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20 essential songs for your Chris Stapleton playlist
Ron Elkman/USA TODAY NETWORK/Sipa USA

20 essential songs for your Chris Stapleton playlist

Both a prolific songwriter and hitmaking solo artist, Chris Stapleton is one of the biggest names in Nashville. Before his smash-hit solo debut, "Traveller" was released in 2016, Stapleton spent his time writing tunes for artists like Luke Bryan, Kenny Chesney, and more top country artists. Now, he's selling out stadiums in his own right. 

Flip through the slideshow packed with that booming baritone and killer lyrics, for 20 essential songs to include on your Chris Stapleton playlist. 

 
1 of 20

"Tennessee Whiskey"

"Tennessee Whiskey"
Rick Diamond/Getty Images

Arguably Stapleton's most recognizable hit, "Tennessee Whiskey" is a cover of an old country song that's been recorded by David Allan Coe and George Jones. The soulful Stapleton put his own twist on the song, which shot to mainstream popularity after Stapleton performed it alongside pop superstar Justin Timberlake at the 2015 CMA Awards. 

 
2 of 20

"You Are My Sunshine," with Morgane Stapleton

"You Are My Sunshine," with Morgane Stapleton
Jason Davis/Getty Images

Written by the one-time governor of Louisiana, this classic children's song is transformed into a stunning vocal showcase of the husband-and-wife duo of Chris and Morgane Stapleton. Recorded for Dave Cobb's collaborative album "American Family," this version of "You Are My Sunshine" is not to be missed. 

 
3 of 20

"Broken Halos"

"Broken Halos"
John Lamparski/WireImage

Written by Stapleton and released as part of 2017's "From A Room: Volume 1," the stirring "Broken Halos" is now an essential part of the artist's repertoire. In addition to being a #1 hit, the song also earned Stapleton a Best Country Song Grammy Award. 

 
4 of 20

"Traveller"

"Traveller"
Christopher Polk/Getty Images for NARAS

The title track of Stapleton's smash-hit debut album, "Traveller" might also be an ethos for an artist who lives his life out on the road. "I'm just a traveler on this earth, sure as my heart's behind the pocket of my shirt," he sings on the chorus. "I'll just keep rollin' 'til I'm in the dirt, cause I'm a traveler." 

 
5 of 20

"Fire Away"

"Fire Away"
C Flanigan/Getty Images

Infused with soul and Chris Stapleton's absolutely soaring vocals, "Fire Away" is an emotional enough song on its own — and then there's the music video. The video follows a young couple as they battle the ups and downs of mental illness, and it's an absolute tear-jerker. 

 
6 of 20

"Whiskey and You"

"Whiskey and You"
Joseph Okpako/Getty Images

Co-written by Stapleton, the first version of "Whiskey and You" was actually recorded by Tim McGraw. But it was a personal favorite for Stapleton, who included it on his debut album "Traveller." 

 
7 of 20

"Starting Over"

"Starting Over"
Terry Wyatt/Getty Images for ACM

The title track of Stapleton's fourth full-length album, "Starting Over" was co-written with Stapleton's former bandmate, Mike Henderson of the Steel Drivers. It's a solid anthem for anyone who's looking for a fresh start. 

 
8 of 20

"Parachute"

"Parachute"
Kevin Mazur/Getty Images

Even though it wasn't a massive hit for Stapleton on the charts, "Parachute" has earned a seriously devoted following from his fans since its release on 2015's "Traveller." 

 
9 of 20

"Millionaire"

"Millionaire"
Ebet Roberts/Redferns

Stapleton's version of this track penned by songwriter Kevin Welch blends southern rock, country, and a little bit of blues for a sonic vibe that's casual yet compelling. Released in 2018, "Millionaire" peaked at #2 on the Billboard Hot Country Airplay chart. 

