Few artists in modern music have captured the hearts of fans across genres quite like Chris Stapleton. With his soulful voice, masterful songwriting, and raw, emotional performances, Stapleton has become a defining figure in country music—and beyond. His unique ability to blend blues, rock, and country has earned him a reputation as one of the most authentic and versatile artists of our time. Whether he’s belting out powerful anthems or delivering tender ballads, Stapleton’s music resonates with listeners on a deeply personal level.
From his breakout single Tennessee Whiskey to the chart-topping Broken Halos, Stapleton’s catalog is filled with unforgettable tracks that showcase his unparalleled talent. But which of his songs truly stand out as fan favorites? In this article, we’re diving into the top 10 most popular Chris Stapleton songs of all time—those iconic tracks that have defined his career and left an indelible mark on the music world.
Whether you’re a lifelong fan or a newcomer to his music, prepare to be reminded why Chris Stapleton is a force to be reckoned with. These songs will stir your soul, ignite your emotions, and remind you why his name is etched in the annals of music history. Let’s dive in!
1. Tennessee Whiskey (2015)
A song that redefined modern country music, “Tennessee Whiskey” became an instant classic when Chris Stapleton released it on his 2015 debut album, Traveller. Though originally recorded by David Allan Coe and later popularized by George Jones, Stapleton’s rendition gave the song a whole new life with his signature blues-infused, soulful delivery. His rich, gravelly vocals paired with the slow, seductive groove transformed it into something beyond just a country ballad—it became a genre-blending masterpiece.
The song’s lyrics compare a deep, unwavering love to the smoothness of Tennessee whiskey and the sweetness of strawberry wine, creating vivid imagery that immediately resonates with listeners. Stapleton’s powerful vocal performance, backed by a bluesy, gospel-tinged arrangement, adds an emotional weight that makes every line feel deeply personal. His wife, Morgane Stapleton, harmonizes beautifully in the background, further amplifying the song’s intimacy and raw emotion.
“Tennessee Whiskey” quickly became the defining moment of Stapleton’s career, cementing him as one of the most soulful voices in country music. The song’s viral success following his CMA Awards duet with Justin Timberlake propelled him to mainstream recognition, proving that authenticity and pure talent could still captivate the masses. Today, it remains a staple of his live performances and a beloved favorite among fans.
2. Broken Halos (2017)
“Broken Halos” is one of Chris Stapleton’s most deeply emotional songs, offering a poignant reflection on loss and acceptance. Released in 2017 on his album From A Room: Volume 1, the song was inspired by the pain of losing loved ones and the struggle to understand why life can be so cruel. With its stripped-down acoustic arrangement, “Broken Halos” allows Stapleton’s soulful voice to take center stage, giving the song an intimate and heartfelt quality.
Lyrically, the song speaks of angels—people who touch our lives before they leave too soon—leaving behind only their “broken halos.” Instead of searching for answers that may never come, the song encourages listeners to find peace in cherishing the memories of those who have passed. The simplicity of the lyrics, combined with Stapleton’s raw vocal delivery, makes “Broken Halos” both deeply personal and universally relatable.
The song went on to win a Grammy Award for Best Country Song, solidifying its impact on fans and critics alike. It stands as a powerful anthem of healing and resilience, reminding listeners that even in the face of loss, love and memories endure.
3. Starting Over (2020)
“Starting Over” is a heartfelt anthem about embracing change and new beginnings. Released as the title track of Chris Stapleton’s 2020 album, the song offers a message of optimism wrapped in an easygoing, acoustic-driven melody. Its stripped-back production and gentle rhythm highlight Stapleton’s warm, soulful voice, allowing the lyrics to shine with sincerity and hope.
The song’s narrative centers on taking a leap of faith and leaving the past behind in pursuit of something better. Whether it’s a fresh start in a new place, a rekindled relationship, or a personal reinvention, “Starting Over” speaks to the courage it takes to move forward. The lyrics capture both the uncertainty and excitement of change, making it relatable to anyone standing at a crossroads in life.
