In the world of contemporary country music, few artists have made as significant an impact as Chris Stapleton. With his soulful voice, masterful songwriting, and unique blend of country, rock, and blues, Stapleton has captivated audiences and critics alike. Since his breakthrough debut album, “Traveller,” he has released a plethora of hits that resonate deeply with fans, showcasing his ability to convey raw emotion and storytelling through music.
From heartfelt ballads to foot-stomping anthems, Stapleton’s discography is a treasure trove of unforgettable tracks. Each song tells a story, drawing listeners into a world rich with authenticity and passion. As we dive into the top 10 most popular Chris Stapleton songs of all time, we’ll explore the melodies and lyrics that have defined his career and solidified his status as a modern country music icon.
Join us as we celebrate the songs that have not only topped the charts but also left an indelible mark on the hearts of fans everywhere. Whether you’re a lifelong Stapleton devotee or new to his music, this list promises to take you on an exciting journey through his greatest hits!
1. Tennessee Whiskey (2015)
Chris Stapleton’s “Tennessee Whiskey” is a transformative take on a country classic, turning it into a slow-burning, soulful expression of deep affection and redemption. Originally recorded by David Allan Coe and made famous by George Jones, Stapleton’s 2015 version brought the song back to life with a blues-inspired twist that became iconic in its own right. Backed by a smooth, almost sensual guitar line and his gravelly, heartfelt vocals, Stapleton compares the comfort and warmth of his partner’s love to the soothing burn of Tennessee whiskey. His delivery feels deeply personal, like a quiet confession over a glass of bourbon. It’s more than just a love song—it’s a testimony of transformation, moving from a life of reckless drinking to being “warm as a glass of brandy.” The song’s strength lies in its simplicity and emotional truth. Stapleton doesn’t overcomplicate anything—he just sings it like he feels it, and that honesty has connected with listeners across generations. Whether played at a bar, wedding, or during a quiet evening drive, “Tennessee Whiskey” wraps around the soul and leaves a lasting impression.
2. Broken Halos (2017)
“Broken Halos” is a profoundly moving reflection on loss, healing, and the invisible threads that connect us. Released in 2017, Chris Stapleton delivers this song with a voice full of tenderness and depth, capturing both grief and hope in equal measure. The arrangement is gentle—whispering guitars, soft piano, and restrained drums that leave space for the emotion in every word. Stapleton sings of “angels in the wild,” souls taken too soon, and those left behind trying to make sense of “broken halos.” Yet it’s not a song of despair—it’s an anthem of endurance. The chorus gently lifts, reminding listeners that even when someone’s gone, their love remains, and there is beauty in remembering. It’s this blend of dolor and resilience that makes “Broken Halos” resonate deeply. It becomes more than just a memorial—it’s a tribute to anyone who’s ever lost someone and carried the ache of absence forward with tenderness and courage.
3. Starting Over (2020)
“Starting Over” marks a new chapter in Stapleton’s journey—a song about fresh beginnings and quiet determination. Released in 2020, the track brings together elements of country, blues, and rock for a warm yet lively sound. Stapleton’s vocals are both inviting and resolute, as if coaching listeners to embrace change with open hearts. The lyrics speak directly to the courage required to launch anew: learning lessons, letting go of the past, and accepting that every day is another chance. The production is uncluttered—a steady beat, clean guitar licks, and backing that builds just enough to feel hopeful without overwhelming. There’s optimism in the melody and sincerity in Stapleton’s delivery. “Starting Over” captures that universal moment when you decide it’s time to reshuffle your deck and move forward with grace. It’s not preachy—it’s heartfelt encouragement from one soul to another, offering its message to anyone standing at a crossroads, ready to begin again.
4. Fire Away (2015)
“Fire Away,” from Stapleton’s 2015 debut album, is a quiet storm of emotion about loving someone fully and fearlessly. The song starts softly, with acoustic guitar and a gentle pulse, as Stapleton invites someone to speak their truth—no matter how painful. His rich, tender voice carries vulnerability in every line, promising that even if love brings tears, security matters more than silence. Stapleton sings of standing strong through heartbreak: “Say what you need to say, even if it breaks my heart.” The slow, deliberate build mirrors the layers of trust and fear in a deep relationship. As the track progresses, subtle harmonies and swelling instrumentation underscore his message of unconditional acceptance. The song doesn’t erupt in drama—it remains steady, honest, and grounded. “Fire Away” is the kind of ballad that lingers long after it ends, echoing in the listener’s heart. It’s a tribute to emotional bravery and unwavering love, delivered with humility and strength.
