Chris Stapleton’s name is etched in the hearts of music lovers worldwide. With his soulful voice, unparalleled songwriting, and magnetic stage presence, Stapleton has redefined modern country music while blending elements of rock, blues, and soul. From the smoky honky-tonk bars to sold-out arenas, his songs transcend genres and speak to the raw emotions of the human experience.
Whether you’re a lifelong fan or just discovering the magic of his music, there are certain tracks that have become timeless anthems—masterpieces that showcase his ability to craft heartfelt lyrics and deliver spine-tingling performances. His music isn’t just a collection of melodies; it’s a journey through love, heartbreak, resilience, and triumph.
In this article, we’re diving deep into the top 10 most popular Chris Stapleton songs of all time. These tracks have not only dominated charts but also earned a permanent spot in the hearts of millions. From powerhouse ballads to foot-stomping crowd favorites, each song tells a story that lingers long after the music stops.
Get ready to explore the hits that have made Chris Stapleton a living legend. Grab your headphones, turn up the volume, and let’s celebrate the unforgettable legacy of this musical genius!
1. Tennessee Whiskey (2015)
Chris Stapleton’s version of “Tennessee Whiskey” redefined a country classic when it hit the airwaves in 2015. Originally recorded by David Allan Coe and made famous by George Jones, the song already had deep roots in the genre. But Stapleton’s take infused it with a slow-burning soulfulness that gave it new life. His gritty, heartfelt vocals and bluesy phrasing brought an emotional gravity that’s hard to forget. The smooth guitar lines and steady rhythm create an atmosphere that’s both laid-back and intensely passionate. Instead of just singing about whiskey as a metaphor for a lover, Stapleton turns it into a confessional of redemption and deep connection. The production is minimal yet rich, allowing his voice to shine without distraction. Performed live with Justin Timberlake at the 2015 CMA Awards, the track became a viral sensation and introduced Stapleton to a much wider audience. More than a cover, “Tennessee Whiskey” is a masterclass in reinterpreting a song and making it feel like your own. It’s become one of Stapleton’s most iconic tracks—and for good reason. With its blend of country, blues, and soul, it stands as a timeless love song that showcases the full power of his artistry.
2. Starting Over (2020)
“Starting Over” is a beautifully simple song with a deep emotional core, serving as the title track of Chris Stapleton’s 2020 album. It’s a soft, acoustic-driven tune that speaks to the idea of fresh starts, second chances, and the courage it takes to move forward. With a melody that feels warm and comforting, Stapleton invites listeners into a space of hopefulness, even when the road ahead is uncertain. The lyrics reflect a willingness to leave the past behind and embrace a journey into the unknown, especially when shared with someone you love. His signature raspy voice delivers the words with a mixture of tenderness and grit, making the message feel sincere and grounded. The instrumentation is minimal—just enough to support the vocal without overshadowing it. The result is a song that feels deeply human and instantly relatable. “Starting Over” arrived during a time when the world was craving renewal and reassurance, and Stapleton met that moment with grace. It’s a standout track that exemplifies his strength as both a songwriter and storyteller, offering comfort to anyone who’s had to pick themselves up and begin again.
3. Broken Halos (2017)
“Broken Halos” is one of Chris Stapleton’s most emotionally resonant songs, released in 2017 on his album *From A Room: Volume 1*. The track explores the theme of loss and the mystery of life and death, offering comfort without trying to explain the unexplainable. With lyrics like “Seen my share of broken halos / Folded wings that used to fly,” Stapleton pays tribute to people who’ve left this world too soon—friends, family, and strangers alike. The song was inspired in part by real-life tragedy, giving it a weight and authenticity that listeners feel immediately. Musically, it blends Stapleton’s usual mix of country, gospel, and rock influences. The arrangement is clean and powerful, with a soaring chorus that uplifts even as it mourns. Stapleton’s voice carries both strength and sorrow, perfectly suited for such reflective material. “Broken Halos” went on to win a Grammy Award for Best Country Song and became a favorite for live performances, where its message hits even harder. It’s not just a song about grief—it’s a song about faith, healing, and the quiet ways people live on in our hearts after they’re gone.
