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Interview With Jackson Dean

by Eric Althoff

Marylander Jackson Dean shuttles back and forth to Nashville every week to record, perform and get his name out there in the country music scene, but he hasn’t forgotten that Maryland is home. In fact, while still playing high school football in Anne Arundel County last year, the artist showed off his artistic side with a pregame rendition of the national anthem that took the internet by storm and earned him some well-deserved attention.

Dean has a slew of local shows coming up in the next few months, including at Tiki Bar in Solomons (Sept. 21), Sidelines Bar & Grill in Glen Burnie (Sept. 28), Union Jack’s of Annapolis (Oct. 5), Gypsy Sally’s in D.C. (Dec. 7) and Ram’s Head on Stage in Annapolis Jan. 25.

The musician, who has a new EP out called “Ain’t No Saint,” spoke by phone about his influences, racking up those frequent flier miles traveling to Music City USA each week and a very, very special journal that never leaves his side

Can you tell me a little bit about how you first encountered country music?

My dad was big into the blues and a whole bunch of different kinds of music. I’m the youngest of four siblings, so I have two older brothers and an older sister who love music, so I kind of went off what they liked. I was born into classic rock and blues and reggae. 

But I grew up on a dead-end street with a gun range on the end that backed up to a swamp, so that’ll do it, you know.

Who were some of your musical heroes?

Eric Church, the Brothers Osborne. I got to play with [the latter] and hang out with them for a night, which was pretty cool.  

How do you feel about the comparisons that have been made between you and Chris Stapleton?

It’s flattering for sure. I listened to Chris Stapleton a lot when I was in middle school, so I tried to mimic [his sound]. He was like the only thing I listened to when he was with the SteelDrivers. I just loved that kind of sound and ran with it. 

I’ve never wanted to be anybody else. People ask my dad that all the time: “Who does he want to be like?” And my dad just says “himself.” People kind of step back and look at him funny because they’re always expecting an answer like one of the big-time people. And I just want to be myself.

Where do you live these days?

I’m still up here in Maryland for right now, but I’m in Nashville three days a week. And I’m going down there to write. I just got a publishing deal with Little Louder, [whose clients include] Eric Church’s writers, Dierks Bentley’s writers — all those guys. 

I’m down there working three days a week and playing shows. I’m only “home home” like two days a week here in Bowie. So, yeah, I’m a rolling stone, man.

You gather no moss.

That’s right.

How does it feel when you “come home” to Maryland to play?

I always love coming back to play. We’ve been playing a lot in southern Maryland the last few months trying to expand a little bit more and build the following. 

But coming back to the hometown and playing around here is always a good feeling because there’s a lot of familiar faces in the crowd. Every time it’s more and more [who] come to see you that you don’t [recognize] — so people are talking about us and what not. 

It’s always a good feeling.

Why do you think the “countryfied” version of the national anthem you sang at your high school’s football game got so much attention?

I can tell you right now nobody ever did it like that, man. 

It’s funny how that came about: I was asked to sing the national anthem because a friend of ours was the athletic director. He knew I sang, and he was like, “Hey, you should come sing.”  So I put something together, and that was what happened the first time [I performed it]. And then the second time was when it got really big.

I just wanted a really good recording of it, and then Micahel J [of iHeartRadio] got ahold of it and it just went boom.

How do you get back and forth to Nashville each week?

I fly [south] on Monday morning, come back Wednesday or Thursday, and I have practice on Thursday nights with the bands. And then Friday, Saturday, Sunday we play. And then I do it all over again.

Is it exciting to live in two different places at once to pursue your musical goals?

It doesn’t get tiring for me because I’m good when I’m focused and have something to do. If I get stagnant, it’s just not a good place for me. So it keeps me on my toes, and it’s a good way for me to keep moving.

What’s something you absolutely must have with you on the road?

Other than gear? I have a book that I write in and that goes with me pretty much wherever I go.  It’s pretty much like my songbook and for me to write down my thoughts.

And a good pair of headphones. 

Have you ever surprised yourself with something in your notebook becoming a song?

Oh dude, all the time! All the time. That’s how people write, man: You write about what’s going on in your life at the time. Those songs happen when you start writing stuff down like that.

We’ve seen the music industry turned upside down the past few decades, with CD sales not what they once were and artists having to be on the road all the time to make a living.  How hard is it for you? 

We play a lot more than a lot of other people. And we get a lot of our own shows; we book them ourselves. We’re with WME, the booking agency. They helped out with some of the big, big shows like [playing with] Kane Brown that put me in front of thousands of people. 

It’s tough, man. It’s tough when you go from playing for 11,000 people, then to a benefit for 50 people. It’s ups and downs, and that’s just the nature of the beast. 

It won’t always be like that, but right now it is. It’s not like I can turn back now. 

What can people expect at your upcoming DC-area shows?

The Ram’s Head is actually going to be a really cool show this go-around. This’ll be the third time in a row we’ve sold it out, and it’s been a full year since we’ve played there. And we’ve grown so much over the years. It’s gonna be really cool. 

Will you have family and friends in the crowd at these local gigs?

Most likely yeah. I’m not sure about exactly who’s coming. I kind of like to keep it a mystery. 

Do you have a pre-show warmup routine?

I saw a voice coach in Atlanta a few times, and he works with Drake and that dude from Kaleo, the Icelandic rock band. She taught me some routines that I do before the show. A five-minute thing. And it helps a lot: O’s and ah’s and E’s and all that. Just to get ready. 

Maybe have a bottle somewhere nearby of some “necessities.” 


Our hometown hero may yet sing his way to fame in Nashville, but in the meantime, he still has much to share with his fellow Marylanders, as his concert dates over the next few months make plain.  Catch this talented, and humble, rising star of the Old Line State on the way up, as he continues to make Maryland proud. 

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Eric Althoff

A native of New Jersey, Eric Althoff has published articles in “The Washington Post,” “Los Angeles Times,” “Napa Valley Register,” “Black Belt,” DCist, and Luxe Getaways. He produced the Emmy-winning documentary, “The Town That Disappeared Overnight,” and has covered the Oscars live at the Dolby Theater. He lives in Fredericksburg, Virginia, with his wife, Victoria.

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