Unlike some of Stapleton’s heavier, blues-infused tracks, “Starting Over” has a lightness to it that makes it feel comforting and reassuring. It’s a song of renewal, a reminder that even after hardship, there’s always an opportunity to begin again. This uplifting message, combined with Stapleton’s signature soulful delivery, made “Starting Over” one of his most beloved and critically acclaimed songs.
4. You Should Probably Leave (2020)
“You Should Probably Leave” is a masterful portrayal of temptation and emotional conflict, wrapped in Chris Stapleton’s signature blend of blues and country. Released in 2020 as part of his Starting Over album, this Grammy-winning song tells the story of two lovers who can’t seem to resist each other—even when they know their relationship is bound to end in heartache.
The song’s slow, moody groove perfectly complements its lyrics, which describe the tension between desire and self-restraint. Stapleton’s smoky, heartfelt vocals bring out the emotional weight of the story, making it clear that both characters know the right thing to do but struggle to follow through. The clever repetition of the phrase “You should probably leave” throughout the song builds an almost cinematic sense of inevitability.
With its smooth instrumentation and effortless flow, “You Should Probably Leave” showcases Stapleton’s ability to blend country storytelling with a bluesy, soul-infused sound. The song’s universal theme of forbidden love and bad decisions resonated with fans, making it one of his standout tracks from Starting Over.
5. Fire Away (2015)
“Fire Away” is one of Chris Stapleton’s most emotionally charged songs, tackling themes of love, pain, and resilience. Released in 2015 on his debut album Traveller, the song tells the story of someone willing to endure the emotional storms of a troubled relationship. The lyrics paint a picture of unconditional love, where the narrator invites their partner to “fire away”—to unleash their hurt and frustration while he stands steadfast.
The song’s haunting melody and Stapleton’s impassioned vocal delivery create an atmosphere of deep sorrow and devotion. The instrumentation starts off gentle but builds in intensity, mirroring the escalating emotions within the lyrics. While on the surface, “Fire Away” could be interpreted as a song about heartbreak, its meaning runs deeper, touching on themes of mental health struggles and the difficulty of supporting a loved one through their darkest moments.
The accompanying music video further amplifies the song’s weight, depicting the devastating impact of depression on a couple’s relationship. “Fire Away” remains one of Stapleton’s most powerful songs, showcasing his ability to blend raw emotion with masterful storytelling.
6. Millionaire (2017)
“Millionaire” is one of Chris Stapleton’s most uplifting and joyful songs, celebrating the idea that true wealth comes not from money, but from love. Released in 2017 on From A Room: Volume 2, the song showcases Stapleton’s warm, soulful voice and effortless charm, making it an instant fan favorite.
The lyrics paint a picture of a man who feels richer than any millionaire, not because of material possessions, but because of the love he shares with his partner. The chorus, with its catchy melody and feel-good message, radiates happiness and gratitude. Stapleton’s delivery is smooth and heartfelt, with his signature blend of blues, country, and rock adding depth to the song’s simple yet profound theme.
A standout feature of “Millionaire” is the harmony provided by Morgane Stapleton, whose vocals add a rich texture and warmth to the track. Their chemistry is undeniable, creating a sense of intimacy that makes the song feel even more genuine. The lighthearted, easygoing groove makes “Millionaire” a song that fans love to sing along to, and its timeless message ensures its place as one of Stapleton’s most beloved tracks.
7. Whiskey and You (2015)
Few songs capture the raw pain of heartbreak as powerfully as “Whiskey and You.” Released on Stapleton’s 2015 album Traveller, this stripped-down ballad is a haunting reflection on loss, regret, and self-destruction. With just an acoustic guitar and his aching voice, Stapleton lays bare the emotional turmoil of a man turning to alcohol to numb his pain.
