With a voice that cuts straight to the soul and songwriting that spans the entire spectrum of human emotion, Chris Stapleton has taken the country music world—and beyond—by storm. Whether he’s belting out heart-wrenching ballads, delivering raw and gritty Southern rock, or showcasing his smooth, blues-infused sound, Stapleton’s music resonates with millions. His ability to blend genres like country, rock, blues, and soul has made him a household name, earning countless awards and accolades along the way.
But what are the tunes that have truly defined his incredible rise to stardom? From chart-topping classics to deep cuts that showcase his immense range, we’re counting down the top 10 most popular Chris Stapleton songs of all time. Whether you’re a longtime fan or a newcomer to his music, this list will take you on a journey through Stapleton’s greatest hits—songs that have touched hearts and topped charts, leaving an undeniable mark on music history. Get ready to dive into the best of Stapleton’s unforgettable catalog and rediscover why he’s one of the most celebrated artists in modern music!
1. Tennessee Whiskey (2015)
“Tennessee Whiskey,” released in 2015 as part of Chris Stapleton’s debut album Traveller, quickly became a modern-day country classic. Originally written by Dean Dillon and Linda Hargrove and first recorded by David Allan Coe in 1981, the song got its most famous rendition when Stapleton put his soulful spin on it. Blending country, blues, and a bit of Southern rock, “Tennessee Whiskey” became an anthem of love, loss, and redemption. Stapleton’s raspy, powerhouse vocals elevate the song to a new level, infusing it with a raw emotion that resonates deeply with listeners. The metaphor comparing love to whiskey—smooth, intoxicating, and comforting—captures the complexity of relationships in a way that feels both poetic and accessible. Accompanied by a simple yet memorable guitar riff, the song’s slow-burn groove allows Stapleton’s voice to take center stage, making it an unforgettable listening experience. Over time, “Tennessee Whiskey” has become one of Stapleton’s signature songs, beloved by fans across genres and frequently featured in his live performances. Its timeless appeal continues to grow, proving Stapleton’s unique ability to transform a cover song into something entirely his own, while also keeping its classic roots intact.
2. Broken Halos (2017)
Released in 2017 on From A Room: Volume 1, “Broken Halos” is one of Chris Stapleton’s most emotionally charged songs. The track offers a poignant reflection on loss, faith, and the human condition, making it one of the standout moments in his catalog. At its core, “Broken Halos” is a song about accepting life’s hardships, recognizing that some things are beyond our control. The acoustic-driven rhythm provides a simple, understated backdrop for Stapleton’s powerful, gritty vocals, allowing the emotion in the lyrics to take center stage. Despite its heavy themes, the song has a hopeful undertone, urging listeners to find peace in the face of adversity. This balance between sadness and resilience is what makes the song so impactful. The track resonated with fans and critics alike, earning Stapleton a Grammy Award for Best Country Song. Its relatable message about loss, combined with Stapleton’s heartfelt delivery, makes “Broken Halos” a timeless piece of music. It’s the kind of song that not only helps you process grief but also encourages you to keep moving forward—a theme that is both personal and universally understood.
3. Fire Away (2015)
“Fire Away,” featured on Chris Stapleton’s 2015 debut album Traveller, is an emotionally intense ballad that showcases his raw vocal power and profound storytelling ability. The song is a plea for patience and understanding in the face of emotional turmoil, making it a powerful anthem for anyone struggling in a relationship. Stapleton’s gravelly voice carries a weight of sincerity, capturing the vulnerability and frustration that come with loving someone who’s hurting. The song’s minimalist instrumentation—a simple yet haunting melody—gives Stapleton’s voice the space to shine, allowing listeners to feel every word. The accompanying music video amplifies the song’s emotional impact, telling a heart-wrenching story about mental health and the toll it can take on a relationship. “Fire Away” is more than just a song; it’s a deeply moving confession that resonates with anyone who’s ever faced challenges in love. Its powerful lyrics and emotional depth make it one of Stapleton’s most memorable tracks. It reminds listeners that sometimes, the best thing we can do for those we love is to stand by them, even when the situation feels overwhelming and impossible to fix.
4. Traveller (2015)
The title track of Chris Stapleton’s 2015 breakthrough album, “Traveller,” is a deeply personal and reflective anthem that explores themes of self-discovery, loss, and the search for meaning. Written shortly after the death of his father, the song channels Stapleton’s grief into a meditation on life’s journey, capturing the restlessness of someone who’s always on the move, both physically and emotionally. The song’s country-folk melody, paired with Stapleton’s soulful vocals, creates a mood of quiet contemplation. His lyrics reflect on the human experience of searching for purpose and direction, making it a song that resonates with anyone who’s ever felt lost or uncertain. “Traveller” isn’t just about physical travel—it’s a metaphor for the inner journey we all take as we navigate life’s ups and downs. The song helped propel Stapleton into the mainstream, showcasing his ability to blend deeply personal storytelling with universal themes. It’s a track that connects with listeners on a profound level, reminding us that sometimes the journey is more important than the destination. “Traveller” remains one of Stapleton’s most beloved songs, a testament to his gift for crafting meaningful, introspective music.
