Kentucky’s Timeless Vocals
Some artists chase trends. Others create them. But Chris Stapleton? He just stood tall, holding six strings and a voice that could shake mountains. These songs tell the rest of the story.
“Starting Over”
This song was released on August 28, 2020, as the lead single from Stapleton’s fourth studio album of the same name. It came out on November 13, 2020. The track was co-written by Stapleton and his SteelDrivers bandmate Mike Henderson.
Chris Stapleton - Starting Over (Official Music Video) by Chris Stapleton
“Starting Over” (Cont.)
It features background vocals from Chris Stapleton's wife, Morgane. Musically, it brings together acoustic guitar chords with a percussive shake, which creates a sound reminiscent of Willie Nelson's style. It has a "raw, stripped-down, and vulnerable" theme.
Chris Stapleton - Starting Over (Official Music Video) by Chris Stapleton
“Broken Halos”
Here is a piece that got a lot of love from critics and fans, even snagging the Grammy for Best Country Song at the 60th Grammy Awards. It was officially released as a promotional single from his album From A Room: Volume 1 on April 14, 2017.
Chris Stapleton - Broken Halos (Live From TODAY Show Concert Series) by Chris Stapleton
“Broken Halos” (Cont.)
Critics described it as a "tender, lump-in-your-throat reminder to keep the faith”. Co-written by Stapleton and Mike Henderson, "Broken Halos” has an emotional depth that stays with the listeners. As per reports, he recorded it shortly after the demise of a close friend.
Chris Stapleton - Broken Halos (Live From TODAY Show Concert Series) by Chris Stapleton
“Broken Halos” (Cont.)
So, the song also garnered accolades for Single of the Year and Song of the Year at the 52nd Country Music Association Awards. It received the certification of triple platinum by the Recording Industry Association of America (2021), indicating over three million units sold in the US.
Chris Stapleton Wins Entertainer Of The Year | ACM Awards 2023 by Awards Show Network
“Tennessee Whiskey”
Listeners consider this a soulful rendition by Stapleton, as it has become one of his signature songs. It was initially written by Dean Dillon and Linda Hargrove. Stapleton's version is a cover of the song that has been performed by David Coe and George Jones.
Chris Stapleton - Tennessee Whiskey (Austin City Limits Performance) by Chris Stapleton
“Tennessee Whiskey” (Cont.)
However, a breakthrough performance came when Stapleton sang the song alongside Justin Timberlake at the Country Music Association Awards in 2015. Reportedly, as of January 2025, the masterpiece has surpassed one billion streams on Spotify.
“Fire Away”
With a dragging beat that arouses feelings of desire, "Fire Away" has a mournful ballad structure. The remarkable music video ends with a call to action for mental health awareness and displays resources for those in need. Tim Mattia directed it.
Chris Stapleton - Fire Away (Official Music Video) by Chris Stapleton
“Fire Away” (Cont.)
It also won the Music Video of the Year award at the 2016 Country Music Association Awards. Additionally, "Fire Away" peaked at number 25 on the Billboard Hot Country Songs chart and got the sixth position on the Bubbling Under Hot 100 list.
Chris Stapleton - Fire Away (Official Music Video) by Chris Stapleton
“Either Way”
This is a lead single from his 2017 album From A Room: Volume 1. The song was initially recorded by Lee Womack for her 2008 album titled Call Me Crazy. It was co-written by Chris Stapleton, Tim James, and Kendell Marvel.
Chris Stapleton performs Either Way (May 11, 2017) | Charlie Rose by Charlie Rose
“Either Way” (Cont.)
“Either Way” is classified as a country ballad, featuring acoustic guitar prominently throughout. Rolling Stone called it "simple and stunning," praising Stapleton's vocal performance. The song debuted at number 17 on Billboard's Hot Country Songs chart in 2017.
Chris Stapleton On What Either Way Means | Exclusive Interview by iHeartRadio
“Cold”
At the 64th Grammy Awards, this masterpiece bagged the award for Best Country Song. Also, it earned the Platinum certification from the RIAA for over one million units sold in the United States. Stapleton performed "Cold" live at a couple of events.
Chris Stapleton - Cold (CMA Awards 2021) by Chris Stapleton
“Cold” (Cont.)
This included the 55th CMA Awards in November 2021 and the 64th Grammy Awards in April 2022. Producer Dave Cobb and band members J.T. Cure and Derek Mixon also played a role in the song’s writing. It was out for the audience on September 25, 2020.
Chris Stapleton - Cold (CMA Awards 2021) by Chris Stapleton
“Parachute”
“Parachute” is an uptempo love song where the narrator shows his commitment to being there for his partner. The chorus has the memorable line, "Baby, I will be your parachute,” which symbolizes support and safety.
Chris Stapleton - Parachute by McKinnonD
“Parachute” (Cont.)
Stapleton performed “Parachute” live at the CMT Music Awards in June 2016 as well as on Saturday Night Live on January 16, 2016. Country Universe described "Parachute" as a "pretty good song,” while Billy Dukes rated the song a B+.
