Chris Stapleton has cemented himself as one of the most iconic voices in modern country music, blending soul, blues, and Southern rock into a sound that’s uniquely his own. With his raw, gritty vocals and heartfelt lyrics, Stapleton has created a catalog of songs that resonate deeply with fans around the world. Whether he’s belting out a heart-wrenching ballad or lighting up a stage with an electrifying anthem, his music strikes a chord with listeners of all genres. From honky-tonk heartbreakers to soulful serenades, his versatility as a songwriter and performer is unmatched.
In this article, we’re diving into the top 10 most popular Chris Stapleton songs of all time—tracks that have defined his career and left an indelible mark on the music industry. These are the songs that have brought tears to eyes, inspired countless sing-alongs, and earned him Grammy Awards, chart-topping success, and the adoration of millions. Whether you’re a lifelong fan or new to his music, this list is a must-read for anyone who appreciates the artistry of a true musical legend. So, grab your headphones, turn up the volume, and get ready to relive the magic of Chris Stapleton’s greatest hits!
1. Tennessee Whiskey (2015)
Chris Stapleton’s cover of “Tennessee Whiskey” took the music world by storm when it was released as part of his 2015 debut album Traveller. Originally penned by Dean Dillon and Linda Hargrove, the song had been a classic in the country genre, but Stapleton’s rendition took it to new heights, blending the deep, emotional grit of blues with a smooth, soulful country style. His powerful, raspy voice, dripping with sincerity, adds a layer of authenticity and vulnerability that resonates deeply with listeners. The song is about a love so intense that it has the ability to heal and save, symbolized through the metaphor of Tennessee whiskey. Stapleton’s delivery of the heartfelt lyrics is both tender and powerful, capturing the raw emotion of the song’s themes of redemption and the life-altering effects of love. The arrangement is simple yet effective, with slow, sweeping guitar chords and a steady rhythm that complements the song’s reflective mood. “Tennessee Whiskey” quickly became one of Stapleton’s most iconic songs, attracting a wide range of fans from across country and blues circles. It also became an anthem of sorts for a generation of listeners who crave music that connects on a deeper emotional level. The song’s success in both mainstream country and blues circles highlighted Stapleton’s ability to cross musical boundaries, and it cemented his status as one of the most compelling voices in contemporary country music. Its timeless appeal, paired with the raw emotion of Stapleton’s performance, continues to make “Tennessee Whiskey” a fan favorite and a defining moment in his career.
2. Broken Halos (2017)
“Broken Halos,” featured on Chris Stapleton’s 2017 album From A Room: Volume 1, is a hauntingly beautiful ballad that explores the themes of loss, love, and the fragility of life. The song was awarded the Grammy for Best Country Song in 2018, and its deeply emotional lyrics and simple acoustic melody have made it one of Stapleton’s most beloved tracks. In “Broken Halos,” Stapleton reflects on the idea that sometimes, even the people we love and look up to can fall from grace. The imagery of “broken halos” speaks to the imperfections and vulnerability of human existence, with Stapleton singing about how people, though flawed, can still leave a lasting impact on the lives they touch. The song’s stripped-back instrumentation—primarily acoustic guitar and subtle percussion—creates a somber yet uplifting atmosphere, allowing the song’s message to shine through. Stapleton’s soulful delivery is filled with sincerity and pain, matching the poignancy of the lyrics, while also offering a sense of hope and redemption. His voice, rich and full of raw emotion, turns the song into a reflection on the inevitability of loss, but also the beauty found in cherishing the memories of those who have left us. The song resonates with anyone who has experienced the passing of loved ones, while its universal message about the impermanence of life strikes a chord with listeners on a personal level. “Broken Halos” is more than just a song; it’s a tribute to those who have shaped our lives and a reminder that even in brokenness, there is grace and beauty.
3. Starting Over (2020)
The title track from Chris Stapleton’s 2020 album Starting Over is a deeply introspective and hopeful song that captures the essence of fresh beginnings and the courage it takes to embrace change. Released during a time of uncertainty, the song’s gentle optimism and soothing melody struck a chord with fans, providing a sense of comfort and reassurance amid a global crisis. “Starting Over” is about shedding the past and stepping into the unknown with hope, a message that resonated with many who were looking for a new beginning during a challenging time. The song opens with a soft, acoustic guitar riff, gradually building into a full, soulful arrangement that perfectly complements Stapleton’s rich voice. His delivery is warm and sincere, giving the song a feeling of both intimacy and empowerment. The lyrics speak to the idea that no matter how difficult life may be, there’s always the potential for a fresh start. “Starting Over” is a perfect blend of country, blues, and rock, with Stapleton’s distinct style shining through. It captures the vulnerability and resilience that are central to his music, showcasing his ability to turn personal experiences into universal anthems. The song’s reflective nature and uplifting message make it a standout in Stapleton’s catalog, as it encourages listeners to embrace new opportunities and move forward with confidence. For many, “Starting Over” is more than just a song—it’s an anthem for overcoming adversity and finding hope in life’s transitions.
