Behind the Remarkable Rise of Jimmie Allen, Country’s Most Ambitious (And Bowling-Obsessed) New Star

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In 2012 — five years after moving to Nashville to chase his dream of being a country artist — Jimmie Allen had little to show for his efforts. He was working multiple jobs to pay the rent, playing writers’ rounds when he could and taking gigs for tip money. He had already been tossed off American Idol.

Then one day, while searching through his attic for family photos, he found a “trashy” spiral notebook and began filling the empty pages with a list of very specific career goals: Land a publishing deal. Sign a record contract. Get a booking agency to expand his reach into movies and TV. Have No. 1 singles. Play sold-out stadiums. Sing with the world’s greatest musical icons, like Elton John.

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A decade later, Allen still has that notebook. And while he hasn’t quite finished checking off all of the items on that list, sure enough, they all seem to be coming true — from signing with BMG’s Stoney Creek/BBR imprint in 2017 to collaborating with John in 2021 — just like he predicted.

“Everything I accomplish, it doesn’t surprise me. I’m thankful for the opportunity, but I’m not surprised at all,” says Allen, leaning forward in his chair on the spacious fifth-floor patio of his record label as a soft rain falls over Nashville’s historic Music Row in late May. “It’s all part of this plan that has been written down.”

Allen, 37, is fresh from a red-eye, his 13th flight of the week, following a gig in Seattle the night before, and he has stopped at his home south of Nashville just long enough to shower and change before jumping in his black Ford F-150. But he is engaged, focused and alert. Though he’s known for flamboyant, often bedazzled stage get-ups, he’s dressed down today in a Dancing With the Stars sweatsuit — he competed on the show last fall — a DEL Made ball cap and black sneakers, one of more than 1,000 pairs he owns. His trademark diamond studs are missing from his ears (“That’s the ‘show Jimmie,’ ” he explains), but he does sport impressive bling on his left wrist: an engraved Breguet watch that new friend Garth Brooks gave him as a gift to thank him for performing as part of his Kennedy Center Honors induction last year. (Allen’s rendition of “Friends in Low Places” brought the Washington, D.C., crowd — and the star he calls Mr. Brooks — to their feet, though Allen admits to having world-class jitters performing for one of his heroes.) Every few minutes, he spits Grizzly Wintergreen snuff — “If you know them, I’ll take a sponsorship,” he volunteers — into an empty smartwater bottle.

Allen may look relaxed, but he is in full-on work mode. In less than 18 hours, he’ll leave town again. Before then, he’ll head to the Country Music Hall of Fame and Museum to kick off an event, then handle some business calls, then participate in a CMT Twitter Spaces panel about artists and mental health. (He was diagnosed with bipolar disorder when he was 13.) Somehow, he’ll also find time between engagements for his pandemic passion, bowling in nearby Franklin, Tenn., before returning home to his wife, Lexi, and two infant daughters, Naomi Bettie and Zara James. (He also has an 8-year-old son, Aaydn, from a previous relationship.) Then he’ll hop on a tour bus for an overnight ride to Arkansas and the next gig.

“I only sleep about three-and-a-half hours a night,” Allen says. “If I get two, I feel like I’ve slept.”

Over the past few years, Allen’s seemingly inexhaustible supply of energy has proved especially useful — not only as his career has gained velocity since his first single, “Best Shot,” vaulted to No. 1 on Billboard’s Country Airplay chart in November 2018, but also as he has become his own cottage industry. He runs management, production and publishing companies in Nashville, as well as a trio of businesses that include a septic-pump repair company in his hometown of Milton, Del. On top of that, he has launched a TV career, discussing big- and small-screen projects with UTA (he also co-hosted the 2022 Academy of Country Music [ACM] Awards with Dolly Parton and Gabby Barrett); published a children’s book, My Voice Is a Trumpet; and served as executive music producer on Titletown High, a Netflix reality show about a Georgia high school football team.

“There are times when you’re pushing an artist forward and pushing and pushing,” says BMG Nashville president Jon Loba. “With Jimmie, we’re always running to catch up with him.”

Allen’s intense drive would mean nothing if he didn’t possess the talent to back it up. With his honeyed baritone that effortlessly wraps around the everyman anthems he writes — seamlessly blending country, pop and R&B — Allen has become the reigning Country Music Association (CMA) new artist of the year, the ACM’s 2021 new male artist of the year and, at this year’s Grammy Awards, the only country act nominated for best new artist.

On June 24, he’ll release his 17-track third album, Tulip Drive, named for the street where his late grandmother and confidante, Bettie, lived. It’s the final piece of a trilogy that began with his 2018 debut, Mercury Lane (the street he grew up on) and 2020’s Bettie James (which subsequently received an expanded version), a collection of duets with artists beloved by Allen, his grandmother and his father, James, who died in 2019.

