Few artists in modern country music have captivated audiences quite like Chris Stapleton. With his soulful voice, heartfelt lyrics, and a remarkable ability to blend country, blues, and rock, Stapleton has become a powerhouse in the music industry. His songs resonate deeply, telling stories of love, heartache, triumph, and resilience that connect with listeners across generations. From his breakout success with Traveller to his unforgettable collaborations with some of music’s biggest names, Stapleton has carved out a unique space in the hearts of fans worldwide.
In this article, we’re taking a journey through the top 10 most popular Chris Stapleton songs of all time. These tracks aren’t just hits; they’re anthems that define his artistry and have become staples in the playlists of country and music lovers everywhere. Whether you’re a long-time fan or new to his music, this list is guaranteed to remind you why Chris Stapleton is regarded as one of the greatest singer-songwriters of our time. So, grab your headphones and get ready to dive into the unforgettable melodies, raw emotion, and timeless storytelling that make these songs unforgettable. Let’s count them down!
1. “Tennessee Whiskey” (2015)
Chris Stapleton’s rendition of “Tennessee Whiskey,” originally released by David Allan Coe in 1981, quickly became a modern classic when it was featured on his 2015 debut album Traveller. Stapleton’s soulful interpretation of the song blends country and blues in a way that feels both timeless and fresh. His deep, raspy voice delivers the heartfelt lyrics with such emotion that it immediately resonates with anyone who has ever experienced the complexities of love and longing. The richness of his voice, paired with a stripped-back, bluesy arrangement, creates an atmosphere of raw vulnerability. What makes this track so impactful is how Stapleton makes it his own, adding his unique style while staying true to the spirit of the original. The performance was further solidified as a defining moment in his career when he performed it live with Justin Timberlake at the 2015 CMA Awards, a moment that made waves across the music world. Since then, “Tennessee Whiskey” has become an anthem for anyone who has ever sought solace in love or turned to music as a way to cope with heartache. The song’s timeless appeal lies in its emotional depth and Stapleton’s undeniable vocal power, making it a staple in country and blues music alike.
2. “Broken Halos” (2017)
“Broken Halos,” a standout track from Chris Stapleton’s From A Room: Volume 1, is a haunting, introspective ballad that showcases his ability to blend raw emotion with masterful storytelling. The song revolves around themes of loss, the fleeting nature of life, and the search for meaning in difficult times. Stapleton’s gravelly vocals add an undeniable weight to the poignant lyrics, giving the song an emotional intensity that hits listeners on a deeply personal level. The song’s acoustic-driven arrangement, with its sparse instrumentation and gentle rhythm, allows Stapleton’s voice to take center stage. It feels like a quiet conversation with a friend, a reminder of the brokenness that exists in the world, but also the hope that can be found in faith and the connections we make. “Broken Halos” won a Grammy for Best Country Song, and it’s easy to see why—it strikes a balance between sorrow and hope, capturing the universal experience of grief, while also pointing to the belief that even in brokenness, there’s beauty. Stapleton’s ability to express this emotional depth through music is one of the reasons “Broken Halos” has become one of his most beloved tracks, resonating deeply with fans worldwide.
3. “Parachute” (2015)
“Parachute,” from Stapleton’s debut album Traveller, is an energetic and uplifting track that highlights his incredible vocal range and dynamic musical style. The song starts with a lively, rhythmic beat and quickly builds into a full-throttle anthem of devotion and support. The lyrics, which promise unconditional love and unwavering support through thick and thin, are delivered with a fiery passion that matches the intensity of the music. Stapleton’s powerful voice soars above the dynamic instrumentation, conveying a sense of urgency and sincerity. It’s the kind of song that makes you want to stand up and cheer, a reminder that true love is about being there for someone no matter what. The song’s anthemic quality is perfect for live performances, where Stapleton’s energy and charisma are on full display. “Parachute” stands out as one of Stapleton’s most vibrant tracks, offering a refreshing contrast to the slower, more contemplative songs on Traveller. It’s an empowering, feel-good anthem that inspires listeners to lean on one another in times of need, making it a standout moment in Stapleton’s career and a fan favorite in his live shows.
