“I think the truck driver is sort of the last cowboy,” says Jason Lee Wilson, 37, winner of the 2016 Overdrive-Red Eye Radio Trucker Talent Search. “There is some amount of freedom in driving this commodity from one location to another, like cowboys would drive cattle from the fields to the stockyards.”
Wilson’s cowboy affinity covers more than trucking. He loves cowboy music and its not-too-distant cousins. His early musical exposure happened in church and in front of the radio, and his singing and songwriting are influenced by classic country artists such as Dwight Yoakum and John Anderson. That love of music and his later career choice of trucking combined to lead him to the live Trucker Talent Search competition held in August at The Great American Trucking Show in Dallas.
Wilson’s uncle had a grading and hauling business, and Wilson recalls riding in the company dump truck when he was a kid. “I never thought I would do that,” he says.
Nearly seven years into his driving career, he can’t imagine doing anything else. Driving a dump truck locally and dry van regionally, he feels a strong connection to the old-school trucking culture.
Perhaps that’s partly tied to being born and raised in Monteagle, Tennessee, known by truckers for sitting atop a particularly steep grade of Interstate 24 northwest of Chattanooga. The dangerous stretch was immortalized in Jerry Reed’s “The Legend” (from “Smokey and the Bandit”) and Johnny Cash’s “Monteagle Mountain.”
After studying studio art and minoring in music at the University of the South in Sewanee, Tennessee, Wilson worked in aftermarket gauge restoration. He went back to school to take some arts education and German courses and then began teaching art at an elementary school. He then switched to working for the county’s 4-H Club Foundation.
About the time he was finishing up at 4-H, a friend with a trucking company needed more drivers. “My friend helped me get my CDL, and I started driving for him off and on,” he says.
Soon after, he moved to Maryville, Tennessee, to be closer to family. A neighbor there drove for MDM Trucking, the company for whom Wilson now drives a dump truck full time. He still pulls a dry van monthly and bimonthly carrying stage lighting equipment and rigging for his Monteagle buddy’s company, Perfect Tenn Transportation.
During those career changes, even as far back as his childhood, Wilson has had one constant — music.
His father gave him a student-size guitar for his ninth birthday. “It was my dad’s guitar,” he says. “His father had bought it in a pawn shop in the 1950s and gave it to my dad when he was 9, so then I got it when I was 9. I learned how to play a song on it, and it hurt ’cause my fingers were small, and I picked it up again at 13 or 14.”
At that point, he began writing songs. “I’ve got a stack of songs that I wrote as a teenager that were modeled after The Beach Boys’ songs,” he says. “Girls, cars — they were cheesy, but they fit that age.”
A turning point in his songwriting came around age 17 or 18. “I had the desire to make music or to see what I could do (with the guitar), because I needed music to accompany the songs I was writing. I wouldn’t consider myself a musician as much as a singer-songwriter.”
He played in a college band, the Cumberland Runners, and gigs were steady. “We were playing pretty heavily for two or three years after college,” he recalls. “I was making a conscious effort, and it was a priority, and then responsibility took over, and it got put on the back burner.”
However, thanks to contacts made during his senior year in college, his musical interests took him on a long haul. Wilson was awarded a Thomas J. Watson Foundation Fellowship to study abroad for a year. His topic was “automotive design and its relationship with culture.” He interviewed executives with Jaguar and TVR in Britain, Ford in Wales, Volvo in Sweden, Fiat and Pininfarina in Italy, Ford and GM Holden in Australia, and Porsche, BMW and Ford in Germany.
A subtopic of his study was rockabilly music’s influences on “Kustom Kulture,” which refers to custom cars and the associated culture that grew from southern California’s hot rod movement in the 1960s. “Rockabilly music is the soundtrack for that phenomenon, and while I was in Europe, I was visiting car shows and making contacts and picking up information on labels and producers.”
After returning home, he recorded some tracks and submitted his CD to some of those contacts, with hopes of being included in music catalogues. Around 2006, a studio owner in Germany invited him to record. After doing so, he was booked for a short tour in 2009, which included a stop at the Tear It Up!! rockabilly festival in Croatia.
Since then, “I sort of had a creative dry spell, but in the past year, it started opening up. And then I had some productivity, and I had some shows pop up and opportunities, and Trucker Talent Search was one of them.”
Competing for the award brought the usual performance anxiety, but that was no problem. “It keeps you alert and keeps you on your game,” he says. “I have performed for small intimate crowds and large crowds, and I don’t think there’s really a difference. I can be just as nervous performing in church as a crowd in a large amphitheater.”
Radio stations and DJs have expressed interest in Wilson at various times, and he thinks the exposure from the Trucker Talent Search has put him back on their radar. He has been contacted for interviews and is excited about new doors opening.
His dream is for songwriting and performing “to be my profession and trucking to be my hobby,” though one deeply ingrained in his daily life. “I spend days in a dump truck by myself listening to the radio,” he says. That’s the sort of freedom and enjoyment that the cowboy in him would never want to give up.
The second time, it took
Jason Lee Wilson and Aleksandra Bosnjak were in Medulin, Croatia, on the same summer day in 2009. Bosnjak was there visiting her aunt, and Wilson, on a brief European tour, was performing there at the Tear it up!! rockabilly festival.
They discovered the coincidence four years later, when Bosnjak was in the United States on a work exchange program. At the urging of a colleague, she went to one of Wilson’s shows at a Harley Davidson dealership. Bosnjak told Wilson how much she enjoyed his performance, so he offered to get her a CD from his vehicle.
She waited a few minutes, and then a few more. After 15 minutes, she recalls thinking, “Why am I still waiting?”
Wilson had opened the trunk, then accidentally locked his keys in the car. “He had to wait for a police officer to help him open the window, and when he came back, he didn’t tell me about it, but I found out later,” she says.
Wilson and Bosnjak were married a few months later on Sept. 30, 2013. They spent three months in Croatia before settling in Maryville, Tennessee, in April 2014.
“Even though driving a truck is in my mind very serious, responsible and sometimes dangerous, he really enjoys it,” Bosnjak says. “He has a great team of people that he works with, and he gives the best of himself to his job — the same with his music.”