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Chris Stapleton Songs: 12 of the Country Superstar’s Top Tracks

With a voice as smooth as Tennessee whiskey, this talented artist will keep you coming back for more!

You know your vocals and artistry have true power when you can bring football players to tears singing the national anthem, and that’s just what Chris Stapleton did when he crushed his performance of “The Star-Spangled Banner” at the 2023 Super Bowl. Of the Chris Stapleton best songs, the country star dominated the national anthem and his performance. “Chris Stapleton is one of the best singers, to me, that’s ever lived. He’s effortless,” raved P!nk, who’s teamed up with the Kentucky born country star on both “Just Say I’m Sorry” and “Love Me Anyway.”

Still, Stapleton, who just won his record-breaking seventh CMA Male Vocalist of the Year Award on Nov. 8, continues to stay humble about his talents. “I’m always shocked when I win one,” he noted when picking up his latest trophy. Others more eagerly sing his praises. Elton John even personally called Stapleton in 2018 to ask him to be a part of his and Bernie Taupin’s Restoration “reimagining” album.

“He wanted us to do this particular song that we’ve done [“I Want Love”], and what are you going to say if Elton John calls you up and asks you to do something like that other than, ‘Yes, absolutely.’ And, ‘I’ll do my best, Sir Elton,’” Stapleton told Amazon Music of the surreal honor.

H.E.R. and Chris Stapleton perform onstage for the 2021 CMT Music Awards
H.E.R. and Chris Stapleton performing (2021), Chris Stapleton best songsErika Goldring / Stringer / Getty

One of Stapleton’s true strengths is his versatility: While he’s carved out a well-respected songwriting and singing career in country, he’s also been able to branch out into other genres and collaborate with artists from Sheryl Crow, Miranda Lambert and Taylor Swift to Ed Sheeran, Bruno Mars, Santana and H.E.R.

“Ultimately, I’m me. And I’m just trying to be the best version of that that I can be,” Stapleton told CBS News. “Whether that’s playing a song that leans into blues or a song that leans into R&B or a song that leans into really distinctly outlaw country. I love all that music. And I don’t feel limited to playing one type of song.”

“Basically, I’ve been a fan of him since SteelDriver days,” Adele has said of Stapleton, referencing the bluegrass group he was once in. “I’ve been covering SteelDrivers for, like, nearly 12 years now. It’s just… his voice is just fu—ing brilliant,” added the British belter, who duetted with the country star on “Easy on Me” for a bonus track for her album 30. “Our voices work brilliantly together,” she raved.

While that’s certainly true, his voice is powerful and emotive enough on its own. Be sure to check out these Chris Stapleton best songs that are sure to knock your cowboy boots — and socks! — off.

12. “Think I’m in Love With You” (2023)

Slide up next to your favorite dance partner for this slinky, sultry track that allows Stapleton to get playful. “You are my life, you are my world, you are the air I’m breathing, girl,” he sings with a lot of soul in this blues-tinged single co-produced by his wife, Morgane Stapleton. When her husband sings, “You’re all of everything to me, you are the reasons I am” and then belts out, “Woman!,” we’re pretty sure we know who he’s talking about.

11. “Devil Always Made Me Think Twice” (2020)

“The minute that I saw you walkin’ over, I figured I was diggin’ my grave. And you had the shovel, I knew you were trouble, but you’re just the kind of trouble I crave.” Here, the swampy, bluesy tune “shows off Stapleton the singer, who works his way up to a searing roar as he recounts his assorted losing battles with temptation,” as Rolling Stone put it.

10. “You Should Probably Leave” (2021)

More temptation! From its opening line — “I know it ain’t all that late, but you should probably leave” — we all know where this flirty, fun song is headed. “Sun on your skin, 6 a.m., and I been watchin’ you sleep,” Stapleton sings later on, and there you have it! Of Chris Stapleton best songs, this one has a killer groove and frisky but sweet lyrics, which helped win Stapleton a Grammy for Best Country Solo Performance.

9. “Mountains of My Mind” (2023)

“Yes, I’ve been trying all this time and still can’t climb the mountains of my mind.” Unlike the first three selections, this one is a whole different vibe and one that’ll kick you in the gut. “My wife was just bawling in the control room the whole time I was playing it,” Stapleton told Apple Music of the emotional tune that tackles loneliness, self-doubt and personal struggles. “There’s some of that ‘not being able to get through the day’ sometimes. I think everyone has those days,” he shared of the song.

