Thursday, July 18, would be a short day of work for operator Josh Gentry. It began at a leisurely 10 a.m. in Fort Payne, Alabama, outside the Quality Inn. There, Gentry picked me up in his Chevrolet, rolling then to the site of an old auto dealership that, since the 1980s, has been the home base of the fan club and the general headquarters for longtime country-rock group Alabama.

It’s also home base for the group’s tour truck (pictured outside the fan club there), in which Gentry was about to set out on a run.All photos by Todd Dills

Josh Gentry, getting his e-log ready for the pretrip and the run

Josh Gentry is son of one of the last two founding members in the band, bassist and harmony singer Teddy Gentry. After years pursuing music himself, then hauling grain around his home region (some of those years as an owner-operator), Josh today serves as hauler of Alabama’s touring operation, moved in a single truck and 48-foot Great Dane show trailer emblazoned with the band’s insignia and the “Roll On II North America Tour” logo.

Gentry and his mother, Linda Gentry, stage right watching Alabama perform at Bridgestone in Nashville.That truck, a 2021 Kenworth T680 detailed in this week’s podcast, rekindles an old partnership between the Alabama group and the Kenworth company, dormant since a farewell tour marked the end of the band’s first long tenure in the early part of this century. As you’ll hear on this three-hour run to Nashville to load in for Alabama’s July 19 show at Bridgestone arena, Kenworth’s relationship with the band tracks back to the 1980s, when the tour operation was as many as four trucks and trailers, and the band was at the height of its popularity with big hits like “Mountain Music,” “Tennessee River” and, yes, the classic “Roll On (18 Wheeler).”

That last track lives large in the memory of many in Overdrive‘s audience, named in past by readers in the top five for best trucking song of all time. 

Gentry’s come full circle with his growing involvement in the tour operation, immersed as he was in his father’s band’s music at an early age. He idolized longtime Alabama drummer Mark Herndon in those days, he said, and would go on to play drums himself in a few different groups during a time he lived in Nashville and worked in the music business.

Those years are long in the past, though, and since then Josh Gentry’s turned toward another lifelong passion borne in part out of Alabama’s past relationship with Kenworth — namely, all things trucks and trucking, where there’s still plenty opportunity for new experiences. By 11 a.m. Thursday last week, we were pulling out with a lightly loaded trailer toward the Nashville docks of the Soundcheck business to load more gear. 

Soundcheck’s facility is situated a very-short haul across the river from downtown to the day’s final destination — 20,000-seat Bridgestone arena, which would be packed for Friday night’s show.

Docked at the final destination in the bowels of Bridgestone for the Friday show.

Thursday morning, as the truck and trailer merged onto I-59 toward Chattanooga from Ft. Payne, just as I was readying the audio recorder for the talk with Gentry, a voice came over the radio — “Roll on, Alabama!” — invoking the classic trucking song.

Here’s a big thanks to continued support for Overdrive Radio from the fine folks at sponsoring company Howes, longtime provider of fuel treatments like its Howes Diesel Treat anti-gel and Lifeline rescue treatment to get you through the coldest temps, likewise its all-weather Diesel Defender and Howes Multipurpose penetrating oil, among other products.Gentry called tour manager Jeff Davis to mark the moment — a first, he said — and give him an update on progress toward Nashville for load and staging. Yet the over-the-air atta-boy wasn’t the very first bit of attention the wrapped truck and trailer have gotten over going on two years Gentry’s been guiding the tour, taking him as far as, most recently, North Dakota and into Manitoba and elsewhere in Canada. This week, too, he’ll be in Chillicothe, Ohio, for a couple days’ worth of displaying the rig at the Kenworth plant there, he said. 

Dive into Gentry’s trucking history, and otherwise, in this first episode featuring our talk with the operator, the principal interests of his life to date all coming together now in live entertainment hauling with the family business. Take a listen:

Alabama’s Teddy Gentry (right) and Randy Owen onstage in Nashville to a crowd at near capacity.

Alabama bassist Teddy Gentry (third from right) shares a moment with guitarists at the show.

[Related: The top 10 trucking songs of all time]