5. Starting Over (2020)
Released as the title track of Chris Stapleton’s 2020 album, “Starting Over” is a song that carries a message of hope and renewal, which resonated deeply with listeners during a time of global uncertainty. With its gentle acoustic guitar and Stapleton’s warm, reassuring vocals, the song feels like a breath of fresh air—a reminder that no matter how hard life gets, there’s always a chance to begin again. The song’s lyrics speak to the idea of leaving the past behind and embracing new opportunities, making it an anthem for anyone going through a transition or facing the unknown. The simplicity of the song is its greatest strength; there’s no need for elaborate production or complex arrangements when the message is so pure and heartfelt. Stapleton’s voice, full of grit and soul, brings the song to life, making it both comforting and inspiring. “Starting Over” became a timely reminder that life is full of second chances, and its optimistic tone provided solace to many during a challenging year. The track further solidified Stapleton’s reputation as a master of crafting songs that speak to the heart, offering both personal reflection and universal appeal.
6. Parachute (2015)
“Parachute,” from Chris Stapleton’s 2015 debut album Traveller, is a high-energy, rock-infused track that showcases his versatility as an artist. Known for his soulful ballads and deep, emotional storytelling, Stapleton shifts gears with this fast-paced song, proving he can deliver a gritty, powerful anthem just as well. The song’s driving beat and electrifying guitar riffs make “Parachute” stand out as one of the more energetic tracks on the album. Lyrically, the song is about being there for someone no matter what, offering unconditional support and loyalty in tough times. It’s a metaphorical promise to catch someone when they fall, to be their safety net when life gets rough. Stapleton’s signature rasp and raw vocal power elevate the song to an anthem of strength and resilience, making it a favorite among fans who appreciate both his tender ballads and his harder-hitting tracks. “Parachute” shows off a different side of Stapleton—one that’s just as compelling and heartfelt, but with an added edge of intensity. It’s a song that resonates with anyone who’s ever been a rock for someone else, capturing the essence of loyalty and steadfast love.
7. Nobody to Blame (2015)
“Nobody to Blame,” one of the standout tracks from Chris Stapleton’s 2015 album Traveller, is a modern-day country heartbreak song with a raw, confessional twist. The song tells the story of a man who takes responsibility for the breakdown of his relationship, acknowledging that he has “nobody to blame but me.” Stapleton’s gritty voice, combined with the twangy guitars and bluesy instrumentation, gives the song a classic country feel, while the relatable lyrics strike a chord with listeners who’ve been in similar situations. The track is full of vivid imagery, describing the aftermath of the breakup—his belongings are destroyed, his house is wrecked, but he knows he brought it all on himself. “Nobody to Blame” became one of Stapleton’s first major radio hits, solidifying his place as a standout voice in country music. Its honest, straightforward storytelling and infectious chorus made it an instant favorite among fans and critics alike. The song’s emotional depth and Stapleton’s heartfelt delivery resonate deeply with anyone who’s ever had to face the consequences of their own actions, making it a timeless addition to his catalog.
8. Millionaire (2017)
Chris Stapleton’s cover of “Millionaire,” originally written by Kevin Welch and featured on his 2017 album From A Room: Volume 2, is a soulful and heartfelt ode to the richness of love. With its laid-back groove and Stapleton’s smooth, bluesy vocals, the song conveys the message that true wealth isn’t measured in money but in the love and connection we share with others. The lyrics celebrate the idea that feeling “like a millionaire” comes from having someone special in your life, rather than material possessions. Stapleton’s version of the song brings a warmth and sincerity that makes the message feel even more personal. His voice, full of grit and soul, gives the song an emotional depth that resonates with listeners, transforming it from a simple love song into an anthem for romantics everywhere. The stripped-back production allows the focus to remain on Stapleton’s vocals and the song’s heartfelt message, making it a standout track on the album. “Millionaire” is a reminder that the most important things in life can’t be bought, and Stapleton’s rendition captures that sentiment perfectly, creating a timeless love song in the process.
9. Whiskey and You (2015)
“Whiskey and You,” from Chris Stapleton’s 2015 debut album Traveller, is one of his most stark and emotionally raw songs. The track is a slow, haunting ballad that strips everything down to its bare essentials: just Stapleton’s voice and a guitar. This simplicity allows the song’s emotional weight to hit even harder, as Stapleton explores themes of addiction, heartbreak, and loneliness. In the song, he compares the comfort of whiskey to the pain of lost love, acknowledging that neither provides real solace. Stapleton’s raw, unfiltered vocals make the song feel deeply personal, as if he’s baring his soul to the listener. The minimalist production only adds to the song’s intensity, making every word and note feel heavy with emotion. “Whiskey and You” has become one of the most beloved tracks in Stapleton’s catalog, a fan favorite that showcases his ability to convey deep emotion with just his voice and a simple guitar arrangement. It’s a song that speaks to anyone who’s ever tried to numb their pain, only to realize that the hurt still lingers—a theme that’s both personal and universal.
10. You Should Probably Leave (2021)
Released as part of Chris Stapleton’s 2021 album Starting Over, “You Should Probably Leave” is a bittersweet, bluesy track about two people who are irresistibly drawn to each other but know that staying together will only lead to more heartache. The song captures the tension between desire and the need to make the right choice, with Stapleton’s smooth, soulful vocals perfectly conveying the internal struggle. The track’s bluesy groove and catchy melody make it a standout on the album, but it’s the song’s relatable theme of resisting temptation that has resonated so deeply with fans. “You Should Probably Leave” is a masterclass in subtle storytelling—Stapleton doesn’t need to spell out every detail of the relationship for listeners to understand the emotional weight of the situation. Instead, he lets the music and his vocal delivery do the heavy lifting, creating a song that feels intimate and universal all at once. The track earned Stapleton yet another hit, proving his ability to craft songs that connect with listeners on a deeply emotional level. It’s a song that lingers long after it’s over, leaving you thinking about the choices we make and the ones we resist.