We all have a country music story. Well, stories, to be more appropriate: stories of how we discovered the genre, stories of what kept us coming back for more, stories of what keeps us coming back for more even now. Maybe it’s because some artist out there wrote our life story in just three minutes or so. Or maybe they didn’t, and we just greatly appreciate their stories anyway. It was actually the sound and melodic tendencies that got me hooked as a child – still catchy, for sure, but low-key and sweet as well. To shamelessly dive headfirst into a cliché, the sound of fiddle and pedal steel is like a warm calling card back home for me, no matter how far I roam.
Now, I haven’t lost that hunger for new music, and I don’t think I ever will. It would be a great shame to become numb to something so magical. If anything, though, it’s why I don’t take my favorites these days for granted – the artists that have helped shape my tastes and experiences throughout my entire life. I stopped using review scores last year, and the more I distance myself from them, the happier I am I did, because a true connection can’t be measured by a number, and it doesn’t just happen overnight. Once we’ve bonded to a favorite artist, it’s very hard to shake it – regardless of whether their current work measures up to the past work we know and love, it doesn’t really matter, because we owe them more than we can put into words.
And while we can, of course, come together over our love for certain acts, at the end of the day, our own group of favorites and why they’ve connected with us is going to be ours and ours alone. It’s tied to generational divides, both in terms of who’s popular now and who was popular before, and in terms of what our parental figures choose to introduce to us. Maybe it’s even tied to a physical location, though in the modern age, that feels like a fading factor. Country music has been, and still is, everywhere, man.
So today, I’d like to take a walk through my own timeline to discuss six artists that have shaped my life and not only have made me the country music fan I am today, but who keep me invested in all that it has to offer even now. Keep in mind this isn’t a definitive ranking exercise – the artists presented here are presented in order of when their art spoke to me in life, if anything. And it’s not to say there aren’t still more favorites beyond the artists mentioned here. My Fifteen Favorites series alone should offer a deeper glimpse into who’s impacted my love for the genre. This is simply a way of examining artists that have cut as deep as it can go, and I invite you all to share yours, too. Let’s get started.
He’s first on this list, and he is probably the artist I associate most with my early love for the country music genre, but that also goes to show how timeless Alan Jackson’s music is for me. And it comes down to two factors: consistency and simplicity. Jackson’s first album sounds just like his latest, with the only differences coming through in his now more weathered, mature delivery fitting for a veteran’s poise, and the fact that time and experience has naturally made him a more wide-eyed, empathetic writer. Other than that, Jackson’s sound is everything I love about country music; not traditional or neotraditional country music, mind you – though those are the closest categorizations most make with his sound – but just country music in its purest form, full of weighted reflections, cathartic glimpses of joy, and, of course, a good amount of fiddle and pedal steel. There’s always a firm, naturally inviting rollick to his delivery and sound, whether he’s offering a sobering outlook on life through songs like “Remember When” and “Monday Morning Church,” or offering something on the decidedly much more lightweight side with songs like “Chattahoochee” and “Summertime Blues.”
Maybe it’s because my own grandparents were so instrumental in developing my love for the genre, but growing up, I always looked to Jackson as a role model – his songs being my guidebook through life. Ironically enough, I can only really understand his perspective in an older age myself now. But whenever I put on a song of his – any song – I’m back home. I’m back to lazy summer days and watching CMT music videos with my grandparents, remembering Jackson riding his jet ski to “Chattahoochee.” And it’s a timeless feeling that never feels liked wasted reminiscence – not when it’s all presented with this much boundless charisma and heart. I said at the beginning of this piece that there’s no order here beyond when these artists really stamped my life, but I don’t think I’d be the country music fan I am today without Alan Jackson. He is, I think, my all-time favorite country music artist.
If Alan Jackson represents the quintessential heart of country music who invited me into that world, Gary Allan represents, well, basically the opposite side of the coin. He’s not going to make it easy to get a glimpse into his world, and given how dark he’s went with his themes and ideas, maybe it’s for the best.
