Top 10 Chris Stapleton Songs

It’s hard to be a country artist that pleases both genre purists, casual listeners, and the industry alike. One singer who has done all three in spades is Chris Stapleton.

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Prior to becoming an in-demand artist in his own right, Stapleton’s run as a songwriter in Nashville was unparalleled. The likes of Kenny Chesney, Thomas Rhett, Luke Bryan, George Strait, Brad Paisley, Lee Ann Womack, Dierks Bentley, Darius Rucker, and Adele have recorded Stapleton-penned tracks.

After stepping into the spotlight in 2015, Stapleton and his songwriting chops have earned the Kentucky native a lucrative career twice over.

We’ve combed through Stapleton’s releases and picked out a slew of tracks that have bolstered him into the artist we know today. Find our selections for the top 10 Stapleton songs below.

10. “The Devil Named Music”

In “The Devil Named Music,” Stapleton reckons with the life of a touring musician. He sings about weighing the cost of success with missing loved ones. In the end, he cedes that he sold his soul long ago to a six-string and sad melody.

9. “What Are You Listening To?”

You’re in every line / Takes me back in time / Yeah tonight I’m wondering, Stapleton sings in “What Are You Listening To.” In this stand-alone single from 2013, he filters a breakup through the lens of a country song he is listening to. The memory of her comes flooding in with every song that comes through his speakers. It’s a truly unique breakup track.

8. “Daddy Doesn’t Pray Anymore”

“Daddy Doesn’t Pray Anymore” features one of Stapleton’s most intimate choruses. The song was inspired by Stapleton’s father, a religious man who prayed before every meal. On one particular trip back home, he skipped grace prompting Stapleton to pen this lament.

7. “A Simple Song”

Stapleton penned this track with his father-in-law, Darrell Hayes. It’s truly a family affair, with Stapleton’s wife, Morgane, layering a number of harmonies that add a sense of depth to this “Simple Song.”

6.  “Fire Away”

“Fire Away” demands a measure of audience participation. The chorus (Fire away / Take your best shot / Show me what you got / Honey, I’m not afraid) is tailored for a crowd to scream at the top of their lungs.

5. “Whiskey and You”

Tim McGraw was the first to record “Whiskey and You” back in 2007 for his album Let It Go. For his debut album, Stapleton decided to give the track a go, giving it an intimate, broken-down edge. There is raw emotion present in this track that only Stapleton could muster.

4. “Second One to Know”

“Second One to Know” dips into Stapleton’s southern blues roots. As much as his guitar-slinging on this track excites, he levels it out with an equal amount of emotional depth. Hold up my right hand / Swear to the Promised Land / Rather die before I treat you bad, he sings.

3. “You Should Probably Leave”

Stapleton picked up a Grammy for “You Should Probably Leave.” Written alongside Ashley Gorley and Chris DuBois, the track tells the story of an on-again, off-again relationship. Despite knowing they are doomed to fail, they can’t seem to stay away from one another. Stapleton’s powerful vocals are just the ticket for this poignant track.

2. “Broken Halos”

Written with his former SteelDrivers bandmate, Mike Henderson, Stapleton delivers something that is somehow both classic and fresh with “Broken Halos.” It is undoubtedly one of Stapleton’s most radio-friendly tracks. He sings in the ear-worm track, Seen my share of broken halos/ Folded wings that used to fly.

1. “Tennessee Whiskey”

No other song could take the No. 1 spot. “Tennessee Whiskey” launched Stapleton’s career to unimaginable heights. Given Stapleton’s reputation as a songwriter, it’s a bit ironic that his biggest song to date was written by someone else. Though Stapleton wasn’t the first to record “Tennessee Whiskey,” his version has blown past renditions out of the water.

Photo: Andy Barron / ***EBM PR

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