When it comes to modern country music, few artists have made as profound an impact as Chris Stapleton. With his soulful voice and masterful songwriting, Stapleton has captivated audiences worldwide, blending traditional country with blues and rock influences. Since his breakthrough debut album, “Traveller,” he has consistently topped the charts, earning accolades and a dedicated fan base. But which of his songs truly resonate the most with listeners? In this article, we’ll dive into the top 10 most popular Chris Stapleton songs of all time, showcasing the tracks that define his artistry and illustrate his incredible range. From heart-wrenching ballads to foot-stomping anthems, each song tells a story that strikes a chord. Whether you’re a longtime fan or new to his music, prepare to discover the hits that have solidified Stapleton’s status as a contemporary legend. Join us as we explore the melodies and lyrics that have captured hearts, ignited emotions, and made Chris Stapleton a defining voice of a generation. Get ready to sing along and reminisce about the unforgettable moments behind each beloved track!
1. Tennessee Whiskey (2015)
“Tennessee Whiskey” is a smooth, soulful ballad that became Chris Stapleton’s breakout hit, and for good reason. Though originally penned by Dean Dillon and Linda Hargrove and first recorded by David Allan Coe, it was Stapleton’s 2015 rendition that brought the song to life for a new generation. Infused with blues, country, and a touch of southern soul, the track is an intoxicating blend of heartfelt lyrics and rich, velvety vocals. Stapleton likens love to the smooth burn of fine whiskey—sweet, deep, and comforting—delivering every line with raw, emotional power. His gritty yet tender voice carries the weight of every word, making the metaphor feel fresh and authentic. The slow-burning guitar riffs paired with a bluesy organ create a warm, intimate backdrop, drawing listeners into a place of quiet reflection and gratitude. “Tennessee Whiskey” doesn’t just showcase Stapleton’s vocal talent—it captures his ability to reimagine a classic with sincerity and soul. It became a defining moment in his career, turning heads not just in country music circles but across genres. Whether played live or through headphones, the song remains a moving tribute to love, redemption, and the comforting strength found in another’s embrace.
2. Traveller (2015)
“Traveller,” the title track from Chris Stapleton’s debut solo album, is a poignant reflection on life, movement, and the search for meaning. The song paints a vivid picture of a man constantly in motion, both physically and emotionally, yet always yearning for something more. With a mix of country, folk, and blues influences, the acoustic-driven track feels intimate and thoughtful. Stapleton’s raspy vocals deliver each line with a sense of wonder and weariness, capturing the heart of anyone who has ever felt like they were wandering through life looking for answers. Lyrically, “Traveller” isn’t just about roads and destinations—it’s about introspection, the lessons learned along the way, and the pull between freedom and belonging. The understated instrumentation allows the emotion in Stapleton’s voice to shine through, making the song feel both personal and universal. It’s easy to get lost in the mood he creates: that of a dusty highway at sunset, windows down, and a mind full of memories. “Traveller” is more than a song—it’s a journey in itself, one that invites listeners to pause, reflect, and embrace the winding paths that shape who we are.
3. Broken Halos (2017)
“Broken Halos” is a hauntingly beautiful song that speaks to the pain of loss and the mysterious nature of suffering. Written by Chris Stapleton and Mike Henderson, this 2017 track gently urges listeners to accept that some things in life simply cannot be explained. Stapleton’s raw, soulful voice delivers the lyrics with reverence and heartbreak, reflecting on people who came into the world with promise but left too soon. The title refers to those “broken halos”—the fallen or departed—whose stories ended before their time. Musically, the song is stripped-down and understated, with soft acoustic guitar and a subtle gospel influence that adds spiritual depth. The message is tender and reflective, suggesting that not all questions have answers, and that healing often comes through acceptance rather than understanding. “Broken Halos” struck a deep chord with fans, offering comfort to those mourning loved ones or grappling with life’s unfairness. It stands out in Stapleton’s catalog as one of his most emotionally resonant songs—a quiet anthem for anyone who’s carried the weight of grief and still chosen to move forward with hope.
4. Starting Over (2020)
“Starting Over” is a hopeful, feel-good anthem that finds beauty in the idea of fresh beginnings. Released in 2020, this title track from Stapleton’s fourth studio album speaks to the universal desire to leave the past behind and embrace what lies ahead. With an acoustic guitar strumming a steady rhythm and Stapleton’s warm vocals leading the way, the song feels like a road trip into a new chapter of life. The lyrics are simple but heartfelt—there’s no need for grandeur here, just honesty. Whether it’s a relationship, a dream, or life itself, the song encourages us to take that leap, no matter how daunting it may seem. It’s about choosing courage over comfort, optimism over regret. What makes “Starting Over” so powerful is the way it blends that emotional truth with a lighthearted, accessible melody. Stapleton sounds relaxed and energized, capturing the spirit of taking a chance and trusting the journey. The track became especially meaningful during a time when many listeners were navigating change and uncertainty, making it a kind of emotional reset button. It’s a song that reassures us: no matter what we’ve been through, it’s never too late to begin again.
