Few artists can command a stage, tell a story, and stir your soul quite like Chris Stapleton. With his powerhouse vocals, raw emotion, and genre-transcending sound, Stapleton has become one of the most celebrated voices in modern music. From heartfelt ballads that leave you teary-eyed to foot-stomping anthems dripping with grit and soul, his songs have a way of connecting with listeners on a deeply personal level.
This article dives into the top 10 most popular Chris Stapleton songs of all time, showcasing the tracks that have cemented his legacy as a country music icon. Whether you’re a longtime fan or just discovering his music, you’ll find an array of unforgettable tunes that highlight Stapleton’s unparalleled ability to blend blues, rock, country, and soul.
Get ready to relive the magic of songs that have topped charts, won prestigious awards, and become anthems for millions of fans worldwide. From his breakout hits to timeless collaborations, this list is a testament to Stapleton’s artistry and his ability to turn every lyric into an emotional masterpiece. So grab your headphones, crank up the volume, and join us as we explore the very best of Chris Stapleton’s music catalog!
1. Tennessee Whiskey (2015)
Chris Stapleton’s version of “Tennessee Whiskey” didn’t just cover a classic — it redefined it. Originally penned by Dean Dillon and Linda Hargrove and first recorded by David Allan Coe in 1981, the song found new life in Stapleton’s hands. Released on his 2015 debut album Traveller, Stapleton’s rendition is a masterclass in blending country, soul, and blues into something timeless. His gravelly voice, dripping with emotion, wraps around every lyric, turning a simple love song into a deep, heartfelt confession. The way he compares the sweetness of love to the smoothness of whiskey feels so genuine, you can almost taste it. Backed by a slow, bluesy guitar and a restrained, simmering arrangement, Stapleton gives the song room to breathe, making each note and word land with incredible power. “Tennessee Whiskey” became a modern standard almost overnight, introducing Stapleton to a wider audience and showcasing his rare ability to turn a well-worn theme into something profoundly personal. It’s not just a song you hear — it’s one you feel in your bones, a slow dance between heartbreak and hope. In Stapleton’s hands, “Tennessee Whiskey” is a soulful toast to love, longing, and the healing powers of a good song.
2. Broken Halos (2017)
“Broken Halos” stands as one of Chris Stapleton’s most poignant and enduring songs. Released in 2017 on his critically acclaimed album From A Room: Volume 1, it’s a heartfelt meditation on loss, grief, and the mysteries of life. The track’s stripped-back arrangement — just acoustic guitar, soft percussion, and Stapleton’s unmistakable voice — allows the raw emotion of the lyrics to shine through. Singing about those who leave too soon, Stapleton offers comfort without trying to explain the inexplicable. The song’s simplicity is its power; it doesn’t try to make sense of tragedy, but instead honors the pain and resilience that come with it. Winning the Grammy for Best Country Song in 2018, “Broken Halos” resonated deeply with listeners from all walks of life, becoming an anthem for those navigating heartache. Stapleton’s delivery is hauntingly sincere, never overwrought, letting the message sink in naturally. It feels like a conversation with an old friend or a prayer whispered late at night. “Broken Halos” proves that sometimes the most powerful songs aren’t about giving answers — they’re about reminding us we’re not alone in the questions. It’s a beautiful, enduring testament to hope amid sorrow.
3. Starting Over (2020)
“Starting Over,” the title track of Chris Stapleton’s 2020 album, is a heartfelt anthem about new beginnings and the courage it takes to chase a fresh start. With its easygoing acoustic strum and warm, unhurried tempo, the song feels like a breath of fresh air. Stapleton’s voice, rich and reassuring, captures the bittersweet excitement that comes with stepping into the unknown. The lyrics are a love letter to the idea that no matter what’s behind you, there’s always the chance to begin again — as long as you have someone to share the journey with. The song doesn’t sugarcoat the uncertainties; instead, it embraces them, finding beauty in both the struggles and the possibilities. There’s a simplicity to “Starting Over” that makes it deeply relatable — it’s the kind of song you want to play on a long drive with the windows down, thinking about everything ahead. Stapleton’s storytelling shines, creating vivid images of small towns, open roads, and shared dreams. “Starting Over” isn’t just about moving on; it’s about holding onto hope and love when everything else feels unsure. It’s a gentle, uplifting reminder that sometimes, a new beginning is the greatest adventure of all.
