Trey Calloway: Carrying Country’s Heart Into Christmas

Mark White | The Mark White Show

Nashville, Tennessee - Some artists arrive on the scene with a sound. Others arrive with a story. Trey Calloway showed up with both, the voice of a ’90s country jukebox and the heart of a songwriter who still believes in the power of a good line and a good life lesson.

When Trey joined me on The Mark White Show to talk about his new Christmas single, Christmas With You, the conversation quickly became more than just music. It became a window into a man who has lived the life he sings about, the long roads, the long-distance love, the separation, the grit and gratitude that shows up in every note.

Where It All Began

Growing up in North Carolina, Trey’s earliest stage was a church platform. His father was a Pentecostal evangelist, and Trey spent his childhood singing southern gospel out of red-back hymnals. Country music found him at thirteen, courtesy of a Greatest Hits CD packed with Loretta Lynn, Waylon Jennings, and George Jones.

“I always joke that I’m my dad’s second-favorite country singer behind George Jones,” Trey said with a laugh. “And I’m okay being second fiddle to George.”

From that moment on, he didn’t look back. Aside from a few odd jobs along the way, Trey has spent most of his life making a living with a guitar in his hand and a story on his lips.

Finding His Sound

Trey describes his style as “Johnny Cash meets Garth Brooks meets Alan Jackson meets Jason Aldean.” It’s a blend of familiar and fresh, old-school storytelling, modern production, and a commitment to showcasing real instruments.

No gimmicks, no electronic noise, just country music the way country music was built.

“What makes the ’90s sound come back so strong is the storytelling,” Trey said. “It was heart and soul. I try to keep that spirit alive.”

A Songwriter at Heart

Some writers start with a guitar riff. Trey starts with everyday conversation.

“Somebody will say something that sounds like a hook to me,” he said. “I’ve been known to stop mid-sentence and pull my phone out. I never want to lose a good line.”

Trey may be modest about his songwriting talent, but his approach is classic country, clarity, honesty, and a hook that sticks.

The Heart Behind “Christmas With You”

This isn’t just another holiday single, it’s a piece of Trey’s life.

For almost four years, Trey and his wife have lived apart, him in Nashville chasing music, her in Myrtle Beach chasing her own dreams. Add in his son living in Charlotte, and you begin to understand the weight behind the line “All I want is Christmas with you.”

“It’s semi-biographical,” Trey admitted. “I know what it’s like to be away from your family while you’re chasing a dream.”

Written with hit songwriter JP Williams, the song speaks to anyone who has ever spent a Christmas missing the people they love most, military families, truck drivers, touring artists, shift workers, and anyone whose life requires sacrifice.

Christmas Then. Christmas Now.

Trey grew up with big family Christmases, his great-grandparents, cousins, music, food, laughter filling every corner of the house. His great-grandfather, Joe, a singer-songwriter himself, helped shape who Trey would become.

Today, Christmas looks different, not smaller, just different. His wife’s family gathers to bake cookies, singing George Strait’s “Christmas Cookies,” and for Trey, it bridges the past and present.

“It fixes a hole in the heart,” he said.

What’s Next for Trey Calloway

A new album is already in the works, with another studio session coming early in 2026. Trey’s also preparing for a heavy touring schedule, including, he hopes, a stop here in Alabama.

And yes… he’s a Tide fan.

“I know nobody expects a North Carolina guy to say Roll Tide,” Trey said. “But I was raised one.”

A Voice Built on Honesty

What makes Trey Calloway special isn’t just the voice. It’s the intention. He cares more about connection than attention. More about the right song than the perfect set list.

“What gives me the most joy is changing a life one song at a time,” he said.

And with Christmas With You, he’s done exactly that, delivering a reminder that the greatest gift isn’t wrapped under a tree. It’s sitting across the table.