10. Live Oak – Jason Isbell – Southeastern
Catching the tail end of our list is one of the final tracks on Isbell’s iconic solo album, Southeastern. I wouldn’t call this a concept album, but more of a contemplation album on the subjects of sobriety and maturity, a trend from which “Live Oak,” doesn’t break. In it, Jason shows his narrative skill, crafting something of a Western which follows an ex-criminal and cowboy who has now settled down in a small town with the love of his life.
Where the obvious choice is to speak to the ways love has helped him to overcome his old ways and grow up, Jason chooses, instead to write what is ultimately a story of fear. Our subject fears that his settling into domestic life has left him less interesting and impressive to his love, and he wonders if she loves him as he once was more than she loves him as he is now. The whole story, in addition to serving as a unique metaphor for the alcoholism which Isbell had so recently overcome, is riveting and told beautifully, the bare instrumental allowing his lyrics to strike hard.
9. Outfit – Drive-By Truckers – Decoration Day
One of Jason’s many excellent contributions to the Truckers’ discography over his three album stint, “Outfit,” highlights a simpler period is his writing. The bulk of his Truckers songs deal in Southern culture and family dynamic, this song being no exception. The track also functions as a fantastic example of Isbell’s ability to, in one breath, glorify and criticize the same idea.
This song is written from the perspective of Isbell’s father, repeating many of the sayings and bits of advice which he had often given over the years. In the verses he tells the unique story of meeting Isbell’s mother, a teen pregnancy, the struggle to build a life for his family, and ultimately, the rock solid work ethic which allowed him to pull Jason’s family up above the poverty line. While the song explicitly praises the wise words of Jason’s father and his rather ridged code of conduct for oneself, there is an implicit criticism hidden in the rather difficult story his father tells. It seems, almost, to suggest that this masculine rigidity may lead to a few weak points in life which may be avoidable.
8. Goddamn Lonely Love – Drive-By Truckers – The Dirty South
The Dirty South is easily the Truckers’ strongest effort to date, thanks in no small part to the contributions of Jason Isbell. “Goddamn Lonely Love,” is unique in that it doesn’t carry a powerful life lesson, or even a surprising concept or execution. Instead, Isbell plays the part of a drunkard in a bar, rattling off couplets with stark beauty and striking truth, one after another for about five minutes.
Particularly thoughtful on this track is the bridge, which reads as follows: “Stop me if you’ve heard this one before, a man walks into the bar and leaves before his ashes hit the floor.” On the one hand, the turn of phrase reference to the kinds of one liner jokes a drunk at the bar may tell not only establishes his setting, but mimics the simplicity of the couplet structure he’s used across the plot. On the other, the “Stop me,” is sung with such passion because it is a request in of itself. Jason wants to be stopped in story so he can hear the tale of someone who has survived what he’s going through. He also wants the bartender to stop him from spiraling downward so strongly. This song is just an excellent reminder that when an unbelievable songwriter takes on a simple structure, almost invariably, magic happens.
7. In a Razor Town – Jason Isbell – Sirens of the Ditch
Slightly more recent than our previous few entries, “In a Razor Town,” is a highlight to the rather jumbled solo debut that is Sirens of the Ditch. Written in the thick of his struggles with substance abuse, Jason’s lyrical voice is much colder on this and other earlier tracks. He writes about painful topics here from a vantage point of his future self and seems unimpressed by his own emotional tendencies.
The song tells the story of a young relationship in a small, dying town. He tells his subjects that they’ll have to move on, that small town romances don’t last, and that life moves on without regard to their feelings. The topic is unique and Jason seems to realize that this isn’t fair. He writes about what will happen without caring how it feels, and it’s that coldness that makes “In a Razor Town,” such a unique entry to the Isbell catalog.
6. Decoration Day – Drive-By Truckers – Decoration Day
Doubtless Jason’s best contribution to the Truckers, the title tracks from their 2003 LP follows the Hill-Lawson feud, a bloody battle between two families in Alabama in the early 1980’s. The story telling ability Isbell shows throughout this track is unparalleled, even by his contemporaries in the Truckers, and the passion in his performance shows how much he cares about the stories he writes.
As with most of Jason’s writing, his unique and well spoken opinion makes this song what it is. He writes from the point of view of a young son of the Lawson family. The writing takes place many years after the feud, as the subject deals with the fact that his children have never seen his fathers grave, nor visited his hometown. He finally decides that this is for the better, that he’s glad his father was killed, and that these battles do nothing but destroy families. Throughout, Jason contemplates the value of tradition, loyalty, and blood. As with “Outfit,” he settles by questioning the culture with which he was raised, while fully appreciating his upbringing.
5. Dress Blues – Jason Isbell – Sirens of the Ditch
The highlight of his first solo effort, “Dress Blues,” was written in honor of Jason’s high school friend, Matthew Connolley who left for war at a young age to be killed overseas, leaving his wife and baby daughter behind. This is one of his most emotional songs, able to tug tears from even the driest of eyes, and it stands as a touching tribute to a very brave young man.
