Get ready to dive into the soulful world of Chris Stapleton, a powerhouse of modern country music whose voice resonates with raw emotion and authenticity. Since breaking onto the scene, Stapleton has captivated audiences with his unique blend of country, blues, and rock influences, making him one of the most beloved artists of our time. With a remarkable ability to weave storytelling into his lyrics, every song is a journey through love, heartache, and resilience.
From his chart-topping hits to deep cuts that showcase his incredible songwriting prowess, Stapleton’s discography is rich with unforgettable melodies and poignant narratives. Fans and newcomers alike have been drawn to his magnetic stage presence and the way he pours his heart into every performance.
In this article, we’ll explore the top 10 most popular Chris Stapleton songs of all time—each one a testament to his talent and the timeless themes that resonate with listeners. Whether you’re a lifelong fan or just discovering his music, prepare to be inspired by the heartfelt stories and powerful vocals that define Chris Stapleton’s extraordinary career. Buckle up as we celebrate the best of his musical journey!
1. Tennessee Whiskey (2015)
Chris Stapleton’s version of “Tennessee Whiskey” turned a country classic into a soul-infused masterpiece. Originally written by Dean Dillon and Linda Hargrove and first recorded by David Allan Coe, this song found new life in Stapleton’s hands. His smoky, powerful voice lends the track a depth of emotion that elevates it far beyond a typical love ballad. The lyrics compare the warmth and comfort of a lover to the smoothness of a fine whiskey, creating an intoxicating metaphor that perfectly captures the feelings of safety, love, and intimacy. The arrangement is simple yet rich—driven by a slow bluesy groove and gentle guitar licks that echo with feeling. What truly sets this version apart is Stapleton’s vocal phrasing; each word feels deliberate, every note soaked in feeling. The song resonates with anyone who has experienced redemptive love—the kind that calms storms and brings peace to the soul. “Tennessee Whiskey” became a breakout hit for Stapleton, catapulting him into the mainstream and introducing millions to his unique blend of country, blues, and southern soul. It’s more than just a song; it’s a full-bodied emotional experience that lingers like the last sip of something strong and smooth.
2. Broken Halos (2017)
“Broken Halos” is one of Chris Stapleton’s most poignant and heartfelt songs, taken from his 2017 album From A Room: Volume 1. The track explores the pain of loss and the mystery behind life’s tragedies. It’s a quiet reflection on the people we lose too soon—those whose lives are cut short, leaving us with more questions than answers. With lyrics like “Don’t go asking Jesus why / We’re not meant to know the answers,” Stapleton conveys a deep sense of humility and grief, acknowledging that some wounds never quite heal. The song’s stripped-down arrangement—just acoustic guitar, light percussion, and Stapleton’s aching voice—lets the emotional weight of the lyrics shine through. His soulful delivery adds layers of vulnerability and sincerity, making it resonate deeply with anyone who has experienced loss. “Broken Halos” doesn’t offer easy comfort, but it does offer solidarity—a shared space to mourn and remember. It’s a song that reminds us we’re not alone in our sorrow, and sometimes the most powerful thing we can do is honor the broken halos among us by carrying their memory with us as we move forward.
3. Fire Away (2015)
“Fire Away” is a powerful ballad about emotional endurance, taken from Chris Stapleton’s breakout album Traveller. At its core, the song is a raw depiction of being in a relationship with someone who is battling emotional pain. Stapleton sings from the perspective of a partner willing to stand strong, even when love hurts. The chorus—“Fire away”—isn’t an act of defiance, but one of sacrificial love, inviting emotional wounds if it means being there for someone in distress. The instrumentation starts off subdued, then builds slowly into a powerful crescendo, mirroring the emotional escalation of the lyrics. The music video adds another layer, portraying the reality of mental health struggles, particularly depression and suicide, and sparked important conversations when it was released. Stapleton’s gravelly voice captures every ounce of pain, loyalty, and helplessness embedded in the song. “Fire Away” stands out as a testament to the complexity of love—it’s not always pretty, and sometimes it means weathering storms that can’t be fixed with words. This haunting ballad leaves a lasting impact, reminding listeners that standing by someone in their lowest moments can be both heartbreaking and heroic.
4. Millionaire (2017)
With “Millionaire,” Chris Stapleton puts a soulful twist on gratitude and love. Originally written by Kevin Welch, the song was recorded for From A Room: Volume 2, and Stapleton’s version gives it a smooth, laid-back feel that perfectly captures the warmth of its message. Accompanied by his wife Morgane’s gentle harmonies, Stapleton sings about the richness of life that comes from love, not money. The lyrics celebrate the idea that emotional wealth—found in relationships, kindness, and inner peace—is far more valuable than material success. The easygoing, almost gospel-tinged rhythm invites the listener to slow down and appreciate the simple joys of life. Stapleton’s heartfelt delivery makes it all the more genuine. There’s no flash here, just sincerity and soul. “Millionaire” feels like sitting on a porch with someone you love, knowing that no matter what the bank account says, you have everything you need. It’s a refreshing reminder in a world obsessed with status and stuff. The song’s timeless message, combined with its warm musicality, makes it one of Stapleton’s most comforting and uplifting tracks—a celebration of the kind of wealth that truly matters.
