Jason Isbell has had a dynamite solo career in recent years. Not only did the former Drive-By Truckers member marry Amanda Shires, a talented singer-songwriter and fiddle player in her own right, and have an adorable baby girl, but since getting sober, his career has shifted into overdrive.

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 also took home two Grammy Awards and was nominated at the CMA Awards.

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

  • 10

    "Down in a Hole"

    From 2007's 'Sirens of the Ditch'

    The rich, fat-cat protagonist of this early Isbell solo song is "trouble," from his penchant for redevelopment to the way he (mis)treats his daughters and employees. The tune's music emphasizes the lyrical wariness: Organ courtesy of Spooner Oldham and bass from David Hood (the father of Isbell's Drive-By Truckers bandmate Patterson Hood) help create a simmering, sultry-blues vibe.

  • 9

    "Go It Alone"

    From 2011's 'Here We Rest'

    This plugged-in song highlights Isbell's grittier, bar-band country-blues side. Credited to Jason Isbell and the 400 Unit, the song features a protagonist who's come to terms with the fact he has to press restart on his life — in part because he's lost a woman, presumably due to divorce — to try to regain equilibrium: "I'm realizing just how far I had to fall / And taking it home to go it alone again."

  • 8

    "Letting You Go"

    From 2020's 'Reunions'

    Isbell knows how to tug at listeners' heartstrings, but "Letting You Go" is different new look for him. Truly, did anyone ever expect him to write a absolutely perfect father-daughter dance song?

    "Being your daddy comes natural / The roses just know how to grow," Isbell sings in the chorus. "It's easy to see that you'll get where you're going / The hard part is letting you go / The hard part is letting you go."

    Written about, and for, his daughter, Mercy Rose, the darling song finds him recalling his baby girl's first days, and imagining her wedding day. "I wish I could walk with them back through your life to see / Every last minute of every last day," Isbell admits of Mercy's future spouse. "The best I can do is to let myself trust that you know who'll be strong enough to carry your heart."

  • 7


    From 2013's 'Southeastern'

    One of Isbell's most moving, harrowing songs on Southeastern is "Elephant," which describes what happens when one-half of a pair of "drinking buddies" is slowly dying of cancer. Atop strident, braided acoustic guitar and piano, Isbell describes silly joys (complaining about weekend warriors), reality-check side effects (losing hair and singing voice) and the private pain of the "elephant" in the room: "Surrounded by her family, I saw that she was dying alone."

  • 6

    "Alabama Pines"

    From 2011's 'Here We Rest'

    Credited to Jason Isbell and the 400 Unit, this Americana Music Award-winning song presaged the stripped-back, straight-shooting direction that Isbell would take on future solo albums. The protagonist feels unmoored from the place where he grew up — longing for its familiar quirks, but knowing that he can't replicate the past. Longing fiddle weaves through the story, capturing the circuitous lifestyle with which the protagonist has dealt.

  • 5

    "Traveling Alone"

    From 2013's 'Southeastern'

    This 2013 Isbell song acutely captures the crushing loneliness of the open road, especially when you're traveling by yourself and longing for a companion: "I know every town worth passing through," he says. "But what good does knowing do with no one to show it to?" Shires adds elegiac fiddle and subtle backing vocals to the song, amplifying its ache.

  • 4

    "If We Were Vampires"

    From 2017's 'The Nashville Sound'

    A Grammy Awards Best American Roots Song winner, "If We Were Vampires" is a stark admission of a truth we're rarely fully ready to face: Our time on this planet -- specifically, with the one we love the most -- is finite, and when all is said and done, one person is left behind.

    "Maybe we'll get 40 years together," Isbell sings, "But one day, I'll be gone / Or one day, you'll be gone.

    It's not all gloomily upsetting, though. Over gorgeous fiddle played by his wife, Amanda Shires, Isbell points out, "Maybe time running out is a gift," an encouragement to each of us to cherish the time we do get. I'll work hard 'til the end of my shift / And give you every second I can find / And hope it isn't me who's left behind," he pledges.

  • 3

    "24 Frames"

    From 2015's 'Something More Than Free'

    This song finds a character who's humbled by his own shortcomings and trying to reconnect with things that matter — family, love and selflessness — while recalibrating his sense of the world. Musically, it resembles the laid-back alt-country favored by Wilco in the '90s, with a splash of R.E.M.'s jangle thrown in for good measure.

  • 2

    "Dress Blues"

    From 2007's 'Sirens of the Ditch'

    Zac Brown Band popularized this song by covering it on their 2015 album Jekyll + Hyde. It's easy to see why the band was drawn to the song: Isbell's original — which was inspired by a high school acquaintance, Marine Cpl. Matthew D. Conley, who was killed while in the line of duty — is a wrenching, plainspoken remembrance of war's casualties.

  • 1

    "Cover Me Up"

    From 2013's 'Southeastern'

    Isbell's straightforward song about getting sober and opening himself up to wife Shires is one of his best — simply because it is so vulnerable and deeply felt.

    "That was a hard one for me to even get through without breaking down the first time, because that one is really personal," he told NPR in 2013. "It's not easy to sit down and open yourself up and say, 'This is how much I love you,' you know? It's scary to do that."