Letcher County, Kentucky-born Gary Stewart was an outlaw country music legend and the King of Honky-Tonk. Though the star left us in 2003 after passing away from a gunshot wound at his home in Fort Pierce, Florida, his legacy in Nashville and beyond, as well as his hits, still live on.
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Stewart, named after the famed actor Gary Cooper, spent a chunk of his childhood in Florida where his father worked as a coal miner. After marrying his wife Mary Lou when he was just 17 years old, he started playing around town at local honky-tonks. He ended up crossing paths with country singer Mel Tillis who encouraged him to move out to Nashville to find success as a songwriter. Soon after showing up in Music City, Stewart signed with Kapp Records and had numerous country hits written for Stonewall Jackson, Billy Walker, Cal Smith, and he even spent time playing in Charley Pride's band.
The singer ended up returning to Florida where he played country rock around the local clubs. At the peak of his career, he covered songs by the Allman Brothers, songs for Motown Records, and even had his own successes after his new label, RCA Records re-released some of his old material. He developed a strong following throughout the 70s who loved his southern rock sound and continued performing through the 90s, visiting Live at Billy Bob's Texas several times a year.
These are 10 of our absolute favorite Gary Stewart songs.
10. "Little Junior"
From his 1978 album of the same name, "Little Junior" lays out Stewart's honky-tonk history in full.
9. "Drinkin' Thing"
Stewart's 1974 single "Drinkin' Thing" was the debut song from his classic album Out of Hand.
8. "Out of Hand"
Peaking at No. 4 on the charts, "Out of Hand" was one of the many hits off Stewart's album of the same name.
7. "Your Place or Mine"
No one delivered a barroom come-hither quite like Stewart, who recorded "Your Place or Mine" for his album of the same name.
6. "Single Again"
With his signature vibrato, Stewart captured the pain of life after (another) breakup on the down and out tune "Single Again."
Read More: Classic Country Rewind: Gary Stewart's 'She's Actin' Single (I'm Drinkin' Doubles)'
5. "Cactus and a Rose"
This tune about a hard-living man whose way of life won't allow for a relationship is from Stewart's underrated album of the same name. Following this album, RCA teamed Stewart up with Dean Dillon for a series of duets, including "Honky Tonk Crazy," which was later recorded by George Strait.
4. "In Some Room Above the Street"
From his album Steppin' Out, Stewart proves again (and again and again) that he knows how to write about the southern man's social life.
3. "Brand New Whiskey"
From the album Brand New, released in 1988, Stewart wrote this hit with his wife Mary Lou Taylor.
2. "Whiskey Trip"
Stewart's brilliant "Whiskey Trip," about a man attempting to drown his heartache in a bottle of whiskey, was featured on the singer's 1978 album Little Junior.
1. "She's Actin' Single (I'm Drinkin' Doubles)"
"She's Actin' Single (I'm Drinkin' Doubles)" was the biggest Billboard hit of Gary Stewart's career and it's easy to see why. Perhaps there's no better example of Stewart's hurts-so-good country music than when the man with a teardrop in his voice sings "my heart is breaking like the tiny bubbles/ she's actin' single/ I'm drinkin' doubles."
This article was originally published in May of 2019.
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