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10 Songs Behind Chris Stapleton's Award Show Dominance


Few current stars equally appease mainstream country fans, traditionalists and even casual pop listeners quite as effectively as Chris Stapleton.

Ultimately, that's because his musical output casts a wide creative net. 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. As does his most recent LP, 2020's Starting Over. Indeed, while Stapleton is certainly a true-blue 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.

His musical range 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 Rhett, Luke Bryan, George Strait, Brad Paisley, Lee Ann Womack, Dierks Bentley, Darius Rucker and even Adele. It's because they tapped into something that spoke to their vast audiences. When it came time to fly solo, 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 a fixture of industry awards shows.


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

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 because even his grizzled vocals resonate. He channels the raw emotions of a moment with his delivery in ways most singers only dream about.

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

10. "The Devil Named Music" (Traveller, 2015)

AUSTIN, TX - JULY 04: Singer-songwriter Chris Stapleton performs onstage during Willie Nelsons 4th of July Picnic at Austin360 Amphitheater on July 4, 2015 in Austin, Texas.

Rick Kern/WireImage

Much of Traveller, Stapleton's debut album, had him doing just that-- retracing 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 so much for success that's no guaranteed. It's not until the end that he lets out a grizzled vocal wail that shakes through your speakers.


Listen here.

9. "What Are You Listening To?" (2013)

NASHVILLE, TN - OCTOBER 29: Chris Stapleton and Morgane Stapleton attend the 50th Annual ASCAP Country Music Awards at the Gaylord Opryland Hotel on October 29, 2012 in Nashville, Tennessee. (

Rick Diamond/Getty Images for ASCAP

"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 something new. He's thinking about his recent break-up through the lens of what country song she's listening to.

Listen here.

8. "Daddy Doesn't Pray Anymore" (Traveller, 2015)

LOUISVILLE, KY - JULY 18: Chris Stapleton performs during day 2 at the 2015 Forecastle festival at Waterfront Park on July 18, 2015 in Louisville, Kentucky.

Timothy Hiatt/WireImage

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 a haunting yet comfortably warm touch.


Listen here.

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

LAS VEGAS, NV - APRIL 02: Recording artists Chris Stapleton (L) and Morgane Stapleton (R) perform during the 52nd Academy of Country Music Awards at T-Mobile Arena on April 2, 2017 in Las Vegas, Nevada.

Ethan Miller/Getty Images

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

Listen here.

6. "Fire Away" (Traveller, 2015)

LOS ANGELES, CA - FEBRUARY 13: Musician Chris Stapleton attends the charities signings during the 2016 MusiCares Person Of The Year honoring Lionel Richie at Los Angeles Convention Center on February 13, 2016 in Los Angeles City.

Jason Kempin/WireImage

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" provide 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.


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5. "Whiskey And You" (Traveller, 2015)

NEW ORLEANS, LA - MAY 02: Chris Stapleton performs at Fair Grounds Race Course on May 2, 2015 in New Orleans, Louisiana.

Erika Goldring/Getty Images

Tim McGraw first recorded "Whiskey And You" for his 2007 album Let It Go. Thankfully, Stapleton gave it his own spin 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 from any era of country music.

Listen here.

4. "Second One to Know" (From A Room: Volume 1, 2017)

Singer Chris Stapleton performs on NBC's "Today" at Rockefeller Plaza on July 18, 2017 in New York City. *** Local Caption *** Chris Stapleton

John Lamparski/WireImage

A Southern blues-rocker at heart, Stapleton delivered a song that Blackberry Smoke's members probably wish they'd thought of first. Guitar-slinging doesn't completely overshadow the emotional depth we've come to expect from Stapleton co-writes. Bonus points for a music video starring a Lego version of Stapleton and his band.


Listen here.

3. "You Should Probably Leave" (Starting Over, 2020)

NASHVILLE, TENNESSEE - FEBRUARY 10: Chris Stapleton performs at All for the Hall: Under the Influence Benefiting the Country Music Hall of Fame and Museum at Bridgestone Arena on February 10, 2020, in Nashville, Tennessee.

Jason Kempin/Getty Images for Country Music Hall of Fame and Museum

A highlight of Starting Over, this Grammy award-winning song was co-written by Stapleton, Chris DuBois and Ashley Gorley. It 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. Stapleton's emotive voice really brings out the beautiful but tragic lyrics in what's among his best in-studio performances.

Listen here.

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

LAS VEGAS, NV - APRIL 02: Chris Stapleton and Morgane Stapleton arrive at the 52nd Academy of Country Music Awards held at T-Mobile Arena on April 2, 2017 in Las Vegas, Nevada.

Michael Tran/FilmMagic

"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 begs 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.


Listen here.

1. "Tennessee Whiskey" (Traveller, 2015)

NASHVILLE, TN - NOVEMBER 04: Musician Justin Timberlake (L) performs onstage with Singer-songwriter Chris Stapleton (R) at the 49th annual CMA Awards at the Bridgestone Arena on November 4, 2015 in Nashville, Tennessee. (

Terry Wyatt/WireImage

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 perhaps best known for a cover. Written by Dean Dillon and Linda Hargrove, "Tennessee Whiskey" has been cut 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 --and his crossover appeal-- to a whole new level.

Listen here.

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