Chris Stapleton Performs “Parachute” at 2016 CMT Music Awards by CMT
“What Are You Listening To?”
This Stapleton song peaked at #46 on the Country Airplay chart in the year 2013. This track is based on heartbreak and longing as the singer wonders as to what his ex-partner might be listening to after their disturbing separation.
Chris Stapleton - What Are You Listening To (Live Acoustic) by XTU Philadelphia
“What Are You Listening To?” (Cont.)
So, the song has been covered by many artists, such as Megan Moroney and Luke Combs. For instance, Luke Combs covered “What Are You Listening To?” as part of the #DeepCutsChallenge, which was initiated by fellow artist Morgan Wallen.
Megan Moroney Covers Chris Stapleton’s “What Are You Listening To?” | CMT Campfire Sessions by CMT
“You Should Probably Leave”
Apparently, this one was originally written in 2014 but did not make it onto Stapleton's earlier albums. His wife, Morgane Stapleton, encouraged him to include it in Starting Over, which led to its eventual release. It is now the third single from that album.
Chris Stapleton - You Should Probably Leave by McKinnonD
“You Should Probably Leave” (Cont.)
Amidst all those complexities of love and temptation come the key lyrics, which say, "I know it ain’t all that late /, But you should probably leave / And I recognize that look in your eyes / Yeah, you should probably leave”.
2021 CCMA Awards - Chris Stapleton - You Should Probably Leave by CCMAOfficial
“Scarecrow In The Garden”
This song was released as part of From A Room: Volume 2 on December 1, 2017. Its genre includes country with elements of folk and blues. The song is about a farmer questioning his life and the struggles associated with maintaining a family farm.
Sterling Munksgard, Shutterstock
“Scarecrow In The Garden” (Cont.)
The singer himself has considered the song to be "more than a little dark," which indicates that it addresses severe issues faced by farmers, particularly those in Appalachia. He even performed this piece live at Farm Aid 2018.
Chris Stapleton - Scarecrow in the Garden (Live at Farm Aid 2018) by Farm Aid
“Nobody To Blame”
Along with Jesse Frasure and Michael Wilson, Stapleton co-wrote the piece. It's more of a love song that began on the Country Airplay chart at number 46 and landed at number 50 on the Hot Country Songs chart for the week of November 21, 2015.
Chris Stapleton - Nobody to Blame (Acoustic) by NJ-Riggz
“Nobody To Blame” (Cont.)
Quite obviously, “Nobody to Blame” won the Song of the Year award at the Academy of Country Music (ACM) Awards. Billy Dukes from Taste of Country has called it a "200-proof country song" that fits well into any generation's best catalog.
Chris Stapleton - Nobody to Blame (Live at Farm Aid 2018) by Farm Aid
“Second One To Know”
Here’s another song that talks about love, longing, and communication in relationships. It is the chorus that presses on the importance of not putting love on the back burner and wanting to be informed about any potential changes.
Chris Stapleton - Second One To Know (Official Music Video) by Chris Stapleton
“Second One To Know” (Cont.)
The official music video has a unique Lego animation style that presents Stapleton as a Lego mini-figure. Interestingly, Chris Stapleton debuted "Second One to Know" live during the 2017 ACM Awards, which blends country, rock, and blues.
Chris Stapleton - Second One To Know (Official Music Video) by Chris Stapleton
“Midnight Train To Memphis”
This song narrates the story of a man looking back at his time in lock-up and the journey he faces upon release. It was first played at the New Orleans Jazz & Heritage Festival on May 2, 2015, marking an early live performance for Stapleton.
Chris Stapleton - Midnight Train to Memphis (Live at Farm Aid 2018) by Farm Aid
“Midnight Train To Memphis” (Cont.)
As of June 15, 2024, “Midnight Train to Memphis” was performed at Globe Life Field in Arlington, Texas. This "mesmerizing track" is combined with a gritty electric guitar and a memorable percussion beat, complementing Stapleton's awesome vocals.
Chris Stapleton - Midnight Train to Memphis (Live at Farm Aid 2018) by Farm Aid
“A Simple Song”
Co-written by Darrell Hayes and the singer himself, critics have praised “A Simple Song” for its relatable lyrics and heartfelt delivery. It has been stated Stapelton wrote this song in his father's living room many years ago with his father-in-law, Hayes.
Chris Stapleton - A Simple Song (Live From The 54th ACM Awards) by Chris Stapleton
“White Horse”
"White Horse" is a track by Chris Stapleton that dropped as the first single from his fifth album, Higher, on July 21, 2023. It brings us an electric guitar-driven sound with a superb mix of blues and rock elements.
Chris Stapleton - White Horse (Unofficial Music Video) by Elite Eye Productions
“White Horse” (Cont.)