5. Parachute (2015)
“Parachute” is one of Chris Stapleton’s more upbeat, foot-stomping tracks from his album Traveller, showcasing a grittier, rock-tinged side of his sound. With its driving rhythm, dynamic vocals, and rhythmic acoustic strumming, the song feels like a jolt of energy. Lyrically, it’s about being a steady and reliable presence in someone’s life—a “parachute” when the other person is falling. Stapleton promises unconditional support and safety, even when times get rough. The metaphor is simple but powerful: he’s the one who’ll catch you when you’re crashing down. The raw urgency in his voice brings out the strength of that promise, transforming a simple love song into a declaration of loyalty and resilience. The song’s blend of country grit and rock swagger makes it a standout in his catalog, and a crowd favorite at live shows. “Parachute” reminds us that love isn’t just about romance—it’s about being someone’s lifeline, their safety net when the world gets hard. Stapleton’s passionate delivery and the song’s propulsive energy combine to create a powerful anthem for anyone who’s ever needed—or been—a parachute for someone else.
6. Starting Over (2020)
“Starting Over” is the title track of Chris Stapleton’s 2020 album and serves as a hopeful anthem about new beginnings. With its warm acoustic guitar and easygoing rhythm, the song feels like a fresh breeze—optimistic and full of possibility. Stapleton sings about leaving behind the old and venturing into the unknown with someone you love. It’s not just about physical relocation, but emotional renewal—choosing to rebuild and rediscover joy, no matter what the past holds. There’s a comforting sense of companionship in the lyrics: “Wherever we are is where I wanna be.” The simplicity of the arrangement highlights the sincerity of the message. Morgane Stapleton’s harmonies lend a beautiful softness, reinforcing the idea that love is what anchors us in times of change. “Starting Over” arrived during a season of global uncertainty and struck a chord with many looking to reset and find purpose again. The song blends country roots with soul influences, and Stapleton’s signature grit makes it all the more authentic. It’s an anthem for anyone beginning a new chapter—offering reassurance that no matter how uncertain the road ahead is, love makes the journey worthwhile.
7. Cold (2020)
“Cold” is one of Chris Stapleton’s most soul-stirring and vocally powerful ballads. Released as part of his Starting Over album, this haunting track dives into the ache of heartbreak with stunning emotional depth. The song’s orchestral arrangement—with moody piano, sweeping strings, and bluesy guitar riffs—sets the tone for a slow-burning lament that builds in intensity. Stapleton’s voice, gravelly yet tender, cuts through with pure anguish as he questions why someone he trusted left him out in the emotional cold. The lyrics are raw: “Why you got to be so cold? / Why you got to go and cut me like a knife?” It’s more than a breakup song—it’s a cry from someone blindsided by betrayal. There’s a soul and blues influence that evokes the heartbreak ballads of the past, yet Stapleton gives it a modern edge. The emotional weight he carries in every note makes “Cold” unforgettable. It’s the kind of song that leaves you quiet when it ends, not because it’s sad, but because it makes you feel something deeply real. “Cold” showcases Stapleton’s gift for storytelling through music—and his rare ability to make heartache sound beautiful.
8. You Should Probably Leave (2020)
“You Should Probably Leave” tells the story of a complicated relationship full of temptation, emotional history, and blurred boundaries. It’s one of Chris Stapleton’s most relatable songs, wrapped in a bluesy, understated arrangement that complements its emotional tension. The lyrics unfold like a conversation between two people who know they’re not good for each other, yet keep getting drawn back in. “’Cause I know you and you know me / And we both know where this is gonna lead,” Stapleton sings with resigned honesty. There’s a gentle sadness in the delivery—it’s not angry, just tired and wise. He captures that familiar late-night moment where hearts want what heads know they shouldn’t. The song’s strength lies in its subtlety. There’s no dramatic climax, just a quiet pull between desire and restraint. Morgane’s background vocals once again add a layer of intimacy, reinforcing the closeness between the characters. “You Should Probably Leave” stands out as a mature, introspective take on love’s messier side. It’s the kind of song that lingers, not because of big production, but because of how real it feels—honest, nuanced, and painfully human.
9. Daddy Doesn’t Pray Anymore (2015)
“Daddy Doesn’t Pray Anymore” is a deeply personal and emotionally resonant track from Stapleton’s Traveller album. In this gentle ballad, he reflects on the spiritual life and passing of his father. The song is simple in structure but profound in meaning. It opens with the line: “Daddy doesn’t pray anymore / I guess he’s finished talking to the Lord.” At first, the listener might assume this is a song about someone who lost their faith. But as it unfolds, it becomes clear that Stapleton is speaking about death—and the peace that came with it. The minimal arrangement, driven by acoustic guitar and Stapleton’s hushed vocals, enhances the song’s reverent tone. It’s both a tribute and a moment of quiet mourning. The storytelling is tender and free from sentimentality, which makes it even more powerful. Rather than trying to explain grief, Stapleton simply shares a moment that many listeners can identify with. “Daddy Doesn’t Pray Anymore” is not just a song about loss—it’s about legacy, faith, and the quiet impact of a life lived with conviction. It’s one of his most moving works and a reminder of the power of simplicity in songwriting.
10. Joy of My Life (2020)
In “Joy of My Life,” Chris Stapleton delivers a heartfelt love song that feels timeless. Originally written and recorded by John Fogerty, Stapleton’s version appears on Starting Over and adds a tender, country-soul flavor that suits his warm, expressive voice perfectly. The song is a simple declaration of love and gratitude. Stapleton sings with gentle reverence about the woman who brings meaning to his life, describing her as the one who truly completes him. “She takes me by the hand / I am the luckiest man alive.” It’s a quiet celebration of contentment—the kind of love that isn’t flashy but steady and enduring. The acoustic-driven arrangement allows his voice to take center stage, supported by soft guitar and a subtle rhythm section. Morgane’s harmonies once again elevate the song, adding a sense of intimacy and warmth. There’s no drama here—just appreciation for life’s most cherished gift: the love of someone who truly understands you. “Joy of My Life” is a standout track because of its sincerity. It doesn’t try to be profound; it simply is. And in its simplicity, it says everything a great love song needs to say.
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.