4. Traveller (2015)
The title track of Chris Stapleton’s breakthrough album, “Traveller” is a beautifully introspective song that captures the restlessness of the human spirit. Released in 2015, the song paints a portrait of someone always on the move—both physically and emotionally—searching for meaning in the ups and downs of life. With a steady, rolling rhythm and a soulful delivery, Stapleton reflects on the transient nature of time, love, and the roads we travel. His lyrics evoke wide open landscapes and long highways, serving as metaphors for personal growth and discovery. There’s a sense of melancholy woven throughout the song, but it never feels heavy. Instead, it offers a gentle kind of wisdom—accepting life’s impermanence while finding moments of clarity along the way. Stapleton’s vocals, filled with both grit and tenderness, drive home the authenticity of the message. “Traveller” helped define the sound and soul of Stapleton’s artistry, combining traditional country storytelling with bluesy depth and rock-inspired edge. It’s a song that resonates with anyone who’s ever felt the pull to keep moving, searching, and learning—an anthem for the wanderers, the seekers, and those in search of something more.
5. Fire Away (2015)
“Fire Away” stands out as one of Chris Stapleton’s most emotionally raw and courageous songs from his 2015 debut album *Traveller*. On the surface, it’s a slow-burning ballad about enduring pain in a relationship, but dig deeper, and you’ll find a powerful commentary on mental health and the resilience of love. With a haunting melody and a steady, bluesy groove, Stapleton invites his partner to unleash all her frustration—telling her to “fire away”—even if it breaks him. His voice carries a heaviness that lingers, full of empathy and weariness, making every lyric feel personal. The accompanying music video takes the song’s emotional impact even further, portraying a heartbreaking story of a couple dealing with depression and loss. It struck a nerve with fans and critics alike, sparking important conversations about emotional vulnerability and mental well-being. The production is sparse yet dynamic, building slowly to a gut-punch crescendo that mirrors the unraveling of a wounded heart. “Fire Away” proves that Stapleton isn’t afraid to tackle real human struggles in his music. It’s not just a love song—it’s a plea for understanding and a beautifully tragic expression of how far someone will go to hold on to the person they love.
6. Whiskey and You (2015)
Few songs capture heartbreak as starkly and honestly as “Whiskey and You,” a standout track from Stapleton’s 2015 album *Traveller*. Originally recorded by Tim McGraw, Stapleton’s version strips it down to its bare bones—just a mournful voice and an acoustic guitar. The simplicity is deliberate, allowing every lyric to hit with unfiltered emotion. The song draws a brutal comparison between the temporary numbness of alcohol and the lingering pain of lost love, with Stapleton confessing that sometimes the whiskey hurts less than the truth. His gritty voice brings a world-weariness that makes the pain feel real, like he’s singing from the bottom of a glass and the depths of a broken heart. There’s no sugarcoating here—just raw, aching honesty that many listeners have found deeply relatable. It’s the kind of song that feels like it was written at 2 a.m. with a heavy soul and an empty room. “Whiskey and You” is more than just a sad ballad—it’s a haunting portrayal of grief, regret, and the ways we try to dull the pain that just won’t go away. It showcases Stapleton’s unmatched ability to make simple songs feel monumental.