The lyrics give off a vibe of love and being open, where the singer talks about needing some time before he’s ready to enter fully into a relationship. Notable lines include " If that’s the kinda love you wanna wait for / Hold on a tight girl I ain’t there yet”.
“White Horse” (Cont.)
"White Horse" reached number two, where it stayed for two weeks. During this time, it was behind Nate Smith's hit "World on Fire”. The song also topped the Mediabase chart, marking it as Stapleton's fourth career number-one country radio as of January 28, 2024.
Sterling Munksgard, Shutterstock
“Death Row”
Stapleton described this beautiful song as a "straight blues song," diverting from his country roots. He said that he wrote it nearly a decade prior to its release but felt it still resonated strongly and deserved a place on his 2017 album.
Chris Stapleton Death Row Live Toronto Ontario Canada August 17 2019 by TheConcertGoddess
“Death Row” (Cont.)
Apparently, during the recording process, producer Dave Cobb played a riff that inspired the other musicians to join in. This led Stapleton to create lyrics spontaneously over the music. As we know, he isn’t shy of darker subjects, and that's seen in this composition.
Chris Stapleton Death Row Live Toronto August 17 2017 by TheConcertGoddess
“Daddy Doesn’t Pray Anymore”
Here’s an interesting backstory. While Stapleton and his wife were getting ready for an event a while back, Chris started stressing out about being late. He told Willie Geist on Sunday TODAY that Morgane just said, “Write a song or something” to pass the time.
Hear How Chris Stapleton Wrote ‘Daddy Doesn't Pray Anymore’ In 10 Minutes | Sunday TODAY by TODAY
“Daddy Doesn’t Pray Anymore” (Cont.)
And he did just that. “Daddy Doesn’t Pray Anymore” is a part of Traveller. He also said, “I think it was maybe 2005 that I wrote that song. That song's been around that long, but it got weight after my father departed. It felt like time to record it”.
Chris Stapleton sings Daddy Doesn't Pray Anymore live at the Ryman Auditorium by KOKETV
“Daddy Doesn’t Pray Anymore” (Cont.)
It focuses on the changes in a father-son relationship, particularly on the father's loss of faith and the emotional impact it has on the family. The narrator remembers how his father used to pray and express gratitude but no longer does so.
“Blow”
This song is a collaboration between Ed Sheeran, Chris Stapleton, and Bruno Mars, and it was released on July 5, 2019. The famous track was co-written by Ed Sheeran, Chris Stapleton, Bruno Mars, and several others, including Brody Brown and Frank Rogers.
Ed Sheeran - BLOW (with Chris Stapleton & Bruno Mars) [Official Music Video] by Ed Sheeran
“Blow” (Cont.)
It is said that this song was written in a basement in Nashville, where the artists experimented with different sounds. It is characterized by a heavy, distorted electric guitar riff that goes back to the 80s rock and lively drumbeats.
Ed Sheeran - BLOW (with Chris Stapleton & Bruno Mars) [Official Music Video] by Ed Sheeran
“Blow” (Cont.)
Obviously, this track debuted at number 60 on the Billboard Hot 100 and hit number 39 on the Canadian Hot 100. Additionally, the song received silver certification from the British Phonographic Industry and platinum certification from Music Canada.
Ed Sheeran - BLOW (with Chris Stapleton & Bruno Mars) [Official Music Video] by Ed Sheeran
“I Was Wrong”
This one is a song by Chris Stapleton from his album From A Room: Volume 1. Stapleton premiered "I Was Wrong" during his performance on Austin City Limits on February 17, 2018. Also, the beloved Kelly Clarkson covered this song on The Kelly Clarkson Show.
Chris Stapleton - I Was Wrong (Austin City Limits Performance) by Chris Stapleton
“Millionaire”
The song, which Kevin Welch wrote in 2002, talks about how love is way more important than money and stuff. It was launched as a promotional single on October 20, 2017, and then released to country radio as the album's first single on April 23, 2018.
Chris Stapleton Performs Millionaire On The CMT Music Awards by CMT
“Millionaire” (Cont.)
It has a mid-tempo ballad driven by acoustic guitar. Reviewers noted the song's "Heartbreakers-worthy update” when it successfully sold approximately 250,000 copies in the United States in April 2018. “Millionaire” was performed by him on The Ellen DeGeneres Show.
Chris Stapleton performs Millionaire on Ellen by The Morning Hangover
“Whiskey And You”
This is the song you need while dealing with heartbreak or the struggle to move on after a lost relationship. Originally recorded by Tim McGraw, it was released on March 27, 2007. Stapleton later included his version on his album Traveller.
Chris Stapleton - Whiskey and You - ASCAP Experience 2011 by ASCAP
“Whiskey And You” (Cont.)
During the C2C (Country to Country) Festival in London, Stapleton took over the crowd with this one. The singer has also mentioned that he always believed it was one of the better songs he had been part of, leading him to perform it frequently with his guitar.
Chris Stapleton - Whiskey and You by Recorded Live in Concert!