4. Fire Away (2015)
“Fire Away,” from Chris Stapleton’s Traveller album, is a raw, emotional ballad that tackles the complex themes of personal struggle, resilience, and mental health. The song, which features a slow, bluesy rhythm, highlights Stapleton’s ability to convey deep emotion through both his lyrics and his powerful vocal delivery. In “Fire Away,” the singer expresses a sense of vulnerability, confronting the challenges of facing one’s inner demons and emotional scars. With lyrics like “Fire away, fire away,” the song evokes the feeling of standing firm in the face of adversity, refusing to back down from life’s difficulties. Stapleton’s delivery is unwavering, each note dripping with emotion and conviction, making it one of his most powerful tracks. The song’s simple yet striking instrumentation, led by acoustic guitar and a haunting slide guitar solo, perfectly matches the emotional depth of the lyrics. What sets “Fire Away” apart is its ability to tackle mental health issues with raw honesty, something that was largely unexplored in mainstream country music at the time of its release. Its accompanying music video, which focuses on the impact of mental health struggles, further emphasizes the song’s message of understanding and compassion. “Fire Away” became an anthem for many who were grappling with their own internal battles, offering both a sense of solidarity and empowerment. The song is a testament to Stapleton’s songwriting prowess and his ability to address important issues through music, making it one of the standout tracks on Traveller and a crucial moment in his career.
5. You Should Probably Leave (2020)
Released in 2020, “You Should Probably Leave” is a sultry, bittersweet song that tells the story of a complicated love affair. With its smooth, soulful melody and Stapleton’s velvet voice, the song oozes sensuality and yearning, capturing the complexities of a relationship that’s on the verge of coming to an end. The song’s narrative is about two people who are stuck in a toxic situation, caught between desire and the realization that they should part ways. The chorus, with its plea “You should probably leave,” feels like a moment of clarity in an otherwise tangled, emotional web. The song’s smooth rhythm and understated instrumentation create a moody atmosphere, perfectly complementing the emotional weight of the lyrics. Stapleton’s delivery is nothing short of captivating—his voice full of longing, regret, and quiet resignation, making the song impossible to ignore. “You Should Probably Leave” explores the tension between love and heartache, offering a raw, honest take on relationships that aren’t meant to last but are hard to let go of. The song’s understated production and smooth arrangement highlight Stapleton’s vocal prowess, allowing his voice to shine through the music’s subtle intricacies. It became an instant hit among fans who appreciated its emotional depth and relatable subject matter. With “You Should Probably Leave,” Stapleton once again proves his ability to craft songs that speak to the heart, making it one of his most memorable releases of 2020.
6. Parachute (2015)
From his debut album Traveller, “Parachute” is a spirited track that combines Chris Stapleton’s country roots with his dynamic storytelling and fiery passion. The song revolves around the theme of loyalty, with Stapleton likening his love for someone to the safety and security of a parachute. It’s a declaration of unwavering devotion, with Stapleton singing about being there for someone, no matter what life throws at them. The upbeat rhythm and vibrant instrumentation give the song a sense of energy and optimism, which contrasts beautifully with the depth of its message. The powerful rhythm section, paired with the punchy electric guitar, creates a driving groove that keeps the listener hooked from start to finish. Stapleton’s voice is again the centerpiece, and his gravelly yet soulful delivery lends an authenticity to the song that is hard to ignore. His ability to blend raw emotion with upbeat, infectious melodies is a key element in what makes “Parachute” stand out. The track captures the essence of love as a life-affirming force, able to catch us when we fall and help us soar. “Parachute” is a perfect example of Stapleton’s knack for taking familiar country tropes and giving them a fresh, powerful twist. While it may be a lighter, more up-tempo song compared to some of his other tracks, it still carries the emotional weight and sincerity that fans of Stapleton have come to expect. It’s a joyful, confident anthem for those who know that love is something worth falling for—and the safety net that catches us when we do.