5. Parachute (2017)
“Parachute” is a lively, uplifting exploration of trust, adventure, and falling in love wholeheartedly. Released in 2017, this upbeat track pulses with energy—the kind that makes you want to move and feel alive. Stapleton’s soulful voice rides over spirited guitars and a beat that feels like steady wings in flight. Lyrically, the song uses the metaphor of a parachute to describe love that requires courage: letting go, free-falling, and trusting someone to catch you. Lines like “When you fall, I’ll be your parachute” feel simple yet profoundly comforting. The chorus soars with optimism, celebrating the leap that comes with intimacy. The renewed rhythm and joyful instrumentation underscore the thrill of taking emotional risks. “Parachute” isn’t just a romantic song—it’s a celebration of partnership, vulnerability, and the highs of giving someone your trust. It’s bright, bold, and tender all at once—a declaration that true love is both daring and safe.
6. What Are You Listening To? (2015)
“What Are You Listening To?” is a beautifully contemplative song that invites you to pause and remember. Released in 2015, this poignant piece raises the question: which songs shaped your memories? Stapleton’s voice is gentle yet loaded with emotion, asking listeners to recall moments tied to melodies—first dances, heartbreak, joy, and grief. The arrangement is stripped-down, anchored by soft piano, subtle guitar, and atmospheric echoes, giving space to the introspective lyrics. It’s a tribute to music’s power to transport us through time and feeling. With lines like “You won’t hear it now, but someday you’ll hear it,” the song becomes a nostalgic echo for listeners to hold close. Stapleton doesn’t instruct or lament—he simply observes and invites introspection. In doing so, he honors the emotional bond between memory and melody. “What Are You Listening To?” isn’t just a song—it’s a moment of quiet reflection, reminding us that music is woven into the fabric of our most personal stories.
7. Millionaire (2017)
“Millionaire,” a duet released in 2017, blends warmth, depth, and lyrical beauty in a conversation about love and abundance. Stapleton and his duet partner deliver rich, intertwined harmonies over a soulful, slow-burning groove. The song speaks of wealth—not in material terms, but emotional riches: knowing love that’s “bigger than the moon,” grounded in connection rather than money. The instrumentation is lush but restrained—tender piano, yearning strings, and subtle guitar lines that support without distracting. Vocals swell with sincerity, transcending genre labels. Their voices harmonize effortlessly, creating an emotional resonance that feels almost healing. The meaning is clear: true riches come from relationships that feed the heart. “Millionaire” doesn’t preach—it invites listeners to expand their definition of wealth. It resonates with anyone who’s ever found comfort in a partner’s presence, teaching us that love can be the most valuable asset. This track is a testament to Stapleton’s ability to write songs that feel like gentle affirmations, grounded in musical and emotional integrity.
8. Either Way (2017)
“Either Way” is a deeply intimate and emotionally stirring ballad about holding on and letting go. Released in 2017, the song is a raw and honest reflection on love’s complexity, especially when relationships change or come to an end. Stapleton sings from a place of vulnerability, as if in conversation: “Either way, I’ll still care. Either way, I’ll still want you there.” The arrangement is pared back—sparse guitar and soft accompaniment leave room for every word to breathe. His voice, rich and woody, vibrates with empathy and regret. There’s no dramatic crescendo—just a quiet intensity that reverberates long after the song ends. It’s a song of compassion and grief, acknowledging that even when love doesn’t fit, admiration and memory remain. “Either Way” doesn’t offer neat resolutions—it offers emotional truth and presence. That bare sincerity is what makes it so affecting, a gentle elegy for love in all its forms.
9. Nobody to Blame (2015)
“Nobody to Blame” is an achingly honest song about accountability and heartbreak. Released in 2015, it brings forth a raw, bluesy energy that underscores its message of personal ownership in love gone wrong. The rhythm rocks steadily—rooted in classic country–rock tones—with gritty guitar and steady percussion. Stapleton’s voice is rough around the edges, full of regret and introspection as he sings, “I couldn’t even cheat on you the right way.” The lyrics dig into the realization that he alone carried the pain, even when heartbreak hurt them both. There’s no attempt to externalize blame—it’s a solemn, mature admission that the only person at fault was himself. The chorus resonates with brutal honesty, every lyric delivered with emotional heft. “Nobody to Blame” doesn’t feel performative—it feels like a confession. It’s the kind of song that makes you reflect on your own actions and the complexities of love. In just one track, Stapleton turns pain into clarity—and that clarity into art.
10. Outlaw State of Mind (2015)
“Outlaw State of Mind” is an electrifying anthem of independence and identity. Released in 2015, the song channels swagger, grit, and untamed spirit wrapped in a fierce country–rock blend. Stapleton’s voice is commanding—earthy, bold, with a rebel’s edge. The driving beat and electric guitar riffs evoke movement and momentum, like the rumble of an open road. Lyrically, the song celebrates authenticity: being unapologetically yourself, on your own terms. It’s a declaration: “I was born to live free, and free I’ll be.” The chorus soars with defiance and self-assurance, and every note feels fueled by conviction. Behind the bravado, though, there’s a grounded truth: the power to define your own path. It’s not just bravura—it’s belief. “Outlaw State of Mind” is not a gimmick—it’s a philosophy turned into music. And in Stapleton’s hands, it becomes an anthem not only for outlaws, but for anyone who refuses to shrink their identity.
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.
