Chris Stapleton is a name that resonates deeply within the world of country music and beyond. With a soulful voice that cuts straight to the core and lyrics that blend raw emotion with masterful storytelling, Stapleton has become one of the most powerful and beloved artists of our time. Whether it’s heart-wrenching ballads or foot-stomping anthems, his music transcends genres, appealing to fans of country, rock, blues, and soul alike. From his breakout solo album Traveller to his numerous collaborations with icons across the music industry, Stapleton’s songs have not only dominated the charts but also touched the hearts of millions worldwide.
In this article, we’re counting down the top 10 most popular Chris Stapleton songs of all time. These tracks have defined his career, showcasing his immense talent as both a songwriter and performer. Whether you’re a long-time fan or just discovering his music, this list will take you on a journey through his best hits, from the gritty, whiskey-soaked notes of “Tennessee Whiskey” to the hauntingly beautiful “Broken Halos.” Get ready to dive into the songs that cemented Stapleton’s legacy as a true modern-day music legend.
1. Tennessee Whiskey (2015)
“Tennessee Whiskey” is one of those rare songs that feels like it’s been around forever, but Chris Stapleton’s 2015 version gave it new life in a way that’s unforgettable. Originally written by Dean Dillon and Linda Hargrove, this song had been recorded by several artists before Stapleton took it on, but his rendition on the Traveller album made it iconic. His voice, which blends soulful blues with classic country, is perfectly suited to the song’s slow, smooth melody. In Stapleton’s hands, “Tennessee Whiskey” feels like a conversation between a man and his past, comparing the feeling of being loved to the warm, soothing burn of whiskey. His raw, emotional delivery of lines like “you’re as smooth as Tennessee whiskey” elevates the song, turning it into a love anthem that crosses genres, resonating with fans of country, blues, and R&B alike. The track has since become a staple in his live performances, often met with roaring applause. It’s not just a song—it’s a journey through heartache, healing, and love. For many, “Tennessee Whiskey” is the track that defines Chris Stapleton’s career and cements his place as a country music legend.
2. Broken Halos (2017)
Released in 2017 on his From A Room: Volume 1 album, “Broken Halos” is one of Chris Stapleton’s most heartfelt songs, filled with emotion and introspection. Co-written with his longtime collaborator Mike Henderson, the track feels like a deeply personal exploration of grief, loss, and the unanswered questions that often accompany those emotions. Stapleton’s voice carries a weight of sorrow, yet there’s a sense of hopefulness intertwined with the pain. He sings about the “broken halos” of those who have left us, acknowledging the things we can’t fix or fully understand. The song’s simplicity—an acoustic guitar paired with Stapleton’s raw, soulful vocals—gives it a timeless quality, making it resonate deeply with listeners. In 2018, “Broken Halos” went on to win the Grammy Award for Best Country Song, cementing its place as one of Stapleton’s most cherished tracks. Whether you’re mourning a loss or simply reflecting on life’s unpredictability, this song offers both solace and a reminder to appreciate the moments we have. It’s no wonder this powerful track has become a fan favorite and remains a pivotal part of Stapleton’s discography.
3. Fire Away (2015)
“Fire Away” from Chris Stapleton’s Traveller album is an emotional rollercoaster, wrapped in haunting melodies and heart-wrenching lyrics. Released in 2015, the song delves deep into the complexities of love, heartache, and personal battles. Stapleton’s soulful, gravelly voice brings an intense vulnerability to the track, making every word feel raw and real. The song explores themes of mental health, emotional pain, and the toll these struggles take on relationships, which are further amplified in its powerful music video. The imagery in “Fire Away” paints a picture of someone battling inner demons, begging to be understood and supported while at the same time pushing loved ones away. The guitar’s mournful chords, paired with Stapleton’s impassioned delivery, create an atmosphere that resonates with anyone who’s experienced personal struggles or seen a loved one go through dark times. It’s this emotional depth and the graceful way Stapleton handles difficult topics that make “Fire Away” stand out in his catalog. The track is not just a song—it’s a call for compassion and understanding in the face of hardship, and it continues to resonate deeply with fans.
4. Starting Over (2020)
Released as the title track of his 2020 album, “Starting Over” couldn’t have come at a better time. In the midst of global uncertainty, Chris Stapleton delivered a song that felt like a breath of fresh air, offering a message of hope, resilience, and renewal. With its stripped-back, acoustic arrangement, the song puts Stapleton’s rich, soulful voice front and center, allowing the optimistic lyrics to truly shine. The theme of the song—leaving the past behind and embracing new beginnings—is universally relatable, especially in times of change or challenge. It’s a song that speaks to anyone who has ever faced the need to pick up the pieces and move forward, no matter how difficult the journey may seem. The lyrics, simple yet profound, offer a sense of comfort: “This might not be an easy time, there’s rivers to cross and hills to climb.” As with many of Stapleton’s best works, “Starting Over” feels deeply personal yet resonates broadly with listeners. It quickly became a fan favorite, its message of hope striking a chord with those looking for light at the end of the tunnel.
