Celebrate the Heart of Country, Americana, and Roots Music!

Drop Us A Line, Y'all

Y'all interested in advertising, partnering up, contributing stories, joining our team, or just got a question? Well, don't be shy, drop us a line!

Follow Us

Chris Stapleton Songs Are Taking Over The Country Music Landscape

10 Best Chris Stapleton Songs
by
  • Arden is a Senior Country Music Journalist for Country Thang Daily, specializing in classic hits and contemporary chart-toppers.
  • Prior to joining Country Thang Daily, Arden wrote for Billboard and People magazine, covering country music legends and emerging artists.
  • Arden holds a Bachelor of Arts in Journalism from the University of Tennessee, with a minor in Music Studies.

After Chris Stapleton’s breakout performance at the 2015 Country Music Association, he quickly became a household name – and ultimately, an undisputed ruler of country music. Chris Stapleton songs lingered atop the charts and took home awards left and right.

Six years later, the impact and reach of Stapleton’s soulful voice is more prevalent than ever. With that said, let’s check out some of Chris Stapleton‘s greatest hits so far.

1. “Whiskey And You”

From: Traveller (2015)

Stapleton co-wrote “Whiskey and You” with Lee Thomas Miller, where he compared heartache to a hangover from drinking your sorrow away. However, he wasn’t the first one to record the song – Tim McGraw did!

But it was Stapleton’s version that earned attention after it was included on his 2015 album Traveller.

2. “Broken Halos”

From: From a Room: Volume 1 (2016)

Stapleton debuted this country-rock together with his wife Morgane in 2016 during Dolly Parton’s Smoky Mountains Rise: A Benefit for the My People Fund telethon. He dedicated “Broken Halos” – which is about “people who had passed away before their time” – to the fourteen people who died after the Gatlinburg wildfires, including the several families whose homes were destroyed.

3. “Fire Away”

From: Traveller (2015)

Love isn’t always easy, and this song is here to remind you to stick to each other even in those most challenging times. “Fire Away” comes with a powerful music video that follows a young couple’s happy marriage that took a turn for the worse when the woman got affected by severe mental illness.

4. “Traveller”

From: Traveller (2015)

 “Traveller” was released as Stapleton’s debut single in 2015 – introducing his lyrical prowess and extraordinary vocal chops into the world. It went to successfully win a Grammy Award for Best Solo Country Performance.

5. “Tennessee Whiskey”

From: Traveller (2015)

Whiskey is indeed the subject of a myriad of country songs. 

Written by Dean Dillon and Linda Hargrove, “Tennessee Whiskey” is actually a cover that Stapleton took on from country legend George Jones – yet he made it his own with his unique vocal stylings.

6. “Parachute”

From: Traveller (2015)

It may not have climbed as high on the charts as his later release, but the upbeat love song has remarkably captured Stapleton’s sheer vocal prowess. And with lyrics about profession of love even in the hard times – the song captivated many audiences and rapidly expanded his fanbase. 

7. “Second One to Know”

From: From a Room: Volume 1 (2017)

This rock-infused ballad about trying to keep a relationship from fading away showed off Stapleton’s amazing guitar skills while his voice also shines. It comes with a music video wherein Stapleton and his family were animated as Lego people.

8. “Daddy Doesn’t Pray Anymore”

From: Traveller (2015)

A somber acoustic ballad, it finds Stapleton watching his father losing his belief in God. He wrote the song back in the middle of the 2000s when he noticed his father did not say grace in one particular meal. The singer-songwriter only recorded it following his father’s death in 2013.

9. “Scarecrow in the Garden”

From: From A Room: Volume 2 (2017)

This chilling narrative tune tells the story of a desperate West Virginia farmer facing the devastating outcomes of hurricanes that have hit this year. Things turn desperate by the song’s end when the farmer finds himself at the end of his rope.

10. “Was It 26”

From: Traveller (2015)

Written by Don Sampson, “Was It 26” was originally recorded by the Charlie Daniels Band in 1989 for their album Simple Man. Stapleton admitted that he had the song on heavy rotation the first time he heard it. Even though he was only 23 then, the song’s tale of a streak of mid-20s tough living resonated with him.

11. “When the Stars Come Out”

From: Traveller (2015)

Though it was never released as a single, this dreamy ballad off his debut album brought Stapleton’s naturally raspy vocals in a whole new light – something you shouldn’t miss.

12. “Drunkard’s Prayer”

From: From A Room: Volume 2 (2017)

It’s pretty interesting how Stapleton found a way to strongly combine two of the most common themes in country music: alcohol and faith.

13. “Millionaire”

From: From A Room: Volume 2 (2017)

Written by Kevin Welch, “Millionaire” encourages its listeners to appreciate relationship intimacy over material wealth. What makes it even more romantic is that Stapleton’s wife, Morgane accompanies him in the chorus.

14. “Nobody to Blame”

From: Traveller (2015)

Breakups and heartaches have been common in country music, but Stapleton did the right thing in “Nobody to Blame.” It became his first Top 10 single on the Billboard Country Airplay chart and was named Song of the Year by the Academy of Country Music Awards

15. “Outlaw State Of Mind”

From: Traveller (2015)

“This is a song that was born out of the music,” Stapleton said about this track which he wrote with Jerry Salley and Ronnie Bowman – adding that the lyrics contain pieces of his own life that he felt he needed to share.

More Of Chris Stapleton Songs That Are Nothing Short Of Impressive

Indeed, Chris Stapleton’s music is worth celebrating. You’ll find more of his hits below.

  • “The Devil Named Music”
  • “A Simple Song”
  • “Whiskey Sunrise”
  • “Sometimes I Cry”
  • “Arkansas”
  • “Midnight Train To Memphis”
  • “I Was Wrong”
  • “Starting Over”
  • “Might As Well Get Stoned”
  • “Them Stems”

Each time we witness Stapleton sing, it becomes all the more obvious why he is one of country music’s brightest stars to date. We hope you enjoyed this list of Chris Stapleton songs.

Latest Stories

Dolly Parton sings onstage in a rhinestone outfit, embodying the timeless star power celebrated with her official Dolly Parton Day.

Gov. Lee Proclaims January 19 as ‘Dolly Parton Day’ in Honor of Her 80th Birthday

The Queen of Country just got what she has long deserved, and that is her very own day in the state she put on the map. On January 19, 2026, ...

Keith Urban sits for a candid interview, reflective and stripped back, as he opens up about life, healing, and simplicity after his divorce.

Keith Urban Just Sat Down for His First Interview Since the Divorce and Nothing Was Off Limits

Keith Urban is speaking with a clarity that only comes after heartbreak and healing. In his first long-form interview since his split from Nicole Kidman, Keith Urban did not hold ...

Waylon Jennings performs from a seated spot, still commanding the stage with outlaw grit that defined his final chapter in 2000.

Waylon Jennings Took the Stage for the Last Time in 2000 and Country Music Hasn’t Been the Same Since

He might have been sitting in a chair, but Waylon Jennings still owned the damn stage. In January 2000, the outlaw king himself stepped onto the hallowed floor of the ...

Dolly Parton, Lainey Wilson, Miley Cyrus, Reba McEntire, and Queen Latifah in studio recording powerful new version of "Light of a Clear Blue Morning" – star-studded collaboration anthem of hope and resilience.

Dolly, Lainey, Miley, Reba, and Queen Latifah Just Gave Us the Comfort Song of the Year

Sometimes a song hits you straight in the heart, and this one walks right in, takes its boots off, and stays a while. Dolly Parton just gave us a reason ...

Jelly Roll performing in pouring rain on stage with intense passion, singing into microphone under dramatic lights, symbolizing redemption and faith journey in country music.

Jelly Roll Gets Honest About Faith, Forgiveness, and the Two Values He Says the World Needs Most

When Jelly Roll talks about his faith, you stop and listen because it does not sound like a sermon. It sounds like the truth. The “Son of a Sinner” singer ...

Kelly Clarkson delivers a powerful soulful performance of "No One Else Like Me" by The Red Clay Strays on The Kelly Clarkson Show.

Kelly Clarkson Puts Her Whole Soul Into Red Clay Strays Cover and Proves Nobody Can Out-Sing Her

Kelly Clarkson just took a Red Clay Strays song to church and back again, and fans are still picking their jaws up off the floor. It all went down during ...

Country icon Dwight Yoakam sings into microphone under stage lights in cowboy hat and denim, hosting a star-studded benefit "Rockin' for the Kids" at The Roxy on January 28, 2026, to support Children's Hospital Los Angeles with special guests including Charley Crockett, Marcus King, and Lukas Nelson.

Dwight Yoakam to Host Star-Studded Benefit for Children’s Hospital Los Angeles at The Roxy

Country legend Dwight Yoakam is trading the honky-tonk for heartfelt giving with a guitar in hand and a cause close to home. Just ahead of Grammy week, Dwight Yoakam is ...

Country star Megan Moroney sings passionately on stage in short denim dress and boots beside Riley Green strumming guitar in Nebraska cap, fueling rumors her upcoming track "Wish I Didn't" is a sharp breakup anthem directed at Riley Green with hidden clues.

Are Megan Moroney’s New Songs Taking Aim at Riley Green? Fans Think the Clues Add Up

Megan Moroney did not name Riley Green, but her lyrics sure sound like she circled his name in red ink. If you have been anywhere near country TikTok, Instagram comments, ...

Kelly Clarkson shares a rare family update on how her children River and Remington are coping after their father Brandon Blackstock's death, emphasizing snuggles and special bedtime moments that bring joy amid grief in 2026.

Kelly Clarkson Shares a Rare Update on How Her Kids Are Coping After Their Dad’s Death

Even through heartbreak, Kelly Clarkson is doing what strong mamas do best by putting her kids first. Kelly Clarkson may be a powerhouse on stage, but behind closed doors, she ...

Duck Dynasty star Mary Kate Robertson stands on the beach at sunset in a flowy white dress, proudly showing her growing bump with John Luke and their kids, revealing the exciting arrival of twin baby girls.

“Duck Dynasty” Star Mary Kate Robertson Shares Sweet Bump Update as She Awaits Twin Baby Girls

There is just something about the Robertson clan that makes you feel like family, and now it is about to get even bigger with two tiny, pink-bootied blessings. “Duck Dynasty” ...