“I’ll do the, like, ten or fifteen best Jason Isbell songs,” I thought when I set out on the quest that led to what you’re reading right now. “That sounds good. It shouldn’t be that hard.”

Well, then I started digging into Isbell’s catalog and the goal shifted. “Let’s go for twenty,” I now said to myself. Twenty. Now that sounds good. Twenty songs make for a wonderful number of songs to rank, right? “Eh, might want to make it twenty-five,” I soon mumbled as I continued to peruse.

That, my friends, is how I landed on a ranking of my thirty favorite Jason Isbell songs. I’ve been a fan of Isbell’s for a while now but I massively underestimated just how many great tracks he has written over almost two decades during his time with the Drive-By Truckers, backed by The 400 Unit, and all by his lonesome.

There are rockers and there are quiet tunes. There are stories from his own life, stories from other people’s lives, and stories pulled from his imagination. Yet despite the style or the subject matter, there is a calm and serenity to all of Isbell’s music. His songs are often beautiful, frequently meditative, and liable to send you down nostalgia-drenched black holes as you drift off, staring out at the horizon as his music plays.

Back in May, Isbell released Reunions, his fourth studio album with The 400 Unit. It’s more of the same for Isbell in the best possible way. Three songs from the album were able to make into my top 30, and if this list had continued to expand, one or two more could have found their way in.

I told myself I’d stopped at thirty, though, so here’s what I ended up going with.

30. “Dreamsicle” (2020)

This is Jason Isbell right here.

This is a beautiful song that never pushes it too far. It is driving but still restrained within the confines of an idyllic country arrangement; one that bounces and saunters its way across the dance floor. Lyrically, it’s pensive and longing, which is what you’d expect from a tune with a line like “A Dreamsicle on a summer night in a folding lawn chair” in the chorus.

29. “Never Gonna Change” (2004)

Isbell spent six years playing guitar in addition to contributing vocals and songwriting duties to Georgia’s Drive-By Truckers. On each of the three albums he played on, he pitched in a song or two and almost every single one ended up being one of the strongest on the record.

“Never Gonna Change” is equal parts southern, alt-country grit, and soaring Nashville country-rock; a song that would provide a glimpse of what Isbell would do later on with The 400 Unit when they decided to let their hair down some.

28. “Super 8” (2013)

No one—and I mean no one— wants to die in a Super 8 motel. That includes Isbell, who spends a shade over three minutes explaining why he also doesn’t want to suffer such a miserable fate.

To really drive the point home, Isbell gets anecdotal and runs us through a hell of a story about a night when he came pretty damn close to suffering the most unfortunate of lodging-related deaths. It’s also a hell of a rock song (and one that’s best played exceptionally loud).

27. “Never Could Believe” (2011)

Coming from Here We Rest (Isbell’s second album with The 400 Unit), this song seems to pull from the rich musical history of two Southern musical meccas.

The top part—the lyrics and vocals—send their love from Nashville and seem to be having themselves a hell of a time alongside the piano and the scattered and busy drums, which are both proudly hailing from New Orleans.

26. “Soldiers Get Strange” (2009)

Isbell explores the psyche of the soldier returning home here and he digs in deep.

The song is full of pain and struggle, as the soldier tries to figure out where they fit in this world they’ve come home too and even goes as far as to wonder if maybe they should just reenlist. Musically, it’s some solid, rocking alt-country and its lack of polish works well with the chaos of the soldier’s life back home.

25. “Alabama Pines” (2011)

There are few things in life that are more powerful when it comes to making you long for home than spending the night in a shitty hotel. I don’t know if it’s the lack of amenities, the uncomfortable bed, or the serial killer vibe of the bathroom, but there is just something about seedy hotels that make a person pine for the familiar.

On “Alabama Pines,” Isbell finds himself in such a spot. He is longing for someone to “take me home, through those Alabama Pines.” Every once in a while, a song can be almost too relatable and can sound like you yourself wrote it. This is one of those songs (except you’re not Jason Isbell, so your version isn’t nearly as pretty).

24. “Goddamn Lonely Love” (2004)

If you’re gonna write a song called “Goddamn Lonely Love,” it damn best sound something like this song does. This both aches and pains and smells like booze and regret. The swaying it reflexively induces feels like a miracle given how heavy it comes across.

23. “Be Afraid” (2020)

If you follow Isbell on Twitter (which I would highly recommend), then you know he is not a man devoid of political opinions. “Be Afraid” is almost a call to arms; a challenge issued by Isbell to speak your mind, regardless of the consequences.

To call this song political in any way would be doing it a disservice. That’s giving it too narrow of a scope. It’s a song about speaking up and (more importantly) not being afraid to speak up.

Fine, maybe it is political.

22. “Codeine” (2011)

Damn, Jason Isbell, how can you make such a sad song sound so, well…not sad?

If you were just to listen to the music of this tune, you’d think that maybe you were listening to a song that was a cousin of “Wagon Wheel.” Then, you dig in and listen to the lyrics, which tell the story of a woman drugging herself to death and the man helpless to stop her.

At that point, you become very aware this ain’t no “Wagon Wheel.”

