The Musical Divide

Previous: Favorite Hit Country Songs of 1994

---

I didn’t originally plan to redo this list for this series. For those who don’t know, before I revamped this series to work back throughout the years, these used to be far more random and, as a result (or consequence), less focused. It’s why I think few of them have aged well. This was one of the more recent years I had explored prior to the relaunch, given that I looked at it in April 2020, but it’s also one that I think could do with some slight tweaking.

And it’s interesting revisiting this year in a more focused context, because while I think this may actually be the weakest year of the early ‘90s – mostly in terms of quantity and not quality – that still equals out to a mostly excellent year for music. The ‘90s boom had really started to take full effect, and the results, much like the mid-to-late ‘80s, showed in the vastly unique and interesting songs that were able to actually become hits; more on that later, of course. So, as a refresher, regardless of whether you are or aren’t new to this feature, this is a series in which we explore the hits of yesteryear – not necessarily the best or most impactful ones (because that’s just a silly exercise anyway), but rather just personal favorites, meaning I invite you to share yours, as well. If you’re curious as to what qualifies for this particular list, here’s a handy guide. Let’s get started.

---

No. 10 – Trisha Yearwood, “Walkaway Joe” (feat. Don Henley) (written by Vince Melamed and Greg Barnhill)

I’m not sure whether this qualifies as an underrated favorite in Trisha Yearwood’s discography or not. It’s certainly one of her oddest, given that Don Henley’s contributions here don’t really amount to much. But much like Vince Gill, there’s a certain cheat code activated when Yearwood resorts to sweeping piano balladry that allows her voice to shine at the front of the mix.

And while I do, of course, refer to pure power and scope with that statement, I also refer to the empathy displayed for a melancholic situation: a young girl who thinks she knows what love means in falling for the “bad boy,” only to experience her first taste of heartache and defeat instead. The song has always cleverly framed itself as an archetype of a young relationship with specific details used to make its particular story unique, but Yearwood sounds like she’s in that brokenhearted woman’s mindset – the one who didn’t heed her mother’s warning out of a stronger desire for what she thought was love. Sure, the ending to this particular relationship is a bit more brutal than an average high school fantasy, but it only serves to show how deep those scars will run henceforth. It’s sobering and mature in a heartbreaking way, where no one walks away a winner.

No. 9 – Hal Ketchum, “Mama Knows the Highway” (written by Pete Wasner and Charles John Quatro)

Truthfully, I’d say most of my favorite Hal Ketchum songs are of a weightier, darker variety – singles and album cuts – but he was deceptively great at recording some truly cheery, upbeat material as well. And though this is the tale of the road-savvy mama, Ketchum’s weary delivery is enough to add miles to her journey in a way that suggests it may never end. Then again, off the chipper bursts of rollicking piano and mandolin with a great slide guitar groove, it’s not exactly one you’d want to end, either. It’s free-spirited and adventurous that, sure, may be fantasy-driven above all else. But at least for a little while, we can live vicariously through her and Ketchum’s road dog ways, and it’s not a bad way to spend a few minutes. Like the song says, “Good country music will never steer you wrong.”

No. 8 – Sawyer Brown, “All These Years” (written by Mac McAnally)

I’m not sure if I actually personally love this or if I just really, really respect how gutsy it is, especially from this band. That’s not a slight – it’s just that Sawyer Brown were usually known for their upbeat, good-timing mischievous antics, and so to hear them record something this raw and melancholic, with only touches of minor acoustics and strings filling the space … well, you’ve certainly got my attention. And that feeds directly into the setup, where a husband comes home to find his wife in bed with another man. And instead of the usual fury that would typically ensue in a country song, both parties have an honest conversation about their own faults in the relationship.

So, yeah, not exactly a realistic depiction of what would usually ensue (I mean, is the other guy just awkwardly putting back on his clothes while they’re having this heart-to-heart, or…?), but in allowing itself to be a bit fanciful with its melodrama, it’s able to explore the underlying root that typically leads to this sort of malaise: neglect on the husband’s part, and temptation on the wife’s part, never framing either party as necessarily in the right or wrong and feeling surprisingly empathetic as a whole because of it. It’s the sort of complex, challenging song I’m surprised was even a hit then, but it’s powerful, even when sparse and muted.

No. 7 – Mary Chapin Carpenter, “Passionate Kisses” (written by Lucinda Williams)

I originally had “The Hard Way” here instead, but the older I get, the more I understand this song. I always liked it, but it’s always felt like an offbeat single from the usually reserved Mary Chapin Carpenter. Then again, that may be the point – an upbeat country-rocker where she allows herself to let loose and shake the doldrums that have come to define her character’s situation; it’s not selfish to want happiness, after all. It isn’t so much the passionate kisses that’ll do it either: it’s the feeling of stimulation and being alive, in a way where everything is wild and unpredictable rather than boring and settled. It’s no surprise that songwriter Lucinda Williams’ own unbridled energy shines through as a beacon of that unkempt alt-country energy that ran parallel to the mainstream this decade, but it’s the kind of shake-up the format needed. There’s something magical that unlocks with this song.

