Few artists in country music have captured hearts and crossed genres quite like Chris Stapleton. With his gritty voice, soulful lyrics, and undeniable stage presence, Stapleton has become a household name, not just in country circles, but across the music world. Whether he’s belting out an emotional ballad or shredding through a rock-infused anthem, Stapleton’s songs carry a raw authenticity that resonates deeply with listeners.
From his breakout solo debut Traveller to his chart-topping collaborations, Stapleton has delivered hit after hit, each one leaving an indelible mark on the music industry. His unique blend of country, blues, and Southern rock has garnered him accolades, awards, and a devoted fanbase that spans across generations.
In this article, we take a look at the top 10 most popular Chris Stapleton songs of all time. These tracks showcase the very best of his artistry, from the soul-stirring ballads to the foot-stomping anthems. Whether you’re a long-time fan or new to his music, this list is sure to remind you why Chris Stapleton continues to reign as one of the most influential voices in modern country music.
1. Tennessee Whiskey (2015)
Chris Stapleton’s rendition of “Tennessee Whiskey,” released in 2015, took an old classic and made it his own, transforming the song into an unforgettable hit that resonates across genres. Originally penned by country legends Dean Dillon and Linda Hargrove and first popularized by George Jones in the ’80s, Stapleton brought a refreshing new depth and soul to this beloved track. His rich, bluesy voice adds a layer of raw emotion that gives the song a feeling of vulnerability and power, making every note sound deeply personal. With a slow-burning arrangement blending blues, R&B, and country, Stapleton’s version breathes life into a story of love, redemption, and self-discovery.
The song’s groove, built on a steady bassline and smooth guitar, has a soulful intensity that instantly pulls listeners in. Stapleton’s voice is a masterclass in control and emotional delivery, seamlessly moving between tender whispers and powerful belts, drawing out the heartbreak and passion in the lyrics. “Tennessee Whiskey” was not only a commercial success, but it also solidified Stapleton’s place as a force in modern music, crossing the boundaries between country, soul, and blues. His rendition continues to captivate listeners with its timeless quality, proving that true artistry can make even an old song feel brand new.
2. Parachute (2015)
“Parachute,” another standout track from Stapleton’s 2015 debut album Traveller, shows his versatility and ability to blend rock energy with his country roots. This song quickly became a fan favorite, largely due to its driving rhythm, memorable chorus, and Stapleton’s gritty, passionate vocals. “Parachute” tells a story of devotion and resilience, capturing the fierce loyalty of a person willing to be a “parachute” for a loved one—a steady support no matter how far or fast they fall.
Stapleton’s raspy voice carries a sense of urgency, matching the emotional intensity of the lyrics with ease. The song’s relentless beat, powered by rhythmic guitar and energetic drums, adds an edge that keeps listeners hooked. It’s a track that stands out not only for its message of love and support but also for its powerful, almost anthem-like quality that resonates deeply. “Parachute” remains a staple in Stapleton’s live performances, as it perfectly showcases his unique blend of raw energy and soulful storytelling. Fans love the song’s straightforward message and driving force, making it a testament to Stapleton’s ability to create music that’s as relatable as it is electrifying.
3. Fire Away (2015)
“Fire Away,” another hit from Traveller, dives deep into themes of vulnerability, love, and resilience, showcasing Stapleton’s talent for soulful, emotional storytelling. Released in 2015, this hauntingly beautiful ballad invites listeners into an intimate moment between two people facing life’s storms together. With lyrics that encourage openness and honesty, Stapleton encourages his partner to “fire away” with whatever pain or frustration they’re feeling, as he’s there to weather it with them.
Stapleton’s soulful voice is filled with raw emotion, every note carrying weight and authenticity. The song’s stripped-back arrangement allows his voice and the powerful lyrics to take center stage, creating an atmosphere that feels deeply personal. The music video for “Fire Away,” which tackles mental health and loss, amplifies the song’s impact, making it a powerful anthem for anyone who’s struggled with emotional pain. “Fire Away” continues to resonate as one of Stapleton’s most moving pieces, drawing fans with its sincerity and heart-wrenching beauty. It’s a reminder of the power of music to heal, to empathize, and to stand by us in the hardest times.
4. Broken Halos (2017)
Released on From A Room: Volume 1 in 2017, “Broken Halos” is one of Stapleton’s most profound songs, touching on themes of loss, faith, and acceptance. Written in memory of those we’ve lost too soon, the song speaks to the idea of broken halos—those who were once among us but have left a lasting impact. The track’s stripped-back, acoustic arrangement is a perfect backdrop for Stapleton’s soulful, powerful vocals, allowing the song’s message to take center stage.
Stapleton’s voice conveys both pain and acceptance, reflecting on the inevitable hardships of life while encouraging listeners to find peace. The song’s simplicity allows the lyrics to resonate with listeners on a deep, emotional level, as it speaks to universal experiences of grief and resilience. “Broken Halos” was widely praised for its authenticity and earned Stapleton a Grammy for Best Country Song, solidifying it as a modern classic. The song’s blend of hope and sorrow strikes a chord, reminding fans to find comfort in memory and faith, even in the face of loss.
