Few artists in modern country music have the ability to transcend genres and captivate audiences like Chris Stapleton. With his gritty, soulful voice, unmatched songwriting prowess, and raw emotional delivery, Stapleton has become a household name not just for country fans, but for music lovers everywhere. Whether he’s belting out bluesy ballads or delivering heart-wrenching tales of love and loss, Stapleton’s music has a way of reaching into your soul and leaving a lasting impact.
In this article, we’re counting down the top 10 most popular Chris Stapleton songs of all time—tracks that have topped charts, earned awards, and become anthems for fans around the world. From his breakthrough hit Tennessee Whiskey to more introspective gems like Broken Halos, these songs represent the very best of Stapleton’s incredible career. So, whether you’re a longtime fan or a newcomer to his music, get ready to dive into the mesmerizing world of one of country music’s greatest talents. Let’s take a captivating journey through the songs that helped define Chris Stapleton’s legacy and continue to resonate with listeners today!
1. Tennessee Whiskey (2015)
Arguably Chris Stapleton’s most iconic song, Tennessee Whiskey was first released on May 5, 2015, as part of his debut album, Traveller. This cover of a 1981 song originally recorded by David Allan Coe became a massive hit thanks to Stapleton’s soulful reinterpretation. Stapleton infuses the track with bluesy guitar riffs, a slow-burning rhythm, and his signature gravelly voice, making it sound like a completely new creation. The song became a sensation after his unforgettable duet with Justin Timberlake at the 2015 CMA Awards, skyrocketing Stapleton to fame. The blend of country, blues, and R&B elements in Tennessee Whiskey has made it a timeless anthem for lovers of smooth, heartfelt ballads.
2. Broken Halos (2017)
Released on May 5, 2017, from his From A Room: Volume 1 album, Broken Halos is a powerful, emotional ballad that resonates with themes of loss and faith. The song was written by Stapleton and his longtime collaborator Mike Henderson. Its stripped-down instrumentation allows Stapleton’s raw vocals to shine, carrying the weight of the song’s somber message. Broken Halos won the Grammy Award for Best Country Song in 2018, solidifying its place as one of Stapleton’s most beloved works. The song’s poignant lyrics and Stapleton’s yearning delivery make it a deeply touching experience for listeners.
3. Fire Away (2015)
Fire Away is a haunting ballad from Stapleton’s debut album Traveller, released on May 5, 2015. The song deals with themes of love, vulnerability, and emotional resilience. Driven by a slow, steady beat and Stapleton’s aching vocals, Fire Away evokes feelings of both hope and heartbreak. The accompanying music video, which deals with mental health struggles and the impact it has on relationships, added another layer of emotional depth to the song. Fire Away is a testament to Stapleton’s ability to tackle heavy subjects with grace and raw emotion, making it a standout track in his catalog.
4. Parachute (2015)
Released on May 5, 2015, as part of Traveller, Parachute is one of the more upbeat tracks in Stapleton’s discography. This energetic song showcases his versatility as both a vocalist and a songwriter. The lyrics describe the unwavering support offered by a partner, with Stapleton’s voice soaring over a foot-stomping beat and electric guitar riffs. The anthemic quality of Parachute makes it a concert favorite, with its infectious rhythm and Stapleton’s powerful delivery keeping audiences captivated. It’s an exhilarating track that highlights Stapleton’s more rock-infused side.
5. Either Way (2017)
Either Way, released on May 5, 2017, from the From A Room: Volume 1 album, is a heart-wrenching ballad that explores the painful end of a relationship. The minimalist production—just Stapleton’s voice and an acoustic guitar—allows the vulnerability of the lyrics to take center stage. Known for its raw emotional depth, Either Way showcases Stapleton’s ability to convey complex emotions through simple, yet powerful, songwriting. The song was a commercial success and received critical acclaim for its stark portrayal of love lost.
6. Whiskey and You (2015)
Whiskey and You was first published on May 5, 2015, as part of Traveller, but it originally appeared on Tim McGraw’s 2007 album Let It Go. However, Stapleton’s version, stripped of any glossy production, stands out as a deeply personal and reflective track. The song compares the solace found in whiskey to the pain of lost love, and Stapleton’s mournful delivery adds gravity to the already poignant lyrics. It’s a song that perfectly encapsulates Stapleton’s ability to blend heartache with honesty, making it one of his most emotionally resonant tracks.
7. Traveller (2015)
The title track of Stapleton’s debut album, Traveller, was released on May 5, 2015. This song is a reflective, mid-tempo ballad that deals with the themes of self-discovery and life on the road. Written after the death of his father, Traveller captures Stapleton’s sense of being adrift and searching for meaning. The song’s gentle melody paired with Stapleton’s introspective lyrics makes it a standout track that resonates deeply with listeners who have experienced life’s ups and downs. Traveller encapsulates the heart and soul of Stapleton’s debut, setting the tone for his career.
8. Starting Over (2020)
Starting Over, released on November 13, 2020, is the title track of Stapleton’s fourth studio album. The song offers a hopeful message about new beginnings and the courage it takes to start fresh, whether in life or love. The gentle acoustic guitar and Stapleton’s warm, soulful vocals create an uplifting and reassuring atmosphere. Starting Over quickly became a fan favorite for its optimistic outlook and heartfelt lyrics, showing a softer and more hopeful side of Stapleton’s songwriting. It’s a song that speaks to resilience and the beauty of embracing change.
9. Millionaire (2017)
Millionaire, released on May 5, 2017, as part of From A Room: Volume 2, is a cover of Kevin Welch’s original song, but Stapleton makes it his own with his rich, soulful voice. The song’s uplifting message about love being more valuable than money is delivered with a laid-back groove and Stapleton’s signature emotional depth. Millionaire showcases Stapleton’s ability to breathe new life into a song, turning it into a heartfelt celebration of what truly matters in life. Its catchy melody and feel-good lyrics make it a standout track.
10. Nobody to Blame (2015)
Released on May 5, 2015, Nobody to Blame is one of Stapleton’s more traditional country songs, complete with twangy guitars and a driving rhythm. The song tells the story of a man who accepts responsibility for the end of a relationship, admitting that he’s got “nobody to blame but me.” It became a massive hit on country radio, and its relatable lyrics paired with Stapleton’s gritty vocals made it an instant favorite. Nobody to Blame won the ACM Award for Song of the Year in 2016, further cementing Stapleton’s status as a country music powerhouse.
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.
