When it comes to modern country music, few artists have made as profound an impact as Chris Stapleton. With his soulful voice, masterful songwriting, and a blend of country, rock, and blues, Stapleton has captured the hearts of fans around the globe. Since his breakout album, Traveller, he has consistently delivered powerful tracks that resonate with listeners, whether they’re seeking heartache, celebration, or introspection.
His music tells stories of love, loss, and resilience, often drawing on personal experiences that feel universal. As we dive into the top 10 most popular Chris Stapleton songs of all time, prepare to explore the anthems that have defined his career and solidified his status as a country music legend. From chart-topping hits that get crowds singing along to poignant ballads that tug at the heartstrings, each song reveals a different facet of Stapleton’s artistry. Join us as we celebrate the tracks that have not only topped the charts but have also left an indelible mark on the hearts of fans everywhere. Get ready to rediscover the magic of Chris Stapleton’s music!
1. Tennessee Whiskey (2015)
“Tennessee Whiskey” isn’t just a cover—it’s a reawakening of a classic through the soulful fire of Chris Stapleton. Originally written in the early ’80s by Dean Dillon and Linda Hargrove, it found new life in Stapleton’s hands when he released it on his breakthrough 2015 album, Traveller. With a slow-burning blend of country soul and blues, the song unfolds like a heartfelt confession. Stapleton compares the transformative power of love to the smooth burn of fine whiskey, using that metaphor to express the healing he’s found in a romantic partner. His vocals—gravelly, rich, and full of soul—take center stage, carrying both grit and tenderness in every line. It’s not just about heartbreak or addiction—it’s about being rescued from both. The silky guitar riffs and gospel-tinged swells in the background give it a timeless feel, like something old and sacred made brand new again. What makes this version unforgettable is how personal it feels. Stapleton doesn’t just sing it—he lives it, and by the end, you feel like you have too. It’s one of those rare songs that grabs you by the heart and doesn’t let go, no matter how many times you hear it.
2. Starting Over (2020)
“Starting Over” feels like a sunrise after a long night. Released in 2020, this title track from Stapleton’s fourth studio album is a warm, optimistic ode to life’s second chances. It opens with a breezy acoustic strum, gently setting the stage for a message that’s all about renewal, love, and shared resilience. Stapleton, with his signature raspy voice, delivers the lyrics like he’s sitting across from you, reminding you that it’s okay to begin again—even if it’s scary. There’s a sense of peace in the song’s simplicity: it’s not about grand gestures or dramatic change, but about quietly choosing to move forward with someone you trust. The chorus, backed by Morgane Stapleton’s soothing harmonies, offers a kind of emotional shelter—gentle and full of hope. It feels like the soundtrack to a road trip toward something better, something earned. In a world full of noise, “Starting Over” is soft-spoken encouragement. Whether you’re walking away from heartbreak or just ready to close a chapter, the song is a steady hand on your shoulder, reminding you that beginnings aren’t about forgetting the past—they’re about building something stronger because of it.
3. Broken Halos (2017)
“Broken Halos” is a song that feels like a quiet prayer for the grieving. Released in 2017 on the album From A Room: Volume 1, the song is Stapleton’s meditation on loss, healing, and the mystery of why bad things happen to good people. The lyrics speak of “angels come down” and “broken halos that used to shine,” giving voice to the aching questions we all carry when someone we love is taken too soon. But instead of offering easy answers, Stapleton leans into the uncertainty, allowing sorrow and hope to coexist in the same breath. His restrained vocal delivery—raw, weathered, honest—adds a weight that makes each word land like a truth you’ve always known but never said aloud. The production is simple and reverent: acoustic guitar, soft drums, and enough space between the notes to let the emotion breathe. “Broken Halos” doesn’t try to fix the hurt—it acknowledges it. And in doing so, it provides comfort. It’s a song that plays at funerals, in late-night reflections, or during long drives alone. It’s a reminder that while we may never understand all our pain, we can carry it with grace and still find light on the other side.
4. Fire Away (2015)
“Fire Away” is a storm of vulnerability wrapped in slow-burning soul. Released in 2015 on Traveller, this track shows Stapleton at his most emotionally exposed. On the surface, it sounds like a love song, a declaration of loyalty. But dig a little deeper, and you find a raw cry for understanding, for resilience in the face of emotional weight. “Go on and fire away,” he sings—not out of defiance, but out of love that’s willing to weather the worst. The song’s slow build, with its restrained verses and explosive choruses, mirrors the emotional pressure inside a relationship where one partner struggles while the other tries to stay steady. The production is sparse but haunting—steel guitar, piano, and steady drums laying the groundwork for Stapleton’s aching vocals. It’s a plea, a vow, and a confession all at once. The accompanying music video—which deals with mental health and suicide—amplifies the song’s devastating power. “Fire Away” reminds us that love isn’t always easy, and sometimes the strongest thing we can do is stay when it’s hardest. It’s not just a standout on Traveller—it’s a gut-punch of truth wrapped in music.
5. Parachute (2017)
“Parachute” is a rhythmic, heartfelt tribute to loyalty and love’s protective embrace. Released in 2017 as part of From A Room: Volume 1, this track stands out with its punchy acoustic riff and driving tempo, offering a change of pace from Stapleton’s usual slow-burn ballads. From the opening line, he positions himself as the steadfast partner—the one who’ll catch you when life goes into free fall. “You only need a roof when it’s raining,” he sings, “only need a fire when it’s cold.” It’s a reminder that love isn’t just about the good times—it’s about being someone’s anchor when everything else feels uncertain. His raspy, impassioned vocals pair perfectly with the lyrical imagery, painting him not just as a lover, but a refuge. Backed by energetic percussion and warm harmonies, the song becomes a statement of presence and reliability. It’s a toe-tapping affirmation that real love means showing up, especially when it’s hard. “Parachute” captures a universal truth: when life pushes someone to the edge, what they need most is someone willing to break the fall. And Stapleton delivers that message with grit, grace, and a beat you can’t help but move to.
