Few artists in modern country music have had the meteoric rise and widespread impact of Chris Stapleton. With his gritty voice, soul-stirring lyrics, and a sound that blends classic country, Southern rock, blues, and soul, Stapleton has redefined what it means to be a country artist in the 21st century. Since bursting onto the scene with his breakout album Traveller, he’s captivated audiences worldwide, racking up numerous awards and chart-topping hits. Whether he’s tugging at heartstrings with raw ballads or delivering foot-stomping anthems, Stapleton’s music resonates deeply with listeners from all walks of life.
In this article, we’re diving into the top 10 most popular Chris Stapleton songs of all time. These are the tracks that have not only defined his career but have also cemented his status as a living legend in the world of country music. From the heart-wrenching “Whiskey and You” to the soulful anthem “Tennessee Whiskey,” get ready to explore the songs that have made Stapleton a household name. Whether you’re a longtime fan or new to his music, these tracks represent the very best of an artist who continues to push the boundaries of country music.
1. Tennessee Whiskey (2015)
“Tennessee Whiskey” emerged as Chris Stapleton’s hallmark song shortly after its release in 2015, transcending traditional genre boundaries and captivating listeners from various musical backgrounds. Originally penned by Dean Dillon and Linda Hargrove, this track was transformed into a soulful classic through Stapleton’s powerful, bluesy delivery. His smooth vocals meld seamlessly with a slow, sultry melody, creating an atmosphere that appeals universally. The performance Stapleton gave at the 2015 CMA Awards, where he shared the stage with Justin Timberlake, propelled “Tennessee Whiskey” into the spotlight, firmly establishing it as a fan favorite.
The song’s lyrics evoke a sense of longing and reminiscence, drawing listeners into a world where love feels intoxicating and comforting, akin to a fine whiskey. Its masterful fusion of country, blues, and soul captures the essence of late-night introspection, inviting audiences to reflect on their own experiences with love and loss. The song’s resonant themes resonate with those seeking solace and warmth, making it a timeless choice for playlists that aim to evoke emotion.
Stapleton’s soulful interpretation revitalizes this country classic, ensuring that it remains relevant even years after its debut. The song has become more than just a chart-topper; it embodies a spirit of resilience and connection, resonating with anyone who has ever found comfort in a beloved tune. With each listen, “Tennessee Whiskey” continues to remind us of the power of music to heal and unite, solidifying its place as one of Stapleton’s most enduring masterpieces.
2. Broken Halos (2017)
“Broken Halos,” featured on Stapleton’s acclaimed album From A Room: Volume 1, stands out as a deeply moving reflection on themes of loss, healing, and the complexities of life. Released in 2017, this Grammy-winning track illustrates Stapleton’s remarkable ability to weave poignant narratives into anthemic melodies. Inspired in part by the passing of a close friend, “Broken Halos” resonates with a universal message about finding peace in the midst of grief, offering a sense of comfort to those grappling with loss.
The stripped-back instrumentation allows Stapleton’s powerful, soulful voice to shine through, delivering lyrics that linger in the minds and hearts of listeners long after the final note. His emotive vocal delivery captures the essence of vulnerability, emphasizing the importance of acknowledging pain while still searching for light in the darkness. The track invites listeners to reflect on their own experiences with heartache and the healing that can follow, making it a powerful anthem for anyone seeking solace in times of sorrow.
The beauty of “Broken Halos” lies in its raw honesty and relatability, drawing listeners into a shared experience of human emotion. As Stapleton navigates the complexities of life, he encourages his audience to embrace their own journeys of healing and growth. This heartfelt ballad has earned its place among Stapleton’s most cherished works, reminding us all that even in our brokenness, there is hope for redemption and renewal.
3. Fire Away (2015)
From Stapleton’s debut album Traveller, “Fire Away” emerges as a hauntingly beautiful ballad that delves into the intricacies of love and emotional vulnerability. Released in 2015, the song’s lyrics explore the raw, often painful realities of heartache, inviting listeners to embrace their feelings rather than shy away from them. The emotional weight carried by Stapleton’s voice elevates the song, creating a haunting atmosphere that resonates deeply with anyone who has navigated the complexities of love.
The accompanying music video adds a poignant layer to the song’s narrative, addressing crucial issues surrounding mental health and the importance of supporting one another through difficult times. This visual representation amplifies the song’s message, showcasing how love can serve as both a refuge and a battleground for emotional struggles. Stapleton’s ability to intertwine personal experiences with universal themes is what sets “Fire Away” apart, highlighting his unique talent for storytelling through music.
