Fifteen Favorites: The Steve Earle Edition

There are various points in my life I can credit to turning a passion for music and the artists that make it into an obsession – at least one of them is when I discovered Steve Earle and “Copperhead Road.”

And the discovery story for that isn’t as exciting as you’d think. I’m a child of the 2000s, and I found the song by simple accident while scrolling YouTube one day. But what a find it ended up being, a thunderous titan of a song that had only a semi-decent music video. I was in high school, and instead of going through the expected emo phase, I gravitated toward Earle’s angst and firepower. In a way, he was the first artist I really obsessed over – the one where I wanted to collect all of the albums and learn the story, because for those unfamiliar with it, it’s an interesting one we’ll get to soon.

And it’s also why I champion the ‘80s as one of the greatest decades in country music history, because for a brief period of time in the latter half of the decade, it seemed like even the weirdest and most “out there” artists had a chance to make it in Nashville – from quirky songwriters to folk-inspired poets … to even a Texas act like Earle that would never really find his true home in Nashville anyway. His country career really only spans two records and two top ten hits, of which only one is even really still remembered today. And through label conflicts and drug abuse, he stumbled hard in the latter half of the decade and early half of the ‘90s only to roar back with a string of near-classic albums and become an alt-country icon.

Naturally, then, I think it’s time to take a deeper dive into what exactly it is I love about Earle’s style and sound. As always, this feature is simply me expanding upon what makes my favorite songs just that – favorites; not “the best,” because objectivity in musical discussions is pointless anyway. I invite you to share yours if you have any, as well. Let’s get started.

All songs written by Steve Earle unless otherwise noted.

No. 15, “The Tennessee Kid”

To be frank, “The Tennessee Kid” is the only Earle song to be featured on this list past the Transcendental Blues era. Part of this is because his work past that point can be somewhat hit-or-miss, and also because we’re dealing with an incredible first and second half to a career that I honestly couldn’t collectively place any lower than I did. As for the modern song that ended up making my list anyway … well, it’s strange. It comes from a blues album that many were cool on, though it remains a quiet favorite of mine even today. And this is its anchoring point – a slow-rolling menace of a tale that, admittedly, cribs heavily from the iconography of Robert Johnson’s “Cross Road Blues,” but it just delivered with such a sly wit in its story and several excellent solos, that it’s hard to care much. Epic without being campy, it’s one of Earle’s best story songs.

No. 14, “Transcendental Blues”

And from something straightforward we turn to the abstract, where amidst the haze of synthesizers, scuzzy guitars and … bongos (?), we get a philosophical musing and ode to, well, the art of transcendentalism. And whether that’s about confronting everything you’ve encountered on past paths before, rising above mistakes made long ago, moving on to find absolution, or all of the above, I can’t say for sure. But damn, when that outro hits, I feel it all anyway and embrace whatever the hell it is, because “transcendental” is certainly the best way to describe the feeling.

No. 13, “Feel Alright”

And back to the straightforward we go. Earle’s comeback from drug abuse technically resides in the more tempered Train a Comin’ album from 1995. But I’ve always considered the true moment when Steve Earle got back to being “Steve Earle” is when the first notes of that riff played and he roared back with this playfully wry and self-aware ode to feeling alright again. The reflection took place on the album before it, and this was Earle finding a way to have fun again and stay in control of his demons – a shot of glorius euphoria.

No. 12, “Somewhere Out There”

It wont be the first cut from 1997’s El Corázon to make this list (my personal favorite album of his), though it does feel like an extreme wildcard pick in comparison to everything else. And it’s tough to nail down exactly what makes this work for me, be it the more abstract writing about searching and hoping for a partner and kindred spirit one hasn’t even met yet, or the fantastic slow-burn of that guitar work on the solos and especially the outro. Either way, it’s got this restless spirit to it that’s always been a trademark of Earle’s work. And with the more unique framing centering it, it’s an underdog favorite of mine.

No. 11, “You’re Still Standin’ There” (feat. Lucinda Williams)

That chorus. That’s it. In all seriousness, while this is a fairly simple song of love gained and lost, “your memory cannot keep me warm but it never leaves me cold” is one of those all-time great lines for me. And when you have two equally haggard vocalists taking on the role of characters trying so desperately to move on from another – all while that harmonica blasts away – you’ve got an easy formula for success here. Funny how a song about trying to move on from something just won’t leave your head once you hear it or revisit it.

