Who Is Jackson Dean? He’s Not Waiting for You to Figure It Out

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You can make a few assumptions about Jackson Dean: At just 21, the Maryland-raised singer is younger than he sounds in his driving debut single, “Don’t Come Lookin’.”

Dean is the youngest of four kids, so go ahead and lay your characterizations on him for that, too. Then add in the viral nature of his “discovery” and you have a very clear picture of … someone that does not really resemble the person The Boot chatted with in late April.

A spin through the Greenbroke album confirms it. It’s not just that the 10 songs recall his many influences — it’s that his presentation throughout shows a mature understanding of each. There’s a sure-headed edge to the music, and man, that’s rare for any new artist today, especially one wishfully offering a debut single to country radio.

As for the youngest child syndrome? Being the youngest of four did change him, but Dean says he wasn’t really trying to keep up with anyone. His twin brothers were born a decade before he was, and his sister came four years after that.

“I always liked hanging with the older folks,” he shares. “Even growing up I really didn’t vibe with kids my own age. I grew up pretty quick and I led a different kind of life than what the kids in my hometown were doing, just as far as working and being in the woods as much as I was.”

That’s an understatement, as you’ll soon see. Dean presents as the kind of play-by-my-own-rules (or no rules) star celebrity news outlets froth for. He’ll keep details of his past secret for now, but one sees a twinkle as he talks about the kind of partying he used to do in the concrete shack he used to live in.

“I do like my whiskey and I do like my other things,” he offers before standing up to leave. So yeah, make assumptions about Jackson Dean, but leave them in the can outside the front door as you walk in to meet him.

Taste of Country: Your album is called Greenbroke. What does that word mean to you?

Jackson Dean: That song is my story. It’s really just about never losing your wild. As you walk through the world and society, you have to live by some rules, but I see so many people be domesticated, and as soon as that happens, I feel like all wonder kind of goes out the door.

The dictionary definition is more along the lines of partially trained.

It comes from the horse world. A broke horse will do what you want. Most of the time won’t ever step out of line. But a greenbroke horse could run all the way to Canada before it stops. So there’s no telling really what it will do.

Is there an artist out there that has achieved a version of what you’re trying to do musically, sonically and philosophically?

I never really could answer that question. People used to ask me a lot, “Who do you want to be like? Who are you aspiring to be?” It’s not that I don’t admire people, but I wanted to be my own man from the beginning. Of course, I think people have people that they look to, but my family has such a wide musical palette that covers a lot of ground and there’s so many people to look at and be like, “That would be dope. That would be really dope.”

There is a fair amount of — to sum it up crudely — running on this album. We hear that in “Wings.” The single alludes to it with the title and even in “Greenbroke.” What are you running from?

I think everybody’s got things that they wish they didn’t do or wish they weren’t a part of. Those songs are really more about how I’m existing with it. I really can’t stay put for more than a couple of days anyhow, and moving — the motion of it — really seems to help me. Time only works one way: It doesn’t go backwards — it goes forwards.

One of the songs on the album that stands out is “Don’t Take Much.” It’s a different vibe. It’s lighter — where did that song come from?

So I turned 18 and I moved out into a tack room on my granddad’s property. The big house was about 50 yards off. My uncle kept his scaffold and all his stuff for construction down at the bottom of the hill. They had about 35 race horses boarded there at one time. My dad moved there in I think about ’66 or ’67, but it was my uncle’s room, it was my dad’s room, it was my cousin’s room, my brother’s room — this massive party den for like 30 years. Thousands of signatures on the wall, but I lived in there for two years and it was some of the best times of my life. That’s what that song is about.

I’ve heard you describe it as having no running water or heat or A/C. But it looks a bit more decorated than I expected. What did you do to get banished to the tack room?

I was just tired of living by another man’s rules. I didn’t want to do it anymore, so I told my dad one day at work — I worked for my dad — I’m gone, I’m done. I’m 18 now. I’ve done it right thus far and I’m going to start living my life now, like really living my life.

How did you live there day-to-day? At some point you need water and plumbing and to cook.

I had a couple of jugs I would hook up to the spigot on the big house. My brother lived up the street from me for a little while so I had his place to go to. My whole family lives in that area so it wasn’t like I was 30 miles into the wilderness.

What song got you the record deal?

I remember being in a conference room with (Scott) Borchetta. I was at the end of the table and he was probably from me to you and I played “Wings” by myself on the guitar and I finished and he goes, “I don’t know what planet you came from but I want to go there.” About 10 minutes later he was like, “You wanna draw up papers or what?”

Have you ever met another artist whose big break was the National Anthem (In 2018, Dean’s unique performance of the “Star Spangled Banner” in his football uniform was covered nationwide)?

That was a good night. That thing took me places I — I mean it took me to L.A., New York.

Give me a tangible. We see viral videos, but you never hear what that translates into. What did it really do for you?

So I already had two records out that we made up in Baltimore with my band by the time we filmed this. I was already touring regionally, playing shows, selling a couple of places out. My athletic director came to me and said, ‘Hey do you want to sing the National Anthem?’

I was like, “yeah, but I’m gonna do it my way.’ … I just picked up the guitar and said, “How do we make this three chords and the truth?”

We filmed it, and two days later it was going. That was a magical night. We went out and kicked their asses right after that. I was leaving ball games like two weeks later — I remember I left a ball game one night, drove all the way the up to New York, got in at like 5AM and came back down and went to school the next day. Went to L.A. … I was on the Steve Harvey Show out in L.A. I thought the town gazette was gonna be the end of it. It was not. It was a really, really nice jump forward for us.

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