“I was a pirate for one year” – KIK-FM 100.7

2022 Big Machine Music City Grand Prix

Danielle Del Valle/Getty Images

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…



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