24 of Chris Stapleton's Best Songs: A Definitive List

Chris Stapleton’s rise to prominence is a testament to raw talent and unwavering dedication. Emerging from a background as a highly respected session singer and songwriter, he eventually broke through to solo stardom, captivating audiences with his powerful vocals and deeply resonant songwriting. His career is marked not only by chart-topping hits, but also by consistently soulful performances that showcase both his vulnerability and his immense vocal range. From the heart-wrenching ballad that perfectly captures the bittersweet sting of lost love, to the anthems celebrating resilience and finding strength amidst adversity, Stapleton's music consistently touches the soul. This exploration of his best work isn't just a ranking of songs; it's a celebration of a songwriter and performer who has redefined what it means to be authentic in modern country music and a chance to discover or rediscover some truly timeless tracks.

His ability to craft songs that are both intensely personal and universally relatable is a rare gift, resonating with listeners across generations and musical preferences. This list aims to shine a light on the diverse tapestry of his musical output, from the brooding intensity of some tracks to the uplifting hope found in others. Whether you're a longtime fan or just discovering the power of his voice, exploring this collection promises a journey through the emotional landscape of one of country music's most compelling artists, offering a powerful reminder of music's ability to connect us through shared experiences. Prepare to be moved.

  • Tennessee Whiskey
    1

    Tennessee Whiskey

    Chris Stapleton

    2015

    Traveller

  • Fire Away
    2

    Fire Away

    Chris Stapleton

    2015

  • Starting Over
    3

    Starting Over

    Chris Stapleton

    2020

  • Broken Halos
    4

    Broken Halos

    Chris Stapleton

    2017

  • What Are You Listening To
    5

    What Are You Listening To

    Chris Stapleton

    2017

  • Parachute
    6

    Parachute

    Chris Stapleton

    2015

  • I Was Wrong
    7

    I Was Wrong

    Chris Stapleton

    2017

  • Might As Well Get Stoned
    8

    Might As Well Get Stoned

    Chris Stapleton

    2015

  • Traveller
    9

    Traveller

    Chris Stapleton

    2015

  • Daddy Doesn’t Pray Anymore
    10

    Daddy Doesn’t Pray Anymore

    Chris Stapleton

    2017

  • Your Man
    11

    Your Man

    Chris Stapleton

    2015

  • Outlaw State of Mind
    12

    Outlaw State of Mind

    Chris Stapleton

    2015

  • Sometimes I Cry
    13

    Sometimes I Cry

    Chris Stapleton

    2015

  • Nobody
    14

    Nobody

    Chris Stapleton

    2015

  • Cold
    15

    Cold

    Chris Stapleton

    2015

  • Was It 26
    16

    Was It 26

    Chris Stapleton

    2015

  • If It Hadn't Been for Love
    17

    If It Hadn't Been for Love

    Chris Stapleton

    2015

  • Friendship
    18

    Friendship

    Chris Stapleton

    2015

  • More Of You
    19

    More Of You

    Chris Stapleton

    2015

  • Second One To Know
    20

    Second One To Know

    Chris Stapleton

    2015

  • Hard Livin'
    21

    Hard Livin'

    Chris Stapleton

    2015

  • Them Stems
    22

    Them Stems

    Chris Stapleton

    2015

  • Nobody's Lonely Tonight
    23

    Nobody's Lonely Tonight

    Chris Stapleton

    2017

  • Love's Gonna Make It Alright
    24

    Love's Gonna Make It Alright

    Chris Stapleton

    2017