Chris Stapleton is a name that has become synonymous with raw, soulful storytelling and unparalleled vocal talent. Since bursting onto the scene, Stapleton has taken the country music world by storm, blending blues, rock, and traditional country in a way that feels both timeless and refreshingly new. His gravelly voice, coupled with deeply personal lyrics, has resonated with millions of fans across the globe. Whether you’re a longtime fan or just discovering his music, there’s no denying the impact Stapleton has had on the genre. From heart-wrenching ballads that tug at your soul to foot-stomping anthems that make you want to sing along, his songs have a way of leaving a lasting impression. In this list, we’ve compiled the top 10 most popular Chris Stapleton songs of all time—a collection of tracks that showcase his incredible range as an artist and storyteller. These are the songs that have not only topped the charts but have also become a soundtrack to the lives of his listeners. So, grab a glass of Tennessee whiskey, sit back, and let’s dive into the music that has made Chris Stapleton a legend in the making.
1. Tennessee Whiskey (2015)
“Tennessee Whiskey” is perhaps Chris Stapleton’s most iconic song, a soulful ballad that redefined the classic country genre. Released in 2015 on his debut solo album Traveller, the song is a cover of a 1980s track originally recorded by David Allan Coe and later George Jones. However, Stapleton’s rendition, with its bluesy twist and sultry vocals, brought new life to the song. The smooth combination of country storytelling and bluesy guitar riffs, paired with Stapleton’s powerful, emotion-laden voice, creates a sound that is both timeless and deeply moving. It’s a song about the transformative power of love, comparing it to the soothing effects of Tennessee whiskey. Stapleton’s version became a massive hit, further cementing his status as one of the most important voices in country music today.
2. Fire Away (2015)
“Fire Away” is one of the emotionally charged tracks from Chris Stapleton’s Traveller album, released in 2015. The song is a poignant exploration of love and vulnerability, delivered with Stapleton’s signature soulful intensity. Its lyrics speak of unconditional love and the willingness to endure pain for the sake of a partner, making it a hauntingly beautiful ballad. The instrumentation is rich and layered, with a steady drumbeat and melodic guitar that complement Stapleton’s raw, heartfelt vocals. “Fire Away” has resonated deeply with fans, becoming a standout track in Stapleton’s discography. Its powerful message and emotional depth have made it a favorite for both live performances and private listening sessions.
3. Broken Halos (2017)
Released as a single from From A Room: Volume 1 in 2017, “Broken Halos” quickly became one of Chris Stapleton’s most beloved songs. The track, which earned him a Grammy Award, is a reflection on life’s hardships and the loss of loved ones. It’s a song that balances sorrow with hope, offering a message of understanding and acceptance. The melody is simple yet powerful, driven by acoustic guitar and Stapleton’s unmistakable voice. “Broken Halos” is both a tribute and a reminder that some things are beyond our control, and it’s this universal theme that has resonated with so many listeners. The song’s accessibility and emotional depth have made it a staple in Stapleton’s live shows and a favorite among fans.
4. Parachute (2015)
“Parachute” is one of the more upbeat tracks from Chris Stapleton’s 2015 album Traveller. With its driving rhythm and electrifying guitar riffs, the song showcases Stapleton’s versatility as an artist. The lyrics describe a steadfast love, where the narrator promises to be there to catch his partner when they fall, much like a parachute. It’s a song about assurance and loyalty, delivered with a punchy, rock-infused energy that makes it stand out in Stapleton’s catalog. “Parachute” is a testament to Stapleton’s ability to blend genres seamlessly, combining elements of rock, blues, and country into a sound that is uniquely his own. The song’s infectious energy and powerful message have made it a fan favorite, often featured in his live performances.