Tulip Drive bolsters Allen’s growing cross-genre appeal, with collaborations featuring Cee Lo Green, T-Pain and Jennifer Lopez, but it’s also his most personal work yet. The first single, “Down Home,” takes the form of a stirring yet never maudlin conversation with his deceased father, updating him on Allen’s accomplishments: “I promise I’m working/With this guitar about as hard as I can/I met a girl, bought a house/Put a nice little payment/Down home is still where my heart is.”

Loba felt the song was so strong he wanted to put it out last year, before Allen’s most recent Country Airplay No. 1, the Brad Paisley duet “Freedom Was a Highway.” But Allen asked him to wait: “Jimmie said, ‘I can’t right now, Jon. It’s so personal. The wound is still open, and I need some time to heal,’ ” Loba recalls. “I said, ‘Enough said. We’ll go with it whenever you’re ready.’ And as we approached the top 10 with ‘Freedom Was a Highway,’ he said, ‘I’m ready.’ ”

Allen was also prepared to expose a darker chapter of his family history on Tulip Drive. “Habits & Hearts” (written by Steven McMorran, Derrick Southerland and Jess Cates) reminded him of his father’s struggles with substance abuse and the toll Allen saw it take on his mother. “Just hearing the song and remembering him wanting to get better and then falling short a few times — I felt like I was in a time and place to sing it now and be honest with it,” Allen says. “Because even though my dad had his issues, he always reminded me that I shouldn’t do it. He said, ‘I’m telling you, this can cripple you.’ ”

Allen says he inherited his dad’s addictive personality but that he channels it into his competitive drive — the fuel that got him from broke unknown to bright rising star with three No. 1 Country Airplay singles, his own headlining tour earlier this year, a growing shelf of awards and names like Keith Urban, Tim McGraw, Darius Rucker, Pitbull and Shaquille O’Neal in his phone contacts.

And sometimes, it lets him play as hard as he works. Even when it comes to fun, Allen has goals: say, at least an hour of NBA2K or Madden on his PlayStation each night, or (amid the pandemic) becoming not just a bowling hobbyist, but an expert. After former pro football player Cortland Finnegan and Los Angeles Dodgers baseball player Mookie Betts introduced him to the sport, he would spend “five days a week, seven, eight hours at a time at the bowling alley,” Allen recalls. He now belongs to five bowling leagues, keeps three different sets of balls (for home, the tour bus and flights — Brunswick Hammers and DV8s all — so he’ll always be prepared for a few pre-meet-and-greet games) and, in January, plans to try out for the Professional Bowlers Association.

This May, in fact, Allen left his own SESAC party celebrating his second and third No. 1 records early to go bowling. His league average is 215, but he still grimaces remembering the perfect 300 game that eluded him: He got a spare and ended at 288. “It was all strikes until the 10th frame,” he says. “I was sick for a week.”

Somewhere between the ages of 8 and 11 — he can’t remember for sure — Allen was riding in the car with his father and told him he dreamed of becoming a country music performer. “But I can’t,” he added. “They’re all white dudes.’” His dad popped in a CD and played “Does My Ring Hurt Your Finger” by Charley Pride, the first Black country superstar. “That’s when it all made sense,” Allen recalls with a smile.

Allen’s parents divorced when he was 12, but his father remained a constant in his life. “Something broke, he came and fixed it. [My mom has] never had a boyfriend or anything since,” he says. After discovering Pride, music became a constant, too. Allen played drums in the church choir and picked up piano as well. “That’s one of the perks about playing, especially in a Black church: You learn to play off of a feeling,” he says. “You hear and you feel it. I can’t tell you what notes I’m playing, but I can tell you if it’s wrong or right.”

In high school and college, Allen started performing in musicals, landing lead roles like Ren in Footloose and the King of Siam in The King & I. He regularly traveled to New York to perform in talent shows — enough to realize early on that the Big Apple wasn’t the place for him. Instead, after dropping out of Delaware State University, he packed his late-’90s Chevy Malibu and moved to Nashville to pursue music as an artist in his own right. He rented a trailer from a couple, then moved into his car when they wanted him to buy it for $300. He showered and did laundry at the gym where he worked. At 22, he saved up to buy his first guitar and taught himself out of sheer necessity: “I couldn’t afford somebody to play for me [at gigs], like $50 every time,” he says.

Several years of dead ends later, in 2010 Allen tried out for American Idol after losing a bet with a friend. He made it to Hollywood, but got cut short of the top 24. He did, however, become pals with his season’s winner, Scotty McCreery, who years later would tap Allen to open on his own tour. “I saw him around Nashville often through those [subsequent] years,” McCreery remembers now, “and he was always grinding. He’s such a hard worker.”

