Chris Stapleton has a message for everyone who says, “I could do that.” “Anyone who says it’s so easy to write a country hit and that it’s just a formula—well, try it sometime. If it was that easy, everybody would be doing it.”
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Chris Stapleton, though, has figured it out. The Kentucky singer/songwriter/musician/producer has had success with songs written for himself, written for others, and written with others. He wrote or co-wrote No. 1 hits for Kenny Chesney, George Strait, Luke Bryan, and Josh Turner. He secured a publishing deal, put in the hours playing live, pursued multiple styles of music, got a record deal, and then delivered when the spotlight shined the brightest. Here are five moments that shaped the career of Chris Stapleton.
1. The Jompson Brothers and The SteelDrivers
After moving to Nashville in 2001, Stapleton signed with Frank Rogers and Brad Paisley’s publishing company, Sea Gayle Music. He started to have success as a songwriter and started a rock band called the Jompson Brothers. Stapleton then joined the bluegrass band The SteelDrivers. He sang lead on that group’s self-titled debut album on Rounder Records.
Stapleton left the bluegrass band in 2010 and devoted more time to The Jompson Brothers. No Depression magazine called the band “the future of rock ‘n’ roll.” The Jompson Brothers also released a self-titled album, and the Zac Brown Band selected them to open shows for their Sailing Southern Ground Cruise.
2. Traveller
In 2013, Stapleton signed a record deal with Mercury Records. Like what happens so many times in Nashville, his first album was shelved, and the first single they released did not perform well at radio. Stapleton regrouped and released Traveller in 2015.
This time it all clicked. Dave Cobb produced the album and encouraged the singer to record “Tennessee Whiskey.” The song had become a regular addition to Stapleton’s live show. The album was recorded in Nashville at the legendary RCA Studio A. The first couple singles did well at country radio, reaching the Top 20. But then Stapleton had a “coming-out” party of sorts.
3. CMA Awards
On November 4, 2015, Stapleton was nominated in three categories at the Country Music Association Awards. Not only did he win all three, but he also performed “Tennessee Whiskey” with famous pop star, and famous Tennessean Justin Timberlake.
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On the strength of that performance, the song went to No. 1 on the Billboard Hot Country Songs chart. The Traveller album, which had dropped off the charts, quickly returned and was certified platinum by February.
4. Saturday Night Live
On January 16, 2016, Stapleton performed on Saturday Night Live. Riding the wave of notoriety he got from the CMA Awards, the singer performed “Parachute” and “Nobody to Blame.” From a Room Volume 1 and From a Room Volume 2 were released in 2017, and saw strong sales.
On January 27, 2018, Stapleton returned to Saturday Night Live and sang “Midnight Train to Memphis” and “Hard Livin’” with fellow Kentuckian Sturgill Simpson. In 2020, the album Starting Over was released. All of Stapleton’s first four albums hit the top spot on the Billboard Top Country Albums chart.
5. Super Bowl National Anthem
In 2023, Stapleton performed the “Star Spangled Banner” at Super Bowl LVII. Once again, when the moment was big, Stapleton stepped up. Singing the National Anthem at the Super Bowl can be a tough gig, but it’s a chance to reach people who weren’t aware of your music previously. It’s also possible a poor showing could alienate viewers. Stapleton got great reviews, though, for his bluesy, sultry version, which got a great reaction from the live crowd, as well.
Stapleton has tapped into the formula for success. He’s correct when he says that it’s not something that everyone can do, but he, for one, has proven he has the ability to write a hit song, record a hit album, and deliver under pressure.
And I’m just a traveller on this earth
Sure as my heart’s behind the pocket of my shirt
I’ll just keep rollin’ ’til I’m in the dirt
‘Cause I’m a traveller, oh, I’m a traveller
I couldn’t tell you honey, I don’t know
Where I’m goin’ but I’ve got to go
‘Cause every turn reveals some other road
And I’m a traveller, oh, I’m a traveller
Photo by Rick Diamond/Getty Images
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