Essentials: The Top 10 Jason Isbell Songs

Jason Isbell is no hidden secret. The Alabama native is undeniably one of our most talented songwriters and sits somewhere between the Southern Gothic of William Faulkner and the character-driven narratives of John Prine. Finding his feet solidly in Southern rock band Drive-By Truckers, Isbell then found space to be telling his own tales with his first project with backing band The 400 Unit in 2009. It was in 2013 that Isbell released “Southeastern”, and his potential became undeniable.

Above anything else, Isbell is defined by his stories. His lyrics are rooted in deep, raw emotional honesty to the point of bridging on painful at times; there aren’t many artists that come to mind in comparison. Isbell is in a league of his own, and perhaps that’s why once his words are tangled up in your life, it can be hard to let them go again. He can deliver a sentence that digs down and settles under your skin; it can be uncomfortable, but ultimately, Isbell is a lifetime artist and a lifelong artist.

In relation to a career creeping into two decades (without Drive-By Truckers included), I’m a relatively new Isbell fan – his music only finding its place in my life over the last year or so, but there is no part of me that doubts its place or its longevity. It’s tangled up in who I am now, and is there anything more that you can ask for from music?

For the purpose of this list, Drive-By Truckers songs aren’t being included – in fact, Americana UK already has a list of essentials from the band. I will be including solo songs and songs with The 400 Unit – to me, they’re all equally Isbell. I’m also bearing in mind that this is an ‘essentials’ list; this is a place to start for new listeners and to disagree with for those who have their own memories attached to Isbell songs. It’s a list of ten songs to take to a desert island, but it’s not just my desert island – if it was, this list might be ever so slightly different. These are the ten I think you should listen to, but that list could go miles beyond ten. And on that note, please disagree. I think Isbell would be happy about that.

Number 10: ‘Dreamsicle’ from “Reunions” (2020)
‘Dreamsicle’ finds its grounding in the positive moments within the darkness. With a relatively carefree chorus of “A dreamsicle on a summer night/ In a folding lawn chair” playing against the narrative of a home breaking apart, it’s anchored in the small positive moments, ones that can make memories a little less painful to return to. Especially from the perspective of a child, Isbell gives notoriety to the fleeting moments that are just right. A summer night, having a popsicle, doing nothing other than daydreaming? That’s what a child should be doing, and memories of simple goodness are of no less importance than the big memories that can be tough to look back on; in fact, they work together pretty fundamentally.

Number 9: ‘Last of My Kind’ from “The Nashville Sound” (2017)
Some songs just make perfect album openers, and as Isbell explores the anxiety that comes with a changing world, ‘Last of My Kind’ makes a beautiful introduction to his Grammy award-winning album. Isbell’s Alabama roots have spread throughout his discography, and it seems like he’ll always be tied to those that grew in his rural life – but this track captures just how out of place he feels, pretty much, anywhere else. “Am I the last of my kind?” he asks after stringing together a list of things that just don’t feel right. 

On the first chorus, Isbell’s honesty brings a painful level of nostalgia and longing: “Daddy said the river would always lead me home/ But the river can’t take me back in time and Daddy’s dead and gone/ And the family farm’s a parking lot for Walton’s five-and-dime/ Am I the last of my kind?”. It’s those minute details that others would pass by that makes Isbell’s writing as special as it is; knowing the family farm has been torn apart and forced into a perfect sized piece in the puzzle of modern society, well, that does feel like existential heartbreak. It’s no wonder the Alabama native is questioning his place.

Number 8: ‘Ride to Roberts’ from “Foxes in the Snow” (2025)
Isbell is pretty known for being able to shatter a heart with a few words, but ‘Ride to Roberts’ from 2025’s solo album “Foxes in the Snow” exemplifies his skills for locational writing – and in not quite so devastating of a way. As he sings of taking a trip to Nashville’s legendary Robert’s Western World, he includes just enough intricacies – like the mention of honkytonk legend Don Kelley – to immediately transport the listener. As he notes that “Tennessee’s looking after you” and that there can be a “ride to Robert’s when we crave a steel”, this one has a comfort to it. It’s nice to know that Isbell “ain’t lost yet”; he’s “headed home”.

Number 7: ‘Relatively Easy’ from “Southeastern” (2013)
Another one from “Southeastern”, ‘Relatively Easy’, may ring especially true for the time we’re living in now when everything feels just a little unsteady. It feels like there’s a bit of a dangerous trend at the minute of “competing” with who has it worse; Isbell isn’t leaning into that sentiment, though, but is doing quite the opposite: “You should know compared/ To people on a global scale/ Our kind has it relatively easy”. If there’s anything to take from this song, it’s that Isbell is encouraging empathy; when life can be overwhelming, we shouldn’t be finding reasons to make it more difficult. “Watch that lucky man walk to work again/ He may not have a friend left in the world/ See him walking home again to sleep alone/ Or step into a shop to buy a postcard for a girl”. That’s something special right there.