21. “Danko/Manuel” (2004)

This is another tune from Isbell’s Trucker days and it’s one with the kind of easy beat that can lull you to sleep if you’re not careful. Isbell was inspired by Levon Helm’s book This Wheel’s On Fire and draws from the many stories about his times with The Band. Isbell seemed to have seen a lot of himself in the lives of Band members Rick Danko and Richard Manuel, singing “Then they say Danko would have sounded just like me / Is that the man I want to be?”

Both Danko and Manuel saw their lives fall apart after their time with The Band, and with Isbell dealing with his own struggles with substance abuse, it’s easy to see how he was able to draw some parallels between his career and theirs. Thankfully, he was able to right the ship to avoid befalling the same fate as the men who lent their name to the title of this song.

20. “Last of My Kind” (2017)

The opening track of Isbell and Co.’s Grammy-winning album The Nashville Sound features him laying it all out on the table and coming to terms with who he is and (perhaps more importantly) who he has always been.

He was always a little different; not one to fit in while at college, uncomfortable in the big city, and—as he says with an early-morning resignation—maybe “the last of my kind.” It’s a song full of subject matter not unfamiliar to someone approaching forty, but as per usual, Isbell approaches it with such heartfelt honesty that it feels more genuine and real than it should.

19. “Dress Blues” (2007)

Back in 2007, the War in Afghanistan was still going on (it still is, but it was then, too) and artists had begun tackling the toll the conflict was taking on a new generation of soldiers and the families they left back home.

This is what Isbell does in “Dress Blues,” where he tells the story of a soldier killed in combat told from the perspective of the life he left behind in America. It’s a beautiful, haunting song and fairly rare (especially for when it was written and released) in the sense that it’s entirely non-partisan, as Isbell isn’t taking a side but simply telling a universal story about loss.

18. “Different Days” (2013)

Isbell again tackles the passage of time in “Different Days,” although this time it’s not as close to home as it was in “Last of My Kind.” It’s a story of runaways and troubled souls making their way through the world, either together or apart. It’s a song about relationships and the ones that might seem strong but still fall by the wayside as the days go on.

Ah, how our younger selves liked to make promises, huh?

17. “Try” (2007)

“Try” is off of Sirens Of The Ditch, which was his first solo effort after parting ways with the Drive-By Truckers.

You can still hear the influence of the band throughout this song, ranging from the blistering guitar parts to the barroom harmonizing in the chorus. Isbell eventually drifted away from the Truckers’ style of country grit rock, but it’s nice to know that it’ll always be part of him.

16. “Flagship” (2015)

Basically any musician can use a song to tell a story, but what truly separates an artist from the pack is not just telling a story but transplanting listeners directly into that story. This is exactly what Isbell does with “Flagship.”

The lyrics and the voice of the man singing them are simply hypnotic, drawing you in to the point where you can’t think of anything else. It’s a sparse song but one that still has plenty going on and only gets better with every listen.

15. “Only Children” (2020)

“Only Children” is easily the best song off of Reunions; a haunting, yet blissful tune about struggling artists finding themselves headed down two different paths. It’s a song about reconnecting and reminiscing (I love the line “Cold coffee on the fire escape / bet it all on a demo tape”) and it’s anchored by a beautiful guitar, which clears the way for some well-placed harmonies and some light brushwork.

14. “Outfit” (2003)

Again, if you follow Isbell on Twitter, you know that he’s a dad now. That was not the case back in 2003, which is when he wrote “Outfit,” a song about a son running through the advice he had been given by his father.

It’s solid advice too, advice like, “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.” This tune is a prime example of the pleasures that come with watching an artist grow and get older, as you see the subject matter evolving over time and perspectives shifting.

13. “Daisy Mae” (2011)

It’s a song that starts out so promising: “Lay down beside me / Close your eyes and feel the noonday sun.”

However, it soon becomes a song about a person dealing with a history of being sexually abused and the damage left behind. Isbell sings around the subject matter but he gets close enough to get his point across and tell the story he’s looking to tell to create a track that lures you in and sticks with you.

12. “Maybe It’s Time” (2018)

Everyone wants to talk about “Shallow” when they talk about A Star Is Born (specifically when they talk about the music from A Star Is Born), and while “Shallow” is a good song, it’s not as good as “Maybe It’s Time.”

Isbell was initially reluctant to write this wistful and somber song for the movie but some gentle nudging from his wife and bandmate Amanda Shires made him change his mind (and by that I mean she told him “You’re an idiot” for not wanting to).

That usually does the trick.

11. “Stockholm” (2013)

“I’ve heard love songs make a Georgia man cry,” Isbell sings to open what is the kind of barroom anthem that has everyone swaying along with the beat, humming through the verses, and then belting out the chorus.

It’s another relatable tune about being far from home and longing to return and perfectly highlights why Isbell doesn’t just tell good tales—he roots them in a place that gives his stories that much more of a punch.

10. “Decoration Day” (2003)

Decoration Day was the first Drive-By Truckers’ album to feature Isbell on vocals and guitar and he made his presence felt right away, writing two tunes for the album—including the title track.

