Trucker allows Alabama to ‘Roll On’

Josh Gentry is a trucker with a story that’s similar to that of most men and women behind the wheel.

From an early age, he loved big trucks and heavy machinery. That fascination laid the foundation for the career he’s had for the past two decades.

“It’s been almost an addiction,” he said. “It was just something that I always truly loved.”

Although Gentry’s story may strike a familiar chord, the 43-year-old trucker from Fort Payne, Ala., does have one notable difference from your everyday Joe. His father, Teddy, is the bassist for the band Alabama.

Rolling with the band

If trucking is Gentry’s addiction, then model trucks were his gateway drug.

“I could fill up Iowa 80 truck stop with all the die-cast trucks I had,” he said.

That addiction would soon reach the next level. When Gentry was on breaks from school, he had the opportunity to travel with Alabama. This prospect would excite practically anyone, but Gentry’s excitement was over something other than the band.

“I would schmooze Dad over and would be like, ‘Let me go on the road with you. I haven’t been out with you in a while,’” he said. “Well, by the time we got to the first show, I’d be in the truck.”

And that’s where he’d stay, from the first show through the last. Just a truck-crazy little boy bugging the driver about what all the lights and buttons were. Gentry said he’s still close with the drivers he met as a child.

He added that after those experiences, it was inevitable he’d end up in the trucking industry. His first trucking job came when he was 23, working on his cousin’s farm. While the majority of his time has been spent hauling cattle, he’s also pulled produce, dry van and hopper bottom.

“It’s just always been a love and a passion … That’s pretty much the sum of it,” he said. “It’s just a love. I can’t explain it.”

The ‘full-circle’ moment

For the Gentrys, their two worlds are now converging. With Alabama embarking on its 2023 “Roll On 2 North America Tour,” the band needed some heavy hauling ability.

At that same time, truck company Kenworth – which has a long-standing relationship with the band – was celebrating its 100th anniversary. To mark that occasion, the company decided to provide Alabama with a T680 76-inch mid-roof sleeper for the concert tour. Of course, now the band needed someone to drive it.

That’s when Josh got a call from his dad asking if he’d like to drive for the tour. Needless to say, he jumped at the opportunity and has been on that job since June.

While the job descriptions may be similar, Gentry said the tight time constraints along with some unique challenges make hauling musicians a little more stressful than hauling cattle or produce.

“The worst part is, some of these venues were built in the early 1900s or maybe even been 1800s, and their loading docks – they’re just not the easiest to get into,” he said.

Gentry added that he’s had to put his “thinking cap” on more than a few times when it came to navigating his way into a venue. But despite the challenges, coming full circle from being the little kid bugging the driver to being the one behind the wheel has been an incredible experience.

“Actually, it’s surreal. Because in a broader picture – when you’re a kid and you love trucks and love trains or anything that has anything to do with heavy machinery – the things that I loved when I was a kid, I still love them today,” Gentry said. “So it’s just been absolutely 100% an incredible thing to get to not only spend more time with Dad at home, but getting to spend more time with Dad on the road too.”

He added that working alongside him also has provided a new perspective on his famous father.

“Then you’re not looking at it from just him being Dad. You’re looking at it from the standpoint of this is his career, this is what he does, this is how he makes a living,” Gentry said. “I’ve actually gotten to where, as I’ve gotten older, I see the joy that it brings him – the happiness that he does enjoy being out there playing music with five or six of his close friends. And getting to actually enjoy the whole aspect of what he does. So to me, (before this experience) I don’t think I could ever look at my dad as being Teddy Gentry from the group Alabama, because I’ve never been able to look at him any other way than just Dad.” LL