Ten Chris Stapleton Songs Within Country Music’s Greatest Success Stories

These Chris Stapleton songs are the results of the long, tough road behind him before becoming an overnight sensation.

Stapleton had been working behind the scenes in Nashville for many years, leading the progressive bluegrass acoustic quintet the SteelDrivers, at the same time working as a professional songwriter – scoring hits for renowned stars like Kenny Chesney, Luke Bryan, Darius Rucker, George Strait, and Thomas Rhett.

But in the autumn of 2015, Stapleton soared to superstar status after making his solo debut as an artist. From that moment on, everything has changed for the troubadour. Let’s take a look at some of his best songs so far!

1. “The Devil Named Music”

From: Traveller (2015)

“The Devil Named Music” is the outcome of driving all night from Wyoming to Billings, Montana, when Chris Stapleton was still with the band, The SteelDrivers – playing gigs in different cities.

The singer explained the story behind the song, revealing that most of it “is all real stuff”– like how he doesn’t remember stopping in Denver because he was so drunk. When the group got to Salt Lake City, Stapleton started missing his family. He found out in that very moment what lies ahead for him as a touring musician.

Stapleton calls the song “pretty autobiographical.”

2. “Whiskey And You”

From: Traveller (2015)

Though “Whiskey And You” was co-written by Stapleton, he was not the first to lay down the track – Tim McGraw did. 

McGraw recorded the song for his 2007 album Let It Go; however, it was never released as a single, so it did not bring out lots of attention. A bigger spotlight was cast on it eight years later, after Stapleton included it on his debut album.

Stapleton revealed that they went through various of versions when they recorded the song until he finally decided it would be best to present it in its original form, with just a guitar in the background. Over time, it became the song he was hardly ever allowed to leave the stage without singing.

3. “Broken Halos”

From: From A Room, Vol. 1 (2017)

Stapleton recorded “Broken Halos” on the day his friend died of pancreatic cancer. He debuted this track, together with his wife Morgane, during the Dollywood Foundation’s Smoky Mountains Rise: A Benefit for the My People Fund telethon – which has been set up for the East Tennessee wildfires’ victims. The song was performed as an earnest tribute to the fourteen people who lost their lives and the more than 2,400 homes and businesses devastated by the terrible fires.

“Broken Halos” – which title was taken from a chapter name of Keith Richards’ autobiography – went on winning several awards after it was released. It took home a Grammy Award for Best Country Song, as well as Country Music Association Awards for Single of the Year and Song of the Year.

4. “Fire Away”

From: Traveller (2015)

“Fire Away” is a “song about the frustration of commitment,” Stapleton said. 

It is accompanied by a music video that delivers a poignant message, featuring a young married couple played by Ben Foster and Margarita Levieva. The short clip follows the couple – from courtship to their marriage – as they go through some of the most fascinating life events, such as purchasing their first house and adorning it together. However, the joyful moments started fading. The woman suffered from mental illness, even tried to take her own life a couple of times.

It received the 2016 Music Video of the Year Award from the Country Music Association.

5. “Sometimes I Cry”

From: Traveller (2015)

The troubadour is closing his debut album with “Sometimes I Cry,” where he bravely let his voice cut to the most moving, powerful tip. 

Stapleton co-wrote the bluesy song with Clint Ingersoll in the old, windowless EMI writer room – which he revealed to be the place his early Nashville songwriter happened. 

6. “Tennessee Whiskey” 

From: Traveller (2015)

“Tennessee Whiskey” is undoubtedly the song that helped Stapleton make a massive breakthrough to country music’s major league.

David Allan Coe was the first to record the song in 1981 and was followed by George Jones’ version, two years later, reaching No. 2 in the country charts. But it was definitely Stapleton’s breathtaking performance of the song – as a duet with Justin Timberlake – during the 2015 CMA Awards that propelled “Tennessee Whiskey” to No. 1 on Billboard’s Hot Country Songs chart, putting Stapleton on the map.

7. “Traveller”

From: Traveller (2015)

Released as the title track of his debut solo album, Stapleton took the inspiration from his soul-searching in a desert somewhere in New Mexico.

It was in 2013 when Stapleton was feeling a little down after the death of his father. As Stapleton was driving home, he started “thinking about life and how we’re all just passing through it, and that’s what the song is,” the singer said.

8. “Parachute”

From: Traveller (2015)

“Parachute” is another remarkable example of how Stapleton works as a songwriter. In this song, he turned a long-standing sentiment into something new and distinctively different.

9. “Might As Well Get Stoned”

From: Traveller (2015)

This is one of the first songs Stapleton wrote when he first moved to Nashville, along with one of the first friends he made in the Music City, singer-songwriter Jimmy Stewart. The two talented songwriters would often hang out at Stapleton’s garage apartment, playing fiddle tunes or listening to bluegrass songs.

And on one special night, they started talking about what a man would do if he runs out of whiskey – in which they ultimately concluded that he “Might As Well Get Stoned.”

10. “When The Stars Come Out”

From: Traveller (2015)

Though the country superstar never released “When The Stars Come Out” as a single, it’s hard to miss how Stapleton brought his usual raspy vocals to a whole new light in this song.

Stapleton shared the story behind it, which began while walking the streets of Los Angeles. During that night, he noticed that “everybody looked like somebody” – everyone is looking like famous stars. It was then he started toying with the idea that perhaps all of the stars in the city are walking around and, “on some nights, they shine brighter than the city lights.”

Is there anything more amazing than Chris Stapleton songs? Every time we listen to him, it becomes even more apparent why he’s one of country music’s brightest stars today.