No. 10, “Guitar Town”

I mean, it kind of had to be here. But it’s also ironic to hear Earle in country shuffle mode as he takes on the role of the young, green singer/songwriter on the road trying to make it in Nashville. I’ve always considered Earle’s career to have its phases. The mid-’90s saw the triumphant return and new form of an artist who was always destined for more, and everything afterward has added to that legacy in its own way, from tributes to fallen icons to passion projects alike. And before that return you had the angsty rock star that was riding that freight train to hell and churning out great art from his suffering – we expect that a bit too often from our favorites, sadly. And this is where it all started. But even knowing he’d move far past this, there’s something undeniable about that riff, and the way he charges ahead with big dreams and possible delusions of grandeur that, nevertheless, feel well-earned in hindsight.

No. 9, “Poison Lovers” (w/ Siobhan Kennedy)

Another duet, only this time around it’s hard to ignore how much of a toll time has taken on Earle’s voice. This is certainly not a song I enjoy for its chemistry, because in truth, it’s Siobhan Kennedy who steals the spotlight here, where if Earle sounds worn-out and haggard from another bout with bad love, she’s the one who’s had enough and lets listeners know. Couple that with a fantastic slow-burn of a bass groove, and you have a track where that frustration feels like it lets loose and spills over to a point for which there is no turning back for either one of them.

No. 8, “The Devil’s Right Hand”

From an era in which Earle was adding as much muscle as he could to his production and writing, we have a song with one of the greatest hooks to ever live and fire excellently on all counts – a tried-and-true tale of disappointing dear old mom by going against her wishes and living a life on the run that always comes back to that one fatal lesson: “Mama said the pistol is the devil’s right hand.” And it’s going to hammer that point in with a key change toward the end for emphasis, damn it. 

No. 7, “Someday”

If there’s an obvious influence on Guitar Town, Steve Earle’s debut album, it isn’t really a country one; it’s a rock one. And there’s almost something cathartic about the Bruce Springsteen influence evident in the yearning for freedom from one’s life in a small town on “Someday.” Earle’s work has always followed suit, never content with itself and always looking for that next stop. And it’s all the more ironic that it was released in a format where you’re supposed to love your small towns. Like most tracks here, I could just scream that chorus and hook and point to them as the primary factors for why I love this, but it’s one of those tracks that just awakens something primal within.

No. 6, “Billy Austin”

Younger me adored Earle’s The Hard Way album, released in 1990 and right as his spiral out of control came to a screeching halt – one that led to jail time and, eventually, redemption. Older me can’t deny the cracks in the facade, though, or how fried Earle sounded on tracks that were almost disturbingly revealing, like “West Nashville Boogie.” But even at the darkest point, we got this gem, a track told from the perspective of an inmate on death row who doesn’t beg or even ask for our sympathy. He’s just some faceless soul that was dealt a bad hand in life and played it as well as he could, and resorted to thievery for survival and, sadly, murder. Between the reverb echoing off the buzzy acoustics and the deliberately sluggish pace that forces listeners to hear this man’s story, it’s a track that’s supposed to be uncomfortable, and perhaps it’s best that it’s all told as a fictional story, so that we don’t have to truly understand someone like this.

But it’s those last few lines toward the end that always get me: “Could you pull that switch yourself, sir? With a sure and steady hand? Could you still tell yourself, sir, that you’re better that I am?” It always stops me in my tracks, and considering Earle has never been shy about crafting songs from uncomfortable perspectives, this just may still be his best example.

No. 5, “Goodbye”

If an album like Feel Alright was Earle learning how to forgive himself, an album like Train a Comin’ before it was the moment of hard confrontations needed to move on, however uncomfortable they may be. And really, this is yet another Earle song where I can point to that main hook – “I can’t remember if we said goodbye” – as what just drives it all home, where both the joyous memories and painful derailments with a former partner stick with him for better and worse, but the actual end is just a blur he may not want to remember anyway, even if he could. Painfully vulnerable, sad, and personal in a way Earle has only rarely touched in his career, it’s a moment of owning up and letting go, finally offering a deserved goodbye to remember.

No. 4, “I Ain’t Ever Satisfied”

There’s a part of me that knows Earle wrote this exact same song better numerous times afterward in an arguably more poetic or prettier form, but the early moment of direct declaration will always remain my favorite. It’s a theme song – likely for him and definitely for me, where the main conceit is in the title itself and the final verse is another all-time great for him, never content with where one is at but content to chase the everlasting flame anyway, wherever it leads next. And it’s just such a phenomenally catchy and well-balanced composition, right down to the damn “woahs” to boot.

No. 3, “Taneytown”

The pure audacity to release a song like this – a track presumably set in an earlier time yet still depressingly relevant today, where Earle plays the role of a black boy who ventures outside of his home to the wrong side of town and pays for it simply for the color of his skin. Not to resort too much to hyperbole, but this is a track where the thumping intensity of the guitar work and writing is relentlessly goosebump-inducing, always full of danger and despair for the wrong reasons, right down to a twist end that still ends the song on a somber note. It’s a simultaneously angry and fearful song where the roots of that unfounded rage are still noticeable, and it’s a good reminder of how some aren’t so unfortunate to escape the evils of that oppression.

