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The Best Jason Isbell Songs, Ranked

Jason Isbell is extremely good at writing songs.

Not exactly the most controversial statement for a music critic to make, I know. After all, Isbell is commonly recognized as one of the best — if not the best — singer-songwriters working right now. He can write intimate character studies about fictional people who feel as real as your neighbors, as well as broader, statement-driven numbers that reflect the lives of millions of Americans. He’s the closest thing that millennials and young Gen-Xers have to their very own Bruce Springsteen. (If this were an era in which people like Springsteen became pop stars, he would be a household name.)

But there’s something about doing a deep dive into his catalogue — including the Drive-By Truckers albums he played on and contributed songs for before launching his solo career in 2007 — that re-affirms, again, that Jason Isbell is extremely good at writing songs. On May 15, his discography will grow by another album, Reunions, his seventh overall. It speaks to his consistency and reliability that one of the new LP’s singles, “Only Children,” deserves to be ranked among his very best tunes.

But what about his other best tunes? After greatly enjoying my recent swing through his back pages, I compiled this list of my 30 favorite Jason Isbell songs, which was accompanied by about 30,000 tears.

30. “Try” (2007)

Isbell’s first album after leaving Drive-By Truckers, Sirens Of The Ditch, unsurprisingly is the LP that sounds the most like his former band. This slow-boiling rocker is centered on precisely the sort of heavy guitar riff that would have fit perfectly on The Dirty South, which might be why Isbell tended to pursue less bombastic sounds on his subsequent records. But on “Try,” the riffage is more than welcome, providing an explosive counterpoint to the simmering romantic paranoia and fitfully contained rage of the lyrics.

29. “Soliders Get Strange” (2009)

Isbell’s second album, Jason Isbell And The 400 Unit, is the most underrated in his catalogue, with a sweet-sour combination of power-pop and bleak lyrics about addiction and self-hatred that recalls Wilco’s Summerteeth. Many of the songs unfold like Bukowski short stories, with alcoholic protagonists attempting to survive their own self-destructive natures in a haphazard pursuit of redemption (or, at the very least, a moment’s relief). The character in “Soliders Get Strange,” like the person in the similarly themed “Tour Of Duty” from 2011’s Here We Rest, is a veteran struggling to re-acclimate to civilian life. Is he about to become unhinged? As is the case in so many Isbell songs, “Soldiers Get Strange” takes place somewhere between the start of the story and the climax, hinting at bad things on the horizon without fully spelling them out.

28. “Cigarettes and Wine” (Live From Alabama version, 2012)

Another gem from Jason Isbell And The 400 Unit, “Cigarettes And Wine” is about a down-and-out loser who finds a temporary port in the storm after the bars close, in the company of a woman who “lives down inside of me still / Rolled up like a twenty dollar bill.” The gentle blues-rock of the studio version is nice, but this song achieves its full realization on the excellent Live From Alabama, the 2012 release that functions as a kind of greatest hits album for Isbell’s pre-Southeastern work. “This one is a country song, sort of,” Isbell says at the start, and his delivery does the hard-luck narrative justice.

27. “Last Of My Kind” (2017)

Since his early 20s, Isbell has been preoccupied as a writer with the passage of time, and accounting for what is gained and what is lost as we age. While he wrote great songs as a younger man working in this mode, the gravitas he attained in middle age shows in “Last Of My Kind,” the gently philosophical opener from The Nashville Sound. A meditation on the old Thomas Wolfe quote about how “you can never go home again,” “Last Of My Kind” is about coming to grips with suddenly being the adult in the room, and witnessing the world you once knew disappear before your eyes. “Daddy said the river would always lead me home / But the river can’t take me back in time / The family farm’s a parking lot for Walton’s five and dime / Am I the last of my kind?”

26. “Go It Alone” (2011)

The first of Isbell’s great “Alone” songs, “Go It Alone” is also an example of the “life on the road” genre that dominates Isbell’s pre-Southeastern songwriting. (Though he would continue to write classic “life on the road” tunes for that album and beyond.) Over a rollicking guitar riff pitched squarely between the early ’70s Stones and Neil Young’s “ditch” era records, “Go It Alone” front-loads plenty of sleazy rock ‘n’ roll exhaustion, setting the stage for Isbell’s narrative about a touring musician wearily eying a solitary post-tour existence.

