Chris Stapleton has redefined modern country music with his raw, soulful voice and authentic storytelling that bridges traditional country, southern rock, and blues. The Kentucky native burst onto the mainstream scene in 2015 after years as a celebrated songwriter, immediately establishing himself as one of the most compelling voices in contemporary music. His ability to convey deep emotion through gritty vocals and stripped-down arrangements has earned him multiple Grammy Awards and a devoted following that spans across genre boundaries. These 20 best Chris Stapleton songs showcase his incredible range, from heart-wrenching ballads to foot-stomping rockers, representing the essential tracks that have solidified his status as country music royalty.
Tennessee Whiskey
The song that launched Chris Stapleton into superstardom remains his signature masterpiece. This soul-stirring love song draws brilliant comparisons between romance and smooth whiskey, delivered with a vocal performance that channels classic R&B influences while maintaining country authenticity. Stapleton’s raspy, emotional delivery transforms what could have been a simple metaphor into something transcendent, with production that allows his voice and guitar work to take center stage. The 2015 CMA Awards performance of this track alongside Justin Timberlake became legendary, introducing millions to Stapleton’s undeniable talent and fundamentally changing the trajectory of mainstream country music toward more authentic, roots-oriented sounds.
White Horse
Released from his 2023 album “Higher,” this powerful track showcases Stapleton’s ability to craft anthemic rockers that maintain country soul. The song features driving rhythms and electric guitar work that demonstrates his southern rock influences, while his vocals deliver lyrics about resilience and refusing to give up with commanding authority. White Horse represents Stapleton’s evolved sound—more muscular and expansive while retaining the emotional honesty that defines his best work. The production incorporates layered instrumentation that builds to explosive choruses, proving that Stapleton can dominate both intimate ballads and arena-ready rock numbers with equal mastery.
Starting Over
The title track from his 2020 album arrived during a period of global uncertainty, offering hope and renewal through its message about embracing new beginnings. Stapleton’s vocal performance balances vulnerability with determination, supported by gentle acoustic guitar and understated production that gradually builds emotional intensity. The song’s universal themes about leaving the past behind and finding courage to start fresh resonated deeply with listeners navigating their own transitions. Starting Over earned widespread critical acclaim and multiple award nominations, demonstrating Stapleton’s continued relevance and his ability to capture complex emotions with deceptive simplicity in both lyrics and arrangement.
Broken Halos
This contemplative ballad from “From A Room: Volume 1” addresses loss and remembrance with mature perspective and gentle grace. Stapleton explores the idea that the best people often leave too soon, delivering philosophical lyrics with a vocal warmth that provides comfort rather than deepening sorrow. The stripped-down acoustic arrangement allows the profound message to resonate without distraction, while subtle harmonies add depth during key moments. Broken Halos showcases Stapleton’s growth as a songwriter willing to tackle life’s most difficult subjects, offering listeners a musical space for reflection and healing that feels both personal and universal in its emotional reach.
Cold
A standout track from “Starting Over,” this song features one of Stapleton’s most powerful vocal performances, conveying the emotional devastation of a relationship’s end. The production builds from sparse verses to a soaring chorus where Stapleton’s voice cracks with genuine anguish, creating moments of raw vulnerability that few contemporary artists can match. The metaphor of coldness representing emotional distance and loss permeates the lyrics, enhanced by atmospheric production choices that create sonic space around his voice. Cold demonstrates why Stapleton has become the go-to artist for listeners seeking authentic emotional expression in country music, as he transforms personal pain into universally relatable art.
Fire Away
Perhaps Stapleton’s most emotionally devastating composition, this ballad addresses mental health struggles and unconditional love with rare sensitivity and depth. His vocal delivery conveys both the pain of watching a loved one suffer and the unwavering commitment to stand beside them, creating a powerful statement about loyalty during life’s darkest moments. The production wisely remains minimal, allowing the profound lyrics and Stapleton’s aching vocal performance to carry the emotional weight without manipulation or overproduction. Fire Away has become an anthem for mental health awareness within the country music community, demonstrating music’s power to address difficult subjects while offering hope and understanding to those who need it most.