No. 2, “Ft. Worth Blues”

Of all the Earle tracks here, this is the one I find hardest to revisit, even as a fan of Townes Van Zandt, the artist who served as a mentor to Earle and whose death inspired this track. And the irony behind why is actually of a simpler variety, where the offbeat references made here are ones that could really only be understood by two close friends and the relatable core of simply missing a loved one is what ultimately resonates. It’s a tribute for a singer/songwriter whose news, as the first verse indicates, would have shut down the town, had he received the proper and deserved recognition in life to do so. It’s a sendoff to a misunderstood figure that undoubtedly hits harder for the few that did understand him. And there’s only one Earle song that means just a bit more to me.

Of course, before we get to that, let’s roll through several honorable mentions that just barely missed the cut for this list, because the exclusions this time around were brutally difficult:

“Oxycontin Blues”

“Down the Road” (written by Tony Brown, Steve Earle, and Jimbeau Hinson)

“The Galway Girl”

“It’s About Blood”


“Tom Ames’ Prayer”


“Billy and Bonnie”

And now, my No. 1 pick:

No. 1, “Copperhead Road”

OK, so I spoiled it in the introduction. But sometimes the most obvious pick really does feel like the right one. It’s a signature epic, but it almost feels wrong to crown it as that, knowing that this was the first step toward darkness Earle almost didn’t crawl back from. And I think that ominous nature is almost caught with a sense of self-awareness on “Copperhead Road,” where the creaking cry of bagpipes at the beginning signals a very different turn for Earle and his sound compared to his country hits. But this tale of moonshine and contraband isn’t part of a long list of bluegrass staples; it’s a track that borrows from Celtic influences and transitions into a straight-up rock epic, right when the climax hits and the family operation goes sideways. And for all that talk about finding an escape in his other songs, Earle finally penned a character who found it, only to return home to carry on the family legacy anyway … you know, in his own way. Seedy in a way that’s pulse-pounding and epic in all of the best possible ways, it’s a classic that rightfully defines an artist.

And hell, if all that wasn’t enough, maybe it’s just a classic because of the associated line dance. But I think there’s more to its genius than that. To this day, it remains my favorite Earle tune, even if I can’t heed the advice and stay away from Copperhead Road for too long.

2 thoughts on “Fifteen Favorites: The Steve Earle Edition

  1. Steve Earle is such an interesting artist to me. I used to listen to “Guitar Town” (the album) a lot and “Copperhead Road” (the album) almost as much. Then, I really got into “The Mountain,” which I think is his best (and my favourite) album. Since I haven’t listened to it in a number of years, I had it in my head that “Transcendental Blues,” while very good, was nowhere near the quality of “The Mountain;” however, listening to it again recently reminded me how good it is. I also really enjoyed “So You Wanna Be an Outlaw” when it came out and I think his tribute albums are great (particularly “GUY”).

    However, until the past couple of weeks, I don’t think I’d ever listened to most of the rest of his albums. Now that I have, I’m glad I did. Obviously my list is heavily weighted towards the albums I’m most familiar with, but one of the songs from the new-to-me albums made my Top 15 at #11.

    My list doesn’t have a lot of overlap with yours, but that just serves to highlight the consistent quality of Steve Earle’s career.

    Honourable Mention (in alphabetical order):
    – Ain’t No God in Mexico
    – Another Town
    – Someday
    – Union, God and Country

    Top 15:
    15. This is How it Ends (w/ Miranda Lambert)
    14. Dublin Blues
    13. Hillbilly Highway
    12. Nowhere Road (I know this from the Black Dog soundtrack and I didn’t realize it was on the “Exit 0” album)
    11. Mystery Train, Pt. II
    10. Walkin’ in L.A.
    9. Telephone Road
    8. Dixieland
    7. Copperhead Road
    6. Johnny Come Lately
    5. The Galway Girl
    4. Carrie Brown
    3. Down the Road
    2. The Mountain
    1. Guitar Town

    It was really difficult for me to choose between #1 and #2, but I sometimes think #3 might be his best song.

    Liked by 1 person

    1. I know what you mean in regards to the bias toward the albums you’re most familiar with; his post-2000s work is still excellent … but I just couldn’t place most of it above his ’90s work, which really says a lot. Even though we don’t share a ton of similarities with our lists, for example, I can still safely say many of these just missed the cut for my own list and might easily make it on a different day, given that my favorites tend to fluctuate!

      Thanks for the comment and for sharing your own favorites!


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