Jackson Dean Reflects on 2023 Whirlwind: “I’m Just Doing the Best I Can”

Jackson Dean has been writing songs for the past decade. The 23-year-old Maryland native credits inspiration for his early songs to his older brother, whom Dean frequently wrote about while his sibling was at sea. In an interview with American Songwriter backstage at the Grand Ole Opry during the Opry NextStage Live concert in early December, Dean recalls penning his first song, details the meaning behind his single “Fearless (The Echo),” and shares what’s in store for 2024.

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“He worked on a pirate ship in Annapolis for a decade. It’s funny, the career kind of started with him,” Dean says of his brother’s inspiration. “I wrote a song when I was about 14 about him. I wrote him a letter. Then he wrote back and I wrote a song about it. He was out at sea in the Gulf somewhere near the British Virgin Islands. He would take boats out of Eastport and go down to South America and race across the Gulf. I wrote two songs about him and that was a cornerstone of sorts to where I am now.”

[Jackson Dean Shows in 2024 – Get Tickets]

Around age 15, Dean recorded some of his earliest songs at Wolf Stream Studios, located in a row home in Baltimore. Much of his demos today mimic how he made those early songs, with two microphones recording his guitar and vocals separately. He then builds the track on top of there.

While Dean says his songwriting has changed “drastically” since those early songs, his brother still serves as inspiration in other ways. That same brother he wrote about a decade ago stars in the music video for Dean’s current top 20 and rising single, “Fearless (The Echo).” The clip transports the viewer back in time to an 1863 odyssey that shows how far a man will go for his family. The video features Dean’s brother, sister-in-law, and niece. 

Dean penned “Fearless (The Echo)” with Jonathan Sherwood and his producer, Luke Dick, four days before they went to the studio to record his debut album Greenbroke. He recalls Dick having the drum part programmed and a guitar pick pattern when they arrived. 

“He was just like, ‘I want you to soar. I want you to scream,’” Dean recalls Dick saying. “Fearless is the word and we wrote this thing in about two hours and tracked it.” 

The singer eventually did another mix of the song in the studio ahead of releasing it as a single. He renamed the track “Fearless (The Echo)” and says he feels fortunate to be able to return to the song. 

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‘Cause I’m fearless
I’ll jump off the ledges
Burn all the bridges, walk on the edges
I’m fearless
I don’t mind the shadows
Take all the arrows, ride in the echoes

“When we named it ‘The Echo’ I thought about it a good bit,” he says of the song’s lyrics. “Not only is it the most trippy line in the song, really visually trippy, like what does your version of riding an echo look like? That’s most often how I feel running around the world. You show up for the moments and then you’re still there in the after time. Where you end up in the after time is quite unique, at least where I end up is pretty unique. 

“I get to go to some really awesome places and be in some unique spots,” he continues. “Then when we named it ‘The Echo’ I thought about that a lot and I thought about the in-between of going from one beckoning to another. The in-between of that, the snake of that, also visually looks like a soundwave. … The video put the weight of it in perspective and definitely put the emotion and how fierce the emotion was.”

The country singer/songwriter’s debut single “Don’t Come Lookin’” hit No. 1 in late 2022. Since then, he’s spent most of 2023 introducing country fans to his dynamic live show, including a stint on the road as part of Blake Shelton’s 2023 Back to the Honky Tonk Tour. He also traveled overseas to Royal Albert Hall for a performance with Kip Moore, Morgan Wade, and Stephen Wilson Jr., which he calls “the best 30 minutes of my life.”

In 2024, he’ll embark on his headlining trek, the Head Full of Noise Tour, before he hits the road with Lainey Wilson. He kicks off the new year with a performance in Denver on January 12, 2024.

“The bus leaves the 11th,” he says. “For 11 weeks, I’m going to be putting together a record and we’re going to be playing a headline tour. Everywhere we’re not going on our headline tour between the festival season and Lainey Wilson in the fall, we’re going to be hitting everywhere else. I’m going to be putting together a whole big project of music, we got a very big song bank to let the world see. A lot of good things happening for next year.”

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When it comes to writing for his next project, Dean says his two cents on songwriting and performing is: “Make it worth saying and make it worth singing.” 

He’s come a long way since his solo writing as a teenager a decade ago. Now, Dean is well-versed in co-writing but says he still loves to write alone or with his band on the bus. He’ll be taking all the lessons he’s learned into his next project.

“When I figured out how to handle myself in a room, you figure out what your role is real quick,” he says. “I’m a linguist interpreter. So you give me what you want to say, I’m gonna say it like this. This is the dialect and this is this is the drawl that I’m going to put on it. Sometimes you put a different hat on in the room. Coming from a place where I was already wearing all those hats, now I’m like, ‘Okay, I can relax off of that and make this part of it better than it would have ever been.’

“There’s a lot that I’ve learned over my time. I’ve thought about words differently,” he adds. “When I get around Luke [Dick] I feel inferior in terms of language. It’s not like $15 words. It’s simple. I hate when they go in and count the syllables. I understand that but all I’ve ever known is how it rolls off the tongue, not how it looks on paper. Some dudes write like that, and I don’t. But then again, my job is to put the life in it. … I’m just doing the best I can.”

Photo Credit: David McClister / Courtesy Big Machine Label Group

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