At one time country music’s best-kept secret, Kentucky-born Chris Stapleton had been writing hits behind closed doors in Nashville for nearly 15 years, before he broke through with Traveller in 2015.
Thomas Rhett's ‘Crash and Burn’ was written by Stapleton, as was Josh Turner’s ‘Your Man’ and Luke Bryan's ‘Drink a Beer’, in addition to songs for Tim McGraw, George Strait, Lee Ann Womack, Alan Jackson and even Adele.
It was the night of the CMA Awards in 2015 that the cat was finally let out of the country bag, when Stapleton picked up three awards – after an iconic duet with Justin Timberlake - and pretty much changed the course of the country mainstream overnight.
He’s released some of the genre’s most extraordinary albums in a little over half a decade. Here is Holler's list of the Best Chris Stapleton songs.
The second-to-last song on Traveller found Stapleton mining his own autobiography for this gritty slab of country rock.
Letting the lyrics pour out of him - learning to play on his dad’s old Gibson guitar, a snakeskin guitar strap his friend made for him, a dark coal mine, a dog, a knife – he magically weaves each one together like a trippy memory association game.
Written with his SteelDrivers bandmate Mike Henderson, Stapleton wiped all his social media pages clean before sharing the title track from his fourth album.
With Tom Petty and the Heartbreakers’ Benmont Tench on Hammond organ, the gently hopeful tone signals a fresh beginning for Stapleton and a light at the end of the tunnel for a world turned upside down by the coronavirus pandemic.
Written on a mandolin – an instrument that he admits he still can’t really play - in the old EMI writer rooms where he started out as a songwriter, Traveller’s closer is a belting country soul break-up ballad in which he lets on that it’s actually him who does most of the weeping around here.
Inspired by a chapter in Keith Richards’ autobiography, and by "people who have passed away before their time", this heartfelt spiritual from his second studio album picked up a Grammy award and a brace of CMA awards in 2018.
Here, Stapleton offers up an emotional reminder to keep the faith in the midst of tragedy.
He debuted the song during Dolly Parton's Smoky Mountains Rise telethon, in tribute to the 14 people who lost their lives in the Gatlinburg wildfires.
Stapleton has us tearing up again as he parts ways with the city that he moved to almost 15 years earlier. Written with his wife Morgane, it’s a breakup ballad unlike any other, as he explains to the city that it’s time he moved on.
“You be you and I'll be me / So long, Nashville, Tennessee”, he sings, as he takes one last lingering look at the place that helped make him one of contemporary country music’s most successful artists.
“The song is kind of about loving somebody unconditionally, through not so easy times”, Stapleton said about this slow-burning ballad from Traveller, as he brings some of the most evocative lyrics of his career to the table.
Despite cutting his teeth in Nashville as a songwriter for other artists, this is one of the songs in his collection that you can only ever imagine him singing himself.
Stapleton channels his inner Waylon on this barnstorming slice of outlaw country funk from the second volume of From A Room, proving that it’s not all just brooding soul ballads and lump-in-the-throat tearjerkers round here.
When the mood takes him, Chris Stapleton can throw down and tear it up with the best of them.
"It's a song about a man getting what he deserves, for not doing the things that he knows he should and doing things he knows he shouldn't", Stapleton said about this 2015 CMA Song of the Year.
His wife has thrown all his clothes out, torn up their wedding photo, broken all his fishing rods, driven his car into a pond, filled his lawnmower with sugar, poured his whiskey down the drain and burnt his guitar - and he’s got nobody to blame but himself.
Fittingly, for a song about being kicked out of the house, it was written in a shed.
“I love my life, man it's something to see / It's the kids and the dogs and you and me / It's the way it's alright when everything goes wrong”, sings Stapleton in this homely reminder to try to look on the bright side.
Written in his father's living room with his father-in-law Darrell Hayes, this gently strummed easy goer does exactly what it says on the tin, as the two songwriters take stock of all the things they’ve got going on in their lives.
Written on a spur-of-the-moment road trip across America in an old jeep with Morgane and photographer Becky Fluke, the title track from Stapleton’s debut album became the point of entry for his breakthrough masterpiece.
“It was kind of a dumb trip to take in December, but we drove the jeep halfway back across the country to Nashville”, Stapleton explained later.
“I only wrote one song on that trip, and it was ‘Traveller’. Along the way, just driving through the desert, I was thinking about life and how we're all just passing through it, and that's what the song is".
Written with Tim James and Kendell Marvel, this achingly sad ballad was originally recorded by Lee Ann Womack in 2008 for her Call Me Crazy album.
Stapleton stripped the song back even further and doubled down on the desperation to include it on From A Room Volume 1.
This version features one of his most perfectly measured vocals – shifting from softly sung verses up to the belting powerhouse chorus - deservedly winning Best Country Solo Performance at the Grammy Awards in 2018.
In many ways, ‘Tennessee Whiskey’ is the song that changed everything for Chris Stapleton.
Written by Dean Dillon and Linda Hargrove, it had already been cut by David Allen Coe in the 70s, before George Jones almost took it to the top spot in 1983.
Stapleton performed the song 32 years later with Justin Timberlake at the CMA awards, delivering a show-stopping performance on a night that turned country music on its head.
Nashville’s best-kept secret went on to win Male Vocalist of the Year, New Artist of the Year and Album of the Year. A week later, Traveller was sitting atop the Billboard Top 200, becoming the first-ever album to re-enter at no.1 after having dropped out of the chart.
This unsettlingly perky murder ballad was originally written and recorded with Stapleton’s bluegrass band The SteelDrivers, before it found its way to Adele and she recut it as an earthy delta soul song.
Explaining why she was so drawn to it, she said, “I love this song because the sentiment is about killing his wife. I would certainly kill some of my ex-boyfriends, for fucking sure! I reckon all of you would as well!”
Written in about 10 minutes while Chris Stapleton was waiting for his wife to get ready, he waited another 10 years to finally record it.
Written after his usually devout father had skipped saying grace before a meal, it gained extra weight after his father died in 2013.
The sublime stripped-back version on Traveller was recorded outside on the lawn of RCA Studio A.
Originally cut by Tim McGraw in 2007 for his Let It Go album, Stapleton peeled away the gloss of McGraw’s version and took ‘Whiskey And You’ back to its bare essentials.
Always one of the standout moments of any Chris Stapleton live show, it’s a firm fan favourite and proof that the best things don’t always have to come in the fanciest packaging.
Subscribe and listen to Holler's The Best Chris Stapleton Songs playlist below: