15 Best Chris Stapleton Songs: The Ultimate Playlist

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Last updated on June 1st, 2023 at 09:26 pm

Chris Stapleton started in country music as a songwriter in Nashville, cranking out several number-one hits for many country music singers such as Tim McGraw and Luke Bryan, and even beyond with the likes of Justin Timberlake and Ed Sheeran.

With his captivating sound and his phenomenal song lyrics, he quickly became Number-one in our hearts as he brought us some hot country songs to add to our playlist.

From songs about love to ballads to even a little outlaw country, his signature rustic vocal sound and pure country twang have captivated millions.

Here’s our list of the top 15 best Chris Stapleton songs.

15 Best Chris Stapleton Songs

15. Joy of My Life (2022)

Chris Stapleton channels John Fogerty for this cover of the singer’s 1997 single “Joy of My Life.”

It’s clear Stapleton is a happily married man. Although he didn’t pen this song himself as he has so many others, he could’ve fooled us.

We want to feel like the luckiest person alive, too.

14. Daddy Doesn’t Pray Anymore (2015)

You can almost hear the heartbreak in Chris Stapleton’s spot-on vocals when he sings “Daddy Doesn’t Pray Anymore.” It brings tears to our eyes.

Although he wrote in 2005, Stapleton never recorded until after his father passed away in 2013. While talking to Taste of Country, Stapleton spoke about the story behind the song.

“I had gone home for some holiday or something to my parents’ house. My dad was a very straight arrow, prayed-at-every-meal kind of guy,” Stapleton said.

“For whatever reason, whether he was tired or wasn’t feeling well, he didn’t say grace at this particular meal, which he had done at every meal that I’d ever eaten with him.

And he said it at every meal after that, but this particular meal, he didn’t, and it struck me that daddy doesn’t pray anymore.”

If you’re looking for Chris Stapleton songs that’ll make you cry, look no further.

13. Parachute (2016)

This catchy, upbeat song makes us swoon every time as the banjo and acoustic guitar accompaniment, played by Chris Stapleton himself for the album, accompanies the promise of the narrator that he’ll always be there for the one he loves.

The third single from his debut album, “Parachute” may not have received any accolades, but it has been certified platinum twice.

We only hope we find that person that will be our parachute, too.

12. Either Way (2017)

Chris Stapleton recorded this 2008 LeAnn Womack song for his second studio album.

Stapleton’s version of “Either Way” would earn the singer one of many Grammy Awards over the years for Best Country Solo Performance.

This country ballad, on the surface, is simply about a relationship that has ended.

Still, many critics have said Stapleton takes it further as it also highlights the unfortunate events that led to its end.

His smooth vocals on the song break our hearts right along with him.

11. Last Thing I Needed, First Thing This Morning (2017)

We’ve all had bad mornings, but this one takes the cake.

Chris Stapleton covered country legend Willie Nelson’s 1982 hit “Last Thing I Needed, First Thing This Morning” for his second studio album, From A Room: Volume 1.

It’s bad enough when you wake up to a “past due” bill or you wake up late because your alarm clock didn’t go off, but waking up only to have your lover walk out on you is probably the worst.

We agree with Chris Stapleton (and Willie) when he sings that classic line: “The last thing I needed the first thing this morning was to you have walk out on me.”

Don’t worry, Chris. Your fans will never walk out on you.

10. You Should Probably Leave (2021)

It’s reminiscent of an up-tempo version of Chris Young’s 2011 hit single “Tomorrow,” and we’re all about it.

Chris Stapleton’s “You Should Probably Leave” describes a couple constantly in an on-again, off-again relationship. Although they know it will probably not end well, they keep coming back to one another.

Much like the couple is to each other, we’re addicted to this song and want to listen to it over and over again.

Thankfully, we don’t have to worry about it ending in something bad.

9. Traveller (2015)

“Traveller” had to make it on our list of one of the best Chris Stapleton songs.

The Grammy Awards certainly thought so since it was nominated for Best Country Song and Best Country Solo Performance at the 58th Grammy Awards.

No matter what we’re doing or where we’re at in life, in this debut single, Stapleton brings the truth that we’re all “a traveler on this earth” trying to figure out what road to take next.

8. Nobody to Blame (2015)

The first Top 10 Single that he achieved on the U.S. Country Airplay chart, “Nobody to Blame,” has to be considered one of Chris Stapleton’s best songs.

This mid-tempo track with a country rock feel gives us the perspective of a man following a particularly ugly breakup.

We can’t help but feel bad for the man whose girlfriend kicked him out and proceeded to sadistically destroy everything he owned.

We also have to give him props if, even then, he believes there’s “nobody to blame” but himself.

7. Millionaire (2018)

Add this to your list of the best wedding songs. “Millionaire” is a new twist on the old sentiment that love conquers all.