7. You Should Probably Leave (2020)
“You Should Probably Leave” is a smooth, blues-infused track that showcases Chris Stapleton’s knack for telling complex emotional stories with a conversational touch. Released in 2020 on his *Starting Over* album, the song tells the story of a couple caught in a familiar cycle—they know being together isn’t right, but the attraction is too strong to resist. Stapleton’s lyrics walk a fine line between desire and self-control, capturing the inner tug-of-war that comes when you’re trying to do the right thing but your heart—and chemistry—says otherwise. His delivery is equal parts sly and weary, like he’s been here before and knows exactly how it’ll end. The bluesy guitar work and laid-back rhythm give the song a classic vibe, but it’s the subtly clever lyrics that make it stand out. Lines like “I know it ain’t all that late, but you should probably leave” manage to be both playful and heartbreaking. It’s a song full of tension and quiet drama, and Stapleton handles it with the kind of finesse that makes you lean in and really listen. “You Should Probably Leave” is modern, relatable, and perfectly understated—another gem in Stapleton’s rich catalog.
8. Millionaire (2017)
With “Millionaire,” Chris Stapleton delivers one of his most feel-good songs—a breezy, joyful tune that celebrates love over material wealth. Released in 2017 on *From A Room: Volume 2*, this cover of Kevin Welch’s song is filled with warmth, optimism, and that unmistakable Stapleton soul. Right from the first strum, the track exudes positivity. Backed by his wife Morgane’s harmonies and a gentle acoustic groove, Stapleton sings about the richness that comes from being with someone who truly loves you. The lyrics, “Love is more precious than gold,” feel timeless and sincere, and his delivery makes it sound like he’s smiling through the whole song. It’s a refreshing reminder that happiness isn’t found in money or possessions—it’s in the relationships we hold close. The song also shows a softer, more playful side of Stapleton, proving he’s just as effective at singing about contentment and gratitude as he is about heartbreak. “Millionaire” is the kind of track that makes you want to roll the windows down and take a slow drive, soaking in the simple joys of life. It’s heartwarming, catchy, and proof that sometimes, less really is more.
9. Nobody to Blame (2015)
“Nobody to Blame” is a barn-burning track from Stapleton’s 2015 *Traveller* album, filled with gritty guitar riffs, stomping rhythm, and a hefty dose of post-breakup honesty. This song is all about owning up to your mistakes—even when the fallout includes busted windows, burned clothes, and a trashed car. The lyrics paint a vivid picture of a man who’s clearly been thrown out and left to pick up the pieces—but instead of playing the victim, he admits it’s all his fault. Stapleton’s vocal performance is fiery and full of swagger, turning regret into something oddly empowering. The song’s energy is contagious, combining traditional country grit with Southern rock attitude. It’s both humorous and heartfelt, striking a balance that makes it a fan favorite. Whether you’re laughing at the chaos or nodding in agreement, it’s hard not to appreciate the honesty. “Nobody to Blame” stands out because it’s a rare kind of breakup song—it doesn’t point fingers at anyone but the man in the mirror. And with Stapleton’s powerful voice driving it home, it becomes a toe-tapping anthem for accountability wrapped in a honky-tonk beat.
10. Parachute (2015)
“Parachute” is one of the most electrifying tracks on Chris Stapleton’s *Traveller* album, showcasing his ability to blend country, rock, and soul into something bold and heartfelt. From the opening beat, the song kicks off with an energetic urgency, carried by a fast-paced acoustic riff and a driving drumbeat. Lyrically, it’s a passionate pledge of support—Stapleton declares that no matter how far or how hard someone falls, he’ll be there to catch them like a parachute. It’s a love song, yes, but not the soft, sentimental kind. This one comes with a fiery intensity, full of grit and muscle. Stapleton’s vocals soar, growl, and charge through the chorus, matching the relentless tempo of the track. It’s also a crowd favorite at his live shows, where its energy takes on a whole new life. “Parachute” taps into themes of loyalty and resilience, reminding us that real love is about showing up when it counts. It’s one of those songs that makes you want to stomp your foot, raise your glass, and shout the lyrics at the top of your lungs. Bold, brash, and full of heart, it’s Stapleton at his most electrifying.
Edward Tomlin is a frequent contributor to Singers Room. Since 2005, Singersroom has been the voice of R&B around the world. Connect with us via social media below.
