The 6 Chris Stapleton Songs with the Most Gut-Wrenching Lyrics

Chris Stapleton‘s voice is so otherworldly that he landed his first record deal after singing the phone book—literally—in front of Capitol Records executive Mike Dungan.

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“Chris played some songs for us,” music publisher Liz O’Sullivan told American Songwriter in 2015, “and Mike said, ‘Wow, you could literally sing the phone book and it would sound good.’ So Chris got out the White Pages and flipped to a random page and started singing the names. It was hilarious. Like, Saturday Night Live skit hilarious. Mike loved it, and he offered him a record deal that night.”

The record deal didn’t work out, and Stapleton wound up joining the Steeldrivers instead. Years later, when he finally found commercial success with his own music, it wasn’t just his booming vocals that got him there. It was his storytelling, too. 

We’ve rounded up some of the most powerful lyrics in Stapleton’s catalog, from drinking songs to heartbroken ballads.

6. “The Devil Named Music

“I miss my son, I miss my wife, but the devil named music is taking my life,” Stapleton sings during the chorus, like some modern-day Robert Johnson at the crossroads. A countrified cousin of Bob Seger’s “Turn the Page,” “The Devil Named Music” traces the highs and lows of a touring musician’s life on the road, tackling everything from imposter syndrome to jet lag.

5. “Hard Stuff

No, “Hard Stuff” isn’t a drinking song. Justin Timberlake (who co-wrote this track with Stapleton) isn’t singing about hard liquor; instead, he’s referring to the challenges that come with any relationship. Anybody can be in love on a sunny day / Anybody can turn and run when it starts to rain / And everybody wishes all the skies were blue / But that ain’t the kind of love I’m looking to have with you, he sings. Released on Timberlake’s 2018 album Man of the Woods, “Hard Stuff” is a tribute to the challenges that prove a relationship’s merit, as well as a showcase for Stapleton’s ability to write a song in any genre.

4. “Them Stems”

Sure, Stapleton is referring to the dregs of his marijuana stash, but this deep cut from From a Room: Vol. 1 is much more than a stoner’s anthem. Instead, it’s a track about bad luck, hard times, and the desperate measures people will take to find some temporary relief.

This morning, I smoked them stems / Yeah, that’s the kind of shape I’m in / I’m in a bad, bad way again / ‘Cause this morning, I smoked them stems, Stapleton sings, backed by honking harmonica from Willie Nelson’s longtime bandmate Mickey Raphael. During the course of the song, he doesn’t just lose his high; he loses his girlfriend and possibly his job, too. “Them Stems” has become a crowd favorite at Stapleton’s shows, beloved by fans who want to cut loose, get down, and fire up, but it isn’t a celebratory anthem. Dig beneath the surface and you’ll find the underlying message is more buzzkill than buzz-worthy. 

3. “You Should Probably Leave

This Grammy-winning single from Starting Over finds Stapleton and a would-be lover on the verge of getting busy. We both know where this is gonna lead…so you should probably leave, he sings in a cautionary tone, worried about the mess that a hook-up might cause.

That’s standard fare for a country song, but Stapleton flips the script during the final verse. Suddenly, it’s early morning and he’s literally singing a different tune, no longer worried about taking things too fast. Sun on your skin, 6 a.m., and I been watching you sleep / And honey, I’m so afraid you’re gonna wake up and say that you should probably leave, he admits. It’s a clever twist, and the song’s white-hot bluesy guitar riffs are an added bonus.

[RELATED: The Meaning Behind Chris Stapleton’s Hopeful Hit “Starting Over”]

2. “Whiskey and You” 

Traveller, Stapleton’s multi-platinum debut, arrived in 2015, after he’d already logged more than a decade as a successful songwriter for other artists. “Whiskey and You,” one of the album’s underrated highlights, is a master class in old-school country balladry.

The production is threadbare, leaving the storyline itself to pack a bigger punch. The first two lines—There’s a bottle on the dresser by your ring / And it’s empty, so right now I don’t feel a thing—supply all the background information we need, introducing the listener not only to the narrator’s drinking problem, but to his broken heart, too. His wife is gone, and the only thing that remains is the drinking problem that drove her away in the first place. I drink because I’m lonesome and I’m lonesome ’cause I drink, he laments by way of explanation.

The real kicker arrives during the chorus, when Stapleton compares and contrasts the two loves of his life:

I wonder if they ain’t both the same
But one’s a liar that helps to hide me from my pain
And one’s the long-gone bitter truth
And that’s the difference between whiskey and you

If that doesn’t break your heart and pickle your liver, you must not have internal organs. 

1. “Fire Away

A fight is brewing between Stapleton and his lover, and he knows there’s going to be carnage. Rather than fight back, he offers to be a punching bag.

Honey, load up your questions
And pick up your sticks and your stones
And pretend I’m a shelter
For heartaches that don’t have a home

By the time the chorus arrives, he’s encouraging his lover to “rear back and take aim.” Laced with harmony vocals from his wife, Morgane, “Fire Away” doesn’t shy away from the destruction caused by a lovers’ spat, but it does find some tender beauty amongst all the rubble.

Photo by Jason Merritt/Getty Images

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