By Andrew West

HARRINGTON – This time, Jackson Dean will be rolling into the Delaware State Fair as the headliner.

And, for an hour-and-a-half show Sunday night, the country singer plans to be less constrained than he was four years ago as a teenager when he was the fair’s opening act for Brothers Osborne.

He packed a lot of music in his 25 minutes that night. In the crowd were scores of fans from Anne Arundel County, Maryland, where he grew up.

“That was the first time I had ever been to those grounds, and my God, they are huge,” he said Monday in an interview with the Delaware State News. “At the time, that was most people I had ever played in front of.”

It was the summer after his senior year of high school. He had already had 15 minutes of fame the fall prior when he sang a bluesy, contemplative version of the national anthem on his football team’s senior night. The video went viral, of course.

Fast forward to the present, he is now 22 and enjoying growth as a soulful, country troubadour.

His concert will feature original songs such as “Don’t Come Lookin’” and his second and latest to chart, “Fearless.”

Both are on his album “Greenbroke.”

The album name comes from a song he wrote on his grandfather’s horse farm in Odenton, Maryland.

Like a horse that’s not ready to ride, he likes the freedom it represents. That free-spirited nature is what led him to move into an old cinder block building on that farm with no heat and no running water.

“It was a place where laws did not exist,” he said.

He was following a family tradition. His uncle, father and cousins all spent time there before him. “It was a massive party den for something like 40 years,” he said.

In a sense, it was something like the “Hell House” where Lynyrd Skynyrd developed its sound in Florida.

“There was a lot of inspiration, a lot of juju in that place,” he said. “And, not all of that was good.
“I started writing ‘Greenbroke’ in there,” he said. “I was in the doorway in a lawn chair and I just had three (wisdom) teeth ripped out of my head. It was a summer day and I just started picking. It’s a good place for peace.”

The opening lyrics:

Ever since I can remember
All I wanted was to be my own man
Find out what it means to live forever
Draw my own damn line in the sand
I’d kick myself if I didn’t kick down one more wall
Leavin’ home at eighteen, never to look back at all
Just a wild child lookin’ for a wilder blue

The breakthrough for Mr. Dean was “Don’t Come Lookin’” after it got a strong minute of exposure on the hit TV show “Yellowstone.”

It played in the background of a cattle roundup scene before cutting to Kevin Costner.

“I’m just someone who is trying to walk a certain distance between lines,” said Mr. Dean. “I’m not Timmy Childers and I’m not Luke Bryan, either. So, for someone trying to have their noise be heard, it’s very flattering.”

The song grew out of Mr. Dean’s mother often saying she would find him if he wandered off in the countryside. He would sass her, saying, “If I don’t come back, don’t come looking for me.’”

It turned out to be a hook for another song about living free.

You can count on it to being on the playlist Sunday.

“We’re coming back to give you a show,” he said. “It’s a really big honor to be coming back. I remember that place very well. “

He hopes to thrill his friends and family that will make the trip across the Chesapeake Bay Bridge to hear a full set.

“Being that close to home and having it be our show,” he said, “it’s going to be awesome.”