5. Millionaire (2017)
“Millionaire,” released as part of From A Room: Volume 2 in 2017, is a feel-good love song that celebrates the richness of life through love rather than wealth. Originally written by Kevin Welch, Stapleton’s version radiates warmth and sincerity. His smooth, soulful voice combined with gentle guitar work creates a sound that’s both relaxing and uplifting, making “Millionaire” a favorite at weddings and celebrations.
The song’s easygoing rhythm and heartwarming lyrics convey a simple but powerful message: true wealth lies in love and connection, not material possessions. Stapleton’s voice brings a sense of contentment and gratitude to the track, capturing the essence of happiness found in the everyday moments shared with loved ones. “Millionaire” is a refreshing reminder of what really matters in life, and its positive message resonates with fans looking for music that uplifts. Stapleton’s heartfelt performance gives the song an enduring appeal, proving that sometimes, the most valuable things in life can’t be bought.
6. Nobody to Blame (2015)
“Nobody to Blame,” a standout track from Stapleton’s 2015 album Traveller, is a classic country song that dives into the theme of heartbreak and self-reflection. The lyrics tell the story of a man who realizes he’s to blame for the breakdown of his relationship, with Stapleton confessing his regrets and owning up to his mistakes. His gritty, powerful vocals perfectly capture the anguish of lost love and the sting of self-inflicted wounds.
The song’s catchy chorus and relatable lyrics struck a chord with fans, making it an instant hit. The raw emotion in Stapleton’s voice, combined with a driving rhythm and memorable melody, earned “Nobody to Blame” widespread acclaim, including a CMA Award for Song of the Year. The track remains a favorite among fans who appreciate Stapleton’s honesty and his ability to tap into the emotional core of his lyrics. It’s a song that’s both heart-wrenching and captivating, showcasing Stapleton’s talent for storytelling.
7. Starting Over (2020)
“Starting Over,” the title track from Stapleton’s 2020 album, is a song that speaks to new beginnings and the courage it takes to embrace change. Released during a time of global uncertainty, the song’s message of hope and resilience resonated deeply with listeners. Stapleton’s soulful vocals, accompanied by acoustic guitar and understated instrumentation, create a comforting atmosphere that feels both timeless and current.
The lyrics encourage listeners to find strength in fresh starts, offering a reminder that even in the face of challenges, there’s always an opportunity to begin again. “Starting Over” was praised for its honest, heartfelt message, blending folk, country, and Americana influences to create a sound that’s uniquely Stapleton’s. The song is a beacon of hope, capturing the spirit of resilience and reminding listeners that no matter how hard life gets, there’s always a way forward.
8. Traveller (2015)
“Traveller,” the title track of Stapleton’s debut album, released in 2015, is an introspective anthem about the journey of life. The lyrics reflect a desire to explore, to seek purpose, and to embrace the unknown with open arms. Stapleton’s powerful voice, combined with the song’s expansive arrangement, creates a feeling of wanderlust and introspection that resonates with anyone who’s ever set out on a journey, whether literal or metaphorical.
The track captures the essence of self-discovery, blending Stapleton’s soulful vocals with a wide-open sound that feels both grounding and freeing. “Traveller” set the tone for Stapleton’s career, marking him as an artist capable of blending deep emotion with masterful musicianship. It’s a song that speaks to the soul, inviting listeners to reflect on their own paths and the beauty of life’s journey.
9. You Should Probably Leave (2020)
“You Should Probably Leave,” from Stapleton’s Starting Over album, is a track that explores the complicated emotions that arise when love and logic collide. The lyrics capture the tension of knowing it’s time to walk away from a relationship, but feeling the undeniable pull of attraction that makes leaving hard. Stapleton’s smooth, soulful vocals bring both warmth and vulnerability to the song, making the listener feel the conflict in every line.
The song’s delicate guitar work and laid-back rhythm add to the bittersweet vibe, creating an atmosphere that’s both intimate and relatable. “You Should Probably Leave” was praised by fans and critics for its honest depiction of love’s complexities, showcasing Stapleton’s knack for tapping into the human heart. It’s a song that resonates with anyone who’s ever faced a difficult goodbye, proving that Stapleton knows how to capture those moments of tenderness and tension with finesse.
10. Whiskey and You (2015)
“Whiskey and You” is a stark, introspective ballad that showcases Stapleton’s raw vulnerability as he grapples with themes of loneliness, regret, and addiction. Released on Traveller in 2015, the song is stripped down to just Stapleton’s voice and an acoustic guitar, creating an intimate atmosphere that highlights the haunting lyrics. In this song, Stapleton tells the story of a man caught between the solace of whiskey and the pain of lost love.
The simplicity of the arrangement allows Stapleton’s powerful voice to shine, every line heavy with emotion. “Whiskey and You” has become a fan favorite, with its honesty and relatability drawing listeners who appreciate Stapleton’s willingness to confront life’s darker moments. The song is often cited as one of his most emotionally resonant tracks, a testament to Stapleton’s ability to capture the raw, unfiltered truth of heartache and the struggles that come with it.
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.
