Jackson Dean’s strangest job was on the high seas: “I was a pirate for one year”

Before pursuing his country music career, Jackson Dean spent most of his time working in his dad’s construction business.

“Me and my brothers, from birth, worked for our father,” the singer recounts, explaining that they were part of a crew of bricklayers and stonemasons that once numbered about 300 workers. “I always worked construction. Just manual labor. Never worked in a restaurant, never did anything like that,” he continues.

However, there was at least one other job he held, and it involved some aspects of performance that just might have helped him prepare for a career in the entertainment industry.

“I was a pirate for one year,” he reveals. Specifically, he worked on a tourism ship in his hometown of Annapolis, where kids could sail the high seas and try their hand at shooting the treasure-hunting, parrot-wielding Pirate Pete.

“You got, like, a 45-passenger boat, and you’d go out in the bay and shoot water cannons at Pirate Pete,” Jackson remembers. “You got to find treasure. It was like theater, but improv.”

It was also a whole lot of fun, especially because his co-worker was his brother. “Me and my oldest brother would run trips. He would drive. I would ride up front,” the singer says. “Somebody would fall off the boat, or we’d just have dance parties. It was a good time. Like, blaring David Bowie or something.”

These days, Jackson’s not opposed to another venture into the world of acting. His song “Don’t Come Lookin’” was featured on the Yellowstone soundtrack, and he says he’d be game to take on an on-screen role on the show — especially if he got to play a bad guy.

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