar amp, so he went to the music store and bought them. When they wanted to borrow his equipment for a gig, he agreed. “But I come with it,” he insisted. “And I’m singing songs, too.”

Over the next few years, he used his older brother’s ID to sneak into Houston bars to hear musicians like John Prine, the Lost Gonzo Band, David Allan Coe, Jerry Jeff Walker, Michael Martin Murphey, B.W. Stevenson, Shake Russell and John Vandiver. He knew he was passionate about music, but he didn’t think of it as a career path until his dad inadvertently lit the fuse.

“My dad’s ethic was, ‘When you think about what you want to do for a living, think about what you’d do if you didn’t have to work, then figure out how to get paid to do that thing,’” Smith recalls. “One night we were watching Guy Clark on Austin City Limits, and dad said, ‘You see that guy in the middle? He’s probably getting paid.’ And it was like this light went on, and I was like, ‘Oh! I can get paid! I can make this my job!’”

Smith concedes this wasn’t exactly the lesson his father hoped to impart. It wasn’t meant to click. But it did.

Darden Smith / Photo by Michael O’Brien

Climbing and Crashing

Smith began pursuing that dream job in earnest in the ’80s after transferring from Southwest Texas State University to the University of Texas and moving to Austin for good. He released his self-produced 1986 album Native Soil on his own independent label, Redi-Mix Records, but a jump to the majors was right around the corner. His work caught the attention of Ray Benson from Asleep at the Wheel, who helped Smith land a deal with Epic Records and produced his label debut, 1988’s Darden Smith. The album featured guest appearances by Lyle Lovett and Nanci Griffith, who Smith had opened for frequently.

Smith’s career took off after his move over to Columbia Records for 1990’s Trouble No More and especially ’93’s Little Victories. The latter’s “Loving Arms” broke into the Top 100, with a video in steady rotation on VH1. People recognized him as he walked down the streets of New York and London.

“It was cool — very ego-stroking,” he says. “I never made much money, but it seemed like everything was going up. As a young kid, you start believing it. You start thinking it’s gonna last forever.”

Then, in the course of three short days, everything fell apart. He lost his agent and his record contract with Columbia, and he told his wife he was filing for divorce.

“My life just went into a tailspin,” Smith says. “I had a 2-year-old son, I had no money, and I just didn’t see it coming. And you know, when you come off a major-label deal, you’re damaged goods. Nobody wants to hear from you.”

Quick as a wink, he’d gone from up-and-coming to seemingly unemployable in the industry — at least on the level he’d all-too-briefly grown accustomed to. But time and experience have allowed Smith to look back on that period as the catalyst of a critical shift in his life as a musician.

“I wouldn’t wish it on my worst enemy,” he says, “and it’s the best thing that ever happened to me.”

Without the security of a record deal, Smith started drawing upon the scrappy business sense he developed as a child, when his father entrusted him with money to make deals for cattle and chickens. For the next six years, he did whatever he could to make a living. He kept writing songs and playing gigs, and even took a commission writing a piece, “Grand Motion” (1999), for the Austin Symphony.

But peppered in between the small successes were more disappointments. At one point, he successfully negotiated a contract with Lucky Dog Records in Nashville. Then they called him in, told him “We just realized you’re not country” and canceled the deal. Another time he was commissioned by O Vertigo, a dance company in Montreal, to write a dance theater work for a world tour. He was four months into the project when the choreographer changed her mind, and he lost the gig.

Since he had a 6-month-old daughter and an empty work calendar, he called up a friend who did art welding and learned to weld. His first day on the job, while digging a ditch, he found himself facing a barrage of questions about his career from the hungover 21-year-old digging next to him. Smith answered politely as long as he could, but when the young man flat out refused to believe he’d been on TV, his irritation boiled over.