With its aching vocals and timeless melody, “Fire Away” serves as a powerful reminder of the emotional connections that define our relationships. Stapleton’s artistry shines through, revealing the beauty and pain that coexist within love. As listeners engage with this heartfelt ballad, they are reminded of the strength that can be found in vulnerability and the importance of expressing one’s feelings, regardless of how difficult it may be. “Fire Away” remains a poignant testament to Stapleton’s ability to connect deeply with his audience, echoing long after the song ends.
4. Whiskey and You (2015)
Though not an initial chart-topping single, “Whiskey and You” has evolved into one of Chris Stapleton’s most cherished tracks since its release in 2015 on the Traveller album. This stripped-back ballad delves into the painful realities of addiction and regret, showcasing Stapleton’s raw, emotional honesty. With a minimalistic arrangement primarily featuring Stapleton’s soulful voice and an acoustic guitar, the song creates an intimate, confessional atmosphere that draws listeners into his world.
The lyrics poignantly capture the internal battle between numbing pain with alcohol and facing one’s demons directly. Each line resonates with authenticity, reflecting the struggles many face when confronting their addictions and emotional challenges. Stapleton’s vulnerability in expressing these feelings has endeared him to fans, solidifying “Whiskey and You” as a standout track in his repertoire.
The haunting melody and poignant storytelling invite listeners to reflect on their own experiences with love, loss, and addiction. As the song unfolds, it becomes a powerful anthem for anyone grappling with similar struggles, encouraging them to find strength in their vulnerabilities. “Whiskey and You” ultimately serves as a reminder that while pain is an inevitable part of life, there is also hope and healing to be found in honest expression. The emotional depth of this track has cemented its status as one of Stapleton’s most impactful and beloved songs, resonating with audiences long after its release.
5. Nobody to Blame (2015)
Released in 2015, “Nobody to Blame” is an electrifying anthem of regret and accountability that showcases Chris Stapleton’s unique blend of country and rock influences. With its gritty guitar riffs and Stapleton’s unmistakable growl, the song tells the story of a man coming to terms with his mistakes after a relationship crumbles. The energetic beat and catchy chorus elevate the track, making it an instant favorite among fans and helping it ascend the country charts with ease.
Stapleton’s lyrical prowess shines as he narrates the emotional fallout of a broken relationship, skillfully weaving themes of regret and self-reflection into an engaging narrative. The song’s rollicking energy invites listeners to tap their feet and sing along, creating an atmosphere of camaraderie and connection. “Nobody to Blame” not only captures the essence of accountability but also serves as a reminder that embracing one’s flaws is an essential part of personal growth.
The track earned Stapleton his first ACM Award for Song of the Year, a testament to its impact and resonance within the country music landscape. Its infectious rhythm and relatable lyrics ensure that it remains a staple in Stapleton’s live performances, where audiences eagerly sing along, reveling in the song’s raw energy and emotional depth. “Nobody to Blame” has rightfully earned its place in the pantheon of modern country classics, showcasing Stapleton’s remarkable ability to blend storytelling with powerful melodies.
6. Millionaire (2017)
“Millionaire,” a standout track from Stapleton’s From A Room: Volume 2 (2017), is a delightful love song with a simple yet profound message: true wealth comes from love, not material possessions. Originally written by Kevin Welch, Stapleton infuses his rendition with soulful vocals and a laid-back groove that immediately captivates listeners. The upbeat, optimistic tone of the song reveals a lighter side of Stapleton, showcasing his versatility as an artist and appealing to those seeking joy and connection through music.
The lyrics celebrate the richness of love, painting a picture of two people who find their greatest treasures in one another rather than in material wealth. The song’s warm melody and infectious chorus make it an immediate favorite among fans, inviting listeners to embrace the beauty of love in all its forms. As Stapleton croons about the true meaning of being a millionaire, he evokes feelings of happiness and gratitude, encouraging audiences to cherish the relationships that bring them joy.
“Millionaire” serves as a reminder that while society often equates success with financial gain, the most valuable experiences in life stem from our connections with others. The song’s positive message resonates across generations, reinforcing the idea that love is the greatest treasure of all. With its timeless appeal, “Millionaire” continues to uplift listeners, leaving them with a warm sense of fulfillment and a reminder to appreciate the richness of life’s most meaningful relationships.
7. Starting Over (2020)
Released in 2020, “Starting Over” serves as the title track for Stapleton’s fourth studio album, embodying an anthem of hope and new beginnings. Written during a period of personal reflection, the song’s lyrics resonate with anyone who has faced challenges and is seeking a fresh start. With its gentle acoustic guitar and uplifting melody, “Starting Over” offers a breath of fresh air, inviting listeners to embrace change and take chances in life.