25. “Traveling Alone” (2013)

It’s hard to hear “Go It Alone” now and not think of “Traveling Alone” from Isbell’s next album, Southeastern. It’s a more hopeful sequel, in which our hero is rescued from alienation by his soulmate. While “Go It Alone” is somewhat distanced from its writer, “Traveling Alone” (like much of Southeastern) feels like naked autobiography, in which Isbell chucks his former bravado to reveal a lonely man who’s “grown tired of traveling alone.” That Isbell’s wife, Amanda Shires, harmonizes with him on the folky, pleading chorus makes “Traveling Alone” all the more affecting.

24. “Sunstroke” (2009)

“I was certainly dealing with a lot of busted relationships, my career wasn’t really going anywhere, and I wasn’t very happy,” Isbell once said of his life in the late aughts. While Isbell had become a star as Drive-By Truckers’ equivalent to George Harrison — the third-ranked songwriter who contributed a small handful of heaters to each record — he struggled at first to establish himself as a leading man. Part of what makes Jason Isbell And The 400 Unit such a fascinating listen is how that disappointment is baked into songs. Take the piano ballad “Sunstroke” — the lyrics read like a disgusted diatribe directed at the face in the mirror, with a sneaky Dylan reference tossed in for good measure: “Are we supposed to get good at this? / What does it mean to give up? / Why did I call you? I shouldn’t be giving a fuck / Answer these questions for everyone / So maybe they’ll stop asking me / What really happened and where is your masterpiece?”

23. “Streetlights” (2009)

Another great “life on the road” song, “Streetlights” also bears an obvious John Prine influence, writing around the central theme — the feeling of being strung-out and alone at an ungodly hour of the night — with sharply observed narrative details delivered in an off-handed, conversational manner. In order to avoid dealing with himself, the protagonist takes out his phone and starts calling friends and family members. Finally, the bartender kicks him off and he has to figure out how to get to where he’s staying that night: “Think I blocked just a park away, but I can’t really say, it’s been all night. / How I wish you would call me here, but you just disappeared, it wasn’t right.” But there’s something in his voice that tells you that it wasn’t really her fault.

22. “Codeine” (2011)

This deceptively jaunty pop-folk charmer has long been a live staple for the 400 Unit. Isbell moves about the stage to waltz with his crack band, who flash wide smiles as he leans into the sing-along chorus. About that chorus: It’s about a woman slowly drugging herself to death, viewed from the perspective of a lover who can’t keep their relationship from falling apart. That is to say, it is the Platonic ideal for depressing Jason Isbell song subject matter, though the strummy, feel-good music can almost distract you from the tragedy unfolding in your very ears.

21. “Dress Blues” (2007)

This crushing ode to a person killed in combat is the first great song of Isbell’s solo career, and the one tune on his debut, Sirens Of The Ditch, that could sit next to his best work with DBT. Strangely, songs like “Dress Blues” — a nonpartisan, sloganeering-averse narrative that soberly and eloquently recounts the costs of war from an everyday human perspective — were hard to come by in the aughts. Most artists either avoided the subject, even as the country was mired in two major conflicts, or they resorted to simple-minded pandering to bumper-sticker patriotism. Isbell, meanwhile, in each verse just paints heartbreaking scene after heartbreaking scene: “Your baby would just about be here / And your very last tour would be up / But you won’t be back, they’re all dressin’ in black / Drinkin’ sweet tea in Styrofoam cups.”

20. “Hope The High Road” (2017)

The Nashville Sound was among the first rock albums that directly addressed the advent of Trump’s America, a topic that hit particularly close for Isbell given his fanbase and the heartland milieu of his work. The button-pushing anthem “White Man’s World” was among the LP’s breakout songs, tweaking the prejudices of many of his own listeners. But “Hope The High Road” has aged better, in part because of how Isbell leans on positivity in a time of extreme polarization. (The killer guitar lick doesn’t hurt either.) The song’s standout line is among the most quotable in any Isbell song, and perhaps his most Springsteenesque: “Last year was a son of a bitch / For nearly everyone we know / But I ain’t fighting with you down in the ditch / I’ll meet you up here on the road.”