Post-Idol, Allen still couldn’t get paid gigs, so he continued playing for tips at Lower Broadway bars, often calling to book dates under the name of a fake manager, “Landon Jackson.” He worked a series of odd jobs — even appearing in a 2013 Taylor Swift Diet Coke commercial as a singing extra — but decided to never keep one for more than six months: “You get comfortable and are like, ‘You know what? I’m going to stay here,’ ” he says. “I had this insurance company offer me a job that would have started me off at 70 grand a year. Yeah, I can’t do that.”

So the college dropout once again became a student. He read Music Row magazine and, when he couldn’t afford his own subscription, borrowed a friend’s copy of Billboard. He went to South by Southwest not to perform but to hear from industry insiders. And with the dedication of a baseball stats fanatic, he memorized the names of key managers, executives, songwriters, producers, mixing engineers — and their histories, which he remembers to this day. When asked why he eventually signed with BMG, he dives into a detailed recitation of then-president Zach Katz’s résumé, as well as Loba’s.

During those fallow years, Allen recalls sneaking into a WME party with a buddy who also wanted to be an artist but had no idea he was talking to one of the agency’s Nashville heads. “Come on!” he says, seemingly still horrified by his friend’s ignorance. “A lot of people want to get to know the artist. Nah, I want to know the machine that makes the artist because that’s who is doing the work. You have to know so you can make an educated decision on who you work with.”

Eventually, the encyclopedic knowledge he had accumulated paid off. In 2017, after BMG executives saw him at a showcase and brought him in for meetings, “I learned things about our staff that I didn’t even know from him,” Loba says. “One day, we had a couple of employees who had gotten locked in the garage somehow after hours and were trying to figure out how to get out. They were on social media. Jimmie was dialed in enough to have already added them before the deal was signed. He [saw the posts] and said, ‘Hey, I’m right down the street. I’ll come down and help you out.’ He knew about it before any of us at the label did.”

But Allen’s first big break had as much to do with luck as all of his homework. Back in 2015, he had scored a spot in a writers’ round at Puckett’s Grocery in Franklin because another writer had canceled. For the same reason, Ash Bowers — an artist-turned-writer who ran Wide Open Publishing — also found himself on the bill.

“He had an amazing voice, great songs that he had written and seemed very driven to have a career in music,” Bowers recalls of that night. “It was obvious to me that Jimmie is a world-class singer and a natural star.” He offered him a publishing deal on the spot and, shortly thereafter, launched a management division with Allen as his first client.

Now a frequent writing and producing collaborator, Bowers was instrumental in helping rejigger Allen’s first single, “Best Shot,” turning it into the stripped-down, midtempo ballad that reached No. 1 on Country Airplay — and made Allen the first Black artist to do so with his debut single. (Second single “Make Me Want To” would reach the same height.)

Allen is well aware that, as a Black artist played frequently on country radio — no less one notching No. 1s — he’s still in all-too-small company. But “I don’t let my mind go there,” he says when asked if he experiences prejudice in his corner of the industry. “Here’s my thing: Are there people in every genre of music that might not like someone because of their skin color? Yes! [But] everybody’s not like that. If I get that mentality, then I start viewing people with a prejudice the same way, so you start to become what you hate and we’re not helping the issue, we’re perpetuating it.”

And anyway, he credits his meticulous research with both his success thus far and, as he sees it, his ability to meet country music where it is. “So many people haven’t properly done homework or quit too soon. I said country music is what I want to do, country radio is where I want my songs. So I have to be respectful to something that has been there that I’m getting into.” He quotes his own recent tweet that summed up his outlook: “I’m not here to change country music. I’m just here to add to it.”

Last year, when he won the CMA’s new artist award, it was “show Jimmie” that came to the stage, sporting a fluorescent pink and silver lamé three-piece suit, diamond studs flashing. But as he began to speak, he became choked up, recalling his 10 years plugging away without much progress — and how, in 2016, he had spent his last $100 to buy a ticket to the awards’ 50th anniversary just so he could see Pride perform. Four years later, Allen continued, he performed with Pride on the same stage — the legend’s last TV appearance before his death.

Playing with Pride was another notebook goal realized. Allen first met him in 2018 at a trade show in Nashville and the two hit it off; they had a standing phone call every other Sunday. “I’d keep calling till he answered the phone,” Allen says. “He told me he was proud of me and Kane [Brown] and Darius [Rucker] and what we were doing. And he said he was glad to finally see people younger than him that look like him in the business. He said that was one of his fears — he thought he’d be the only one to kind of reach [that] level.”