The tribute to a fallen soldier is far from uncommon in country music, but it’s Jason’s style which sets him apart. He tells Connolley’s story by shifting from broad metaphors to touching detail again and again. In one line he’ll speak ask about the angels coming to meet his friend and he follows by describing crowds drinking “sweet tea in styrofoam cups.” From his writing, it becomes abundantly clear just how incapable he is of processing the emotions of the event, and the anger in the final line which questions why his friend was shipped off to “fight somebody’s Hollywood war,” is gut-wrenching.
4. Speed Trap Town – Jason Isbell – Something More than Free
The only entry on this list from Jason’s most recent solo effort, “Speed Trap Town,” town is an excellent example of his more mature, post-Southeastern phase. The story is unique and personal, and Isbell’s commentary on small-town life is quite moving, yet again. Where his earlier work tended to talk about what was wrong, mature Jason writes about how things are instead. The track is full of large losses and small victories, and the feeling of peace which comes with the conclusion is palpable.
“Speed Trap Town,” follows a man coming home to the small town in which he was raised to visit his father who is dying of a terminal illness. Again, a common country trope is here, this time in the form of the man who comes home to find that his simple hometown isn’t the way he left it, but this time, Jason realizes that it is actually he who has changed. Slowly, our protagonists wrestles with his father’s illness, contemplating his past and what future may be left for him. In the end, Isbell decides to pull the plug on his father and leave the small town behind. As listeners, we’re left with an aching heart, soothed by the vague since of closure in the final few lines.
3. Elephant – Jason Isbell – Southeastern
The second track in a row which is based on terminal illness, “Elephant,” tends to be an introduction to Jason for many new listeners, and what an introduction it is! Again, his narrative skills are simply second to none, and this song in particular is written fearlessly. Themes of love, loss, and pain abound across this tear-jerker and in the end, listeners are left to contemplate how they themselves would handle such a brutally hopeless situation.
The story of a man in love with a woman dying of cancer provides a dark launching point for Jason to muse on the nature of death and finite futures. As the characters grow closer despite the impending doom, he’s able to find beauty, not in spite of the fear and doom of death, but by pushing against it directly. It’s the beauty of positioning love as two doomed drinkers shouting, in harmony, into the void which makes this track so moving. The final line, “no one dies with dignity, we just try to ignore the elephant somehow,” perfectly sums up the powerful story we’ve just been told in a way that only Jason can.
2. If We Were Vampires – Jason Isbell and the 400 Unit – Nashville Sound
The only track on our list which features The 400 Unit, “If We Were Vampires,” is easily Jason’s most commercially successful track to date, and for good reason. This song perfectly incapsulates what makes his current, mature period so excellent, and why he is so worth listening to, still today. Once again, this is a track which benefits from Isbell’s unique view of the world, and more specifically of love.
Trading in the narrative form he frequents for a direct, thoughtful effort, “If We Were Vampires” examines love and death in the same breath with the goal of finding new meaning for both. Jason makes the case that the inescapability of death should not rattle the foundations of true love but, to the contrary, it is precisely the limited time frame of one’s life which endows love with such meaning. He sums this up beautifully with the line, “Maybe time running out is a gift. I work hard till the end of my shift and give you every second I can find. I hope it isn’t me who’s left behind.” Wow.
Flying Over Water
Something More Than Free
Last of My Kind
1. Cover Me Up – Jason Isbell – Southeastern
Could there ever have been a doubt the “Cover Me Up,” would top this list? The opening track to Isbell’s legendary magnum opus, this track did more than set the tone for what would be one of the greatest country albums of all time. With Southeastern’s release set for 2013, one year after he’d chosen to enter rehab for alcohol and drug abuse and just two days after marrying fellow singer/songwriter Amanda Shires, “Cover Me Up,” was tasked with introducing us all to the brand new version of Jason Isbell, and setting the tone for the future of his career. It succeeded in every single way.
The song functions as a love letter to Amanda Shires, presumably written from within the thick of rehab and great change. Jason tells of his adventures, his life on the road, his addictions, and the woman who finally gave him a home, with the skill and passion of one of the greatest songwriters in history. He speaks on the difficulties of sobering up, and that of changing in general, but in the end he simply asks her to cover him up, a reference to the chills which often accompany alcohol withdrawal, and know that she’s enough to use him for good.
In the second verse, Jason speaks to the ways in which he may have treated Amanda unfairly thanks to his addiction. He follows with this line: “But I sobered up and swore off that stuff forever this time.” When this is sung live, every member of the audience raises their glass and cheers, a touching tribute to a man who has cracked open his heart for us for more than fifteen years now, to let him know that we’ve all been listening, and we don’t plan on stopping anytime soon.