4. You Should Probably Leave (2020)
“You Should Probably Leave” captures a familiar yet complicated feeling — being caught in the pull of someone you know you can’t stay with. Released in 2020 on the Starting Over album, this slow-burning track tells the story of two people whose chemistry is undeniable but whose timing is all wrong. Stapleton’s soulful voice breathes life into the tension and tenderness woven into the lyrics. The bluesy, understated arrangement gives the song a simmering energy, like a late-night conversation that both people know is headed toward heartache. What makes “You Should Probably Leave” so powerful is how it embraces the grey areas of love — the way desire and regret can exist in the same moment. Stapleton doesn’t rush the story; he lets it unfold naturally, giving listeners time to sit with the bittersweetness. The honesty in his delivery makes the song relatable to anyone who’s ever faced a tough goodbye. It’s not about anger or blame — it’s about understanding when love isn’t enough to make things right. “You Should Probably Leave” is a standout in Stapleton’s catalog because it shows just how masterfully he captures the complexities of human emotion in a few simple, perfect lines.
5. Parachute (2015)
High-energy and heart-pounding, “Parachute” from Stapleton’s 2015 Traveller album is one of his most electrifying tracks. Driven by a stomping beat and a fiery vocal performance, the song feels like a rallying cry for loyalty and love. Stapleton uses the metaphor of being a parachute — a literal lifesaver — to promise unwavering support to someone he loves. It’s a powerful image, and he leans into it with raw intensity. The fast-paced rhythm paired with his raspy, urgent voice creates a feeling of momentum, as if the song itself is leaping off a cliff, trusting the parachute to open. Unlike some of his slower, more introspective songs, “Parachute” barrels forward with relentless energy, making it a favorite at live shows where the crowd can clap and stomp along. Yet, despite its rock influences, it never loses its country soul. Stapleton proves that he can crank up the tempo without sacrificing the heartfelt sincerity that defines his music. “Parachute” is a reminder that commitment isn’t just about quiet promises — sometimes it’s loud, bold, and fiercely determined. It’s an anthem for anyone who’s ever wanted to be someone’s safe place in a turbulent world.
6. Fire Away (2015)
“Fire Away” is one of the most emotionally powerful songs Chris Stapleton has ever recorded. Released in 2015 on his debut album Traveller, it explores the painful theme of standing by someone through their darkest moments. With just a few simple chords and Stapleton’s aching voice, the song builds a deep sense of vulnerability. He invites his partner to “fire away,” to release all their hurt, anger, and sadness onto him, willing to take the blows if it means offering support. What makes “Fire Away” truly haunting is how understated it is — Stapleton doesn’t shout or over-dramatize; he lets the rawness of the emotion do the talking. The powerful music video, which focuses on the struggles of mental health and suicide awareness, adds even more weight to the track’s meaning, turning it into a quiet anthem for empathy and resilience. The way Stapleton sings it, you can feel every ounce of exhaustion and unconditional love in his voice. “Fire Away” isn’t just a sad love song; it’s a testament to how deep devotion can run even when it hurts. It’s a reminder that sometimes, love is about simply being the one who stays when everything else falls apart.
