The Owensboro Times
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By Ava Hyland
September 21, 2025 | 12:13 am
Updated September 20, 2025 | 9:53 pm
Jeremy Calloway
Gospel singer and Owensboro-based vocalist Jeremy Calloway has spent decades performing across the country, from small-town churches to international stages, while staying rooted in the values he learned growing up in the rural community of Magan Station, Kentucky.
Calloway, who began singing at age 9 in his family church, has since released four solo albums, appeared on nine compilations, and collaborated with icons of gospel and country music. His music spans gospel, country, jazz, and classic American standards, but his foundation, he said, has never changed.
“Southern gospel is where I started, and it’s still what grounds me,” Calloway said. “But I’ve loved being able to explore different styles and reach people in different ways.”
Raised just outside Fordsville, Calloway’s first performances came alongside his cousins in a church quartet.
“We would sing every church service and at any special events going on in the community,” he said. “That’s really how it all started.”
At 18, he joined a semi-professional group based near Columbia, South Carolina. After time performing with them, he returned to Owensboro, where a surprising opportunity awaited at the Executive Inn.
“They had me fronting a band five nights a week, Tuesday through Saturday,” Calloway said. “I loved the variety — Frank Sinatra, George Jones, Elvis. Even though gospel is my first love, I liked taking the American songbook and doing it in my own voice.”
One night at the Executive Inn, a request caught him off guard.
“Someone handed me a tip and said, ‘Sing your favorite song,’” he recalled. “It was late, and the first one that came to mind was ‘How Great Thou Art.’ I just started playing it on my acoustic guitar, and the whole place joined in. That’s when I realized no matter the setting, gospel is in me. It’s part of who I am.”
For Calloway, music is not only a career but a calling.
“My upbringing really formed my sense of purpose,” he said. “If I can bring peace or joy through a song, even just for 90 minutes, that’s what I was meant to do.”
A deep sense of patriotism also runs through his work, rooted in a family legacy of military service. That made one particular performance especially meaningful.
In 2009, Calloway sang at the 50th anniversary of Alaska’s statehood at Elmendorf Air Force Base in Anchorage, performing with Palmetto State Quartet and The Judds.
“We were on stage in this giant hangar, packed with thousands of people, F-16s flanking the stage,” he said. “As we hit the final note of ‘America the Beautiful,’ these jets did a flyover. You could see the snow-covered mountains in the background. It was overwhelming — pride, gratitude, tears. One of those moments you never forget.”
These days, Calloway and his wife Lena, a writer and director, are collaborating on a new chapter. They recently released their original single “She Ain’t Crazy,” written in a burst of inspiration after a heart-to-heart conversation Lena had with a friend.
“She came in from talking with someone who was going through something hard,” Calloway said. “I was standing at the stove warming up leftovers, and I just said, ‘She ain’t crazy because she loves him, she’s crazy because she’s crying.’ And we knew, this is a song.”
Within 45 minutes, the two had the first draft finished. The song is part of a larger project titled Dancing in the Kitchen, featuring both original tracks and timeless standards. The couple has written or co-written more than 20 songs for the upcoming collection.
In addition to that release, Calloway is working on a Christmas album set to debut later this fall. He’ll perform a special holiday concert on December 6 at Hilton Farms near Utica, with dinner and a full band. The event will benefit Friends of Sinners.
“I’ve had opportunities I never dreamed of,” Calloway said. “A kid from Magan Station doesn’t think he’ll share a stage with The Judds. But here I am.”
Whether it’s a massive crowd in Alaska or a small benefit show back home, his goal remains the same.
“If I can help someone feel peace, love, or joy — even just for a little while — then I’ve done what I’m here to do.”
September 21, 2025 | 12:13 am
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From Magan Station to the main stage: Calloway on faith, music, and finding purpose in every song – The Owensboro Times