19. “Only Children” (2020)

The early singles from Isbell’s forthcoming album Reunions have generally tilted in a broader, more rocking direction — more “Hope The High Road” than “If We Were Vampires.” The delicate “Only Children” is the exception, with lovely finger-picking setting the stage for a haunting story about two aspiring artists whose lives take different paths. Though I wonder if “Only Children” can also be read as Isbell addressing a version of himself from a different timeline, the one with “Hydrocodone in your backpack” who couldn’t ever get his act together. Again, the specifics are what sell this song so beautifully: “Heaven’s wasted on the dead / That’s what your mama said / When the hearse was idling in the parking lot / She said you thought the world of me/ And you were glad to see / They finally let me be an astronaut.”

18. “If It Takes A Lifetime” (2015)

Another fine example of Isbell working in John Prine mode, “If It Takes A Lifetime” is an easygoing southern rock song — the breezy rhythmic roll is straight out of Brothers And Sisters and Second Helping about an everyman learning to adjust to the sort of mundane life that hopefully won’t send him to an early grave. If this doesn’t seem like compelling subject matter — one of the verses is about falling asleep with the TV on — the tension in Isbell’s performance suggests that staying on the straight and narrow can be a life-or-death proposition, in which the fight to keep inner demons at bay is constant and unyielding.

17. “Flying Over Water” (2013)

A thread that connects Isbell’s relationship songs concerns lovers who might be too broken to actually be together. The prospects for these characters brightens as Isbell moves through his career — people you would assume are doomed on his early albums often find solace on his later LPs. The couple in “Flying Over Water,” however, seem resigned to a less certain fate. As they hop on a plane on a whim, to escape old lives and familiar frustrations, the mood is similar to that of the famous ending from The Graduate. The world looks simpler from up here, but you can’t stay “up here” forever. “Did we leave our love behind?” the narrator asks. It depends on how much of a romantic the listener is.

16. “Cumberland Gap” (2017)

Bruce Springsteen’s best “political” songs are the ones that stay focused on characters rather than polemics. (See: Every song on Nebraska.) Isbell apparently closely studied this example before writing his “Trump era” album The Nashville Sound, as he steers clear of direct partisan callouts in lieu of crafting character studies about regular Americans who have been left for dead at the side of the late-capitalism highway. The guy in “Cumberland Gap” — a miner who wonders if his job will one day kill him — might very well have voted for Trump. But for Isbell, the character’s angst feels universal: “There’s an answer here, if I look hard enough / There’s a reason why I always reach for the harder stuff.”

15. “Songs That She Sang In The Shower” (2013)

What 1971’s self-titled is to John Prine, Southeastern is to Jason Isbell — the one in which pretty much every song is a banger and beloved fan favorite. Around this time, Isbell got sober, which along with saving his life had the nice side benefit of allowing him to re-focus on his craft. “The older I get and the more I practice, the more I realize it really helps if you do as much work as possible,” he told me in 2015. “When you stop drinking, that comes in handy, ’cause I can spend eight or nine hours on a song without feeling the need to go out and get drunk and shoot pool.” That attention to craft is evident in “Songs That She Sang In The Shower,” in which the tunes that remind the narrator of the partner who has just stormed out of the door — including Pink Floyd’s “Wish You Were Here” and Dusty Springfield’s “Breakfast In Bed” — are thoughtfully chosen, evoking the feel of a real person’s taste while also providing meta commentary on the song itself.

14. “Alabama Pines” (2011)

From here on out, I’m afraid it’s going to be straight tear-jerkers. Just hearing the title of this song is likely to send a resident of the Deep South into nostalgic hysterics. The set-up of “Alabama Pines” is straight out of John Denver: A guy is trapped in a seedy hotel, and it makes him long for home. But the execution is exceedingly graceful — so much so that it’s a shame that Alabama hasn’t put this song in every tourism commercial. “You can’t drive through Talladega on a weekend in October / Head up north to Jacksonville. Cut around and over / Watch your speed in Boiling Springs/ They ain’t got a thing to do. They’ll get you every time.” He makes his home state sound like heaven. That Isbell has also never shied away from calling out the sins of the region makes this adoring tribute seem all the more heartfelt.

13. “Yvette” (2013)

Isbell originally wrote about childhood sexual abuse on Here We Rest‘s “Daisy Mae,” but he plunged into a whole other level of darkness on this grimly hypnotic Southeastern deep cut. Over a dreamy folk-rock sway, Isbell dispassionately tells the story of a young girl horribly victimized by her father from the perspective of an obsessive classmate who follows her home one night. As the song unfolds, it becomes clear that the boy intends to violently avenge the girl by gunning down the father. But Isbell avoids writing a straight-up country revenge song by calling the mental state of the narrator into question — there’s something about his preoccupation with this girl that seems more akin to Travis Bickle than John Wayne. The result is one of Isbell’s most ambiguous and disturbing numbers.

