Here Are The Best Gary Stewart Songs That Once Dominated The Honky Tonks

With his unmiGary Stewart stood as a

Born in Jenkins, Stewart’s journey to stardom was anything but predictable. In the late 1960s, he walked away from what could have been a lifetime working in an airplane factory. Encouraged by Mel Tillis—whom he met in a honky tonk—Stewart took a leap of faith and brought his songs to Nashville. That decision would change everything.

By the early 1970s, a demo tape featuring his country-infused takes on Motown classics caught the attention of a Nashville producer. From that moment on, Stewart’s rise seemed unstoppable. Yet behind the spotlight, success came at a cost. Personal struggles shadowed his career, culminating in a heartbreaking end—he passed away just a month after losing his wife of more than 40 years. It was a tragic close to a life that had always danced on the edge between brilliance and pain.

Today, we look back—not with sorrow, but with admiration—celebrating a voice that defined an era. Here are some of Gary Stewart’s most unforgettable songs, the very tracks that once ruled the honky tonks and still resonate today.

1. She’s Actin’ Single (I’m Drinkin’ Doubles)

From: Out of Hand (1975)
In 1975, Stewart reached the peak of his career with this chart-topping hit—his only No. 1 on Billboard’s Hot Country Songs. The song captures the loneliness of a man navigating life after heartbreak, wrapped in a melody that feels both bitter and beautiful. Its raw honesty made it timeless.

2. Out of Hand

From: Out of Hand (1975)
A story of temptation and regret, this track channels the spirit of legends like Dolly Parton and Merle Haggard. Climbing to No. 4 on the charts, it stands as a powerful reminder of country music’s ability to tell hard truths with grace.

3. Whiskey Trip

From: Little Junior (1978)
Few themes run deeper in country music than whiskey—and Stewart knew it well. “Whiskey Trip” is a haunting escape into heartbreak and self-destruction, carried by his signature trembling voice that feels like it’s unraveling with every note.

https://www.youtube.com/watch?v=KMQP5-lE_UM

4. Brand New Whiskey

From: Brand New (1989)
After stepping away from recording in the early ’80s, Stewart returned with renewed energy. This track, though a minor hit, became a fan favorite—proof that even after silence, his voice still carried weight.

5. In Some Room Above the Street

From: Steppin’ Out (1976)
This song paints a vivid, cinematic picture of loneliness and longing. With its Southern roots and outlaw edge, it captures the soul of Stewart’s artistry—equal parts rugged and heartbreakingly tender.

6. Your Place or Mine

From: Your Place or Mine (1976)
A restless, emotionally charged classic, this track showcases Stewart’s ability to blend vulnerability with intensity. Featuring talents like Emmylou Harris, it adds depth to an already powerful performance.

7. Drinkin’ Thing

From: Out of Hand (1975)
This was the song that first pushed Stewart into the top ten. It tells the story of a man fighting temptation—and losing. Honest, relatable, and painfully real, it became an anthem for many who saw themselves in its lyrics.

8. I See the Want To in Your Eyes

From: Out of Hand (1975)
Before Conway Twitty turned it into a No. 1 hit, Stewart recorded this emotional ballad with a subtle vulnerability that gave it a unique edge.

9. Ten Years of This

From: Your Place or Mine (1977)
A deeply reflective song about the weight of long-term relationships, this track even caught the admiration of Bob Dylan, who reportedly played it repeatedly. That alone speaks volumes.

10. You’re Not the Woman You Used to Be

From: You’re Not the Woman You Used to Be (1975)
Closing the list is another heartbreaking narrative—one that captures the slow, painful realization of love slipping away. It’s classic Stewart: emotional, honest, and unforgettable.

Gary Stewart wasn’t just a singer—he was a storyteller of life’s rawest moments. His music still echoes through time, reminding us of nights filled with neon lights, broken hearts, and songs that understood us better than we understood ourselves.