When it comes to country music, few artists deliver the heart, soul, and raw power that Chris Stapleton does. With his unmistakable voice, soulful lyrics, and boundary-pushing sound, Stapleton has carved his name deep into the hearts of fans worldwide. From poignant ballads that tug at your heartstrings to electrifying anthems that make you want to sing along, his music transcends genres and speaks to anyone who loves a good story told through song.
Since his breakout moment at the 2015 CMA Awards, where his stunning performance with Justin Timberlake left the world in awe, Stapleton has become a force of nature in the music industry. His songs are an intoxicating blend of country, blues, and rock, showcasing his unparalleled artistry and emotional depth. Whether you’re a longtime fan or just discovering his genius, this list of the top 10 most popular Chris Stapleton songs is sure to remind you why he’s one of the greatest musicians of our time.
So, turn up the volume, grab a drink, and get ready to dive into a playlist that will take you on a journey through heartbreak, hope, and the timeless magic of Chris Stapleton. Let’s get started!
1. Tennessee Whiskey (2015)
Chris Stapleton’s rendition of Tennessee Whiskey is a powerful and soulful anthem that cemented his place as one of the leading voices in country music. Originally penned by Dean Dillon and Linda Hargrove and recorded by legends like George Jones and David Allan Coe, Stapleton’s 2015 version brought the classic to a new generation. His raw, gravelly voice and emotionally charged performance breathed new life into the song, blending blues, soul, and country in a way that resonated deeply with listeners. The slow-burning, sultry melody evokes the warm, smooth feeling of sipping whiskey by a crackling fire, capturing the essence of love as both a comfort and a vice. With his unmatched delivery, Stapleton conveys the song’s themes of heartache and solace in a way that’s deeply personal, making it a standout in his catalog. Tennessee Whiskey is not just a song—it’s an experience, one that draws you in and wraps you in its emotional warmth, staying with you long after the last note fades.
2. Starting Over (2020)
The title track of Chris Stapleton’s 2020 album Starting Over is a beautiful, introspective song about embracing new beginnings with vulnerability and hope. The acoustic-driven melody and soft, tender rhythm provide the perfect backdrop for Stapleton’s soulful voice, which delivers the song’s poignant lyrics with emotional depth. The song speaks to the universal experience of starting fresh—whether in love, life, or personal growth—and the courage it takes to move forward despite uncertainty. Stapleton’s masterful storytelling shines through as he paints a picture of new horizons and the possibility of reinvention. His voice, raw and unpolished, adds a sense of intimacy and honesty, inviting the listener to reflect on their own journey of starting over. The gentle harmonies and stripped-back arrangement further enhance the song’s message of optimism, making it feel both comforting and inspiring. Starting Over serves as a reminder that no matter how difficult life may get, there is always an opportunity to begin anew, making this track one of Stapleton’s most hopeful and uplifting songs to date.
3. You Should Probably Leave (2020)
You Should Probably Leave is a masterclass in emotional depth and subtlety, showcasing Chris Stapleton’s ability to capture the complexities of love and desire. Released in 2020, the song tells the story of a fleeting, yet intense connection—one filled with temptation and emotional turmoil. The track’s minimalistic arrangement, with its gentle acoustic strumming, allows Stapleton’s raspy, gravelly voice to take center stage, pulling the listener into a story of tension, restraint, and unspoken longing. The lyrics explore the painful decision of knowing when to walk away from something that could be harmful, yet undeniably alluring. There’s an undeniable vulnerability in the way Stapleton delivers the words, making the song feel like a quiet confession. The contrast between his soulful voice and the song’s restrained, almost melancholic atmosphere makes You Should Probably Leave one of Stapleton’s most emotionally resonant songs. It’s a beautiful exploration of love’s complexities, capturing the tension between desire and the wisdom of knowing when it’s time to let go.
4. Broken Halos (2017)
Broken Halos, a standout track from Chris Stapleton’s 2017 album From A Room: Volume 1, is a moving tribute to those who have passed before their time. Co-written by Stapleton and Mike Henderson, the song touches on themes of loss, grief, and the resilience to move forward despite the pain. The lyrics, tinged with spirituality, liken the departed to angels whose halos are now broken, offering a poignant image of life’s fragility. The stripped-down arrangement, with its country-gospel undertones, allows Stapleton’s soulful, gravelly voice to deliver the message with raw emotion. Each note is steeped in a sense of both mourning and reverence, creating an atmosphere that is both heart-wrenching and uplifting. The song’s haunting beauty resonates long after the final chord fades, reminding us of the preciousness of life and the loved ones we lose along the way. Broken Halos is a powerful song that speaks to the soul, encapsulating the bittersweet nature of love, loss, and the hope that those who are gone live on in our hearts.
5. Parachute (2015)
Parachute, from Chris Stapleton’s debut album Traveller, is an upbeat, high-energy track that showcases the artist’s versatility and ability to blend genres seamlessly. The song’s infectious energy is driven by a powerful rhythm and bluesy guitar riffs, giving it a rock-infused edge that contrasts with much of Stapleton’s typically laid-back, soulful style. Lyrically, Parachute explores the themes of love and loyalty, with the narrator pledging to be a constant source of support and stability for a loved one. The imagery of a parachute as a metaphor for unconditional trust adds a layer of emotional depth to the song, conveying the idea of being there for someone through thick and thin. Stapleton’s raspy, gravelly voice delivers the heartfelt message with sincerity, while the lively instrumentation propels the song forward, making it one of the most energetic tracks on the album. Parachute stands as a testament to Stapleton’s ability to balance vulnerability with strength, creating a song that is both musically dynamic and emotionally resonant. It’s a feel-good anthem for anyone who believes in the power of love and support in a relationship.