I don’t know what it was about me growing up, though, but I loved dark music (and still do). Not necessarily to the point where it was dark just for the sake of being edgy, however. I think that’s why country music became my preferred medium, because most of the darkness evident within those songs was, and is, just … pain. Genuine pain that we can empathize or sympathize with, especially with a stronger storytelling aspect that can make it feel human. It’s not a song I’d call a favorite of mine of his today, but my first experience with Allan’s music was “Today,” a minor top 20 hit about a guy who’s lost out on love and just has to grin and bear it as his former partner gets remarried. Musically, it’s a pretty fitting picture of late-2000s country, what with the loud, overblown production and all. And yes, I like it in spite of it. But what really connected with me was that gritty voice brimming with an emotional delivery that told me he understood his character’s pain. Those who have followed my Favorite Hit Songs series know that I have a big soft spot for this particular decade of music, but even I can admit there wasn’t quite a lot of that raw vulnerability and passion on display during this time. Despite veering toward rock on quite a few of his compositions, Allan helped me tap into the heart and soul of country music.
And yeah, Allan isn’t much of a writer. Not that he can’t write a great song, mind you, it’s just that most of his compositions tend to be written by other people. But speaking as someone who thinks artists can still craft unique identities through other means regardless, there is a quintessential bedrock to an Allan song. Back in ye old days of CD hunting (if you know, you know), Allan was the first artist where I cared to seek out every recording of his. Smoke Rings in the Dark is a near-classic, and Alright Guy and See If I Care are brooding with swagger. Even an overall happier collection like Set You Free is still characterized by a mature outlook and experience of coming out on the other side of the fray – maybe not in one piece, but here regardless. In recent years, he’s stumbled in trying to recapture that same magic, ironically chasing after radio play after years of standing proudly on his own not needing it. But it’s also that individuality that I’ve always respected about him and will continue to love, especially every time I hear him do that weird growling thing he does.
This will scan as heresy, but there was a time when I didn’t care as much about lyricism in country music. I cared more about how it was presented – both in terms of tone and who was actually presenting it. I suppose that’s still true to a fault for me, but really, it works both ways. A well-written song can fall apart if it’s presented in a boring manner (we tend to call this “coffeehouse folk”), and even the liveliest production techniques and prettiest melodies and compositions can’t mask a lyrical tire fire. My favorite artists tend to be those who can find a happy medium in between – the ones who understand their messages and give them the life they deserve. It’s why I was blown away upon finding an album in 2015 called Blackbirds, which opens with a title track about a daughter who murders her abusive father. Imagine Carrie Underwood’s “Blown Away,” only instead of huge theatrics, it’s carried by a buzzy, gurgling electric simmer and ramps its intensity in more subtly sinister manners throughout (I happen to love both songs, for the record). And then it leads into an atmospheric, very pretty-sounding song aptly titled “Pretty Things” … about depression.
So, OK, I didn’t say it was easy music. But I’ve never known an artist to cut to the bone and beyond it quite like Gretchen Peters. You know her songs if you’re familiar with George Strait’s “Chill of An Early Fall,” or Pam Tillis’ “Let That Pony Run,” or Trisha Yearwood’s “On a Bus to St. Cloud” (you should really know that one), or, well, quite a few others, actually. And her mantra, much like American Aquarium’s BJ Barham, is “sad songs make me happy.” Its meaning is simple, in that there’s beauty in confronting our darkest fears and insecurities head-on, because there will be clarity at the end of a hard-fought battle. Much like contemporary Kim Richey, Peters was mostly known as a writer for other artists throughout the ‘90s. But I found her work through her excellent solo projects from the 2010s, all of which are worth your time, and, at least for me, emblematic of the true power of what a song can make you feel.
I’m slightly cheating with this one, if only because James McMurtry isn’t a country music artist. He’s a folk-rocker with nary a song in his discography I could even point to as somewhat country-adjacent. But he’s another artist, like Gretchen Peters, who has strengthened my love for good storytelling. So if it’s a question of whether or not he belongs here, he absolutely does. I found his music at a similar time in my life to Peters’ music, with an album of heady, minimalist storytelling-driven songs in 2015 called, very appropriately enough, Complicated Game. I loved it then, but McMurtry’s music is the kind that ages better with time – where the layered, emotional resonance becomes more relatable and you start appreciating his eye for detail in the scenes he sets, with enough rock smolder to keep the fire alive. Sure, his pace has slowed considerably over the past decade, but if that’s what it takes to hammer out the finer details and deliver another masterpiece collection of songwriting, it’s worth it every time.
