Interview: Jackson Dean is ‘Fearless’, and a star on the rise

Cait Watters writes:

Highways Festival debut Jackson Dean
Jackson Dean made his UK debut at Highways Festival. Photo credit: Kate Green Getty Images

It’s been an incredible year for the 22-year-old Maryland native, with single Don’t Come Lookin’ becoming the highest charting country single for a new artist since 2015 and popping up on such shows like The Kelly Clarkson Show; Netflix’s The Ice Road; and Paramount’s Yellowstone.

Debut album Greenbroke came out last year and his latest album Live At The Ryman was released via Big Machine Records just last month (April). For a man on the move, Dean has wasted little time in bringing his music over to the UK, wowing fans at the inaugural Highways Festival ahead of a headline tour in a few months’ time.

Jackson sat down with us before Highways to talk about his rise, playing in the UK and more!

It’s pretty awesome getting to talk to you today, Jackson! You’re quite literally a historymaker as your debut single Don’t Come Lookin’ made you the youngest male artist to top Country Aircheck and Radio & Records with their first single! Accomplishing something like that…what was that like?

I remember Jim Murphy from Music Choice…I think we were in Chicago when he told me – he came to a show we were doing. We were hanging out backstage and he [said] ‘I have a stat for you’. He told me [but] my head was in showmode. Afterwards, we got off stage and were talking again and he was like ‘yeah, you’re the youngest to do it [from] a debut’. BadassBadass. All that tells me is that I went out there and busted my ass for it.

Does achieving something like that, especially at a young age and so early in your career, come with a degree of pressure?

I wouldn’t say it’s pressure…more [like] ‘you’re damn right I did’, to me. I don’t feel pressure from that. Do I feel pressure to keep making great music? Absolutely, I think everybody does.

Don’t Come Lookin’ was a massive hit

Don’t Come Lookin’ was a track that burst out, but it wasn’t the first time you’ve gone viral. Before you embarked on your musical career, a video of you performing the national anthem in full high school football kit also blew up. Looking back at that video and looking at where you are at now…did you ever envisage your life going down this route?

A little bit, yes. It’s different…it’s different being on this side of, I guess, the mirror you could call it. There’s a lot of moments [where] I’m like ‘yeah’. It’s not constant. The moments that you dream of, [they] fly by. You have to grab them like they’re a golden nugget and put ‘em in your pocket. Most of the time you don’t have a lot of time to appreciate the nugget you got because you gotta pick up and go to the next place.

You’re no stranger to taking risks in your life – for instance, you moved out at 18 and lived in a cinderblock, concrete floor, one room shack – and it’s fair to say that it’s paying off. Musically, how important is it for you to take risks to continue to stand out in an industry with so much competition?

I didn’t agree to move to Nashville and get signed [to] be like everybody else. I didn’t want to do this with my life because I wanted to be like everybody else in town that was doing it. The reason, I feel, that we’re standing out is because we’re not writing the same songs that everyone else is. Besides, it’s no fun playing it safe. I want to do the unexpected. I didn’t move to Nashville just to be background noise.

Jackson Dean's new album
Jackson’s second album came out in April.
Album art courtesy of Big Machine Records

And those songs you’re writing, you’re very hands on with. On your debut album, Greenbroke, you have a writer’s credit for each and every song. Is it important for you to be that hands on with the stuff you’re putting out?

Absolutely. The first two records I ever did, I wrote them by myself. They’re not up anymore because they’re not who I am now – they’re definitely who I was then *laughs*. The first one was done in Baltimore with a guy who’s now my drummer, with a mic on my guitar and a mic on my voice. They were all one takes and they were young songs…they were so young – every songwriter will tell you you have to write a hundred bad songs to get one good one. I’ve written by myself and I’ve done that.

It was a big commitment to move, get signed to a publishing deal and be [met with] ‘hey, you’re going to walk into this room and write with these two dudes, let them crawl into your head and you’ll crawl into theirs and see what’s what’. I was like ‘you’re out of your mind’. But I did it, like ‘oh, got it’. It is important. I’ve only been pressed a couple of times to cut a song I didn’t write. Don’t get me wrong, I will love a song whether I write it or not. In terms of what I will put my name on, I want to have a bigger hand in crafting it – whether that’ll be lyrical value or composition. It is very important to me, and I think it should be important to every artist.

