For as long as he can remember, Josh Gentry has loved trucks. So much so that he established a career as a professional truck driver. He loves country music too and has deep roots. Josh’s dad, Teddy, is a founding member of Alabama.

Today, Josh drives a Kenworth T680, hauling equipment and staging to support the group’s Roll On 2 North American tour. It’s a family affair.

“My dad called me before the tour started and said they were looking for a truck driver, and asked if I might be interested. I didn’t have to think very long before replying, ‘YES!’

With that, father and son hit the road. And Josh is glad he’s behind the wheel of a Kenworth – the truck brand he literally grew up with. When Alabama and Kenworth began their original 15-year partnership in 1988, Josh was just 8 years old. “I used to travel with the band during the summer,” he recalled. “I would start in the bus with my dad, but I always ended up driving along in one of the Kenworths – I just loved riding in a truck. I have so many stories from that period – it was like yesterday to me.”

Josh said his fascination with trucks actually began when he was five. “Trucks have been my love and passion for as long as I can remember,” he said. “I could tell you the type of truck just by the headlights. I also had a big collection of toy trucks.”

Since Alabama and Kenworth put on an annual concert at the Mid-America Trucking Show, Josh used to always find his way into the Kenworth booth. “I still remember climbing into the cab of the W900L James Bond Limited Edition truck when I was 9 years old. From there, I always knew I wanted a W900.

Josh started his trucking career when he was 23, hauling grain with his cousin. And he transported cattle as well – something he still does to this day. His dad has a 500-acre cattle ranch, and Josh has 100 head of cattle of his own. Josh loved working in agriculture and recalls fondly hauling bottom hoppers full of grain to the feed mills. “The people in agriculture are so down to earth. I’m just a normal country boy who loves talking and working with farmers.”

Today, he delivers to a different audience and is always first to a concert site to help set up. “Being on the road with dad…it’s nice to be part of his career. And I’m having a great time. I’ve always said, ‘if you can’t have fun doing it, it’s not worth doing.’”