These days, Grammy-nominated singer-songwriter Jimmie Allen can often be found in the rural oasis of Milton, Delaware, where he’s been making hits like this year’s “Country Boys Never Learn.” It's all some of the freest music of his decorated career.

The small-town supernova first took the scene by storm in 2018 with his debut “Best Shot.” When it topped the Billboard Country Airplay chart, it made him the first Black artist to achieve the feat with their first single. He made history again when his follow-up, “Make Me Want To,” also shot to the top, making him the first Black artist with two consecutive Number Ones at the onset of their career. Allen has gone on to release three powerful albums, Mercury Lane, Tulip Drive, and Bettie James Gold Edition, the latter featuring intimate collaborations with Tim
McGraw, Darius Rucker, Mickey Guyton, Noah Cyrus and Allen’s personal hero Charley Pride. Allen’s resonant touch has earned him a slew of accolades including the Country Music Association Award for New Artist of the Year and the ACM Award for New Male Artist of the Year. “What I have on my walls are my kids’ awards, though,” says Allen, who treasures their prizes and drawings.
 

While Allen has spent time between Los Angeles, Nashville, Tampa, and Miami, he records all his music back in Milton where it all started and where, to his pleasure, nothing has changed. “I love my hometown because I wouldn't be who I am without the place that raised me,” Allen says. “I get to go out on the water, take the boat out, chill, hang, go to the studio, knock something out, and then head back.” You can catch Allen driving his truck across barren roads that traverse dense crops, or helping out his teammates on the softball diamond, or competing in bowling tournaments across the country. Above all, he prioritizes his kids, who he takes to Disney World often (though he also likes to hit Magic Kingdom alone from time to time).
 

In this era, Allen is writing from a place of contentment. “I definitely use some of the bullshit I had to go through for inspiration, whether it's a song of frustration or a song to motivate myself and other people,” he says, but he’s also inspired by the things he loves, like television. “Probably an unhealthy amount of television,” he says with a chuckle. The two-time platinum sensation “Best Shot,” for example, was the product of that. “A lot of people thought it was about my relationship; Nah, it was about the relationship of Nathan and Haley from that show One Tree Hill,” he says. A forthcoming track ballad of his was inspired by Amazon’s hit coming-of-age series The Summer I Turned Pretty. Allen is letting his mind and pen roam freely, rejecting any boundaries or boxes. “I feel it's really a blank canvas,” he says. “I get to just enjoy, enjoy music again, with no pressure.”

Eager to share with his fans, Allen will head out on the Stories Behind the Songs tour across select cities beginning September 5. His audience runs the gamut from kids to people like the 98 year-old woman who had her great-grandson drive her to Delaware from Valdosta, Georgia to see him play. At his concerts, he always makes it a point to meet with as many of the elders in the audience as possible. “I love the stories and the conversations we get to have,” Allen says. “I was really close to my grandmother and my great grandmother. Man, life is short. If they take the time to come out and see me, I want to go out of my way to show them I appreciate it.” On his rise across Nashville’s country circuit, he would do the same for the few Black faces in crowds where people who looked like them were often made to feel unwelcome. For Allen, that’s what music is about – connection, empathy, and freedom. They’re the rules he’s striving to live by.