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The 10 Best Chris Stapleton Songs, Ranked


No one has flipped the script in recent memory quite as Chris Stapleton has. Chris Stapleton's songs are universally liked, adored, and respected in country music.

Ultimately, that's because his musical output is as diverse as they come. Dave Cobb co-productions Traveller, From A Room: Volume 1 and From A Room: Volume 2 -- two of which are CMA Album of The Year winners -- have pockets of music that were meant for wide listenership. While Stapleton is certainly a country singer, he's so much more than that. His classic country callbacks, southern rock ramblers, and intimate storytelling narratives all resonate. His soulful vocal runs and bluesy guitar grit are refreshing and worthy of critical acclaim.

Much of his diverse sound can be chalked up to his time with the Kentucky bluegrass group The SteelDrivers and the Southern Rock outfit The Jompson Brothers. His career as a Nashville songwriter (we're talking over 100+ songs) is the stuff of legend. But there's a reason those songs were recorded by the likes of Kenny Chesney, Thomas RhettLuke BryanGeorge StraitBrad PaisleyLee Ann WomackDierks BentleyDarius Rucker, and even Adele. It's because they tapped into something genuine. When it came time to release his own, that tap wasn't turned off. In many ways, he let the levee break.

While the catalog of Stapleton songs is diverse in style and story, like the rollicking "Midnight Train to Memphis" or the rhythmic "Trying to Untangle I Mind," it's his genuineness that remains reliable throughout. It'd be easy to dole out a series of paint-by-numbers songs that would find their way to the top of the charts. But Stapleton has rarely, if ever, released a song for the simple fact that he's country music's golden child.


While Stapleton certainly checks off most boxes as an artist -- amazing and powerful vocals, pure raw emotion, heartfelt lyrics and an earnest ear for melody. Perhaps his single greatest gift is his ability to time and again deliver songs that feel comfortable and familiar. Songs become anthems and in turn, those anthems insist on being sung along with. Chorus lines are easily learned. They're identifiable and universal.

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Still, Stapleton doesn't rely too much on that. His most intimate songs are cherished not only because he takes you on "hurt so good" journeys, but even his grizzled vocals resonate. He channels the raw emotions of a moment with his delivery in ways most only dream about.

All being said, Stapleton's country albums are rich journeys that shed light on some of your deepest thoughts, darkest trials, and celebrates your highs of satisfaction and joy. Here are the 10 best Chris Stapleton songs.


Note that this list was written in 2018, so it doesn't incorporate "Arkansas," "Maggie's Song," "Hillbilly Blood," "Worry B Gone," "Watch You Burn," Guy Clark cover "Old Friends" and other selections from new album Starting Over. And like any other top 10 list, there's room for debate over whether or not something like "Nobody to Blame" and "Parachute" from debut album Traveller or Kevin Welch cover "Millionaire" deserved a spot on our playlist. Stapleton released his fourth studio album in November of 2020, Starting Over, which gained several positive reviews from critics.

10. "The Devil Named Music"

Much of Traveller, Stapleton's solo debut, had him doing just that -- the ups and downs that go along with crisscrossing the country as a touring musician. "The Devil Named Music" was the crowning jewel of those sentiments. It's filled with candid lines about missing family and wondering if it's worth sacrificing. It's not until the end that he lets out a grizzled vocal wail that shakes through your speakers.

9. "What Are You Listening To?"


"What Are You Listening To?" was released as a stand-alone single back in 2013. It's a prime example of Stapleton's uncanny ability to create choruses that feel both fresh and comfortably familiar. He also takes a common trope and twists it into new. He's thinking about his recent break-up through the lens of what she's perhaps listening to.

8. "Daddy Doesn't Pray Anymore"

No one pulls you in closer than Stapleton. One minute, he has these grandiose choruses that hinge on fan interaction. The next, he makes you lean in and listen. "Daddy Doesn't Pray Anymore" is one of Stapleton's most humanizing and intimate moments to date. The lamenting harmonica is both a haunting, yet comfortably warm touch.

7. "Fire Away"


Some of Stapleton's greatest moments demand you sing along. "Fire Away" has that magic. You're urged to join in on the chorus. The opening lines of "Honey load up your questions and pick up your sticks and your stones" are some of his most vivid imagery. There's little to no hints on what's caused the quibble. But in just two lines, he frames the scene perfectly. He's ready for the heated argument knowing that their love is an unconditional one.

6. "A Simple Song"

Written with Darrell Hayes, Stapleton's father-in-law, "A Simple Song" is a reassuring pat on the back. The fingerprints of Chris Stapleton's wife Morgane are all over the affectionate number. As they frequently do, her harmony vocals add a layer of depth to the simple song. There's a commonality in Stapleton's examples of when life going awry that are universal. While Stapleton feels the pressures, he never breaks to the pressures of life -- mainly because his foundation is his family.

5. "You Should Probably Leave"


"You Should Probably Leave" was released on May 17, 2021, as the second single from Stapleton's fourth studio album, Starting Over. The song was co-written by Stapleton, Chris DuBois, Ashley Gorley and produced by Dave Cobb. The song beautifully described the story of an on-again, off-again couple who can't help themselves from coming back to one another despite knowing it won't end well. Stapelton's voice really brings out the beautiful but tragic lyrics that you'll be singing at Karaoke.

4. "Broken Halos"

"Broken Halos" is yet another example of Stapleton creating songs that feel familiar and worn in. The chorus of "Seen my share of broken halos. Folded wings that used to fly," just beg you to join in. " Written with former SteelDrivers bandmate Mike Henderson, "Broken Halos" is pure radio gold and is one of Stapleton's best earworms. It's simple, bright, and clear.

3. "Whiskey And You"


Tim McGraw first covered "Whiskey And You" on his 2007 album Let It Go. Thankfully, Stapleton decided to give his own take on Traveller. His broke down version is intimate and transparent. It's as rich as it is dejected and broken down. While most of Stapleton's anthems are built on easily digested choruses and storytelling, his most reserved moments are pure poetry. "Whiskey And You" is just that. It's not just raw emotion either. It's as calculated response to being brokenhearted as you'll hear. His NPR Desk Concert performance of the song still leaves you with goosebumps.

2. "Drunkard's Prayer"

Stapleton plays the part of a drunk better than most. It's not just a party when it comes to alcohol. There's much more to it than that. His "Drunkard's Prayer" is an insightful examination of forgiveness and faith. Stapleton's lyrics aren't just topical or surface level either. They're part of an inner dialogue that feels uncomfortable by nature, but also necessary. It's not just an observation of others. Even if it's not all autobiographical, "Drunkard's Prayer" works because deep down, it's as personal as Stapleton has gotten.

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1. "Tennessee Whiskey"

When it comes down to it, Stapleton is a fan of songwriting first and foremost. There's a little bit of irony in the fact that Stapleton, someone celebrated for their songwriting, is most well known for a cover. Written by Dean Dillon and Linda Hargrove, "Tennessee Whiskey" has been covered by the likes of David Allan Coe and George Jones. But what makes Stapleton's version stand out is his bluesy take on the country standard. And while the studio cut is amazing, his CMA Awards duet with Justin Timberlake took the song to a whole new level.

This story was originally published in 2018.