5. Parachute (2015)
“Parachute,” one of the standout tracks from Chris Stapleton’s 2015 Traveller album, showcases a different side of the artist—a more upbeat, rock-infused sound that still retains his signature soulful grit. The song’s driving guitar riff and energetic tempo make it instantly engaging, but it’s Stapleton’s powerhouse vocals that truly elevate the track. He sings about loyalty and protection, with the lyrics metaphorically offering himself as a “parachute” for someone in need. It’s a promise of steadfast devotion in times of trouble, a message of being there for someone when life gets tough. The urgency in Stapleton’s voice, combined with the gritty instrumentation, creates an anthemic feel that makes “Parachute” one of those songs you can’t help but turn up loud. It’s a testament to his versatility as an artist, seamlessly blending country, rock, and blues into a sound that is uniquely his own. “Parachute” became one of Stapleton’s most popular songs, further solidifying his place as one of the most dynamic and powerful voices in country music today. The track’s energy and heartfelt message continue to resonate with listeners, making it a fan favorite.
6. Nobody to Blame (2015)
“Nobody to Blame” is one of those songs that strikes a chord with just about anyone who’s gone through a tough breakup. Released in 2015, this track from Chris Stapleton’s Traveller album has a bluesy, almost honky-tonk feel, driven by Stapleton’s gravelly voice and raw emotional honesty. The lyrics tell the story of a man who admits that the downfall of his relationship is entirely his own doing. There’s a kind of resigned acceptance in the way Stapleton sings the chorus, “I got nobody to blame but me,” and it’s this candidness that makes the song so relatable. The catchy melody and blues-infused guitar riffs give the track a lively, toe-tapping rhythm, making it hard not to sing along, even if the subject matter is bittersweet. “Nobody to Blame” quickly became a staple on country radio and earned Stapleton the 2016 CMA Award for Song of the Year. It’s a standout track not just for its musicality, but for its ability to capture the complexities of taking responsibility for your own mistakes in a relationship, all while keeping listeners hooked.
7. Traveller (2015)
The title track of Chris Stapleton’s breakout album, “Traveller,” is a deeply introspective song that encapsulates the journey of life—both metaphorically and literally. Released in 2015, the song’s wandering melody and reflective lyrics explore the sense of searching for meaning and purpose while traveling down life’s winding roads. The beauty of “Traveller” lies in its simplicity: Stapleton’s soulful voice paired with a sparse arrangement allows the weight of the lyrics to truly sink in. The song was written during a personal time of reflection for Stapleton, who was grappling with the loss of his father while traveling across the country. This sense of longing and soul-searching is palpable in the song, making it resonate deeply with listeners who have experienced similar moments of reflection and uncertainty. “Traveller” has become a fan favorite, not only for its haunting melody but also for its personal significance in Stapleton’s career. It’s a song that perfectly captures the feeling of being in transition—whether it’s on the road or in life—and it remains one of the most poignant tracks in Stapleton’s impressive catalog.
8. You Should Probably Leave (2020)
“You Should Probably Leave” is one of those songs that perfectly captures the tension between desire and knowing what’s right. Released in 2020 on Chris Stapleton’s Starting Over album, this track has a sultry, bluesy vibe that draws listeners in from the first note. The song tells the story of two people who are clearly attracted to each other but know that being together is a bad idea. The push and pull between temptation and logic is palpable in both the lyrics and Stapleton’s smoky, soulful delivery. Lines like “I know you and you know me, and we both know where this is gonna lead” perfectly capture that moment of hesitation before giving in to a familiar mistake. The slow-burn melody adds to the song’s allure, creating an atmosphere of late-night reflection and regret. “You Should Probably Leave” is a standout track not just for its clever storytelling but also for its emotional complexity. It’s a song that many listeners can relate to, balancing vulnerability with strength, and it further proves Stapleton’s skill in crafting deeply human, emotionally resonant music.
9. Whiskey and You (2015)
“Whiskey and You” is one of the most gut-wrenching songs in Chris Stapleton’s catalog, showcasing his ability to convey deep emotion with nothing more than his voice and a guitar. Featured on his 2015 Traveller album, the song strips away any unnecessary frills, leaving just Stapleton’s raw, aching vocals and sparse instrumentation. The lyrics draw a direct comparison between the pain of lost love and the burn of whiskey, with both offering temporary relief but no real solution. There’s a haunting simplicity to lines like “It’s not the whiskey, it’s not the you that makes me feel the way I do,” emphasizing the loneliness and heartache at the core of the song. Stapleton’s delivery is filled with sorrow and regret, making it impossible not to feel the weight of the emotions he’s conveying. “Whiskey and You” has become a fan favorite for its stark honesty and emotional depth, proving that sometimes less is more when it comes to storytelling in music. The song remains a masterclass in conveying heartache through song, with Stapleton’s voice acting as the perfect vehicle for such raw emotion.
10. Millionaire (2017)
Chris Stapleton’s cover of “Millionaire,” originally written by Kevin Welch, is a feel-good love song that brings a refreshing sense of joy and contentment to his otherwise often heavy discography. Featured on his 2017 album From A Room: Volume 2, “Millionaire” is a celebration of love’s riches over material wealth. The song’s catchy, laid-back groove is the perfect backdrop for Stapleton’s soulful vocals, which glide effortlessly over the melody. The lyrics express a sentiment that love is the greatest fortune anyone can have, with lines like “They say love is more precious than gold” reinforcing the idea that true happiness comes from relationships, not money. Stapleton’s version of the song has a warmth and sincerity that makes it feel genuine and heartfelt, a reminder of the simple joys in life. “Millionaire” became a fan favorite for its uplifting message and feel-good vibe, standing out as one of the highlights of Stapleton’s catalog. It’s a song that brings a smile to your face and reminds you of the things that truly matter, proving that Stapleton can deliver joy just as powerfully as he can deliver sorrow.