This first single from Chris Stapleton’s album From a Room: Volume II reminds us how lucky we should feel once we find that extra special someone.

Stapleton’s wife, Morgane, joins him for this soulful mid-tempo ballad making it all the more powerful as we hear the chemistry of their voices combine in the harmonies of the song’s dynamic chorus.

If we didn’t already believe in love with these two, this love song tipped the scale.

6. Whiskey and You (2015)

Is it strange that several of our favorite Chris Stapleton songs have to do with whiskey? Ah, we don’t care! We’re going to sing along anyway.

“Whiskey and You” may not have been released as a single, but we love it all the same and couldn’t have a best Chris Stapleton songs list without it.

This one goes right up to the top with “Whiskey Lullaby” by Brad Paisley and Allison Krauss and “Wine After Whiskey” by Carrie Underwood.

5. Cold (2020)

“Cold” was the 64th Grammy Award Winner for Best Country Song, and we have no doubts about why.

It’s a heartbreaking song about losing the love you thought would last forever and wanting to hang on for dear life even though your partner has freezed you out.

Stapleton’s vocals on this single shatter us like a rock through a window, too, but in the best way.

It’s undoubtedly one of the best Chris Stapleton songs yet.

4. Starting Over (2020)

Chris Stapleton truly was “Starting Over” when he released this 2020 single.

It had been two years since we’d heard a new single from Stapleton following 2018’s “Millionaire,” but it was worth the wait and lands high on our list of the best Chris Stapleton songs.

He stripped everything away for this raw vocal, promoting the song with the wipeout of all his social media pages just a few weeks before the single was released.

It’s a fun, heartfelt song about just stepping back and seeing where life takes you.

Whether you’re the lucky penny or the four-leaf clover, we’ll take this country superstar’s advice and consider starting over, too.

3. Fire Away (2015)

“Fire Away” is another classic from Chris Stapleton’s debut album that has continued to stick with us.

It’s only become more prominent in our lives with the release of its accompanying music video on Feb. 26, 2016, which took us down a whole different path but just as powerful.

The rustic vocals captivate us through the tragic story of a couple that is portrayed by Ben Foster and Margarita Levieva.

The video earned Stapleton two music video awards from the Country Music Association and the Country Music Television awards, and we can see why.

Rolling Stone’s Jon Freeman said of the video: “Though the video isn’t a literal interpretation of Stapleton’s lyrics, the video captures the song’s weary sadness and brings the doomed resilience of his narrator to life in [Ben] Foster’s performance.”

It was praised for shining a light on mental illness as the video concludes with the website for the Campaign to Change Direction.

The organization’s five signs of emotional suffering are visually portrayed throughout the video.

Nash Country Daily’s Jim Casey said, “Through a heartbreaking conclusion, it shows just how serious mental health issues can be.”

2. Tennessee Whiskey (2015)

It may be a cover song, but Chris Stapleton has certainly made “Tennessee Whiskey” his own.

Originally recorded by David Allan Coe in 1981 and covered by country legend George Jones in 1983, it became the title track for Stapleton’s debut album.

Bringing a little R&B influence to the classic cover song, Stapleton made headlines as delivering “the best moment of the night” when he performed the song at the 2015 Country Music Association Awards alongside former Nsync star Justin Timberlake.

That performance led to its rise on the Hot Country Songs Chart, where it peaked at Number-one and has been certified platinum six times.

“Tennessee Whiskey” is 100 percent one of the best Chris Stapleton songs ever.

1. Broken Halos (2017)

What isn’t there to love about “Broken Halos.”

We’ve all heard the phrase “only the good die young,” which makes it even more painful when we lose those we love before it seems as though it’s their time to go.

It’s those people that Chris Stapleton pays tribute to in his 2017 single “Broken Halos” for his From A Room: Volume 1.

Earning the top spot on our list, the mid-tempo country rock ballad won the Grammy for Best Country Song and Single of the Year and Song of the Year at the 52nd Country Music Association Awards and has been certified 3x platinum by the RIAA.

In a heartbreaking twist, it was later revealed that the song was recorded the day after Stapleton lost a close friend. During an emotional performance at the Ryman Auditorium, Stapleton addressed the audience.

“This is sort of a new song, an old song for me, but it’s a song about people who have passed away before their time,” Stapleton said.

“I recorded this on a day when a friend of mine passed away from pancreatic cancer. He was the same age as me. We played little league together and stuff like that. He was 38 years old, so this is for my buddy, Mike.”

Knowing that makes this deep, emotional song cut even deeper, but we don’t mind.

“Broken Halos” is the perfect example of the truth of what country music is and has always been, and it’s undoubtedly the best of all the Chris Stapleton songs.

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