 
10 of 20

"Last Thing I Needed, First Thing This Morning"

"Last Thing I Needed, First Thing This Morning"
Taylor Hill/Getty Images

Stapleton's take on this country classic, written originally by Gary P. Nunn and Donna Farar for Willie Nelson in 1982, is nothing short of gorgeous. Quietly heartbreaking and straightforward, the song appears on the first installation of the artist's two-part "From A Room" series. 

 
11 of 20

'Them Stems"

'Them Stems"
Tim Mosenfelder/Getty Images

This country-rocker about being in such rough shape that you're willing to smoke the dregs of your weed appears on "From A Room: Volume 1." Even if you're not a pot smoker, this song's catchy lyrics can still be relatable. 

 
12 of 20

"You Should Probably Leave"

"You Should Probably Leave"
Jason Kempin/Getty Images for Country Music Hall of Fame and Museum

Plenty of us have found ourselves in the kind of on-again, off-again relationship that just doesn't seem to end, which makes "You Should Probably Leave" so damn relatable. The harmonies from Morgane Stapleton, Chris Stapleton's wife, and frequent backup singer, sure don't hurt. 

 
13 of 20

"Midnight Train to Memphis"

"Midnight Train to Memphis"
Rich Fury/Getty Images for iHeartMedia

Appearing on the second volume of his double-album "From A Room," "Midnight Train to Memphis" is a deeper cut that's worth listening to. Fans of Stapleton's work with bluegrass outfit The Steel Drivers might recognize the tune — he first recorded it with the band in 2008. 

 
14 of 20

"Second One To Know"

"Second One To Know"
Erika Goldring/Getty Images

As much as Chris Stapleton loves to belt a ballad, he also really enjoys rocking out on songs like "Second One To Know." With hints of Skynyrd and other southern rock influences, it's perfect for fans who aren't as into Stapleton's slower stuff. 

 
15 of 20

"Either Way"

"Either Way"
John Shearer/Getty Images

Originally written by Stapleton, Kendall Marvel, and Tim James for Lee Ann Womack, Chris Stapleton won a Grammy Award for Best Country Solo Performance with his recording of the raw, emotional "Either Way" in 2018. 

 
16 of 20

"When The Stars Come Out"

"When The Stars Come Out"
Kevin Winter/Getty Images

This anthem to the beauty of starlight against the intensity of big-city lights appears on Stapleton's 2015 debut "Traveller." "Running on hope and a tank of gas, like dreams, ain't just for dreamers," he sings. "We couldn't wait to leave that life behind, trying to find salvation in that city limit sign." 

 
17 of 20

"Joy Of My Life"

"Joy Of My Life"
Jason Kempin/Getty Images for Country Music Hall of Fame and Museum

This cover of a John Fogerty classic appears on Chris Stapleton's 2020 album "Starting Over." Bolstered by his ridiculously powerful voice, it's a must-listen for Stapleton fans. 

 
18 of 20

"Nobody To Blame"

"Nobody To Blame"
Rick Kern/WireImage

In this break-up anthem written from the side of the person who's being dumped, "Nobody To Blame" finds Chris Stapleton taking accountability when the lady who's just left him put his guns in hock, threw out all his good whiskey, and — gasp! — broke his fishing rods. 

 
19 of 20

"Watch You Burn"

"Watch You Burn"
Mike Windle/Getty Images for Country Music Hall of Fame and Museum

This powerful ballad, featuring vocals from Stapleton and his wife Morgane, is an angry rebuke of people who spew hatred in violence in the world. The song was written in the aftermath of the Route 91 Harvest Festival shooting in 2017, which left 60 people dead and more than 400 injured. 

 
20 of 20

"If It Hadn't Been For Love," with the Steel Drivers

"If It Hadn't Been For Love," with the Steel Drivers
Michael Loccisano/FilmMagic

Well before his stratospheric solo career, Chris Stapleton was making killer tunes with the Steel Drivers, a bluegrass band born in Nashville. If you're not familiar with his work with the Steel Drivers, 'If It Hadn't Been For Love" is an excellent place to start. 

Amy McCarthy

Amy McCarthy is a Texas-based journalist. Follow her on twitter at @aemccarthy

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