The song’s optimistic tone is infectious, capturing the essence of renewal and the excitement of embarking on new journeys. Stapleton’s soulful voice infuses the lyrics with warmth and sincerity, making it easy for audiences to connect with the message. The narrative encourages listeners to look beyond their past struggles and embrace the possibilities that lie ahead, offering reassurance that it’s never too late to begin anew.
As the song gained popularity, it resonated deeply with fans, becoming a chart success and further solidifying Stapleton’s reputation as a master of heartfelt ballads and uplifting anthems. “Starting Over” reflects the universal experience of resilience, reminding us that life is a continuous journey filled with opportunities for growth and transformation. With its hopeful message and captivating sound, the track has carved out a special place in the hearts of listeners, encouraging them to celebrate new beginnings and the promise they hold.
8. Parachute (2015)
“Parachute” stands out as one of the more energetic tracks from Stapleton’s Traveller album, showcasing his rock influences while staying true to his country roots. Released in 2015, the song features a driving rhythm and an infectious chorus that compels listeners to move. Lyrically, “Parachute” serves as a heartfelt declaration of loyalty and love, with Stapleton promising to be a safety net for his partner in times of need. This powerful message of devotion resonates deeply, making it a fan favorite at live shows.
The electrifying guitar work, combined with Stapleton’s gritty, passionate vocals, creates an atmosphere of excitement and energy that is hard to resist. As the song unfolds, listeners are drawn into a narrative that celebrates the strength of love and the commitment to support one another through life’s ups and downs. “Parachute” encapsulates the feeling of being in a relationship where trust and loyalty create a solid foundation, providing reassurance in an unpredictable world.
This track highlights Stapleton’s ability to blend various musical styles, resulting in a sound that is both fresh and familiar. The energetic vibe of “Parachute” makes it perfect for those moments when you need a boost of adrenaline, whether you’re driving down the highway or dancing in your living room. Its uplifting message and infectious rhythm ensure that it remains a standout in Stapleton’s discography, reminding us all of the power of love and commitment.
9. You Should Probably Leave (2020)
From Stapleton’s Starting Over album, “You Should Probably Leave” is a slow-burning, seductive song that encapsulates the complexities of a relationship teetering on the edge. Released in 2020, the track features a bluesy vibe and clever lyrics that deftly capture the push-and-pull dynamic between two individuals who know they’re not right for each other yet are drawn together irresistibly. Stapleton’s smooth, evocative vocals elevate the song, creating an intimate atmosphere that resonates with listeners.
The understated arrangement allows the lyrics to take center stage, enhancing the emotional weight of the narrative. As Stapleton navigates the tension between desire and reason, he invites audiences to reflect on their own experiences with love that feels both exhilarating and dangerous. The song’s intricate storytelling and relatable themes make it a standout on the album, leaving listeners both captivated and contemplative.
“You Should Probably Leave” has become a defining track for Stapleton, showcasing his ability to blend country, blues, and soul seamlessly. The nuanced emotions expressed in the song resonate with anyone who has grappled with a tumultuous relationship, making it a powerful anthem for those caught in similar situations. With its sultry sound and compelling narrative, “You Should Probably Leave” solidifies Stapleton’s status as a masterful storyteller, capturing the complexities of love and attraction with authenticity and depth.
10. Traveller (2015)
“Traveller,” the title track of Stapleton’s 2015 debut album, offers a reflective journey through the nuances of life and self-discovery. Written during a poignant road trip following the passing of his father, the song captures the essence of searching for meaning and direction amid grief. With its haunting melody and introspective lyrics, “Traveller” delves into the themes of loss, discovery, and resilience that are prevalent throughout Stapleton’s work.
The song’s reflective tone invites listeners to embark on their own journeys, encouraging them to confront their emotions and embrace the experiences that shape their lives. Stapleton’s soulful vocals convey a sense of longing and hope, weaving together narratives that resonate deeply with audiences. As he explores the complexities of existence, “Traveller” becomes a meditation on the importance of embracing both the highs and lows of life.
Since its release, the song has become a fan favorite, embodying the spirit of resilience and self-exploration. Its profound lyrics and captivating melody set the tone for an album that would ultimately become a modern country classic. “Traveller” serves as a testament to Stapleton’s ability to connect with listeners on a personal level, reflecting the shared experiences that unite us all. Through this powerful track, Stapleton encourages us to embrace our journeys, celebrating the moments that define who we are and the paths we choose to follow.
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.