5. Nobody to Blame (2015)
“Nobody to Blame” is a quintessential country song from Chris Stapleton’s critically acclaimed album Traveller, released in 2015. The song tells the story of a man who realizes that his own actions have led to the end of his relationship. With its classic country storytelling, twangy guitar, and Stapleton’s gritty, soulful voice, “Nobody to Blame” quickly became a hit on country radio. The song’s relatable theme of regret and accountability struck a chord with listeners, earning Stapleton widespread acclaim. It’s a prime example of Stapleton’s ability to take traditional country themes and infuse them with a modern, yet authentic, sound. The song’s success helped solidify Stapleton’s reputation as a leading voice in contemporary country music.
6. Starting Over (2020)
“Starting Over,” the title track from Chris Stapleton’s 2020 album, is a song about new beginnings and the courage it takes to embrace change. Released during a time of global uncertainty, the song resonated deeply with listeners. The track is built around a simple acoustic guitar melody, allowing Stapleton’s soulful vocals to shine. The lyrics offer a sense of hope and optimism, encouraging the listener to take a leap of faith and start anew. “Starting Over” is a reminder that it’s never too late to make a change, and Stapleton’s heartfelt delivery gives the song an emotional weight that has made it an instant classic. The song’s message of resilience and hope has made it a standout track in Stapleton’s discography.
7. Millionaire (2018)
Originally written and recorded by Kevin Welch, “Millionaire” was given new life when Chris Stapleton covered it on his 2018 album From A Room: Volume 2. Stapleton’s version of the song is a celebration of love and the richness it brings to life, far beyond material wealth. The song’s upbeat, bluesy feel is complemented by Stapleton’s warm, gravelly voice, making it a feel-good anthem that quickly became a favorite among fans. The lyrics express the idea that true wealth comes from the love and happiness shared between partners, a theme that resonates deeply in Stapleton’s music. “Millionaire” showcases Stapleton’s ability to take a song and make it his own, infusing it with his unique blend of country and soul.
8. Whiskey and You (2015)
“Whiskey and You” is one of the most poignant tracks on Chris Stapleton’s Traveller album, released in 2015. The song is a stark, raw ballad about heartbreak and the ways people cope with pain. With just an acoustic guitar and Stapleton’s powerful voice, the song strips down to the bare essentials, allowing the emotion in the lyrics to take center stage. The song contrasts the temporary solace of whiskey with the enduring pain of lost love, creating a powerful narrative that resonates with anyone who has experienced heartache. “Whiskey and You” is a masterclass in storytelling, showcasing Stapleton’s ability to convey deep emotion with simplicity and honesty. It’s a song that has become a favorite among fans for its raw, unfiltered portrayal of sorrow.
9. More of You (2015)
“More of You” is a tender love song from Chris Stapleton’s 2015 album Traveller. The song features a duet with Stapleton’s wife, Morgane Stapleton, adding a layer of intimacy and warmth to the track. The lyrics express a deep, abiding love, with the narrator longing for more time and connection with their partner. The song’s gentle melody and heartfelt lyrics make it a standout track on the album, showcasing Stapleton’s softer side. “More of You” is a beautiful, understated ballad that captures the essence of true love, making it a favorite for weddings and romantic moments. The song’s simplicity and sincerity have made it a cherished part of Stapleton’s catalog.
10. You Should Probably Leave (2020)
“You Should Probably Leave” is a standout track from Chris Stapleton’s 2020 album Starting Over. The song tells the story of a complicated relationship, where the narrator knows that staying will lead to heartbreak, but the pull of desire is hard to resist. The song’s bluesy melody and Stapleton’s soulful vocals create a sense of tension and longing, perfectly capturing the conflict at the heart of the lyrics. “You Should Probably Leave” is a masterful exploration of temptation and the difficulty of making the right choice in the face of strong emotions. Its relatable theme and Stapleton’s powerful delivery have made it a favorite among fans. The song’s blend of country, blues, and soul is a testament to Stapleton’s versatility as an artist, making it one of the standout tracks on Starting Over.
Samuel Moore 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.