5. Fire Away (2015)
“Fire Away” is one of Chris Stapleton’s most emotionally charged songs—a stirring ballad about enduring love in the face of emotional turmoil. Released in 2015 on his debut solo album Traveller, the track builds slowly and steadily, beginning with a delicate piano line that soon swells into a full, passionate arrangement. Lyrically, it’s a plea and a promise all in one. Stapleton tells a story of unwavering support, inviting his partner to release all their pain and anger, even if it means taking the brunt of it himself. His vocals are achingly sincere, moving from soft restraint to a powerful, soaring chorus that aches with emotion. It’s a performance that showcases his vocal range not just technically, but emotionally. The music video, which addresses themes of mental health, adds even deeper layers to the song’s meaning, resonating with listeners who have felt helpless in the face of a loved one’s struggle. “Fire Away” is more than a love song—it’s a testament to the patience, vulnerability, and strength it takes to love someone through the darkest moments. Stapleton doesn’t just sing about heartbreak; he sings about standing in its storm, unwavering and unafraid.
6. Parachute (2017)
“Parachute” is a high-energy, foot-stomping track that captures Chris Stapleton’s ability to fuse traditional country with rock and blues flair. Released in 2017, the song stands out for its driving rhythm, punchy acoustic riffs, and the gritty edge in Stapleton’s voice. The lyrics center around loyalty and love—he compares himself to a parachute, always there to catch his partner when they fall. It’s a metaphor that works beautifully with the song’s upbeat tempo, making it both catchy and meaningful. There’s a strong sense of devotion in every line, and Stapleton’s raspy, impassioned delivery gives the song its emotional weight. It’s not just about being someone’s safety net; it’s about being ready to stand strong in tough times. The chorus is instantly memorable, and the energy never dips, making it a crowd favorite at live shows. With its blend of heart and grit, “Parachute” captures that rush of knowing you’re someone’s anchor. It’s the kind of song that gets your foot tapping and your heart feeling full—a celebration of commitment, strength, and the powerful kind of love that shows up, no matter what.
7. What Are You Listening To? (2015)
“What Are You Listening To?” is a beautifully introspective song that delves into the emotional aftermath of a breakup. Released in 2015, it was Chris Stapleton’s first solo single, and though it flew under the radar initially, it showcases his signature storytelling style and deep emotional range. The song follows a narrator who is haunted by memories and wonders what his ex might be hearing—sad songs, love songs, or anything that might echo their lost connection. There’s something deeply relatable about the way music becomes a mirror of our emotional state, and Stapleton taps into that vulnerability with poignant sincerity. His voice is smooth and aching, effortlessly drawing the listener into the longing and confusion that come with heartbreak. The gentle guitar and subtle instrumentation let the lyrics take center stage, creating an atmosphere that feels intimate and honest. “What Are You Listening To?” is more than a question—it’s a window into the soul of someone trying to make sense of love lost. It’s reflective without being overly sentimental, and it stands as an early sign of Stapleton’s ability to craft songs that linger long after the final note fades.
8. Either Way (2017)
“Either Way” is a soul-stirring acoustic ballad that strips everything down to the bare essentials: voice, guitar, and unfiltered emotion. Released on the 2017 album From A Room: Volume 1, the song is a gut-wrenching portrayal of a love that has faded, where two people share the same space but not the same heart. Stapleton’s voice carries the weight of every word, moving through the verses with a haunting clarity that makes the silence between the notes just as powerful as the lyrics themselves. The simplicity of the arrangement is what gives “Either Way” its depth. There are no frills—just raw truth. The pain in his voice is palpable as he admits that the relationship is over, whether they choose to stay or leave. It’s a slow burn that hits hard, especially for anyone who’s experienced the quiet collapse of something once beautiful. There’s no blame in the song—only resignation and sorrow. “Either Way” shows just how powerful minimalism can be when it’s driven by authenticity. It’s a reminder that sometimes, the most devastating songs are the ones that whisper rather than shout.
9. Midnight Train to Memphis (2015)
“Midnight Train to Memphis” is a gritty, blues-infused track that pulses with frustration and fire. Originally recorded with his earlier band, The SteelDrivers, Stapleton reimagined the song for his solo career on Traveller in 2015, injecting it with even more attitude and energy. The song tells the story of a man locked behind bars, listening to the distant sound of a midnight train and yearning for freedom. The powerful guitar riffs, thundering drums, and Stapleton’s unrelenting vocal growl make it one of the rawest and most intense songs in his catalog. It’s a song of confinement—both physical and emotional—where every note feels like a hammer hitting the walls of a cell. The imagery is vivid and unapologetic, drawing listeners into the protagonist’s world of regret, anger, and longing. Stapleton doesn’t hold back, channeling every ounce of tension into his performance. “Midnight Train to Memphis” is cathartic and hard-hitting, the kind of track that demands to be played loud. It’s not just a prison tale—it’s a blues-rock anthem about being trapped in circumstances beyond your control, and the burning desire to break free.
10. More of You (2022)
“More of You” is a tender love song that glows with warmth, sincerity, and longing. Released in 2022, it’s a quieter entry in Chris Stapleton’s catalog, but one that carries immense emotional weight. The song centers on the deep yearning for closeness in a relationship—not for material things or fleeting thrills, but for deeper emotional connection and intimacy. Backed by soft acoustic strumming and delicate harmonies, Stapleton’s vocals take on a gentle, almost vulnerable tone, adding to the authenticity of the message. The lyrics express a simple truth: when love is real, no amount of time together ever feels like enough. It’s a sentiment that resonates deeply with listeners who know what it’s like to crave not just someone’s presence, but their heart. “More of You” is an ode to the kind of love that grows richer over time—the quiet, enduring kind that doesn’t need grand gestures to be felt. The beauty of the song lies in its simplicity and honesty. It’s a comforting reminder that in a world full of noise, sometimes the most powerful thing we can say to someone we love is, “I just want more of you.”
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.
