The 10 Best Chris Stapleton Songs

Becky Fluke

The 10 Best Chris Stapleton Songs

Becky Fluke

For years, Chris Stapleton had been an unstoppable force in Nashville — but one working mostly behind the scenes as a songwriter and member of his bluegrass group the Steeldrivers, letting others take the limelight with his words. Writing for everyone from Patty Loveless to Luke Bryan, he gave country music a lot of its heart, soul, and southern-rock swamp from the early 2000s on (yes, even for Luke Bryan). But on his 2015 solo debut, Traveller, Stapleton broke all the norms: He found stardom in his thirties, put country music — not pop country or bro country — back on the map, sang with Justin Timberlake, and sold millions of records in the process. He’s now not only one of the genre’s biggest stars, but he’s managed to create a wave of interest in country traditionalism in his wake.

The follow-up to Traveller was a set of two records, From A Room: Volume 1 and 2, both made with producer Dave Cobb at his home base of RCA Studio A. Less identity-driven albums and more collections of songs, they were food for hungry fans who were eager for a backlog — at the end of the day, their most important function seemed to be to give Stapleton plenty of material to pick from as he stayed eternally on the road.

Times have changed, of course, and Stapleton — or anyone who doesn’t believe COVID-19 is a liberal conspiracy — is off of touring for the foreseeable future, waiting for immunity or at least a vaccine. Stapleton must have felt a stillness in the air when he recorded the 14 tracks on his new album Starting Over in late February 2020, right before life went on hold. Because while some of them feel born for a live show (like “Arkansas”), they are also ripe for slow, at-home introspection and careful ponderance over the subject matter that Stapleton is always most drawn to: mulling human imperfections, praising the “good stuff,” and thanking the gift of love while chiding the lure of intoxicants. He also, in the tradition of his massive hit, “Tennessee Whiskey,” offers up some covers: John Fogerty’s “Joy Of My Life” as well as Guy Clark’s “Worry B Gone” and “Old Friends.” But, as usual, there’s no denying the words that Stapleton puts down himself. Here, we rank 10 of his all-time best.


"Arkansas" (from Starting Over, 2020)

If Stapleton’s going to do something, he’s gonna do it whole hog — and “Arkansas,” off of Starting Over, is absolutely whole hog southern rock, the kind that could blaze Lynyrd Skynyrd clear off the stage but still make Merle Haggard and Waylon Jennings smile. It’s short, raucous, and a polar opposite of gauzy ballads or bluesy rambles. It proves that he’s an artist that can simply do it all.


"Sometimes I Cry" (from Traveller, 2015)

Recorded live to tape at RCA Studio A, “Sometimes I Cry” might be the last track on Traveller, but it’s the album’s biggest clue as to where Stapleton’s heart lies: gritty, gut-wrenching Muscle Shoals R&B. While country music’s biggest bros — the Lukes, Jasons and Dustins of the world — try to make their tight-jeaned masculinity their biggest commodity, Stapleton isn’t ever afraid to let his voice cut to the most tender, emotional tip. “Sometimes I cry,” he wails, with the force of someone baring their truth. You believe those tears, and he’s in no rush to dry the evidence.


"Drunkard’s Prayer" (from From A Room: Volume 2, 2017)

Country music is as enamored with alcohol as it is with making frank observations on, and dedications to, faith. And on “Drunkard’s Prayer,” Stapleton finds a way to potently combine them both. Recorded raw and direct, like a lingering message passed on over time, “Drunkard’s Prayer” finds a man torn between surrendering to the bottle and a higher power — or maybe the two are more closely in cahoots than he could have thought. A woozy, waltzing, and intoxicating confession.


"Whiskey Sunrise" (from Starting Over, 2020)

There’s a bit of that lonesome sound in “Whiskey Sunrise,” one of Starting Over’s most forceful tracks that rolls in with a quiver of the guitar like some saloon doors swinging open. “I’m lost and I’m lonesome when I look in the mirror,” he sings. “And I don’t like the man that I see.” It’s that journey for self-awareness over self-acceptance that makes Stapleton’s songs ring so true, especially when you can’t really have one without the other.


"A Simple Song" (from From A Room: Volume 2, 2017)

Stapleton recorded two songs co-written by Guy Clark on Starting Over, but this track off From A Room: Volume 2 is perhaps his truest notch in furthering the legacy of the late, great songwriter. Like Clark’s finest, “A Simple Song” isn’t presumptuous or showy — it’s a stripped-down meditation on the things that make life worth living, delivered with enough minor keys to remind us that every good thing is temporary and precious. It’s appreciative but not saccharine, solemn but celebratory, and, above all, the story of a common man just trying to find the will to get through the worst through music.


"Traveller" (from Traveller, 2015)

It’s a simple story, really — the tale of a wayward wanderer, following the road and the music wherever it may go. Country is no stranger to a travelin’ song like that, but Stapleton is able to take what could be a tired trope in the hands of another and turn it into his breakthrough moment. The first single from his debut album of the same name, “Traveller” may praise letting yourself journey where the muse may take you, but it’s also a road map of exactly what Stapleton is all about: subtle and evocative metaphors, a perfect brew of relaxed country vamps and soul swagger, and a voice that can cross state lines. It’s a classic theme, and now a straight-up classic, too.


"Fire Away" (from Traveller, 2015)

Stapleton, of all people, knows the power of words to heal — but he also understands their ability to destroy us, too. Traveller’s “Fire Away,” thanks in part to the always-gorgeous harmonies of his wife Morgane Stapleton, finds him wrestling with, and learning to accept, the poison and heartbreak that can come from the mouths of others. It’s the combo of traditional sounds — steel guitar, southern waltz — with full-force vocal acrobatics (who else can draw that many beats out of the word “fire”?) that cements it in classic Stapleton territory. “Pretend I’m a shelter for heartaches that don’t have a home,” he sings, proving that he’s not just a country singer but a poet, too.


"Tennessee Whiskey" (from Traveller, 2015)

When one of our greatest songwriters tries to plant his flag in the words of another, you know it must be something worth your time. Stapleton didn’t write “Tennessee Whiskey” — Dean Dillon and Linda Hargrove did, and both David Allan Coe and George Jones performed it — but Stapleton brought the song, at the suggestion of producer Dave Cobb, into his soul-country wheelhouse. And it’s at a CMA Awards performance with Justin Timberlake that the whole thing went positively electric (and viral). Vocally, it’s still one of his finest moments, and one of country’s best covers of all time.


"Broken Halos" (from From A Room: Volume 1, 2017)

Despite Stapleton’s immense star power and critical acclaim, he still hadn’t scored a hit atop Billboard’s Country Airplay until “Broken Halos,” which managed to work its way up after 37 long weeks on the chart. Not a truck song nor an ode to tailgates, it’s Stapleton once again finding a perfect balance between a catchy, lingering chorus and his predisposition to never let us forget about the tangles and tears tied up in the mortal coil. Heroes die — both literally and metaphorically — and “Broken Halos” manages to make allowance for both the loved ones who have left us and the Godlike figures who had let us down. And why, no matter what, that’s all just part of being human.


"Whiskey And You" (from Traveller, 2015)

Stapleton can be unstoppable when he unleashes into a southern rock boogie (see: “Nobody To Blame”), but he stands alone in a somber ballad like Traveller’s “Whiskey and You” that lets him melt deeply into his repentant words. “I drink because I’m lonesome, and I’m lonesome because I drink,” he sings alongside a simple acoustic guitar. Sometimes he’s near a whisper, sometimes he’s hollering to the heavens, and he’s heard either way. And, finally, so are we.

Listen to the playlist at Spotify:

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