6. Nobody to Blame (2015)
“Nobody to Blame” is a bluesy confession set to a twangy country groove, drenched in self-awareness and regret. Released on Stapleton’s 2015 breakout album Traveller, the song captures the fallout after a breakup—but instead of finger-pointing, it leans hard into personal accountability. The lyrics list a series of escalating acts of destruction: burning clothes, smashing guitars, driving a car into a pond—and yet, the refrain always circles back to one truth: “I got nobody to blame but me.” It’s clever, it’s catchy, and it’s surprisingly mature. Stapleton doesn’t wallow or beg for sympathy. Instead, he owns every bit of it with a shrug and a soulful growl. Musically, the track has a gritty stomp—slide guitar, steady rhythm, and a bit of southern grit that gives it bite. The song walks the line between humor and heartache, acknowledging that sometimes, we self-destruct and have to deal with the wreckage. What makes it powerful is the honesty—it’s not about looking good; it’s about being real. “Nobody to Blame” is a standout not just because it sounds great, but because it speaks the truth plainly—and sometimes, that’s exactly what we need.
7. Midnight Train to Memphis (2015)
“Midnight Train to Memphis” feels like it was born in a smoky roadhouse—gritty, fierce, and unapologetically raw. Originally co-written with his old band The SteelDrivers and later featured on Traveller, this 2015 version roars with outlaw energy. The lyrics tell the story of a man locked behind bars, counting the days and watching life pass him by as the train rumbles through each night. The imagery is striking: confinement, regret, and a distant, unreachable freedom symbolized by the midnight train. Stapleton’s vocal delivery is electric—gravelly and ferocious—full of pent-up frustration and soul. The bluesy guitar riffs and thunderous rhythm section propel the song like a runaway engine, driving home the tension and longing at its core. What makes this track resonate isn’t just its sound, but its humanity. It’s not just about prison—it’s about feeling stuck, powerless, and haunted by time slipping through your fingers. Yet through all of that, there’s a pulse of resilience. “Midnight Train to Memphis” is a reminder that Stapleton isn’t just a country singer—he’s a storyteller who taps into the ache of the human spirit and transforms it into something fiercely alive.
8. Either Way (2017)
“Either Way” is one of Chris Stapleton’s most devastatingly intimate songs—a bare-bones ballad that lays emotional truths bare without flinching. Released in 2017 on From A Room: Volume 1, it features nothing but Stapleton’s voice and an acoustic guitar, and that’s all it needs. The song captures the hollow ache of a love that’s gone emotionally dry. “We can just go on like this, say the word, we’ll call it quits,” he sings with a quiet resignation. It’s not a dramatic breakup anthem—it’s a soft-spoken acknowledgment that the heart has left the room. What’s haunting is how matter-of-fact it feels; there’s no anger, just silence, distance, and the slow realization that staying might hurt more than leaving. His vocals tremble with sadness, but there’s no begging—just the truth, plain and heavy. It’s one of those songs that hits hardest in the quiet moments, when you’re trying to make peace with something slipping away. “Either Way” doesn’t offer a resolution, and that’s what makes it real. It’s a painful mirror for anyone who’s ever sat across from someone they once loved, unsure of what to say—or if there’s anything left to say at all.
9. What Are You Listening To? (2017)
“What Are You Listening To?” is a reflective, quietly heartbreaking song that speaks directly to anyone who’s ever tried to move on while still holding onto the past. Released in 2017, it’s one of Stapleton’s more underappreciated gems, filled with subtle emotion and lyrical depth. The song revolves around a simple, poignant question: when you’re hurting, what music do you reach for—and does it reflect where your heart still lingers? The narrator wonders what his lost love is listening to, imagining that maybe it’s a sad song, a memory, or something that once belonged to them. It’s an achingly human way to frame heartbreak—not through shouting or blaming, but through quiet curiosity. The melody is smooth and mellow, with gentle guitar strums and Stapleton’s warm, raspy voice carrying the emotion like smoke curling in the air. What makes it so effective is how real it feels—how one question can unravel a thousand memories. “What Are You Listening To?” captures that universal truth: music doesn’t just soundtrack our lives—it becomes part of the way we remember, heal, and sometimes, ache. It’s a soft-spoken stunner that lingers long after the last note fades.
10. More of You (2020)
“More of You” is a love song at its most tender—a gentle, soul-stirring ballad about intimacy, longing, and the quiet moments that make a relationship meaningful. Released in 2020, this track finds Stapleton trading in big emotions for quiet devotion. With soft acoustic strumming and subtle string flourishes, the production keeps the spotlight on the lyrics, which are simple but profound. “When I think I can’t go on, I get more of you,” he sings, echoing the reassurance and strength that comes from deep emotional connection. Unlike songs about grand gestures, “More of You” celebrates the small, everyday acts of love—the kind that builds trust over time. Stapleton’s voice is restrained but rich with feeling, sounding like someone who’s not just singing about love, but living it. The track doesn’t need flashy solos or pounding drums to make an impact; its power is in its sincerity. “More of You” reminds us that sometimes the strongest kind of love is the quiet kind—the kind that stays, listens, and chooses you again and again. It’s a lullaby for grown-up hearts, and one of Stapleton’s most emotionally satisfying songs.
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.