He’s not going to compete for a spot on Rolling Stone’s greatest singers list, but his craggy, expressive tone has always gone underrated for just how much charisma he’s able to convey, both as a shit-stirring rapscallion and as a more tempered, observational poet. And I think therein lies the nugget, he’s a poet who shares stories that are rarely ever his own. He writes novels that can span anywhere from three to maybe seven or eight minutes but feel lived-in and complete, introducing and ending characters we come to care about in a relatively short amount of time; “Rachel’s Song” is one of my favorites in that regard. One could make the argument that McMurtry is an artist you might not truly appreciate until much later in life, and indeed, what I love about his work now will likely only deepen with experience and time. But I can happily run through any album of his at any time and still find a thrill.
It took me far longer than it should have to truly explore Patty Loveless’ work, though the reason as to why mostly just boils down to an issue of timing. Unlike Alan Jackson or even George Strait, Brooks & Dunn, and Reba McEntire, I didn’t grow up hearing new music from Loveless on the radio, nor did I hear the rare recurrent hit in the 2000s. It was up to me to take that plunge … and what a delightful trip, indeed. I guess the biggest common thread between every artist for me is simply a strong sense of consistency, where I’m inspired to devour any work of theirs I can get my hands (ears?) on and can happily revisit any of their songs and albums at any point.
But in searching for the individual takeaway I get from Loveless, it’s just a sense of command and grace with how to approach country music. She’s got her lighthearted moments, for sure, but she pulls no punches in making everything of hers feel mature and thoughtful. She’s another artist one could easily brand as neotraditional, but she’s also another artist for me who transcends any label to deliver everything I love about country music: an emotionally heartfelt delivery, songs that can cut and inspire, a clear-cut grace in tone that can make it all her own, and a sense of strong artistic identity. And she’s just amazingly diverse in what she’s able to tackle. Even after her radio hits dried up, she bowed out gracefully to deliver some excellent projects like Mountain Soul and the testament to her influences that is Dreamin’ My Dreams. And despite building a career that could always call back to country music’s past, she carried it into the modern day and deserved so much better.
Tom T. Hall
I end as I begin, really. It’s Alan Jackson’s warmth, grace, and humility that pulled me in to country music in the first place, and now, at a time where I sometimes struggle in maintaining a balance between growing older and expanding my horizons versus remembering who I am, Tom T. Hall’s music has never clicked with me as much as it does now. There is nothing – nothing – like a Hall song. He’s not the storyteller unraveling his adventures from afar – he’s the regular guy who relays life’s simple observations in a conversational manner, like the person you might end up striking a natural conversation with at a diner (or wherever). Only, he’s not quite a stranger; not for long, anyway. He’s a friend on the same level as you and I who just so happens to be a living country music legend, and my pick for the all-time best writer within the genre.
But even beyond the writing, there’s nothing even quite like a Hall song in approach. There’s nothing flashy added to the hooks or melodies or compositions themselves. Most songs of his excel off of simply picked acoustic instrumentation, a rare country-folk mix that was only ever Hall’s and devoid of trends of the time, or any time, for that matter. I guess the other common thread with these artists I’ve picked, though, is a timelessness to their music, and that’s definitely true with Hall. Whenever I need a way to settle me down, I put on any song of his – it’s usually “That’s How I Got to Memphis,” but any will do – or I reread his own The Storyteller’s Nashville for the forty billionth time, and I’m home again. Not home in terms of feeling young again – unlike the aforementioned Jackson, I can’t say Hall’s music was ever part of my childhood – but home as in … grounded. I remember to value what I’m hearing and the magic that enables it in the first place. Since Hall’s death, too, I haven’t went a day without revisiting something of his, taking in every virtue of grace and humility extolled through the perspective of a true leader.
And a few other honorable mentions: Lee Ann Womack, Steve Earle, Shania Twain, Brad Paisley.