Parachute
This upbeat love song from “Traveller” showcases Stapleton’s ability to craft joyful, celebratory tracks that maintain his signature soulful delivery. The metaphor of a lover being a safety net provides the framework for lyrics that express complete trust and devotion with genuine warmth rather than saccharine sentimentality. Stapleton’s vocal performance rides the groove with infectious energy, supported by production that incorporates elements of classic soul and funk into his country foundation. Parachute has become a favorite for those seeking authentic country music recommendations that celebrate love without resorting to clichés, proving Stapleton excels at both heartbreak and happiness with equal conviction.
Millionaire
An uptempo celebration of love over material wealth, this track from “From A Room: Volume 2” delivers its message with rollicking energy and authentic joy. Stapleton’s vocal performance exudes confidence and contentment as he details how emotional richness surpasses financial prosperity, backed by driving rhythms and spirited instrumentation. The song’s production incorporates elements of classic country-rock, with prominent guitar work and a rhythm section that propels the track forward with irresistible momentum. Millionaire represents Stapleton’s ability to craft radio-friendly hits that don’t compromise his artistic integrity, maintaining the raw authenticity that defines his catalog while delivering undeniable hooks and memorable melodies.
Think I’m In Love With You
From his 2023 “Higher” album, this track finds Stapleton exploring the uncertainty and excitement of new romance with youthful enthusiasm. His vocal delivery balances vulnerability with hopeful anticipation, creating an emotional honesty that makes even familiar romantic themes feel fresh and genuine. The production incorporates contemporary elements while maintaining Stapleton’s roots-oriented approach, featuring clean guitar tones and a steady rhythm that supports without overwhelming his voice. Think I’m In Love With You demonstrates that even as Stapleton’s career has reached superstar levels, he remains grounded in fundamental human experiences, crafting songs that connect with listeners through shared emotions rather than gimmicks.
What Are You Listening To?
A meta-commentary on music’s power to evoke memories and emotions, this track uses the simple question about someone’s playlist as a gateway to exploring past relationships. Stapleton’s delivery captures the bittersweet recognition that certain songs forever link us to specific people and moments, creating a universal experience for anyone who has associated a soundtrack with lost love. The production maintains a mid-tempo groove that supports the nostalgic lyrics, while Stapleton’s vocal nuances convey layers of meaning beyond the words themselves. This song showcases his sophistication as a songwriter, using a contemporary concept to explore timeless themes about memory, music, and heartache.
Joy of My Life
This tender love song strips everything down to acoustic essentials, allowing Stapleton’s heartfelt lyrics and emotional vocal delivery to create intimate connection with listeners. Written about his wife Morgane, who provides harmonies on the track, the song captures the profound gratitude and deep contentment of finding your person. Stapleton’s performance avoids grand gestures, instead conveying lasting love through understated sincerity that feels more powerful than any dramatic production choices could achieve. Joy of My Life has become a wedding favorite and relationship anthem, demonstrating that Stapleton’s greatest strength lies in his ability to express complex emotions through deceptively simple arrangements and genuine vulnerability.
I Was Wrong
From “From A Room: Volume 1,” this track confronts the difficulty of admitting mistakes and seeking forgiveness with mature introspection. Stapleton’s vocal performance carries the weight of regret without descending into self-pity, creating a powerful statement about accountability and growth. The production features prominent organ and a gospel-influenced arrangement that adds spiritual depth to the personal confession, while maintaining the raw authenticity that defines Stapleton’s best work. I Was Wrong represents the kind of emotionally honest songwriting that has distinguished Stapleton from many contemporary country artists, proving that vulnerability and accountability can create compelling music that resonates across demographics.
The Ballad of the Lonesome Cowboy
Written for Pixar’s “Toy Story 4,” this track channels classic western themes through Stapleton’s contemporary lens, creating a perfect marriage of nostalgia and freshness. His weathered vocal delivery captures the mythology of the American cowboy while the production incorporates traditional western instrumentation with modern recording techniques. The song works both within the film’s context and as a standalone piece, showcasing Stapleton’s versatility and his ability to honor traditional country forms without becoming derivative. The Ballad of the Lonesome Cowboy introduced Stapleton to new audiences while satisfying longtime fans, demonstrating his broad appeal across generations and musical preferences.
