Few artists in modern country music have managed to captivate audiences quite like Chris Stapleton. With his soulful voice, masterful songwriting, and deep connection to his roots, Stapleton has become a powerhouse in the music industry, transcending genres and touching hearts worldwide. From heart-wrenching ballads to electrifying anthems, his songs are a testament to raw emotion, authenticity, and unparalleled talent.
Whether you’re a lifelong fan or a newcomer to his music, there’s no denying the impact Stapleton’s songs have had on country music and beyond. His ability to blend blues, Southern rock, and country into a sound that’s uniquely his own has earned him critical acclaim and a devoted fanbase. With countless awards, chart-topping hits, and unforgettable performances, Stapleton’s music has become the soundtrack to love, heartbreak, and everything in between.
In this article, we’ll take a journey through Stapleton’s incredible discography to highlight the top 10 songs that have defined his career. These tracks showcase his versatility, vocal power, and storytelling prowess, cementing his place as one of the greatest artists of our time. So, grab your headphones and prepare to be swept away by the unforgettable sounds of Chris Stapleton!
1. “Tennessee Whiskey” (2015)
Chris Stapleton’s rendition of “Tennessee Whiskey” turned a decades-old country ballad into a modern classic. Originally written by Dean Dillon and Linda Hargrove, and previously recorded by David Allan Coe and George Jones, the song found new life in Stapleton’s blues-infused interpretation. His slow, soulful delivery, combined with a rich, smoldering melody, transforms the lyrics into a deeply intimate love song. His version feels like a smooth sip of whiskey itself—warm, strong, and lingering long after it ends. The song’s breakout moment came when Stapleton performed it alongside Justin Timberlake at the 2015 CMA Awards, sending it skyrocketing up the charts. The track helped establish Stapleton’s reputation as a genre-blending artist, effortlessly fusing country, blues, and soul into something timeless. “Tennessee Whiskey” became one of his most recognized songs, cementing his status as one of country music’s most powerful voices. His ability to take a song and make it uniquely his own is what sets him apart, and with this track, he gave the world a version of “Tennessee Whiskey” that will be remembered for generations.
2. “Broken Halos” (2017)
“Broken Halos,” from From A Room: Volume 1, is a heartfelt song about loss, faith, and the mysteries of life. With its gentle acoustic instrumentation and Stapleton’s raw, emotional vocals, the song delivers a powerful message about the fleeting nature of life and the people who pass through it. The lyrics suggest that some things, like why we lose the ones we love, are beyond our understanding, urging us to accept life’s sorrows rather than question them. Written by Stapleton and his longtime collaborator Mike Henderson, the song was inspired by personal experiences with loss, giving it an authentic emotional weight. The simplicity of the arrangement allows the sincerity of the lyrics to shine through, making it one of Stapleton’s most moving tracks. “Broken Halos” resonated deeply with listeners, earning widespread acclaim and winning the Grammy Award for Best Country Song. The track serves as a reminder of Stapleton’s ability to turn deeply personal emotions into music that feels universal, offering comfort and understanding to those who have faced grief. It’s a song that doesn’t just entertain—it heals.
3. “Starting Over” (2020)
The title track from Stapleton’s 2020 album, “Starting Over,” is an uplifting anthem about embracing new beginnings. With a stripped-down arrangement driven by acoustic guitar, the song carries an easygoing, road-trip-like feel that perfectly complements its hopeful lyrics. It speaks to the excitement and uncertainty of moving forward in life, whether that’s chasing a dream, taking a risk, or simply leaving the past behind. Stapleton’s warm, earnest vocals make the song feel intimate, as if he’s sitting beside the listener, offering words of encouragement. His wife, Morgane Stapleton, provides harmonies that add to the song’s rich texture. In a world filled with struggles and setbacks, “Starting Over” serves as a reminder that change isn’t just inevitable—it’s necessary. The song resonated deeply with listeners, offering a sense of optimism during difficult times. With its folk and country influences blending seamlessly, “Starting Over” showcases Stapleton’s ability to write songs that feel both deeply personal and universally relatable. It’s a testament to his skill as a songwriter and his ability to make even the simplest melodies feel profound.
4. “Nobody to Blame” (2015)
From his breakout album Traveller, “Nobody to Blame” is a hard-hitting country song that captures the sting of a relationship gone wrong. The song’s narrator acknowledges that his mistakes cost him everything, from his home to his truck, but he doesn’t hold any grudges—he knows exactly who’s responsible. With its gritty, blues-infused instrumentation and Stapleton’s soulful delivery, the song embodies classic country themes of regret and loss. The lyrics are filled with vivid imagery, describing how his ex took revenge by destroying his belongings, leaving him with nothing but himself to blame. This sense of self-awareness and accountability gives the song an emotional weight that resonates with listeners. The track became one of Stapleton’s early hits, earning a CMA Award for Song of the Year and further solidifying his status as a powerhouse in country music. Fans connected with its mix of humor, heartbreak, and classic country storytelling, making it a staple in his live performances. “Nobody to Blame” is a perfect example of Stapleton’s ability to blend traditional country with his own signature grit and soul, creating music that feels both timeless and fresh.