“I stood up, leaned on my pick ax and said, ‘Dude, I’ve done the Tonight Show twice, I’ve been on Austin City Limits twice, I’ve done the Today Show. I’ve done videos, I’ve had a top 10 VH1 video. I have two Top 10 hits. And he asked, ‘So what are you doing here?’”

For Smith, it was a watershed moment. “That was when I realized it doesn’t matter what you think you deserve,” he says. “The music business builds you up to where you think you deserve this stuff. But at the end of the day, it just matters where you are.”

Darden Smith with veteran Jeffery Hutcherson during a SongwritingWith:Soldiers session / photo by Ed Rode

A New Way to Work

From that point forward, Smith’s ambitions as a musician began to change. With the glitz of big-name record companies in his rear view, Smith was able to think more creatively about what he could do with music other than put it on the radio.

“I write songs, that’s what I do,” he recalls thinking. “How can I use this talent in the world? Not just to sell records and get famous. I don’t care about that anymore. Music can be used in the world in so many ways, and it’s up to me to decide how I want to use it.”

In that spirit, Smith has designed projects not just to support himself but also to help others. In 2003, he founded the Be An Artist program, where he went into schools to write songs with children and inspire them to be creative. In 2012, with his friend Mary Judd, he co-founded SongwritingWith:Soldiers (SW:S), a nonprofit that pairs veterans with songwriters who help them tell their stories in song. A study conducted by Harvard Massachusetts General showed these kinds of sessions reduce PTSD among participants by 33% and depressive symptoms by 25%.

The spark that kindled SW:S is “Angel Flight,” a song Smith wrote with his friend Radney Foster to honor the Red River 44, a Texas National Guard aircrew lost in Iraq. The song debuted on Smith’s 2013 album Love Calling and proceeds from Foster’s accompanying video go to the Texas National Guard Family Support Foundation.

Foster notes he’s written more with Smith than he can remember and that the process is always intense. “He’s a beast,” Foster says, “and I mean that in the best sense of the word. His mind works so quickly. If you don’t like a line, he’ll hit you with five more.”

But when working on “Angel Flight,” Foster says he was particularly struck by the care Smith put into research and preparation. “Darden had done his homework, sitting down with soldiers and talking to them,” Foster says. “He’d transcribed everything, and it was all spread out on sheets of paper in my studio. The first line, ‘All I ever wanted to do is fly,’ is straight out of a guy’s mouth.”

That loyalty to soldiers’ language and stories gives “Angel Flight” and other SW:S songs undeniable poignance and creates a transformative experience for vets, families and songwriters alike. Mary Gauthier produced her Grammy-nominated album Rifles and Rosary Beads from songs she wrote with vets and their families, all of whom are credited on the album.

“In these songs, the songwriter is just really transcribing someone else’s story,” Gauthier says of her SW:S experience. “We’re brought into the story in a way that few civilians ever get to experience. It’s sacred.”

To date, more than 500 soldiers and family members have participated in SW:S collaborative songwriting sessions. When Smith reflects on the program that’s benefited so many people, he remembers that if things had been different, it might never have happened.

“If I hadn’t crashed, I’d never have started the Be An Artist program, never have started SongwritingWith:Soldiers,” he says. “In New York, L.A. or Nashville, the glare on you makes it intimidating to step outside the norm. But here, nobody cares. So I became more of an explorer, following a route that made sense to me.”

That explorer spirit followed him into the COVID crisis, when writing songs for other people took on a whole new importance. When a friend’s wife was in a coma and dying of the disease, Smith offered to help him write a song for her birthday. He told his friend to speak every thought he had about her into his phone, and then text it all to him. “I told him, ‘Just spend all day. Text me every thought you have about her. Everything. Just speak it into your phone and text it to me.’”

By day’s end, he had a long thread of texts. That night Smith wrote the song and recorded a demo. His friend sent it to the nurses who were caring for his wife at the hospital, and they played it for her. “Her heart rate changed. Her breathing changed,” Smith says. “She ended up dying. But for that moment, what better use of my skills?”