7. Traveller (2015)
“Traveller,” the title track from Chris Stapleton’s breakout 2015 album, is pure wanderlust captured in a song. With a laid-back tempo and soulful vocals, Stapleton reflects on the journey of life, touching on the highs, lows, and everything in between. It’s a song about searching — for meaning, for peace, for something just out of reach. Stapleton’s lyrics paint vivid pictures of highways stretching out in front of him and the pull of the unknown calling his name. There’s a bittersweetness to it all, a feeling that no matter how far you travel, you’re always chasing something that can’t quite be pinned down. Musically, “Traveller” blends elements of country, rock, and soul seamlessly, showcasing Stapleton’s incredible range not just as a vocalist, but as a storyteller. His voice carries the kind of wisdom that sounds earned, not learned, making every word feel authentic. The song resonates with anyone who’s ever felt restless, who’s ever packed up and hit the road without knowing exactly why. “Traveller” isn’t just a song about moving from place to place; it’s about moving through life, embracing the journey even when the destination is unclear.
8. Whiskey and You (2015)
“Whiskey and You” is Chris Stapleton at his most raw and vulnerable. Released in 2015 on Traveller, the song strips everything down to the bare essentials: a broken heart, a bottle of whiskey, and the aching honesty of Stapleton’s voice. The lyrics draw a heartbreaking comparison between the numbing burn of alcohol and the lingering pain of lost love. Every line feels like a confession whispered in the dead of night, heavy with regret and loneliness. What’s striking about “Whiskey and You” is its simplicity — there’s no big production, no fancy instrumentation. Just a stark acoustic guitar and a voice that carries the weight of the world. Stapleton’s delivery is so genuine, you can almost smell the whiskey and feel the ache in your own chest. It’s a song that doesn’t just talk about pain — it lives in it. “Whiskey and You” has become a fan favorite because it taps into something universal: the way we all reach for something, anything, to dull the hurt. It’s a reminder that sometimes, the quietest songs can be the loudest in our hearts. Stapleton doesn’t just sing the blues here — he embodies them.
9. Midnight Train to Memphis (2017)
“Midnight Train to Memphis” is Chris Stapleton at his grittiest and most electrifying. Originally written during his time with The SteelDrivers, Stapleton reimagined the song for his 2017 solo album From A Room: Volume 2, giving it a heavy, blues-rock edge that hits like a freight train. The song tells the story of a man serving time in jail, straining to hear the whistle of the train he can’t ride, dreaming of freedom just beyond reach. Stapleton’s raspy, powerhouse vocals bring a fierce urgency to the narrative, making you feel every ounce of frustration and longing. The guitar riffs are thick and growling, perfectly matching the raw energy of his voice. “Midnight Train to Memphis” doesn’t just tell a story — it throws you right into the middle of it, dust and all. There’s a restless spirit running through the track, a burning need to escape that’s palpable. It’s one of Stapleton’s most electrifying performances, especially when played live, where the intensity seems to double. This song proves that Stapleton isn’t just a balladeer — he’s a force of nature when he leans into his rock and blues roots.
10. Millionaire (2017)
With “Millionaire,” Chris Stapleton reminds us that true wealth isn’t counted in dollars and cents, but in love, gratitude, and the simple joys of life. Released in 2017 on From A Room: Volume 2, this cover of Kevin Welch’s song is pure, unfiltered joy. Stapleton’s warm, soulful voice paired with the sweet harmonies of his wife, Morgane Stapleton, makes for an irresistible listen. The arrangement is easygoing — an acoustic guitar, a gentle drum beat, and a whole lot of heart — creating a breezy, feel-good vibe that feels like sunshine on your skin. Lyrically, “Millionaire” speaks to the richness found in relationships and contentment, rather than material success. Stapleton doesn’t preach or boast; he simply shares a little slice of wisdom with an easy charm. It’s the kind of song that makes you want to slow down, hold your loved ones close, and count your blessings. In a world where everyone’s chasing more, “Millionaire” is a refreshing reminder that sometimes, the greatest treasures are already right in front of you. It’s a simple song, but one with a heart big enough to fill an entire room — or maybe even a lifetime.
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.
