When I interviewed Trey Calloway at CRS 2025, there was an instant kindred spirit, and I knew I wanted to do a full feature on him once the opportunity arose. Like so many of the artists I have interviewed, Calloway got his start singing at church. He knows that singing at church, especially when it's not one of those mega churches, is a safe place to try out your voice.
He explained, "A little kid starts singing at six or seven years old, and by the time they are nine or ten, they are singing solos. It's a safe place to practice in front of a crowd where even if you aren't that great, people will still love and support you."
Young Calloway took to singing quite naturally. He shared, "Being in front of crowds and singing for the Lord was a big motivator for me to get into music. It was baseball and music early on for me. And I guess music won out in the end."
Although southern and contemporary gospel were his first musical loves, as a teen, the North Carolina boy developed a deep understanding and passion for the rocking, boot-stomping storytelling of '90s country legends and has been writing and performing country music ever since.
The first album that Calloway released at the age of 19 was called Carolina Man. And while he had recorded music in his uncle's little recording studio, this was his first experience making an album in Nashville. "I was just a baby," he joked.
The album, which he called "Ramblings of a Teenage Boy," was full of 4½-minute-long songs. However, he still plays songs from his debut record, and the single "Carolina Man" is a requirement when he is playing on home turf. "It's basically my signature song," he stated.
That debut album was followed by years of releasing singles and EPs, proving that Calloway is/was a songwriting machine.
Songs like "Worth A Shot," "When You Walk In," "She Loves Me," and "Nothing Wrong With a Love Song" have made an impression in the country music world.
Calloway's song, "One Tough Job," earned him the Texas Country Music Association songwriter of the year in 2023.
In 2024, he released his sophomore, album, Wanted Man that produced singles like "That Was Us," "I Miss Country Music," "Forgotten Man" (a tribute to famers) and one of my favorites, the title track, "Wanted Man" as in "All I ever wanted was to be a wanted man."
Released on Memorial Day this year, Calloway's song, "She Misses Being Mrs." will pull on your heartstrings. The song tells the story of loss while paying tribute to those who have made the ultimate sacrifice and the loved ones they left behind.
If the lyrics Now she misses his heart/ His tender touch/ The warmth of his arms/ Wrapping her up/ The memory of every smile/ And a thousand goodnight kisses/ But most of all she just misses/ Being Mrs. don't move you, you don't have a soul.
But being the powerhouse singer/songwriter that he is, Calloway continues to roll out singles. He has released "Miss Gone By Morning," a song about girl who won't be tied down, the Latin-inspired "The Ballad of Righteous and Wrong," the wildly popular, "Your Love Is Safe With Me," and most recently "She Don't Break It," that tells the story of healing after heartbreak.
The energetic "Must Have Had a Good Time" is his latest single. It is the first song in the ten years he has been singing professionally, which he didn't write. It was written by Anthony Smith, Chris Young, and Frank Myers. Chris Young had made a demo for it, but for some reason, he never released it. When Calloway found out it was available, he jumped at the chance to cut his own version of the song.
Back in the day, artists like George Strait and Patsy Cline never wrote their music, but songwriters knew the best way to get sales was to get someone like that to record their songs. "I want to help bring back the trend of using outside cuts," Calloway shared.
He continued, "I love playing 'Must Have Had a Good Time' live. It feels like it's my song. The crowd goes nuts over it. They love it. Everybody must have had a good time. If the song feels honest to me, I don't care who wrote it."
I jokingly asked how two kids (he and I) who grew up being Pentecostal ended up liking party songs so much. Calloway quipped, "I think all the shouting and hand clapping and running up the pews that we do puts that in us from a young age."
What I like about Trey Calloway and his music is that he brings the '90s country vibe to his newer songs, which he plays regularly in bars up and down Broadway.
Calloway has opened shows for Joe Diffie, Tracy Lawrence, McBride & The Ride, Pat Green, Edwin McCain, and Craig Campbell, and has played for audiences at the Charlotte Speed Street NASCAR Festival, the House of Blues, Billy Bob's Texas, and the Tennessee State Fair Opry Stage.
Calloway will be releasing new music every 6-8 weeks. But if you get a chance, you will want to see him play live. He and his band are a favorite in the Nashville music scene. This is the music you come to Nashville to hear.
You can follow Trey Calloway on his website, Facebook, Instagram, YouTube, TikTok, and all streaming services.
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Bethany Bowman is a freelance entertainment writer. You can follow her blog, Instagram, and X.
