After recording three records as a member of Drive-By Truckers, Alabama native Jason Isbell emerged as an artist in his own right with his debut solo album Sirens of the Ditch in 2007. During those early years, he went through a divorce, got sober, and later married talented singer-songwriter and fiddle player Amanda Shires. Through it all, he lived a tale worth a thousand songs.

Isbell teamed up with producer Dave Cobb for 2013's critically acclaimed Southeastern, which led to him winning Album of the Year and Artist of the Year at the 2014 Americana Music Awards, and the momentum continued with 2015's Something More Than Free. The latter LP won the Grammys trophy for Best Americana Album, while the record's "24 Frames" won Best American Roots Song. And as if that wasn't enough, Isbell's 2017 album The Nashville Sound with his band The 400 Unit also took home two Grammy Awards and was nominated at the CMA Awards. With the release of his stellar 2020 album Reunions and 2021's Georgia Blue, Isbell has proven that he has no plans of slowing down, even through a global pandemic.

Isbell's catalog is full of gems, but the following are The Boot's picks for his Top 10 tunes:

This list was originally written by Annie Zaleski, and revised by Blake Ells and Lorie Liebig.

  • 10

    "Palmetto Rose"

    From: 'Southeastern' (2013)

    Relatively speaking, a deep cut from Something More Than Free, “Palmetto Rose” managed to be the type of song that Isbell spent years writing about Alabama and Alabamians, but for South Carolinians. It is an anthem about a home that Isbell never lived in.

  • 9

    "Flying Over Water"

    From: 'Southeastern' (2013)

    “Flying Over Water” is the exact intersection of the versions of Jason Isbell & the 400 Unit. It’s a rock and roll song, but it’s also an Americana song. It’s about the fear of trying something new and overcoming it. It’s about walking the line of sobriety. It’s about leaving home and remembering where home was. If someone was given just one 3:30 minute song to be introduced to Jason Isbell & the 400 Unit, this is the one that best accomplishes the task.

  • 8

    "Something to Love"

    From: 'The Nashville Sound' (2017)

    There’s something special about the hopeful songs that Isbell writes, because they don’t come often. This one, which was the last track on The Nashville Sound, is one of many he’s written about his daughter as she’s grown.

    “Just find what makes you happy girl / And do it til you’re gone.”

  • 7

    "Tour of Duty"

    From: 'Here We Rest' (2011)

    “Tour of Duty” is arguably the most joyful song ever written about war. It tells the story of a man that has returned home to his partner and the plans that they can now make together, reunited. In recent years, it has made a consistent return to the band’s set lists, stripped down as a duo with Isbell and guitarist Sadler Vaden.

    “I’ve been eating like I’m out on bail / Collard greens and chicken wings and oysters by the pail / Eating oysters by the pail / Making up for those lost days.”

  • 6

    "Dress Blues"

    From: 'Sirens of the Ditch' (2007)

    A song from Isbell’s solo debut, Sirens of the Ditch, “Dress Blues” is about a native of Isbell’s hometown named Matthew Conley who died at war. It’s about the way that kind of loss plays out in a small town, which really isn’t the way it’s often politicized in national news media.

    This track was later recorded by Zac Brown Band, but stands as another cover version of an Isbell tune that lacks something when stripped of context. The story that Isbell shared was one that was close to him, and it laid the groundwork for what his own sound apart from Drive-By Truckers would be.

  • 5

    "Something More Than Free"

    From: 'Something More Than Free' (2015)

    Much like the next song on this list, the title track of Something More Than Free found Isbell shaping personal experiences into universal themes that everyone —especially those across the rural south, in places similar to his hometown — could relate.

    “I don’t think on why I’m here or where it hurts / I’m just lucky to have the work / Every night I dream I’m drowning in the dirt/but I thank God for the work.”

  • 4

    "Speed Trap Town"

    From: 'Something More Than Free' (2015)

    This track from 2015’s Something More Than Free was clearly inspired by specific events to Isbell, but it’s the beginning of a new way that he had begun writing at the time where he found ways to connect his own stories to a wider audience. Everyone in every state knows a speed trap town, one that celebrates their high school football team as if its’ on a national stage. As such, it was a breakthrough for his own craft and the way he’d move ahead.

  • 3

    "Alabama Pines"

    From: 'Here We Rest' (2011)

    “Alabama Pines” was the song that let AAA and Americana know that Isbell had fully arrived as a solo artist. He has penned plenty of songs about his home state, but this one has become a de facto state anthem strong enough to rival Lynyrd Skynyrd’s “Sweet Home Alabama.”

  • 2

    "Elephant"

    From: 'Southeastern' (2013)

    “Elephant” is about the narrator’s relationship with a friend that has been diagnosed with cancer. Isbell speaks of trying to carry on with everyday life, while ignoring a lingering reality that will alter our time together.

    “There’s one thing that’s real clear to me / No one dies with dignity / We just try to ignore the elephant somehow.”

  • 1

    "Cover Me Up"

    From: 'Southeastern' (2013)

    The breakthrough track from 2013's Southeastern, “Cover Me Up” was written by Isbell about his own struggle with sobriety and his relationship with his wife, acclaimed singer-songwriter and multi-instrumentalist Amanda Shires.

     

    Morgan Wallen recorded his own version of "Cover Me Up" for inclusion on his 2021 album Dangerous after frequently performing it at his live shows. Although Wallen's is devoid of the personal connection that makes Isbell's original version shine, it earned some airplay on country radio although it was never formally released as a single. Shortly after Wallen’s use of a racial slur in early 2021, Isbell pledged to donate all proceeds he earned from Wallen’s version to the NAACP.