Around the same time, Smith was talking to a friend who worked as a doctor in a Boston hospital. Together they hatched a plan to start Frontline Songs, an organization that allows songwriters to help healthcare workers heal through songwriting.

Gauthier was one of the first artists to sign on to the new project. She’s conducted songwriting sessions at Cedar Sinai Hospital in Los Angeles and Beth Israel Deaconess Medical School in Boston. “The doctors and nurses are deeply traumatized,” she says. “They’re struggling and they’re exhausted, and they’re still in it right now. So being able to be of service to them has been tremendous.”

Though the project is still in its early stages, Smith has a clear idea of its significance. “This is not about career,” he insists. “I’ve got that sussed. This is true art, true collaboration.”

Western Skies

Like the outside-the-box projects he does with kids, soldiers and healthcare workers, Smith’s 16th album, Western Skies (out April 1), is as bold as they come. It features 11 songs, some brand new and others remade from 10-year-old bits and pieces he found in his piano bench. True to his hard-to-nail-down style, the songs reflect a variety of influences, from folk to Great American Songbook-inspired pop and jazz. And the themes — impermanence, hanging on and letting go, a yearning for kindness and justice — ring especially true in the COVID era.

“There’s a lot of mortality in the record,” Smith says. “I lost a lot of people, a lot of things, and these songs were written conscious of the transition. I also just felt like, ‘Hey, man, we’re all mortal, and if you got something to say, say it now.’ It’s actually quite freeing.”

That sense of urgency is felt in the lyrics, which range from direct to poetic but are always honest to the bone.

The songs are deeply satisfying, but they’re only part of a larger project. The album’s companion piece is a book that features song lyrics, short essays, prose poems and Polaroid pictures Smith took on trips through West Texas during the pandemic. Near Marfa, Marathon, Tornillo and El Paso, he snapped black-and-white images of gas stations, train cars, water tanks, mountains, cloudscapes and bridge trestles — the stuff of road trips across the Trans-Pecos region.

“I’ve always loved that part of the world,” he says. “There’s a danger and a beauty that has a stillness. When I close my eyes and think about a landscape, it’s got a big flat horizon. Western Skies is about the sort of mythology of Texas and the visual landscape of it.”

True to Smith’s exploratory spirit, the project didn’t emerge from a well-defined plan. He’d been making trips to Arizona to work with Songwriting With: Soldiers and stopping at Sonic Ranch in Tornillo to record some songs. But on the third night in the studio of a three-night recording session, he saw the full scope of the big picture he wanted to paint with words, music and pictures.

To ensure that each part can stand alone, Smith has partnered with people in various fields who understand his vision and push him to do his best work. Album producers Michael Ramos and Stuart Lerman have collaborated with him on projects across the highs and lows of 30 years. DJ Stout, a partner at Pentagram Studios, designed multiple album covers for Smith, as well as his book Habits of Noticing (2018), before taking on design duties for Western Skies.

“Darden’s great to work with,” says Stout, “because he’s an artist, but he’s also not afraid to say, ‘You’re an artist, too, and you do a different kind of art than I do. Here’s my idea about this record and my photographs, but I want you to design it.’’’

Western Skies also ventures into territory brand new to Smith. He contracted Burning Bones Press to turn 13 of the Polaroids into lithographs, which have been shown at Redbud Gallery in Houston since March 5. And after the album was cut and the book was at press, he also decided to record the essays and prose-poems from the book as a separate album.

While an artist with a more controlling personality might shy away from developments like these, particularly late in production, to Smith they’re all just part of his creative process that continually shifts and expands.

“Every seven to 10 years,” he says, “I need a big rambling, problematic, expensive, borderline unwieldy project to push myself beyond anything I’ve ever done before.”

It’s fair to say Western Skies fits that bill. And it really makes one wonder where Darden Smith’s next great big leap will take him.

Lead photo by Jeff Fasano