7. Millionaire (2017)
“Millionaire,” from From A Room: Volume 2, is a feel-good, toe-tapping track that flips the script on what it means to be rich. Rather than focusing on material wealth or possessions, the song emphasizes that true richness comes from the love we give and receive. Written by Kevin Welch, Stapleton’s rendition of this song is a perfect mix of country, blues, and rock. With its playful melody and catchy rhythm, “Millionaire” radiates a sense of contentment and appreciation for life’s simple pleasures. The lyrics, which describe the narrator’s contentment in being “rich in love” rather than “rich in gold,” offer a perspective that many people can relate to—especially in today’s world, where the pursuit of money often takes precedence over personal connections. Stapleton’s delivery is laid-back yet filled with warmth, and his voice carries a sense of authenticity that makes the song’s message even more powerful. The instrumental arrangement, driven by gentle guitar strumming and a lighthearted rhythm section, creates a sense of comfort and familiarity. “Millionaire” is an uplifting, celebratory song that reminds us that the things that truly matter in life—like love and happiness—are priceless. The song became a fan favorite thanks to its catchy chorus and feel-good vibe, as well as its universal message that speaks to anyone who values relationships over material wealth. In “Millionaire,” Stapleton shows his ability to take a classic concept and turn it into something meaningful and relatable, further cementing his status as one of country music’s most compelling storytellers.
8. Nobody to Blame (2015)
“Nobody to Blame,” from Traveller, is a powerful country ballad that speaks to the heart of regret, loss, and self-reflection. The song is about a man who’s come to terms with the end of a relationship, acknowledging that he is the one responsible for its downfall. The lyrics paint a vivid picture of heartache and accountability, with Stapleton singing about how his actions led to the inevitable separation. The rawness in Stapleton’s voice conveys the pain of looking back and realizing that sometimes, we’re the ones who let things slip through our fingers. Musically, “Nobody to Blame” features a stripped-down, classic country arrangement that lets the emotion of the song take center stage. The mournful steel guitar and steady rhythm give the track a sense of melancholy and reflection, perfectly complementing the somber nature of the lyrics. Stapleton’s delivery is gritty and soulful, and his voice resonates with authenticity and vulnerability. The song’s relatability lies in the way it speaks to the universal experience of feeling responsible for a lost love and the painful process of moving forward. “Nobody to Blame” was one of the standout tracks on Traveller, earning critical acclaim for its honest portrayal of the human condition. It’s a song that resonates with anyone who has experienced heartache and self-doubt, and its timeless themes of regret and redemption make it one of Stapleton’s most impactful works.
9. Whiskey and You (2015)
“Whiskey and You,” another track from Traveller, is one of Chris Stapleton’s most emotionally charged songs. This haunting ballad is about heartbreak, loneliness, and the solace that comes from drowning your sorrows in whiskey. It’s a raw, unflinching look at how people often turn to unhealthy coping mechanisms to numb the pain of a broken heart. The song’s slow, mournful melody sets the tone for Stapleton’s soulful performance, with his voice filled with raw emotion and vulnerability. The lyrics express the narrator’s feelings of isolation and despair, as he grapples with the end of a relationship and turns to alcohol as a temporary escape. The interplay between the mournful piano, the subtle guitar, and Stapleton’s voice creates an atmosphere of heartache and resignation. “Whiskey and You” stands out as one of the most poignant songs in Stapleton’s catalog, as it taps into the universal experience of feeling alone and heartbroken. There’s a bittersweet beauty in the way the song explores the complexity of grief and the fleeting comfort that substances like whiskey can provide. Stapleton’s delivery is unmatched, and his ability to convey such vulnerability through his voice makes the song hit even harder for listeners. “Whiskey and You” has become a fan favorite because of its emotional depth and relatability, as it speaks to the pain and healing that come with the end of a love.
10. Traveller (2015)
As the title track of his debut album, “Traveller” offers a glimpse into Chris Stapleton’s personal journey and his love for the open road. The song is a reflection on the freedom and self-discovery that come with traveling, as well as the emotional weight of leaving behind the past. The lyrics paint a picture of a man who is searching for something—whether it’s inner peace, a sense of belonging, or simply a new chapter in life. With its stripped-down instrumentation and acoustic guitar-driven melody, the song has an intimate, reflective quality that makes it feel like Stapleton is confiding in the listener. His raspy, soulful voice, combined with the vulnerability in his delivery, gives the song a sense of honesty and authenticity. “Traveller” isn’t just about physical travel; it’s a metaphor for personal growth and the process of learning who we are along the way. The song captures the spirit of adventure and the desire to break free from the constraints of everyday life. For Stapleton, the road symbolizes a path to self-discovery and freedom from past struggles. The song’s poignant message resonates with anyone who has experienced the longing for new beginnings or the feeling of being lost yet driven to keep moving forward. “Traveller” became a defining moment in Stapleton’s career, setting the tone for the rest of the Traveller album and establishing him as a voice for those seeking meaning in their lives. It’s a timeless anthem for anyone on a journey of self-exploration and transformation.
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.