12. “Danko/Manuel” (2004)

As a writer who has long been fascinated by the dark side of the touring musician’s life, it was natural that he would be attracted to the two most tragic members of The Band. “I was reading This Wheel’s On Fire, the Levon Helm book about his time with The Band. He talks about how they had this pact on the road — it was kind of a joke — that whoever died first, they would take his body, take him home, and bury him and all of that,” Isbell once told me. “I saw a lot of myself in that book.” In retrospect, “Danko/Manuel” seems prescient — he wrote it near the start of his career, and it seems to lay out the next decade or so of his life. “Then they say Danko would have sounded just like me / ‘Is that the man you want to be?’” Thankfully, Isbell found a different, better path for himself.

11. “Relatively Easy” (2013)

Along with allowing him to pay more attention to his craft, sobriety also imbued Isbell’s songs with a sense of wisdom that eschews easy resolutions. As the last song on Southeastern, “Relatively Easy” functions as a summation statement for the entire album. In short, life is hard, but it’s still life, which means it’s all we have. Whereas Isbell’s earlier work is marked by doom-laden fatalism, “Relatively Easy” posits that transcending struggle — if only in your mind — might very well be the point of existence. It’s hardly a moment of unfettered triumph, but it’s truthful, which makes this song especially nourishing.

10. “Maybe It’s Time” (2018)

Isbell has said that he initially didn’t want to write a song for Bradley Cooper’s 2018 remake of A Star Is Born. When his producer Dave Cobb, who assembled the soundtrack, asked him, Isbell said, “‘No, Dave. I don’t have time for that shit.’ And my wife said, ‘You’re an idiot,’” he recently related to GQ. He had reason to be skeptical, though in the end Isbell is one of the only credible country-rock analogues to Jackson Maine that exists in real life. In a way, A Star Is Born is a bizarro-world version of Isbell’s story, only Isbell had the good sense not to self-destruct when he met his own Ally. Also, while Isbell has clearly carved out a successful niche for himself, it was nice to see him score an actual hit on one of the biggest albums of recent years.

9. “Super 8” (2013)

The best flat-out rocker in Isbell’s catalogue, “Super 8” is also his funniest song, even if it happens to be a three-and-a-half-minute tour of his personal hell. Essentially a compendium of drunken tour stories compressed into one terrifying night, “Super 8” barrels forward like a roller coaster that’s going a little too fast on a rickety track that appears to be on the verge of collapsing. All the while Isbell’s story keeps getting worse: He’s drinking and doing blow in his crummy hotel room, a guy busts in with a baseball bat, he wakes up bleeding, and now he’s having trouble breathing. Then comes one of the best lines in the song: “Well, they slapped me back to life / And they telephoned my wife / And they filled me full of Pedialyte / Saw my guts and my glory / It would make a great story / If I ever could remember it right.” There’s nothing funny about any of this, and yet Isbell’s desperation and bemusement that he survived it all turns “Super 8” into a classic black comedy, like After Hours set at the world’s worst after-party.

8. “24 Frames” (2015)

It’s one thing to write a compelling song about almost dying in a hotel room. That sort of thing is inherently interesting. But in “24 Frames,” Isbell writes about the existential fear that grips all of us in our daily lives, the mundane terror that’s difficult to put into words. “24 Frames” is about anticipatory tragedy. What happens when something terrible inevitably happens to you? What will that be like? How do you deal with it? Again, Isbell avoids platitudes and instead supplies truth with a side of empathy. “You thought God was an architect, now you know / He’s something like a pipe bomb ready to blow.” In the meantime, you just try to keep your loved ones close, so you can appreciate a moment of calm while it’s here.

7. “If We Were Vampires” (2017)

Is it dusty in here? Is someone chopping onions? Why do I suddenly feel like I am drowning in a sea of my own tears? This is Isbell’s greatest “anticipatory tragedy” song. It works because it’s imminently relatable — who among us with the good fortune of being paired up with a soulmate hasn’t thought about the day when this will all end? The line that always gets me is when Isbell sings, “And hope it isn’t me who’s left behind.” He’s choosing death over loneliness! I know I would do the same.

