Trucker helps famous father and his band ‘Roll On’

Josh Gentry is a pretty down-to-earth guy. The 43-year-old trucker has a fun, easy-going personality and is quick with a story – drawing from his nearly two decades of experience behind the wheel. Gentry, by many standards, is the ‘run of the mill’ blue-collar guy, with one subtle difference. Gentry’s father Teddy is the bassist for a little band you may have heard of – Alabama.

For the Gentrys, their two worlds are now converging. With Alabama embarking on their 2023 “Roll On 2 North America Tour” the band needed some heavy hauling ability. At that same time, truck company Kenworth – who’s had a long-standing relationship with the band – was celebrating their 100^th anniversary. To mark that occasion, the company decided to provide the band with a T680 76-inch mid-roof sleeper for the concert tour. Of course, now they needed someone to drive it.

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

I recently had a chance to catch up with Josh in between tour stops. The down-to-earth Gentry told me about growing up with a passion for trucking and why the industry means so much to him.

“I’ve just always felt that the Lord put the desire in my heart to have a love for it and appreciation for it, and that’s where it’s just always been,” Gentry said. “And to me, it’s not just the machines themselves, it’s the people I’ve met through the amazing, incredible industry.”

Listen to the full interview with Josh Gentry below.

From his start in the industry, to whether or not he ever felt pressure to follow in his father’s footsteps, Gentry shares his stories from the road and growing up with a famous father. Josh also shared with me a hilarious story about his first trip to the Mid-America Trucking Show, an event he says he hasn’t missed since 1988. LL