Whiskey and You
A devastating comparison between alcohol and a lost love, this early track from “Traveller” showcases Stapleton’s blues influences and his mastery of the traditional country heartbreak song. His vocal performance drips with anguish as he details how even whiskey can’t numb the pain of lost love, delivered with conviction that suggests deeply personal experience. The stripped-down production allows every vocal nuance to land with maximum impact, while subtle guitar work adds texture without distraction. Whiskey and You represents pure, uncut country blues that refuses to compromise or pander, establishing Stapleton as an artist committed to authentic emotional expression regardless of commercial considerations.
Blue Side of the Mountain
A cover of a SteelDrivers song (Stapleton’s former band), this track highlights his bluegrass roots and showcases his ability to deliver high-energy traditional country with modern production values. The driving rhythm and prominent mandolin create infectious momentum, while Stapleton’s vocals maintain clarity and power throughout the uptempo arrangement. Blue Side of the Mountain bridges the gap between Stapleton’s bluegrass past and country-rock present, demonstrating the consistency of his artistic vision across different contexts and band configurations. The song’s energy makes it a live favorite, proving Stapleton can command attention with both quiet introspection and rollicking performance numbers.
Nobody to Blame
This self-reflective track examines personal responsibility after a relationship’s end, with Stapleton acknowledging his role in driving his partner away. The production features a memorable guitar riff and groove-oriented arrangement that creates movement while supporting lyrics about regret and accountability. Stapleton’s vocal delivery balances resignation with understanding, creating a mature perspective on failed relationships that avoids both victimhood and villainy. Nobody to Blame became a significant radio hit, proving that audiences respond to Stapleton’s honest approach even when the subject matter acknowledges uncomfortable personal truths, and helping establish him as more than just a ballad specialist.
Traveller
The title track from his breakthrough album established Stapleton’s aesthetic and artistic vision with crystalline clarity. This song about moving forward after loss combines literal travel imagery with emotional journey metaphors, delivered through Stapleton’s most vulnerable vocal performance. The production gradually builds from stark acoustic beginnings to a powerful electric guitar solo that releases the song’s accumulated emotional tension in a cathartic instrumental statement. Traveller encapsulates everything that makes Stapleton special—authentic emotion, masterful musicianship, poetic lyrics, and the courage to let songs breathe and develop naturally rather than forcing them into radio-friendly formats.
Devil Always Made Me Think Twice
From “Starting Over,” this track addresses temptation and moral struggle with bluesy grit and rock attitude. Stapleton’s vocal performance conveys the internal conflict between doing right and giving in to darker impulses, backed by muscular production featuring prominent electric guitar and driving rhythms. The song demonstrates Stapleton’s comfort exploring complicated human experiences without offering easy answers or moral certainties, creating space for listeners to recognize their own struggles. Devil Always Made Me Think Twice showcases his versatility as both vocalist and songwriter, proving he can deliver hard-rocking tracks with the same emotional authenticity he brings to tender ballads.
Maggie’s Song
A heartbreaking tribute to Stapleton’s deceased dog, this track might seem like an unusual choice for a serious artist, but Stapleton transforms pet loss into profound meditation on love, loyalty, and grief. His vocal performance captures genuine heartbreak without embarrassment or irony, honoring the bond between humans and animals with touching sincerity. The production remains gentle and supportive, allowing the emotional lyrics to resonate without manipulation, while Stapleton’s delivery conveys the universal experience of losing a beloved companion. Maggie’s Song demonstrates remarkable artistic courage, tackling a subject some might consider trivial with the same depth and commitment he brings to any other form of love and loss.