6. “Outfit” (2002)

Isbell is now one of the defining figures of dad rock — dads love his music, and he has assumed a dad-like stature in his songs, dispensing wisdom from a position of genuine gravitas. But when he was in Drive-By Truckers, he wrote one of the great anthems of son rock, “Outfit.” A fond remembrance of fatherly advice, “Outfit” is Isbell paying it forward: “Don’t call what you’re wearing an outfit, don’t ever say your car is broke / Don’t worry about losing your accent, a southern man tells better jokes / Have fun, stay clear of the needle, call home on your sister’s birthday / Don’t tell them you’re bigger than Jesus, don’t give it away.”

5. “Speed Trap Town” (2015)

A low-key strummer from Something More Than Free, “Speed Trap Town” is one of Isbell’s best narratives, unfolding like a four-minute documentary about small-town life that feels like it was carved out of a larger, extensive, unseen history. The storytelling is masterful: “She said, ‘It’s none of my business but it breaks my heart’ / Dropped a dozen cheap roses in my shopping cart,” is a killer opening line, instantly inviting though also vague enough to not spell out what’s coming. Soon, we learn the guy in the song is grieving the loss of his father. We also learn that the dad was a state trooper who assaulted the women he pulled over, and ignored his kids until he got sick. We even learn about the local football team. All in the space of a four-minute song! And it never feels overly dense or heavy-handed.

4. “Cover Me Up” (2013)

It has happened at every Jason Isbell concert I’ve ever seen: Whenever he sings the line in “Cover Me Up” about how “I sobered up and I swore off that stuff / Forever this time,” everybody cheers. And I always get a little choked up. How could you not? There’s real blood and guts in “Cover Me Up.” The country singer Morgan Whalen recently covered this song — his version actually comes up on Spotify before Isbell’s — but with all due respect to Whalen’s reverent take it’s impossible for me to imagine anyone other than Isbell singing it. “Cover Me Up” is the sound of a man exposing the deepest, most vulnerable parts of himself, and expressing gratitude that he’s still around to sing about it.

3. “Children Of Children” (2015)

Relationships between children and parents have been an ongoing thematic concern for Isbell throughout his career, as it was for one of his primary influences, Bruce Springsteen. But “Children Of Children” is his best song of this kind, because it feels like a breakthrough in understanding that all parents essentially are children who are faking it at being grown-ups. (It’s Isbell’s “Used Cars.”) “I was riding on my mother’s hip / She was shorter than the corn / All the years I took from her / Just by being born.” As the tragedy of that lyric sinks in, the music swells like an early ’70s Nick Drake ballad, with a breathtaking string arrangement couching Isbell’s best-recorded guitar solo.

2. “Goddamn Lonely Love” (2004)

The highest compliment I can pay this song is that it sounds exactly like the title. Like, you can’t call your song “Goddamn Lonely Love” and not deliver the emotionally wracked goods without looking like a total chump. Isbell avoids this pitfall but perfectly evoking that “sitting alone on a barstool at closing time when you’ve been drinking all night for the wrong reasons” feeling. (I bet Frank Sinatra would have done an amazing version.) It’s absolutely beautiful without romanticizing this state of mind in the least. Isbell sounds like he’s about to jump off of a bridge the moment he’s done singing.

1. “Elephant” (2013)

My favorite Jason Isbell song is not the one I listen to the most. In fact, it is probably among the songs on this list that I’ve played the least. When I listen to Southeastern, I often skip “Elephant,” because I know I simply cannot handle it. This song has made me cry every single time I’ve ever heard it, and most days I’m just not equipped to put “Elephant” into my life and allow it to devastate me. On paper, it might seem maudlin, even manipulative — it’s about a woman who dies of cancer, sung from the perspective of the man who loves her. But “Elephant” works precisely because Isbell doesn’t write it like a Terms Of Endearment-style melodrama. He inhabits the character in the song so fully that it feels like someone talking to you about his life from across the kitchen table. Which is why the part that always gets me — and I do mean always, like I’m tearing up as I type this — is the line where he sings, “If I’d fucked her before she got sick, I’d never hear the end of it.” It’s the precise lack of sentimentality of that lyric, and the well of suppressed emotion that Isbell vocal evokes, that just destroys me. Wow, now I’m a mess. Thanks, Jason Isbell! Time to put on some Imagine Dragons so I can go back to feeling a little more numb.