Isbell wrote the song shortly after joining the band and the story—two families involved in an intergenerational feud that has dragged on for so long no one can remember how it actually started—fits perfectly with the rest of the album, which deals heavily with southern folklore.

9. “Cumberland Gap” (2017)

For all of his prowess and skill when it comes to quieter tunes highlighted by intricate finger-picking and detail-laden stories, Isbell and The 400 Unit can sure bust out a barn-burner when the situation calls for it.

“Cumberland Gap” is a fantastic driving song that checks all the boxes, as it’s uptempo, loud, and features a chorus that’s tailormade for singing along to. I’ll always appreciate Isbell’s folksier tunes but my heart will forever be with his barn burners—especially “Cumberland Gap.”

8. “Traveling Alone” (2013)

In some ways, “Traveling Alone” is also a pretty good driving song (albeit a much different kind of driving song than “Cumberland Gap”).

“Traveling Alone” is more of a late afternoon or late at night driving song; the kind that has you staring off into the distance as you go one hand on the wheel and another dangling out of the window while you get as reflective about life as he does. 

7. “If It Takes A Lifetime” (2015)

There is a timelessness to “If It Takes A Lifetime,” a song about a man “learning how to be alone / fall asleep with the TV on / fight the urge to live inside my telephone.” It’s poignant on its own, but if you listen to it with knowledge of Isbell’s battles with substance abuse and the perceived mundane existence that comes with sober living, it comes with a little bit more weight and gravitas.

It might be heavy, but at the same time, it’s also got that 1970s honky-tonk vibe that you can’t help but smile at, which is a testament to the wide array of emotions Isbell is capable of eliciting with a single track.

6. “Cover Me Up” (2013)

“Cover Me Up” is what the kids would call “some real raw shit.” It’s Isbell laying it bare and digging out all those old skeletons and demons and exorcising them in the only way he knows possible.

“I sobered up and I swore off that stuff / Forever this time,” he sings in the song’s second verse. We should always want honesty from the artists we love, and for Isbell, it doesn’t get more honest than “Cover Me Up.”

5. “If We Were Vampires” (2017)

“If We Were Vampires” shows up at exactly the halfway point of The Nashville Sound, which is appropriate because it’s definitely the high water mark for the album. Once again, it’s just Isbell, an acoustic guitar, and backing vocals by Shires, and (also again) though it might sound sparse, that’s just an illusion.

It’s an incredibly sad song, as it looks toward what lies ahead after years and years of happiness together, “knowing that this can’t go on forever.”

It’s tough because we all struggle with getting too far ahead of ourselves and not devoting enough time to the present. At the same time, we’ve also been preconditioned to know that the end is always there, and because of that, it’s always hanging over our heads.

The loneliness will be there. It has to be. The only uncertainty is whether or not you’ll be the one left behind or your partner will be.

4. “Elephant” (2013)

Oof.

That’s just the best way to describe this, which is sung from the perspective of a man who is watching his wife die of cancer (the “elephant” they’re trying to ignore while they attempt to find some peace and happiness before it’s too late).

“We just drink our drinks and laugh out loud / and bitch about the weekend crowd / and try to ignore the elephant somehow.” It’s the kind of song that will make you want to hold your loved ones a little harder after you listen to it. You know, after you wipe the tears from your eyes.

3. “Go It Alone” (2011)

I love the guitar in this song. I love it. I am physically incapable of listening to it and not playing air guitar to it.

“Go It Alone” has all the glorious sights and sounds of vintage Neil Young and Crazy Horse or deep in the swamp Tom Petty. It’s some rugged as all hell, shit-kicking rock. It’s not all fun and games, though, as the song deals with a touring musician warily eyeing a life away from the road once the tour ends.

Loneliness, man. Isbell might work that fickle bastard better than anyone.

2. “24 Frames” (2015)

So you’re listening to this song for the first time. You mostly ignored the lyrics in the first verse and enjoyed the melodies so you’re in kind of a good mood. “This is a pleasant little ditty,” you might say to yourself.

But then the chorus hits. “You thought God was an architect, now you know / He’s something like a pipe bomb ready to blow.” Hmmmm. Maybe this is something darker than you originally thought.

Isbell is tricky because he just doesn’t write songs about a tragedy that already happened or one currently taking place. He writes songs like “24 Frames” that are about something worse: the tragedies yet to happen but that are destined to (and occasionally makes them resemble a feel-good country tune).

Diabolical.

1. “Hope the High Road” (2017)

If you come across someone who is down to compare Isbell with Bruce Springsteen (which I might be depending on the mood), they could point to “Hope the High Road” as a song that helps make their point.

The Nashville Sound is a profoundly interesting album for our current times, and while there’s a song like “White Man’s World” on it that addresses certain topics in an unabashedly overt manner, “Hope the High Road” is more of a keeper and has more staying power thanks in large part to the power of positivity that courses through its veins:

“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.”

“Hope the High Road” might end up being one of the more definitive and enduring songs of an American era defined by divisiveness, and with people on both sides drifting further and further apart with each day that passes, songs about bridging those gaps are all that more important.