8. “Nobody to Blame” (2015)

Out of all the Chris Stapleton best songs, this one earned him his first Top 10 on the country airplay chart, as well as the ACM award for Song of the Year. With its fiddles, steel guitar and lyrics like “She fired up my old hot rod, ran it in the pond. Put sugar in my John Deere, I can’t even mow my lawn,” this is a straight-up country classic and one in which he admirably admits “I got nobody to blame but me.”

7. “Starting Over” (2020)

“This might not be an easy time, there’s rivers to cross and hills to climb,” Stapleton sings in this CMA Single and Song of the Year, which coincidentally came out in the middle of the COVID pandemic. The lyrics tell of a couple looking for a fresh start, as they’re ready to “take our chances and roll the dice.” The No. 1 hit takes on extra sweet meaning with wife Morgane’s superb backing vocals throughout the track. Again, when Stapleton sings “I can be your lucky penny, you can be my four-leaf clover,” we know who he’s thinking of.

6. “What Are You Listening To?” (2013)

This is a love song to music as much as it is a love song, with lyrics like “I put that record on, girl, you know what song, and I let it play again and again. You’re in every line, takes me back in time.” Stapleton’s missing a woman he can’t get out of his head as he’s desperate to figure out what she’s listening to. “Is it a cover band in some college town bar? Where it’s na-na-nas and air guitars, or is it something to get you through? Just a sad song playing on the radio station…” He —and we! — need to know!

5. “Parachute” (2016)

Talk about supportive! “Say the word and I’ll be there for you, baby, I will be your parachute,” Stapleton sings in this hard-driving, rocking tune, which landed at No. 12 on the Hot Country Songs chart. Fittingly, the singer really lets his vocals soar on the choruses before promising, “If you think you’re going down, just know that I’ll be around.”

4. “White Horse” (2023)

This song was conceived as a potential track for 2013’s The Lone Ranger film. “It would be cool to have a kind of rock-driven-western-themed song,” the singer said to his co-writer Dan Wilson, so “we kind of built it around a guitar riff.” The lyrics — “If you want a cowboy on a white horse, ridin’ off into the sunset, if that’s the kind of love you wanna wait for, hold on tight, girl, I ain’t there yet” — weren’t an immediate hit with Stapleton’s wife, though. Morgane thought they were “not the most romantic thing in the world,” he shared, but persistence paid off. “I think she might’ve changed her mind on it,” he added.

3. “Broken Halos” (2017)

“Angels come down from the heavens just to help us on our way. Come to teach us, then they leave us, and they find some other soul to save.” Stapleton struck gold with this masterpiece, which won a Grammy for Best Country song as well as both the CMA Single and Song of the Year. “It’s a song about people who have passed away before their time. I recorded this on the day a friend of mine passed away from pancreatic cancer. He was the same age as me,” Stapleton shared with an audience in 2016. He’d also play it to honor the victims of 2016’s deadly Smoky Mountain wildfires, as well as those of 2017’s Route 91 Harvest music festival mass shooting in Las Vegas.

2. “Cold” (2020)

Despite its title, this track proved to be a red-hot one for Stapleton, who won a Grammy for Best Country song for his efforts. “Oh, why you got to be so cold? Why you got to go and cut me like a knife, and put our love on ice?” he sings to the woman who’s done him wrong before channeling all his pain into one hell of a guitar solo. The track also features some strings that help add some chilliness to the track’s vibe.

1. “Fire Away” (2016)

With a melancholy waltzing beat that winds itself around the story of a couple whose relationship is on the ropes, “Fire Away” is pretty stark and powerful. “Take your best shot, show me what you got, honey, I’m not afraid. Rear back and take aim and fire away,” Stapleton sings, and the video takes things a step further, presenting the story of a troubled wife who’s battling depression and repeatedly attempting to take her own life. “The video aims to bring attention to the culture of mental health awareness throughout the country,” the artist’s website explains of the video, which ends with contact information for people in need of assistance. “Hopefully it has value beyond just being a video for the sake of doing a video,” Stapleton said after it won Music Video of the Year at the CMAs.

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