4. “Fire Away” (2015)
“Fire Away,” also from Traveller, is a slow-burning ballad that delves into the complexities of love, vulnerability, and emotional turmoil. The song’s bluesy groove and stripped-back instrumentation provide the perfect backdrop for Stapleton’s raw, powerful vocals. His voice, full of grit and depth, brings an extra layer of emotion to the song, making every word feel personal and deeply felt. The lyrics explore the emotional challenges of being in a relationship where communication is difficult, and the fear of opening up runs deep. The phrase “fire away” becomes a metaphor for the pent-up emotions and unspoken words that need to be released. Stapleton’s delivery is unflinching, capturing the angst and rawness that comes with letting down one’s guard. The song’s slow, deliberate pace allows the listener to fully absorb the weight of the message, making it one of the most emotionally intense tracks on Traveller. “Fire Away” highlights Stapleton’s ability to tackle the tough, messy sides of relationships and human emotion with honesty and depth. It’s a song that continues to resonate with listeners who’ve experienced the vulnerability that comes with truly letting someone into your heart.
5. “Starting Over” (2020)
The title track from Chris Stapleton’s 2020 album Starting Over is a heartfelt anthem about embracing change and finding hope in new beginnings. With its warm acoustic arrangement and optimistic lyrics, the song offers a sense of reassurance for anyone going through a challenging transition. Stapleton’s voice, as always, is the focal point of the song—smooth and soulful, yet raw and full of life. His delivery conveys a sense of resilience and tenderness, making it clear that while starting over can be daunting, it also holds the promise of growth and renewal. The song’s gentle rhythm and optimistic vibe create a feeling of comfort and encouragement, as if Stapleton is offering a musical hug to anyone feeling uncertain or lost. The lyrics speak to the process of letting go of the past and embracing the unknown, a universal theme that resonates with people from all walks of life. “Starting Over” captures the essence of Stapleton’s artistry—he’s able to take a simple idea, like the idea of beginning again, and turn it into something both deeply personal and universally relatable. It’s a beautiful reminder that every ending is also a new opportunity, and a celebration of the courage it takes to start fresh.
6. “Nobody to Blame” (2015)
“Nobody to Blame,” from Chris Stapleton’s Traveller, is a gritty, blues-infused breakup anthem that explores the raw emotions of regret, responsibility, and heartbreak. With its stomping rhythm and soulful instrumentation, the song has a tough, no-nonsense energy that matches the blunt honesty of the lyrics. Stapleton’s raspy vocals, tinged with both sorrow and defiance, tell the story of a man who owns up to his mistakes in a failed relationship. The song’s straightforward approach—taking accountability for the end of a relationship without shifting blame—is refreshing in its honesty. There’s no sugar-coating here; instead, Stapleton embraces the painful truth that sometimes, we are the ones responsible for the breakdown of something that mattered. The song’s steady, bluesy beat and Stapleton’s vocal performance make it a cathartic experience for anyone who’s gone through a breakup and had to face their own shortcomings. “Nobody to Blame” stands as a reminder that sometimes the hardest thing to do is admit fault and move on. Its gritty, honest tone and relatable theme make it a powerful track in Stapleton’s catalog, one that resonates deeply with listeners who appreciate raw, unvarnished truth.