Pride, who collaborated with Allen and Rucker on the Bettie James track “Why Things Happen,” also encouraged Allen to trust his power. “His big advice was you never shy away from who you are. You’re not here to wake up every day and say, ‘How can I make myself smaller to make someone else bigger?’ No. Inspire people from greatness.”

Last year, Allen put that message into practice. “We all are where we are because someone created an opportunity for us,” he says. “It’s our job, just as humans, to have a platform and find ways to share it and create other opportunities for other artists.” In September, he formed Bettie James Music Publishing, a partnership with Sony Music Publishing Nashville, with songwriter (and his own bassist) Tate Howell his first signee. Then in December, Allen joined forces with former Spotify executive John Marks and producer Aaron Benward to launch JAB Entertainment, a management and production company; its first client, country duo Neon Union, has since signed with Red Street Country, the imprint founded by Rascal Flatts’ Jay DeMarcus.

And Allen, who will open for Carrie Underwood on tour this fall, has his eye on the live sector, too. On Aug. 13, his second Bettie James Fest will take place in his hometown, with himself, Lainey Wilson and We the Kings on the bill, among others. The tug to return to Delaware is ever present. “I’d move back now if my wife was ready to go, but she just moved from Delaware two years ago,” he says. “She’s not ready to go back. I am.”

Be that as it may, his myriad interests keep him on the road. He loves dancing, so he competed on Dancing With the Stars; he also loves game shows, so he made stops on Celebrity Family Feud and Let’s Make a Deal. But for Allen and his team, these aren’t just whimsical side projects — they’re ways to build his audience.

Dancing With the Stars was very impactful,” Bowers says. Over the eight weeks that Allen competed, “we saw a huge uptick in social following and streaming audience. It’s about expanding his fan base in areas where he also has interest. It’s proven to be successful in creating new fans that haven’t discovered him on country radio.” Now, Allen has his eye on more hosting gigs as well as acting roles, citing Jamie Foxx and Wayne Brady as inspirations. “We have been approached with several opportunities that lead me to believe we are on the right path with that,” says Bowers, who surveys them with Allen’s agent at UTA, Josh Garrett. Allen is even considering returning to his stage roots: “I want to play Aaron Burr in Hamilton,” he told Billboard last December.

Most of the time, Allen’s laser focus allows him to keep his music career front and center. “When I’m writing, I’m writing. When I’m performing, I’m performing,” he says. “I compartmentalize my whole life. Sometimes it’s a good thing, sometimes it’s bad. But I feel like my personal issues should never interfere with work. And work should never interfere with my personal life. Wherever I’m at and what I’m doing, that’s who I am.”

Still, maintaining such clear-cut divides isn’t always straightforward. Allen has talked candidly about his bipolar diagnosis and addresses it in “Untitled,” an as-yet-unrecorded song that he has posted twice on his Instagram. “Truth is that I’m always on the edge/Trying to find the point of living/I’m barely hanging on/And no one can see that I’m constantly fighting with me … It’s like two different people live inside my mind/Which voice do I follow, the dark or the light,” he sings, sounding weary. When he posted it in April, he wrote, “Mental illness is something I have struggled with my entire life. Every day is a constant battle with myself.”

Today, Allen says he has learned “to take time when I need time” for a mental break. “Whether it’s a show or interview or something, if I’m not in the right space to do it, I’ll cancel it,” he continues. “And it’s always a few days ahead of time or a week in advance because I know me, I can kind of feel it: ‘Yeah, I’m not going to be good on this day. Let’s move it.’ ”

But while Bowers says he and Allen see eye to eye on that front, nothing seems likely to stop Allen’s relentless drive forward and upward. “I think the ultimate goal is to headline stadiums as an artist and become an A-list actor,” Bowers says. “I think we will be very close to accomplishing that in five years from now.”

It sounds like a milestone straight out of that old notebook. But Allen quit writing in it after he signed his record deal; at that point, he figured, he had finalized his list of career goals and it was time to focus on accomplishing them. There’s one final entry, he says: his plan for how to, eventually, walk away. He won’t reveal when, but makes it clear he’s not interested in a slow fade. When he leaves, it’ll be with the same kind of intention that drove him in the first place.

“I look at my music career like sports. If I’m not able to perform or create at a level that I’ve always done it, I won’t do it anymore,” he says. “Imagine [Michael] Jordan in the NBA right now. You would easily forget about his greatness. You’d easily forget about everything he accomplished … because people are all about the right now.”

And Allen has never been only about the present. He speaks slowly and deliberately as he envisions what that final chapter might look like. “I want to do it at a level for a while. After I step away and retire, I might do a pop-up thing twice a year,” he muses. “But the time of grinding and building will be over. It’s more enjoyment, to where if I want to put out a song, I might. But I probably won’t.”

This story originally appeared in the June 25, 2022, issue of Billboard.

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