Chris Stapleton is more than just a country music icon—he’s a storyteller, a powerhouse vocalist, and a soul-stirring artist whose music transcends genres. From heartfelt ballads to foot-stomping anthems, Stapleton’s songs are a beautiful blend of raw emotion, striking lyricism, and his signature raspy, blues-infused voice. With a career that has earned him countless accolades, including Grammy Awards and multiplatinum records, Stapleton has become a household name not just in country music, but in the broader world of music lovers everywhere.
In this article, we’ll dive into the top 10 most popular Chris Stapleton songs of all time—tracks that have defined his career and captured the hearts of millions. Whether you’re a die-hard fan or a newcomer looking to explore his greatest hits, this list showcases the very best of Stapleton’s artistry. From soulful serenades like “Tennessee Whiskey” to hard-hitting tunes like “Parachute,” each song tells a story that resonates deeply with listeners. Get ready to be swept away by the magic of Chris Stapleton’s music as we count down his most iconic songs that have left an indelible mark on the music world. Let’s dive in and celebrate the genius of this modern legend!
1. Tennessee Whiskey (2015)
When Chris Stapleton released his rendition of “Tennessee Whiskey” on Traveller in 2015, he took a classic country song and turned it into something entirely his own. Originally written by Dean Dillon and Linda Hargrove, and first recorded by David Allan Coe in 1981, the song later gained recognition through George Jones’ version in 1983. However, it was Stapleton’s blues-infused, slow-burning performance that made it an instant classic for a new generation. His smooth, soulful vocals, paired with a stripped-down arrangement reminiscent of an R&B ballad, gave the song a fresh, deeply emotional feel. The lyrics compare a woman’s love to the warmth of Tennessee whiskey and the sweetness of honey, making it an intoxicating love song in every sense. The live duet with Justin Timberlake at the 2015 CMA Awards further propelled the song to mainstream success, showcasing Stapleton’s raw talent and cementing his place as a powerhouse in modern country music. His version of “Tennessee Whiskey” is more than just a cover—it’s a transformation, blending country, blues, and soul in a way that makes it one of the most unforgettable tracks of his career.
2. Broken Halos (2017)
“Broken Halos,” from From A Room: Volume 1 (2017), is a beautifully poignant song that resonates with themes of loss, grief, and faith. The song, co-written with Mike Henderson, was inspired by personal experiences, including the loss of Stapleton’s close friend. With its stripped-down acoustic arrangement and gospel-tinged harmonies, “Broken Halos” carries a weight of sorrow but also a sense of comfort. The lyrics paint a picture of angels who have done their work on Earth and moved on, serving as a reminder of the fleeting nature of life. The simplicity of the melody allows Stapleton’s raw, emotional vocals to take center stage, making every word hit with profound sincerity. The song won the Grammy for Best Country Song in 2018, further solidifying its impact. “Broken Halos” isn’t just a song—it’s a heartfelt tribute to those we’ve lost, offering solace to anyone who has ever struggled to understand the mysteries of life and death. It stands as one of Stapleton’s most moving and deeply personal works.
3. Parachute (2015)
“Parachute,” one of the standout tracks from Traveller (2015), showcases Stapleton’s ability to seamlessly blend country, rock, and blues into something truly electrifying. The song kicks off with a driving rhythm and an urgent energy that sets it apart from his slower, more introspective ballads. Lyrically, it’s a declaration of unwavering love and devotion—he promises to be there for his partner no matter what, like a parachute in times of need. The strong imagery and metaphorical depth make it a powerful love song, but the rough-edged delivery gives it an anthemic, almost rebellious feel. Stapleton’s raspy vocals, paired with the song’s pulsing beat, create an infectious energy that makes it one of his most dynamic performances. “Parachute” is a testament to Stapleton’s versatility, proving that he can craft both heartfelt ballads and high-energy tracks with equal mastery. Whether performed live or played through speakers, this song never fails to captivate.
4. Starting Over (2020)
“Starting Over,” the title track of Stapleton’s 2020 album, is a beautifully optimistic song about new beginnings and taking chances. Unlike some of his more intense, blues-heavy tracks, this one has a light, almost breezy feel, driven by acoustic guitar and heartfelt lyrics. Co-written with longtime collaborator Mike Henderson, the song speaks to the universal desire for fresh starts and second chances, making it especially poignant in a world that constantly changes. The simplicity of the arrangement allows Stapleton’s warm, soulful voice to shine, creating an atmosphere of hope and renewal. The lyrics acknowledge life’s difficulties but emphasize the beauty of moving forward, making it a song of encouragement for anyone facing change. “Starting Over” resonated deeply with listeners upon its release, as many found comfort in its hopeful message. It stands as a testament to Stapleton’s ability to capture real-life emotions in a way that feels deeply personal yet universally relatable.