Your latest single Fearless (The Echo) is an evolution of the version of Fearless that was on the album. You mentioned having that bigger hand in crafting the songs you’re putting out so was it important for you to release this slightly different, evolved version of the album track? Why did you decide to go down that route?

Yes…ish. Fearless and Don’t Come Lookin’ were done in the first half of GreenbrokeGreenbroke was done in two halves. The first half was done when I was 18, 19 – probably 19 – and we always thought that DCL and Fearless would be one hell of a one-two punch.

We were trying to figure out something to kick out to radio to back up Don’t Come Lookin’. Trailer Park was too similar so everyone was pushing for Fearless – honestly, so was I. My only hiccup was [that] my vocals sound[ed] very, very young. We wrote that song about two weeks before we went in and cut it. I had played about 350 to 400 shows [since] that time. You get to sing it every night and make it better, and your voice starts to dance more and more as the song gets easier to sing and you wrap your head around it. I asked if I could re-sing [it] and that’d be what we’d put out to radio. It was a cool thing as you don’t really get to do that very often, you don’t get to put something out in the world and go back and make it better so I feel very fortunate. The fact that it is doing as well as it is right now is very exciting and very awesome. It is a powerful song and I’m grateful for it.

Jackson Dean at the Royal Albert Hall
Jackson Dean on stage at the Highways Festival. Photo credit: Kate Green Getty Images

Your big year is just continuing as I’m talking to you the day before you play your first ever UK show at Highways Festival…at the Royal Albert Hall, no less! How exciting is it for you to make your UK debut at such an event at such an iconic venue?

We drove past it on the way here today. We were in the back of a cab and I looked out the window and, out loud, I was like ‘holy sh*t, there it is!’.

Me and my boys, we’ve been dreaming about playing not just here but overseas for a long, long time. I don’t think any of us have played overseas [so] the fact we’re doing it together is even more exciting. They’re my family and getting to do that with them is really awesome. So many people that we idolized have played here and it’s one hell of an honor to get to step on that stage.

And the line-up? Stephen Wilson [Jr] is going to be making the best music in our genre for a long time to come. We just cut a couple of me and Stephen songs for the last round of recordings we did. He’s amazing and deserves every bit of what he gets. I’m so excited to play with him. He’s an incredible player and writer and a wonderful singer. Morgan [Wade] is just a badass. I’ve never seen her play live, never met her. I remember seeing a video of her playing acoustic and she played The Night and I was like ‘hell yeah, that’s what I’m talking about’. And Kip Moore…I’ve been a fan since I was ten. One of my favorite songs, one that I wore out, is Crazy One More Time. He’s been very influential on me, for sure.

You’re here for Highways but, of course, you’ve got your own UK tour in just a few months too! What’s it like for you to get these opportunities to not just come here but to, already, have the opportunity to keep coming back?

It’s a dream come true…a dream come true. I’m honoured and humbled. It goes to show that y’all get it. Not everyone can come over here and do that. So for me to be able to come over here and y’all be accepting of it is awesome. We’ve been saying that the last couple of weeks, [I’m] Mr Worldwide, Pitbull *laughs*. It’s really cool. It’s weird when your dreams come true as you gotta live them. It makes my heart happy.

Live At The Ryman Track List:
1. “Greenbroke (Live at the Ryman)” | Jackson Dean, Jeff Hyde
2. “Trailer Park (Live at the Ryman)” | Jackson Dean, Cary Barlowe, Jesse Frasure
3. “Fearless (Live at the Ryman)” | Jackson Dean, Luke Dick, Jonathan Scott Sherwood
4. “Wings (Live at the Ryman)” | Jackson Dean, Park Chisolm
5. “Heavens To Betsy (Live at the Ryman)” | Jackson Dean, Benjy Davis, Driver Williams
6. “1971 (Live at the Ryman)” | Jackson Dean, Brandon Aksteter, Rich Kolm, Sean Mercer
7. “Don’t Come Lookin’ (Live at the Ryman)” | Jackson Dean, Luke Dick
8. “Red Light (Metal Version / Live at the Ryman)” | Jackson Dean, Jonathan Scott Sherwood, Ryan Tyndell
More information including tour dates can be found at

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