5. “Fire Away” (2015)
“Fire Away,” one of the most emotionally intense tracks on Traveller, explores the complexities of love, pain, and emotional struggle. The song tells the story of someone who is willing to take all the emotional blows from a loved one, despite the deep hurt they endure. Stapleton’s soaring vocals and the slow-burning instrumentation create an atmosphere of raw vulnerability, making the song one of his most powerful ballads. The lyrics, filled with a sense of quiet desperation, capture the feeling of loving someone who is battling their own inner demons. The accompanying music video adds another layer of depth, portraying the heartbreaking reality of mental health struggles and the impact they have on relationships. “Fire Away” isn’t just a love song—it’s a profound commentary on the sacrifices we make for those we care about. The track showcases Stapleton’s ability to infuse deep emotion into every note, proving why he is one of the most compelling artists in country music today. Its haunting beauty and powerful message make it a fan favorite, touching the hearts of listeners in a way few songs can.
6. “You Should Probably Leave” (2020)
“You Should Probably Leave” is a beautifully bittersweet track from Starting Over that captures the push and pull of an on-again, off-again relationship. The song’s gentle groove, subtle blues influences, and Stapleton’s smooth vocals create an atmosphere of quiet tension. The lyrics tell the story of two people who know they shouldn’t be together but can’t resist falling into old patterns. As they find themselves once again drawn to each other, they acknowledge the inevitable heartbreak ahead, making the song both relatable and heartbreaking. Stapleton’s delivery is filled with warmth and restraint, perfectly balancing desire and self-awareness. The song’s laid-back yet emotionally charged tone makes it stand out on the album, showcasing his ability to craft deeply personal, narrative-driven music. “You Should Probably Leave” demonstrates Stapleton’s talent for capturing complex emotions in a way that feels effortlessly real. The track resonated with fans who have found themselves in similar situations, making it one of the highlights of his 2020 album. With its smooth melody and evocative lyrics, it’s a song that lingers long after it ends.
7. “Traveller” (2015)
The title track of Traveller serves as a defining statement of Chris Stapleton’s musical journey. The song paints a picture of a restless soul, always searching, always moving, never quite settling down. With its sweeping melody and introspective lyrics, “Traveller” captures the essence of a wandering heart, making it one of Stapleton’s most personal and reflective songs. Inspired by a cross-country road trip he took after his father’s passing, the song embodies themes of self-discovery and the ever-changing nature of life. The instrumentation blends elements of country, folk, and blues, creating a rich, immersive soundscape. Stapleton’s soulful voice carries a sense of longing and wisdom, making the song feel both deeply personal and universally relatable. “Traveller” set the tone for Stapleton’s career, proving that he wasn’t just another country singer—he was a storyteller with an unmatched ability to connect with listeners on a profound level. The track remains a fan favorite, encapsulating the spirit of adventure, reflection, and the pursuit of something greater. It’s a song that speaks to anyone who has ever felt like they were searching for their place in the world.
8. “Cold” (2020)
“Cold” is one of the most hauntingly beautiful songs in Chris Stapleton’s catalog, showcasing his incredible vocal power and emotional depth. Featured on Starting Over, the song is a slow-burning, blues-infused ballad that conveys the deep sting of heartbreak. With its dramatic string arrangement and chilling piano melodies, “Cold” stands apart from the more traditional country tracks in Stapleton’s discography. The lyrics describe the devastation of being abandoned by someone who once loved you, leaving behind an emotional emptiness that feels almost unbearable. Stapleton’s voice soars with pain and frustration, making each note feel like a gut punch. The song’s orchestral build-up adds to its cinematic quality, making it one of the most intense listening experiences on the album. “Cold” is a masterclass in musical storytelling, using both lyrics and instrumentation to immerse the listener in a world of sorrow. It’s a song that doesn’t just tell a story—it makes you feel every ounce of its heartbreak. The raw vulnerability of “Cold” proves why Stapleton is one of the most compelling voices in music today.
9. “Parachute” (2015)
“Parachute” is one of the more energetic tracks on Traveller, blending country, rock, and blues influences into a powerful anthem about loyalty and commitment. With a driving beat, electrifying guitar riffs, and Stapleton’s signature gritty vocals, the song carries a sense of urgency and passion. The lyrics speak of unwavering devotion, promising to be there for someone no matter what life throws at them. This theme of steadfast love, combined with the song’s infectious rhythm, makes “Parachute” a standout track. The blend of rock and country elements showcases Stapleton’s versatility, proving that he can deliver high-energy anthems just as effectively as slow-burning ballads. The song’s intensity builds as Stapleton’s voice soars over the pulsating instrumentation, creating a dynamic and exciting listening experience. “Parachute” became a fan favorite due to its electrifying energy and heartfelt message, proving that Stapleton can craft songs that hit just as hard musically as they do emotionally.
10. “Whiskey and You” (2015)
“Whiskey and You” is one of the most emotionally raw songs on Traveller, showcasing Stapleton’s ability to convey heartbreak in its purest form. The song strips everything down to just an acoustic guitar and his aching, soul-drenched vocals, allowing the lyrics to take center stage. The song compares the pain of lost love to the burn of whiskey, with the narrator using alcohol as a temporary escape from heartache. The raw honesty in the lyrics, paired with Stapleton’s sorrowful delivery, makes “Whiskey and You” one of the most devastating breakup songs in modern country music. It’s a song about trying to numb the pain but ultimately realizing that nothing can truly erase it. Originally recorded by Tim McGraw, Stapleton’s version feels far more intimate and gut-wrenching, making it the definitive rendition. The stripped-down arrangement makes the emotion feel even more real, turning the song into a heartbreaking confession rather than just another country ballad. “Whiskey and You” is a testament to Stapleton’s ability to take simple themes and turn them into something deeply moving and unforgettable.
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.
