In October 2018, an Arundel High School football game in Gambrills, Maryland, kicked off with the unlikely spectacle of the team’s defensive end, Jackson Dean Nicholson, walking onto the 50-yard line in uniform, acoustic guitar in tow, to perform the national anthem. The senior’s soulful, countrified take on “The Star-Spangled Banner” went viral, racking up national media coverage and a million views on YouTube, and led the teenager to repeat his performance at an NFL game a couple months later.

“I’d been at it a while by the time the anthem video had got going,” said Jackson Dean, now 22 and recording under his first and middle name. In fact, Dean had already self-released two albums of original songs by the time he became famous as the singing football player. By the end of the school year, it was clear that he was headed to Nashville, not college. “I think I had graduation, and I was playing with [country star] Kane Brown the next day,” Dean recalled.

Dean, who was born and raised in Odenton, Maryland, signed with Big Machine Records soon after, becoming labelmates with stars such as Tim McGraw and Carly Pearce. His major label debut, “Greenbroke,” released in early 2022, belies his age: Dean has the gravitas of another generation of country stars, sounding like someone who couldn’t possibly have been born in the 21st century. His deep growl of a voice is more in line with artists twice his age, like Chris Stapleton, and his contemplative songs were influenced by cult singer-songwriters born decades before him, such as Chris Knight and Fred Eaglesmith.

By the end of 2022, Dean’s swaggering single “Don’t Come Lookin’” was on the Billboard Hot 100 and became a top 3 hit on country radio, driven in part by a prominent placement on one of the most popular shows on television, “Yellowstone.” This year, as a rising star in high demand, Dean is spending most of his time on the road, crisscrossing America this summer before heading to Europe and Australia. “We’ve got like four different tours bouncing around this year,” Dean said in a phone call last weekend from Columbus, Ohio, where he opened for Kip Moore.

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This week, Dean begins a stint on country superstar Luke Bryan’s current tour, which will bring Dean to his home turf Friday for a show at Merriweather Post Pavilion in Columbia. It’s a full-circle moment for the Maryland native, who sang “Last time I saw you was at a Luke Bryan concert” on the 2019 song “Don’t Let Me Go,” in reference to a time he saw Bryan at Merriweather in high school. “My God, I’ve passed out on that lawn once or twice,” Dean laughed. “My sister pulled a tooth out of her knuckle after a brawl there.”

Despite Maryland’s location below the Mason-Dixon Line and a healthy number of country music lovers in the state, Dean is one of the first mainstream country stars from Maryland, following in the footsteps of Maggie Rose from Potomac and Brothers Osborne from Deale, who Dean has played shows with. “John and T.J. [Osborne] are wonderful,” Dean raved. “I like who they are as individuals and people, they’re cool as shit.”

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Through it all, Dean has kept close with some of the Maryland musicians with which he started this journey. He stepped into a Baltimore recording studio for the first time almost a decade ago, when a young singer asked him to play guitar on an Adele cover she was recording. “It got to the end of the session and his parents asked if he could just sing a song a cappella,” remembered Sean Mercer, who produced the recording. “And so I set up a mic, had him sing, and my jaw hit the floor. I wasn’t really prepared for it. Then after that, we became friends, and he ended up coming back and doing some more records.”

Mercer, a veteran of Baltimore’s indie rock scene who’s played drums in bands such as Teen Suicide and Us And Us Only, became part of Dean’s backing band, The Outsiders. Mercer brought in Rich Kolm of Hollywood Blanks, and Dean recruited Brandon Aksteter, a guitarist he’d jammed with at Old Bowie Town Grille. That quartet has played hundreds of shows together over the last six years. “No matter where we go, we end up with people coming and saying, ‘Hey, he sounds better than the album live,’” Mercer said.

In true Nashville tradition, Dean recorded “Greenbroke” with professional session musicians, though Aksteter contributed a guitar solo to the album’s title track. The Outsiders got a chance to show off their band chemistry recently, however, with the April release of “Live At The Ryman,” recorded at Nashville’s legendary Ryman Auditorium.

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The concert was originally recorded so that a couple of live tracks could appear on a deluxe edition of “Greenbroke.” “Then [Scott] Borchetta, the head of my label, heard the rest of it, and he was like, ‘Oh wait, we should put this out,’” Dean said. The album features a couple of previously unreleased songs, including a longtime fan favorite, “1971,” co-written by the entire band, and a “metal version” of the “Greenbroke” standout “Red Light.”

Another “Greenbroke” song got a makeover when Dean decided to re-record “Fearless” for a single release, with the new version, Fearless (The Echo),” currently climbing the country charts. Dean had recorded the original “Fearless” within days of writing it, and after a couple years of performing it, he knew he could sing it better and display his growth as a vocalist.

“I wanted to start unleashing and showing the direction of what is to come,” Dean said.

“You spend 120 days playing shows in a year at that age, your voice changes,” Mercer agreed. “Plus, there was probably some whiskey involved.”

While opening for big names is growing Dean’s fanbase, he admits that he most enjoys playing headlining shows for his own fans. “That’s our jam, man. When I can really see the whites of their eyeballs and feel their breath on me is when we have the most fun. That’s the fastest way to get their energy to you,” he said.

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Looking ahead to recording a second album for Big Machine, however, he knows he needs to beef up his catalog to become a full-time headliner first. “We’re goin’ back for more,” he said. “You gotta have songs to build a show.”

Al Shipley is a Maryland-based music and culture writer.