7. “You Should Probably Leave” (2020)
“You Should Probably Leave,” from Starting Over, is a bittersweet ballad that captures the emotional complexity of a relationship on the brink of imploding. The song’s smooth, soulful melody perfectly complements the sense of uncertainty and longing in the lyrics. Stapleton’s delivery is nothing short of mesmerizing, as he paints a picture of a relationship that’s both intoxicating and doomed. The lyrics speak to the internal conflict of wanting to stay in a passionate, yet ultimately unsustainable relationship, where both parties are aware that it’s time to let go. Stapleton’s voice, with its rich, emotive quality, expresses the tension and heartache of the situation, making it a relatable experience for anyone who has been in a similar scenario. The song’s slow-burning groove creates a sense of melancholy, making the moment of decision feel all the more significant. “You Should Probably Leave” perfectly captures that in-between moment of desire and resignation, where everything feels uncertain, and the future is unclear. It’s a masterful example of Stapleton’s ability to blend soul, country, and blues, creating a timeless song that resonates deeply with listeners. The song’s smooth, reflective mood makes it a standout track on Starting Over, showcasing Stapleton’s depth as an artist.
8. “Millionaire” (2017)
“Millionaire,” from From A Room: Volume 2, is an infectious, feel-good track that radiates joy and gratitude. The song, originally written by Kevin Welch, is a celebration of love and the simple pleasures in life. Stapleton’s version infuses the song with his signature soulful delivery, making it impossible not to smile as you listen. The upbeat, toe-tapping rhythm creates an instant sense of happiness, while Stapleton’s rich vocals provide the perfect vehicle for the song’s message. The lyrics remind us that love is the ultimate wealth, far surpassing any material riches we might accumulate. The beauty of “Millionaire” lies in its simplicity; it’s a reminder that the most valuable things in life aren’t things at all, but the connections we share with others. Stapleton’s performance brings warmth and sincerity to the song, creating an uplifting atmosphere that makes it impossible to stay still. “Millionaire” is a refreshing departure from the heavier, more introspective tracks on From A Room: Volume 2, offering a moment of lightness and joy. It’s a perfect example of Stapleton’s ability to take a simple concept—love—and turn it into something that feels both deeply personal and universally relatable.
9. “Whiskey and You” (2015)
“Whiskey and You,” from Traveller, is a raw, stripped-down ballad that delves deep into the pain of heartbreak and self-reflection. The song is built around a mournful acoustic guitar and Stapleton’s emotive, gravelly voice, which conveys the weight of the lyrics with remarkable intensity. The song speaks to the feeling of being haunted by the past, and the way we sometimes turn to vices—like whiskey—to numb the pain of lost love. The narrator reflects on his own role in the heartbreak, acknowledging his struggles with addiction and emotional vulnerability. There’s a profound sense of loneliness in the song, as the narrator is left to confront his demons on his own. Stapleton’s delivery is both haunting and beautiful, perfectly capturing the desolation and regret that comes with losing someone important. “Whiskey and You” is a masterclass in simplicity; it doesn’t rely on flashy instrumentation or complicated arrangements. Instead, it lets the lyrics and vocals do the heavy lifting, creating a raw and powerful emotional experience for the listener. It’s one of the most deeply emotional tracks on Traveller, a true showcase of Stapleton’s ability to express pain and heartbreak through music.
10. “Traveller” (2015)
“Traveller,” the title track from Chris Stapleton’s debut album, is an introspective journey through the highs and lows of life. The song’s reflective lyrics explore themes of searching for one’s place in the world, facing personal challenges, and the bittersweet realization that the journey itself is what truly matters. Stapleton’s soulful voice, rich and resonant, carries the weight of the lyrics with a depth that makes each word feel significant. The music itself is equally soulful, with a warm, acoustic arrangement that complements the introspective nature of the song. “Traveller” captures the essence of Stapleton’s artistry—his ability to take personal experiences and turn them into universal stories that connect with listeners on a deep level. The song speaks to the feeling of being on the road, both literally and metaphorically, trying to make sense of life’s journey and the lessons learned along the way. The understated beauty of “Traveller” lies in its simplicity; there’s no need for grandiosity here—just heartfelt storytelling and emotion. This track sets the tone for the rest of the album, establishing Stapleton as an artist with the rare ability to blend authenticity with musicality. It’s a song that stays with you long after the last note fades, resonating deeply in its quiet sincerity.
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.