The lyrics compare whiskey to a lost love, highlighting the painful reality that both offer comfort, but neither can truly heal a broken heart. Each verse is filled with sorrow and desperation, as the narrator struggles with the realization that drinking is only a temporary escape. Stapleton’s voice, filled with grit and longing, makes every word hit hard, bringing the song’s deep sadness to life.
Unlike some of his more polished productions, “Whiskey and You” thrives in its simplicity. The rawness of the performance makes it feel incredibly personal, as if Stapleton is pouring his soul into every note. This authenticity has made it one of his most emotionally resonant songs, deeply connecting with listeners who have faced their own battles with loss and heartache.
8. Traveller (2015)
“Traveller,” the title track of Chris Stapleton’s groundbreaking 2015 debut album, is a soulful anthem about self-discovery and the journey of life. With its introspective lyrics and soaring melody, the song perfectly captures the restless spirit of someone searching for meaning and direction.
The song’s verses tell the story of a wandering soul, someone who doesn’t stay in one place for too long, always chasing the horizon. The chorus, with its sweeping melody and evocative imagery, reinforces the idea that life itself is a journey, filled with twists, turns, and unexpected detours. Stapleton’s raspy, heartfelt delivery adds a layer of wisdom and experience, making it feel like he’s singing from a place of deep understanding.
Musically, “Traveller” blends country, blues, and folk influences, creating a rich and textured sound that mirrors the song’s themes. The instrumentation is warm and organic, allowing the song’s message to shine through without distraction. As the opening track on Traveller, this song set the tone for the entire album, showcasing Stapleton’s unique ability to blend storytelling with soul-stirring melodies. It remains a defining song in his career and a favorite among fans.
9. Nobody to Blame (2015)
“Nobody to Blame” is a fiery, blues-infused country song about facing the consequences of one’s own mistakes. Released in 2015 on Traveller, this track tells the story of a man whose bad decisions have cost him everything—including his relationship. With its driving rhythm and confessional lyrics, the song captures the pain of regret in a way that feels both personal and universal.
The lyrics paint a vivid picture of a breakup gone wrong, with the narrator watching as his ex systematically destroys everything he owns—from burning his clothes to throwing his guitars out into the yard. But instead of blaming her, he admits that he brought this on himself. This honest approach to heartbreak is one of the reasons “Nobody to Blame” resonated so deeply with fans—it’s a song about owning up to your mistakes, even when it hurts.
Stapleton’s gritty, soulful vocals bring an intensity to the song, making the emotion feel raw and real. The bluesy guitar riffs and steady beat give the track a sense of movement, almost like the wheels turning in the narrator’s mind as he reflects on what he’s lost. “Nobody to Blame” quickly became a fan favorite and one of Stapleton’s most recognized songs, earning critical acclaim and a CMA Award for Song of the Year.
10. Parachute (2015)
“Parachute” is one of Chris Stapleton’s most dynamic and high-energy songs, blending country, rock, and blues into a powerful anthem of devotion. Released on Traveller in 2015, the song tells the story of a man promising to be his lover’s unwavering support—her safety net when life gets tough. With its driving beat and passionate delivery, “Parachute” stands out as one of Stapleton’s most electrifying tracks.
The lyrics use the metaphor of a parachute to describe the singer’s commitment, reassuring his partner that he’ll always be there to catch her when she falls. This imagery, combined with Stapleton’s raw, impassioned vocal performance, creates a song that feels both deeply personal and universally relatable. The chorus, with its soaring melody and powerful rhythm, makes it anthemic—perfect for blasting on long drives or during moments of reflection.
Musically, “Parachute” leans into rock influences more than some of Stapleton’s other tracks, with its heavy drumbeat and gritty guitar riffs adding a sense of urgency and intensity. This fusion of sounds showcases his ability to push the boundaries of country music while still staying true to his roots. As a result, “Parachute” remains one of his most exhilarating and memorable songs, proving that Stapleton is just as skilled at delivering energetic, full-throttle performances as he is at crafting soulful ballads.
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.