5. Fire Away (2015)
“Fire Away,” from Traveller (2015), is one of Stapleton’s most emotionally powerful songs, tackling themes of love, pain, and the struggles that come with both. The song’s swelling instrumentation, combined with Stapleton’s impassioned vocal delivery, makes for a truly heartbreaking listening experience. The lyrics depict a man willing to endure the emotional pain inflicted by his lover, showcasing a raw and vulnerable side to love that isn’t always easy to talk about. While the song itself is moving on its own, the accompanying music video—depicting the struggles of mental illness and the devastating impact it can have on relationships—adds an even deeper layer of meaning. Stapleton’s ability to convey emotion through his voice is unparalleled, and in “Fire Away,” he delivers a performance so intense that it lingers long after the song ends. It’s a testament to the depth and authenticity of his songwriting, proving that country music can be just as powerful and thought-provoking as any other genre.
6. Millionaire (2017)
Originally written and recorded by singer-songwriter Kevin Welch, “Millionaire” found new life in Chris Stapleton’s hands when he included it on From A Room: Volume 2 in 2017. Stapleton’s version takes the song’s already warm, feel-good energy and amplifies it with his signature blend of country, blues, and soul. The song’s lyrics revolve around the idea that true wealth isn’t measured in money but in love and happiness, a sentiment that Stapleton delivers with effortless charm. His wife, Morgane Stapleton, provides stunning harmonies that add an extra layer of depth and richness to the track, making it feel even more intimate and heartfelt. The lighthearted acoustic arrangement, complete with a bluesy groove, gives the song a laid-back, easygoing feel that makes it impossible not to smile while listening. “Millionaire” is a perfect example of Stapleton’s ability to take a great song and make it even better, infusing it with his own soulful touch. It stands out as one of his most joyful and uplifting tracks, a reminder that the best things in life can’t be bought.
7. Whiskey and You (2015)
Few songs capture heartbreak as honestly and painfully as “Whiskey and You.” Originally written by Chris Stapleton and Lee Thomas Miller, the song first appeared on Tim McGraw’s 2007 album Let It Go before Stapleton recorded his own stripped-down version for Traveller in 2015. With nothing but an acoustic guitar and his raw, aching vocals, Stapleton delivers a gut-wrenching performance that lays bare the pain of lost love and self-destruction. The lyrics compare the temporary relief of whiskey to the lingering hurt of a breakup, creating a powerful metaphor for emotional pain. Every line is heavy with regret, and Stapleton’s voice carries the weight of a man who has been through it all. The stark simplicity of the song makes it all the more effective—there’s no need for elaborate production when the storytelling is this strong. “Whiskey and You” is a masterclass in songwriting and performance, proving that sometimes, the simplest songs are the most powerful.
8. Traveller (2015)
As the title track of his breakthrough album, “Traveller” is a deeply introspective song that captures the restless spirit of a man always on the move. Written while Stapleton was on a road trip following the death of his father, the song reflects on life’s journey—both literally and metaphorically. With its steady rhythm and thoughtful lyrics, “Traveller” feels like an anthem for those who are constantly searching for something more. Stapleton’s rich, weathered voice brings a sense of wisdom and experience to the song, making it resonate with anyone who has ever felt like they don’t quite belong in one place. The production is simple yet effective, allowing the song’s message to shine through without distraction. “Traveller” serves as the perfect introduction to Stapleton’s music, encapsulating everything that makes him such a compelling artist—his honest storytelling, his soulful voice, and his ability to blend genres effortlessly. It’s more than just a song; it’s a statement of who he is as an artist and as a person.
9. Nobody to Blame (2015)
“Nobody to Blame” is one of the most hard-hitting songs on Traveller, blending country storytelling with bluesy grit. The song tells the story of a man who has lost everything in a breakup, from his house to his car to even his fishing pole, yet he acknowledges that he has no one to blame but himself. It’s a classic country theme—heartache, regret, and self-inflicted misery—but Stapleton’s passionate delivery makes it feel fresh and deeply personal. The song’s slow-burning intensity builds with every verse, culminating in a chorus that feels both defiant and full of sorrow. The rawness of Stapleton’s vocals, combined with the bluesy guitar work, gives the song a haunting quality that lingers long after it ends. “Nobody to Blame” became one of Stapleton’s first big hits on country radio, introducing him to a wider audience and proving that his brand of country music had a place in the mainstream. It’s a song about mistakes, consequences, and the painful process of owning up to them—something nearly everyone can relate to.
10. You Should Probably Leave (2020)
“You Should Probably Leave,” from Stapleton’s 2020 album Starting Over, is a beautifully bittersweet song about two people who can’t resist each other—even though they know they should. The song captures the push-and-pull of an on-again, off-again relationship, where the attraction is undeniable, but the outcome is always the same. The smooth, almost jazzy melody sets it apart from some of Stapleton’s grittier tracks, giving it a laid-back yet emotionally charged feel. His vocals are tender and controlled, perfectly conveying the tension between desire and self-restraint. The storytelling in this song is particularly strong, painting a vivid picture of two people caught in a cycle they can’t break. “You Should Probably Leave” is proof that Stapleton excels not only at powerhouse ballads but also at subtle, nuanced performances. The song’s gentle groove, combined with its relatable lyrics, makes it one of his most compelling and memorable tracks. It’s the kind of song that stays with you, echoing the struggles of knowing what’s right but wanting what’s wrong.
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.
