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7 Greatest Gary Stewart Songs

7 Greatest Gary Stewart Songs

Gary Stewart songs are country tunes best heard over and over again. 

At first, you may not hear the magnificence and wild abandon. 

But after a while, these honky-tonk southern country tracks will leave you wanting more.

Which Gary Stewart songs are the best, though? Let’s find out!

About Gary Stewart

Born on May 28, 1944, Gary Stewart was one of nine children born and raised in the south. By 16, Gary was playing music professionally. His first band was The Tomcats, a swaggering rockabilly band. He also married his wife, Mary Lou, during this time. 

In the mid-60s, he was discovered by outlaw country singer Mel Tillis. With his idol’s encouragement, Stewart began songwriting, eventually moving to Nashville in 1971.

When his 1973 demo tape made the rounds in the country circuit, producer Roy Dea scooped him up and signed him to RCA.

Gary Stewart’s voice was one of a kind. His hillbilly vibrato and lonesome Kentucky howl could leave you wounded but coming back for more. With a touch of rock and a little soul, he gave country music a boost. 

As a result, it wasn’t long before Stewart became a famous country artist. His second album, Out of Hand, produced three top ten hits. It became known as one of the best honky tonk records of all time.

But Stewart was an outlaw country artist in more ways than one. Musically, he was influenced by both outlaw country and southern rock. Personally, he was a feral creature who could not be contained. 

The Dark Side of Gary Stewart

Full of wild fervor and unrelenting heartache, Stewart had a thirst for the dark side. He drank heavily and did loads of drugs. For years. According to friend and writer Jimmy McDonough, the battle to get Stewart to be good to himself was endlessly uphill.

“​​Everybody but the mailman got sucked into trying to help Gary kick the many monkeys on his back,” says McDonough. A car accident in 1980 didn’t help. After a string of hit songs and five well-received albums, Gary Stewart’s success slowly faded away. Although he would go on to record 13 albums, Stewart’s relationship with the music industry was always problematic.

His personal life in his Florida sanctuary was what he loved. Unfortunately, the darkness was inescapable even there. His son, Gary Jr, committed suicide in 1987. Although Stewart sobered up for a brief period, he fell back off the wagon a few years later. 

He never quite recovered from the loss of his son. And when Mary Lou, his wife of 43 years, died in November of 2003, Stewart was inconsolable. He committed suicide one month later.

Gary Stewart was a true country classic with all of the heartache and tough southern living. Artists like Bob Dylan went out of their way to meet him. People today still discover him.

Here are the Gary Stewart songs that stand out the most.

#7 Single Again

About the Song: Single Again is a perfect intro to Gary Stewart. We’re starting with a lesser-known but well-crafted song. You’ve got the guitar twang, the slow country sway, and that lost love theme that goes far in the hearts of country music lovers.

Greatest Lyric

Single again.
Born to lose, dying to win. 
The only thing I'm a'running from
Is the alimony man.

First Appearance: Single again debut on Stewart’s 1978 album, Little Junior

#6 Your Place or Mine

About the Song: You can’t get more straightforward than this. Gary Stewart’s blend of honesty and nervous vibrato might charm the pants off many listeners. Honky tonk and sway the night away to this undomesticated classic.

Greatest Lyric

Now, honey, I'm not pretending. 
A here's my bottom line. 
Where are we going?
Your place or mine?

First Appearance: Stewart released Your Place or Mine on his highly successful album of the same name in 1977.

#5 In Some Room Above the Street

About the Song: The lyrics to this track remind listeners of Stewart’s ties to the south. It’s no wonder that southern rock had such a significant influence on him. A little outlaw, a little lovesick, this might be the most cinematic piece in Stewart’s honky tonk jukebox.

Greatest Lyric

In some room above the street. 
Like thieves and beggers when we meet.
We'll wake before the break of day. 
Then like the night we'll steal away

First Appearance: This sweet story was released in 1976 on Stewart’s album Steppin Out.

#4 Out of Hand

About the Song: Out of hand starts with a potent reminder of classic country tunes by greats like Dolly Parton, The Carter Family, and Merle Haggard. Its composition hits the spot with a brilliant chorus/verse timing. The lyrics are about an extramarital affair. 

Greatest Lyric:

Out of hand, out of hand.
I'm a hard-living kind of a man. 
I need more to keep me goin', 
Than this gold wedding band.

First Appearance: Written by Tom Jans and Jeff Barry, Gary Stewart first recorded Out of Hand in 1974 for his album by the same name.

#3 Brand New Whiskey

About the Song: Gary Stewart wrote and released Brand New Whiskey after a six-year hiatus. Back in the saddle, Stewart’s new batch of songs was a little more rockin’ and rowdy. With some slick slide guitar from Warren Haynes of Allman Brothers, this ditty brings you right into the bar.

Greatest Lyric

When a goodbye hits him like a hurricane. 
Make it sweet, as sweet as her lips.
Something special like champagne.

First Appearance: This rugged little tune first appeared in 1988 on Stewart’s comeback record entitled Brand New.

#2 Whiskey Trip

About the Song: You can’t have too many songs about whiskey in the land of country! This popish jingle is about drinking your broken-hearted blues away. The serene sounds of the xylophone might remind you of Jimmy Buffett’s Margaritaville. But the waver in Stewart’s voice takes this whiskey trip miles away, in another direction.

Greatest Lyric:

Whiskey, you're a friend of mine.
You can blow away my mind.
To some other place and time.

First Appearance: Whiskey Trip set sail in 1978, on Gary Stewart’s fifth album, Little Junior.

#1 She’s Actin’ Single

About the Song: The greatest Gary Stewart song was easy to pick. She’s Acting Single (I’m Drinkin’ Doubles) was Stewart’s third top-ten country hit, reaching number one in 1975. Written by Wayne Carson, Stewart worked long and hard on this heartbreaker to get it just right. 

Record producer Roy Dea drove the hammer down, insisting on complex overdubs and an intricate arrangement. But the work paid off. With brilliant steel guitar and lush backing vocals added to Stewart’s pleading voice, it’s no wonder this remains an outlaw country classic.

Greatest Lyric

My heart is breakin', 
Like the tiny bubbles. 
She's actin' single,
I'm drinkin' doubles.

First Appearance: She’s Actin’ Single was released in March of 1975. It’s track one on side two of the album Out Of Hand, Stewart’s defining Honkey Tonk record.

Which Gary Stewart Song is Your Favorite?

King of honky tonk and crooner of the wild country, Gary Stewart was one of a kind. His music catalog is worth a deep dive. Apparently, there are many Gary Stewart songs recorded but not yet released. Let’s hope someone rounds them up onto a CD soon. Until then, what do you think of our list? What’s your favorite Gary Stewart tune?