Either Way
This philosophical ballad examines the uncertainty of whether a relationship will survive or end, accepting both possibilities with mature resignation. Stapleton’s vocal performance captures the emotional complexity of hoping for the best while preparing for the worst, delivered with understated power that allows nuance to shine through. The production features beautiful chord progressions and subtle instrumental layering that creates atmosphere without overwhelming the introspective lyrics. Either Way represents Stapleton’s growth as a songwriter willing to embrace ambiguity and complexity rather than forcing resolution, creating songs that mirror the messy reality of human relationships rather than simplifying them for commercial appeal.
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Frequently Asked Questions
What is Chris Stapleton’s most famous song?
Tennessee Whiskey remains Chris Stapleton’s most famous and commercially successful song. Released in 2015 from his debut solo album “Traveller,” the track became a cultural phenomenon after his legendary CMA Awards performance with Justin Timberlake. The song’s blend of country and soul influences, combined with Stapleton’s raw vocal power and the timeless metaphor comparing love to smooth whiskey, captured audiences across genre boundaries. Tennessee Whiskey topped multiple charts, earned widespread critical acclaim, and fundamentally changed mainstream country music’s direction toward more authentic, roots-oriented sounds. The track continues to define Stapleton’s career and serves as his signature song at live performances.
What genre is Chris Stapleton’s music?
Chris Stapleton’s music defies simple categorization, blending traditional country, southern rock, blues, and soul into a distinctive sound that honors roots while feeling contemporary. While marketed primarily as country music, his work incorporates blues guitar techniques, R&B vocal styling, rock energy, and bluegrass instrumentation from his time with The SteelDrivers. This genre-blending approach has made Stapleton appealing to diverse audiences beyond traditional country fans, attracting rock, blues, and soul listeners who appreciate authentic musicianship and emotional honesty. His refusal to conform to contemporary country-pop trends has actually expanded his audience, proving that artistic integrity and commercial success aren’t mutually exclusive when talent and authenticity are this undeniable.
How many Grammy Awards has Chris Stapleton won?
Chris Stapleton has won eight Grammy Awards throughout his career, with five coming from his breakthrough album “Traveller” and additional wins for subsequent releases. His Grammy victories span multiple categories including Best Country Album, Best Country Solo Performance, and Best Country Song, demonstrating the Recording Academy’s recognition of both his vocal performances and songwriting abilities. Stapleton’s Grammy success reflects the music industry’s embrace of his traditional approach during a period when country music had largely moved toward pop-influenced production. These awards have validated his artistic choices and helped establish him as one of contemporary country music’s most respected and acclaimed artists, influencing a new generation of performers toward more authentic, roots-oriented sounds.
Did Chris Stapleton write songs for other artists before his solo career?
Yes, Chris Stapleton enjoyed tremendous success as a Nashville songwriter before launching his solo career, penning hits for numerous major country artists. His songwriting credits include chart-toppers for Kenny Chesney, George Strait, Luke Bryan, and Adele, among many others. Stapleton wrote or co-wrote over 170 songs recorded by other artists, earning recognition as one of Nashville’s most talented and versatile songwriters. This extensive songwriting background provided him with deep industry connections, financial stability to pursue his artistic vision, and refined skills in crafting emotionally resonant lyrics and memorable melodies. His transition from successful songwriter to acclaimed performer demonstrates that his talent extends beyond writing to include the interpretive skills and vocal power necessary for superstar status.
What was Chris Stapleton’s band before going solo?
Before his solo breakthrough, Chris Stapleton fronted The SteelDrivers, a bluegrass and country band that earned critical acclaim within Americana circles. He served as the band’s lead vocalist and guitarist from 2008 to 2010, recording two albums that showcased his powerful voice within a traditional bluegrass context. The SteelDrivers received Grammy nominations and developed a devoted following, establishing Stapleton’s credibility within roots music communities before mainstream recognition arrived. His time with The SteelDrivers provided essential experience in bluegrass instrumentation, harmonies, and traditional arrangements that continue to influence his solo work. Leaving the band to pursue a solo career proved fortuitous, allowing Stapleton to expand his sound while maintaining the authenticity and musicianship he developed during those formative bluegrass years.