6. Fire Away (2015)
Fire Away, from Chris Stapleton’s critically acclaimed Traveller album, is a raw and powerful exploration of love, vulnerability, and emotional struggles. The song’s haunting, stripped-back melody and somber tone create an atmosphere of tension, perfectly mirroring the lyrical themes of facing personal demons and the weight of emotional pain. With his gravelly, soulful voice, Stapleton sings about confronting the challenges of mental health and the struggle to open up to someone you love. The track’s simplicity—both in its instrumentation and arrangement—allows the focus to remain on the depth of the emotions conveyed through Stapleton’s voice and the lyrical honesty that drives the song. The heart-wrenching delivery of the lines “fire away” serves as a metaphor for the emotional volatility that often accompanies self-doubt and inner turmoil. Despite the heavy subject matter, the song carries a sense of hope, suggesting that love can be a powerful force for healing. Fire Away is one of Stapleton’s most vulnerable songs, offering an unflinching look at the darkness that can cloud our minds, while also shining a light on the possibility of redemption and emotional release.
7. Nobody to Blame (2015)
Nobody to Blame, from Chris Stapleton’s debut album Traveller, is a classic country song with a modern twist, blending traditional elements with Stapleton’s signature soul-infused style. The track tells the story of heartbreak and regret, where the narrator comes to terms with the fact that they alone are responsible for the end of their relationship. The song’s catchy chorus and relatable lyrics immediately draw listeners in, with Stapleton’s raspy voice delivering the pain of loss with an honest vulnerability. The upbeat tempo, paired with the strong rhythm section and steel guitar, gives the song a classic country feel, while Stapleton’s raw delivery adds a layer of depth that elevates it beyond a typical breakup song. As the narrator acknowledges their role in the breakup, there’s a sense of self-awareness and accountability that makes Nobody to Blame a refreshing take on the genre. The song’s blend of heartfelt emotion and toe-tapping rhythm has made it a fan favorite, earning Stapleton critical acclaim and solidifying his place in country music’s contemporary scene.
8. Traveller (2015)
The title track from Chris Stapleton’s debut album Traveller is an introspective and reflective anthem that captures the spirit of wandering and searching for meaning in life. The song’s stripped-back instrumentation and soulful delivery highlight Stapleton’s knack for conveying deep emotion through simplicity. Lyrically, Traveller is a meditation on the feeling of restlessness that comes with life’s uncertainties—whether in love, work, or personal identity. The song’s raw honesty invites listeners to reflect on their own journeys and the desire for something more. With his signature gravelly voice, Stapleton paints a picture of someone on the road, both literally and metaphorically, searching for purpose and understanding. The track resonates with anyone who has ever felt like a wanderer, caught between the past and the future, and unsure of where they’re headed. The sparse arrangement and emotionally charged delivery make Traveller a deeply personal song that resonates with those who have experienced the uncertainty of life’s journey.
9. Whiskey and You (2015)
Whiskey and You is one of Chris Stapleton’s most emotionally raw and vulnerable tracks, showcasing his ability to convey heartbreak and longing through both his voice and songwriting. Featured on his 2015 album Traveller, the song speaks to the pain of losing a loved one and the solace found in substances like whiskey. The minimal instrumentation puts Stapleton’s powerful, gravelly voice at the forefront, allowing him to communicate the depth of the emotions behind the lyrics. As he sings about drowning sorrows in whiskey, the song also explores the damaging effects of using alcohol as a coping mechanism. It’s a poignant reflection on the struggle to move on after a broken relationship, and the sense of emptiness that remains in the absence of love. With its haunting melody and stripped-down arrangement, Whiskey and You becomes a heartbreaking meditation on the ways we try to numb our pain. Stapleton’s haunting delivery makes the song one of his most emotionally powerful and universally relatable tracks, resonating with anyone who has experienced the agony of love lost and the fight to let go.
10. Millionaire (2017)
Millionaire, from Chris Stapleton’s 2017 album From A Room: Volume 2, is a feel-good celebration of love and gratitude, wrapped in an upbeat and joyful melody. Originally written by Kevin Welch, Stapleton’s version infuses the song with his soulful, heartfelt vocals and a warmth that makes it an instant favorite. The song’s lyrics express a love so deep that the narrator feels richer than any millionaire could ever be, proving that love and gratitude are the true sources of wealth. The lively tempo, combined with Stapleton’s passionate delivery and the infectious melody, creates an atmosphere of joy and contentment. There’s an undeniable sense of celebration throughout the track, as Stapleton sings about the simple pleasures of life—those that money can’t buy. The song’s uplifting tone and feel-good message make it a perfect anthem for anyone who values the intangible things in life, like love, family, and meaningful connections. Millionaire is a song that radiates positivity and warmth, reminding listeners that sometimes, the greatest riches are found in the simplest moments.
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.