Number 6: ‘Dress Blues’ from “Sirens of the Ditch” (2007)
Chronicling the story of a soldier being lost in action, it’s tracks like this one that remind us of Isbell’s position as a storyteller. Devastation runs through the song as a young soldier leaves behind a wife, a baby and a silence that will last for an eternity. There’s a distinct Americanness in ‘Dress Blues’ that suggests this story may be all too familiar for all too many people, closing the song with “You never planned on the bombs in the sand/ Or sleeping in your dress blues“, the impressions last way longer than its four-minute run-time.

Number 5: ‘Alabama Pines’ from “Here We Rest” (2011)
I don’t think I need to give much of an explanation for this song; it comes from an album called “Here We Rest”, and that’s exactly what Isbell is looking for. “Somebody take me home/ Through those Alabama Pines” it doesn’t have to be Alabama; everyone has a place where their mind quietens, and their heart feels at home. This is one of those lifelong songs I mentioned earlier, it was released in 2011, and it will be around forever.

Number 4: ‘Cast Iron Skillet’ from “Weathervanes” (2023)
Continuing with my incessant campaigning for Isbell to be recognised as a Great American Writer, ‘Cast Iron Skillet’ from the 2023 album “Weathervanes” is inherently Southern. Written as a string of caution and a questioning of truths, the profoundly vulnerable track opens with “Don’t’ wash the cast iron skillet, don’t drink and drive, you’ll spill it”. Don’t let what matters slip through your grasp; take care of them, nurture them, and care for them.

The verses are built on short stories from Isbell’s Alabama life; they’re serious and, dark, and intensely human. Playing against what seems to be a reference to “To Kill a Mockingbird” in the line “That dog bites my kid, I’ll kill it”, these tales seem to weave into one – the one that shaped the things Isbell’s beliefs and the morality he treasures.

Number 3: ‘Elephant’ from “Southeastern” (2013)
Not many artists could bring themselves to write a deeply personal song about a friend dying of cancer, and even less could write one as raw and hard-hitting as Isbell’s ‘Elephant’ from the 2013 solo album “Southeastern”. “We just drink our drinks and laugh out loud/ Bitch about the weekend crowd/ And try to ignore the elephant somehow”, he sings, that “elephant” being the inevitable. The line that hits the hardest and cuts the deepest, though, is, “There’s one thing that’s real clear to me: No one dies with dignity”. It’s a song that will entirely surround you and demands a real, concentrated listen. It’s also one of those songs that, as remarkable as it is, sometimes needs to be skipped – it’s not a casual listen.

Number 2: ‘Strawberry Woman’ from “Weathervanes” (2023)
I very nearly didn’t include this one on the list for worries that it might be turning into the list I would take to my desert island, but if someone asked me to recommend Isbell songs to them, of course, I would share with them my favourite. ‘Strawberry Woman’ is pure stunning simplicity. I could type out every line to this song because I think they’re all as special as the next, but rolling into each other with accordion and slide guitar accompaniment, they make up one perfect song.

“I remember you at that place in Post/ You were thick-cut bacon on Texas toast/ Prairie dogs popping up to see/ That strawberry woman sitting next to me”. I truly couldn’t imagine that verse coming from anyone but Isbell. It’s so deeply personal and feels so quintessentially Southern in its references, but once again, he’s open to sharing. I haven’t dug into the sound of Isbell songs in this list, there’s a beauty in being able to discover that for yourself, and I’m not going to do that too much with this song either, but I will say that The 400 Unit did everything it needed to do to paint the sound of the line “the highway’s straight and the night’s so still/ Barely have to touch the wheel”. ‘Strawberry Woman’ sounds like a clear, star-filled, still night.

There’s a bittersweet note to ‘Strawberry Woman’ as it very much feels like a reflection on a time and relationship gone by. But it doesn’t lose any of the love that sits within each line so comfortably; as the song moves towards an end that comes much too soon, the whole sentiment seems to be captured in the line “We walked through weather, and we walked through time”. Weather changes and time changes and it can’t be stopped, but in that moment, you can’t embrace it any more than simply walking through it.

Number 1: ‘Cover Me Up – Live’ from “Live From The Ryman” (2018)
My final pick goes to ‘Cover Me Up’, easily Isbell’s most well-known song. Heaving with a kind of reflective immediacy that Isbell seems to do all too well, it’s a complete and undying confession of love, a promise of time as Isbell sings, “So girl, leave your boots by the bed/ We ain’t leavin’ this room/’Til someone needs medical help/ Or the magnolias bloom”.

There’s no doubt that this track would make the list, and, if this was to be ranked, has more than enough potential to creep into the top spot, but the version recorded “Live From The Ryman” is simply on a different calibre of phenomenal. When I saw this one live last year, I was blown away all over again. The sheer desperation in Isbell’s voice as he throws those lyrics out on the chorus was mesmerising, as much as life brings changes, there is always going to be a certainty in those lyrics that can’t be removed. The relationship or story that inspired its original meaning could have closed, or it could turn into a memory or a reflection, but Isbell wrote this song with heartfelt certainty; there’s no questioning that every word of ‘Cover Me Up’ is permanent in its own way. And for all it’s worth (and it’s worth a lot), hearing the crowd’s reaction to Isbell singing “I sobered up, I swore off that stuff/ Forever this time” is proof that there’s a personal pride in this song, too.