Few current stars equally appease mainstream country fans, traditionalists and even casual pop listeners quite as effectively as Chris Stapleton.
Videos by Wide Open Country
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 for Stapleton to fly solo, that tap wasn't turned off. Instead, 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 20 best Stapleton songs.
Kevin Kane/Getty Images for The Rock and Roll Hall of Fame You probably don't need to be sold on Stapleton as someone who can make a cover song their own, considering he first made a name for himself with "Tennessee Whiskey." It's still worth revisiting how well he holds his own alongside one of popular music's all-time greats. Terry Wyatt/Getty Images Stapleton's most recent material's strong and sets the stage for yet another award-winning album. The Grammys in particular will eat this stuff up. On "White Horse," he lives out a western rambler fantasy with a rocking number that's basically the modern equivalent of Waylon Jennings fronting a white-hot blues-rock band. Terry Wyatt/WireImage Most of these picks put Stapleton over as a world-class poet and wordsmith. Here, he paints a vivid picture —it's as much historical fiction as it's country music— with prose that utilizes Biblical imagery while spanning multiple generations of a farming family. Adam Hagy/Getty Images for ABA As his shelf of industry awards proves, Stapleton's among the best as bluesy country throwbacks with a punch. He's no less amazing when slowing things down and waxign sentimental, as heard on this and numerous other love and life songs in his growing catalog. Kevin Winter/Getty Images for The Recording Academy Stapleton and his equally-talented spouse Morgane join voices on one of the most tender country love songs in the modern country canon. In short, if love as currency, they'd be millionaires because they've got each other. Kevin Mazur/Getty Images for Roc Nation As Stapleton's legend has grown, he's become a desired duet partner for everyone from Pink and Santana to Taylor Swift and Alana Springsteen. His best duet so far came with Carly Pearce, a fellow Kentuckian with a bluegrass background. Kevin Kane/Getty Images for The Rock and Roll Hall of Fame If you're a fan of some of the country-soul stunners near the top of our list, check out this steel guitar-laden gem that's among Morgane's best harmony vocal performances. Gregory Shamus/Getty Images Another love song that's all the more sweeter because of the Chris-Morgane romance, the couple's got you if you're in the mood for an old-fashioned love song instead of a neo-traditional anthem. Photo by Jason Davis/Getty Images for CMT Listeners first pointed to Stapleton by Timberlake and "Tennessee Whiskey" first got floored by his original material by this, a standout from his first solo album. It's Stapleton at his country-rock star best and among his more traditionally "country" material, putting him in the same "savior" conversation as Sturgill Simpson, Erika Goldring/Getty Images for CMT If you hold up the concept of a sad country song, make sure you didn't overlook "Maggie' Song,' It's a sad one for sure, and you're not likely to fight back tears as the song reaches the end of a beloved family pet's life. Tim Mosenfelder/Getty Images Likening a modern artist to a classic act in sweeping terms tends to be lazy, if not disingenuous. That said, Stapleton sounds like John Fogerty here, with "Devil Always Made Me Think Twice" serving as an example of a song that Creedence Clearwater Revival might record in the 21st century. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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."My Heroes Have Always Been Cowboys" (Feat. Willie Nelson) (Outlaw: Celebrating the Music of Waylon Jennings, 2017)
"White Horse" (Single, 2023)
"Scarecrow in the Garden" (From a Room: Volume 2, 2017)
"Joy of My Life" (Starting Over, 2020)
"Millionaire" (From A Room: Volume 2, 2017)
"We Don't Fight Anymore" (Feat. Carly Pearce) (Single, 2023)
"Fire Away" (Traveler, 2015)
"Without Your Love" (From A Room, Volume 1, 2017)
"Parachute" (Traveler, 2015)
12. "Maggie's Song" (Starting Over, 2020)
11. "Devil Always Made Me Think Twice" (Starting Over, 2020)
"The Devil Named Music" (Traveller, 2015)
"What Are You Listening To?" (2013)
"A Simple Song" (From A Room: Volume 2, 2017)
"Fire Away" (Traveller, 2015)
"Whiskey And You" (Traveller, 2015)
"Second One to Know" (From A Room: Volume 1, 2017)
"You Should Probably Leave" (Starting Over, 2020)
"Broken Halos" (From A Room: Volume 1, 2017)
"Broken Halos" (From A Room: Volume 1, 2017)
"Tennessee Whiskey" (Traveller, 2015)
Editor's Note: This story previously ran on Nov. 9, 2022.