No. 6 – Toby Keith, “Should’ve Been a Cowboy” (written by Toby Keith)

If there’s a recognizable classic from this list, it’s definitely this song, and for good reasons beyond just its iconic riff and hook. For as much as Toby Keith would lean on bravado and swagger in a clumsier manner over the next decade, this is a similar power fantasy that nonetheless feels goofy and sincere in a relatable way. Maybe it’s just my own memories of watching shows like Gunsmoke and Bonanza as a kid with my grandfather fueling some of the love, but there is something to be said for how lighthearted and chipper this feels in wanting to live out the fantasy of the romanticized Hollywood cowboy. Heck, even outside of that specific context, it’s simply about wanting to be the star of our own show and having our glory moments, which, regardless of whether that does or doesn’t happen at some point in life, is always fun to revel in, especially through someone as charismatic as Keith is here. Hey, one can always dream, right?

No. 5 – Patty Loveless, “Nothin’ But the Wheel” (written by John Scott Sherrill)

I sometimes stretch the definition of “hit” with these selections, and I certainly don’t need to include yet another Patty Loveless song on one of these lists. Except, oh yeah, I do, because it’s sad that this was only a minor, forgotten top 20 hit for her: a piano ballad that shifts toward a warm acoustic foundation, with enough atmosphere and lingering fiddle and pedal steel to capture that lonesome feeling of striking out on one’s own that’s just strikingly beautiful.

Escapism for the sake of itself rarely makes for good material – unless, it’s, you know, “Mama Knows the Highway” – but when this trip on the highway is used to frame Loveless’ drive away from a troubled past and dead relationship, the subtext left from that pain is heartbreaking. Though what I think I like best is an overall message of hope and resilience, where that drive may not provide all of the answers she needs right now, but will certainly provide enough temporary solace to push forward; that’s all it takes sometimes. It’s another slice of hardbitten reality from a master of the craft, and that’s why it’s here.

No. 4 – Confederate Railroad, “When You Leave That Way You Can Never Go Back” (written by Steve Clark and Johnny MacRae)

This is another song, like Sawyer Brown’s “All These Years,” that feels like an odd fit for this particular group: a sparse, brittle acoustic ballad with fantastic spacious texture throughout that comes from a band known more for their rowdier, southern-rock-inspired cuts. On the surface, I suppose it’s not that surprising; this decade did favor corny and over sentimental ballads I haven’t exactly showcased, after all. And “When You Leave Like That” is all set to cross that line of being mawkish … and then it doesn’t. There’s no happy ending for the star character who recklessly stumbles through life because of a bad childhood, and redemption only comes when it’s too late.

The song doesn’t ask for sympathy, but it does show how even the tiniest decision can forever alter who we are and who we become, and without that solid foundation, you’re forever doomed to just repeat those mistakes. I’d call it depressingly frank … but it’s more just brutally realistic in its framing and consequences it has for real, everyday – and forgotten – people.

No. 3 – Pam Tillis, “Let That Pony Run” (written by Gretchen Peters)

The opening lines of this song remain some of my favorite of all time: “Mary was married with children / Had the perfect suburban life / ‘Til her husband came clean with the help of Jim Beam and confessed all his sins in one night.” It’s a common theme for country music, but it says so much with so little – and that’s just to start it off, rather than establish the anchoring point. After all, “Let That Pony Run” is more complicated than that anyway. It finds Pam Tillis’ character caught in the aftermath of the situation, free to move on with her life yet unable to find the courage to do so.

Yet the subtext is hopeful, acknowledging how she’ll be fine one day after that shock fades and she finds the strength to explore the freedom to find herself. And there’s never any judgment cast even when there easily could be – partly because she’s not sure what to really make of all of it, but also because the song hints she needed this break anyway; the love died long ago anyway. It’s another song here that feels lived-in and real in a way that can uncomfortable to confront, but at least in the optimistic outlook, there’s enough to hold on to for now – let that pony run wild, indeed.

No. 2 – Dwight Yoakam, “A Thousand Miles From Nowhere” (written by Dwight Yoakam)

There’s nothing quite like this song in country music, even despite its roots: an atmospheric, moody track cut from Dwight Yoakam’s Californian roots, even if I wouldn’t label it an outright Bakersfield sound. It’s a rambling from an isolated wanderer that could easily lose itself to bravado, and yet his tone is mostly withered. Heck, knowing Yoakam, it’s the sort of tale of the lonely drifter that you can imagine him singing while walking through the desert at night, capturing mood and essence in a way through the atmospheric guitar tones and mournful “Oh I’s” that’s always reminded me of Gary Allan’s “Smoke Rings in the Dark” in terms of sheer scope and power.

Beyond that, I’ve never known quite how to capture its magic – it’s the sort of song that awakens something primal within that bypasses any critical faculties I’ve gained over the years. Couple that with some of Yoakam’s most cutting imagery like “in the mirror there’s a vision of what used to be a man,” and you have not only his most convincing display of pain, but easily my favorite song of his. It’s not a song – it’s an experience.

---

As always, before unveiling my No. 1 pick, here are a few honorable mentions that just barely missed the cut for this list, presented in no particular order:

John Anderson, “Let Go of the Stone” (written by Max D. Barnes and Max T. Barnes)

We’ll definitely explore John Anderson’s hits in further depth next time, but this tender cut urging a partner to let go of a dark past is an underrated bright spot in his discography.

Mary Chapin Carpenter, “The Hard Way” (written by Mary Chapin Carpenter)

Another fiery country-rocker from her with a lot of hardbitten truth attached; always welcome.

Suzy Bogguss, “Drive South” (written by John Hiatt)

The highest-charting single from an underrated talent who deserved better.

Pam Tillis, “Cleopatra, Queen of Denial” (written by Pam Tillis, Bob DiPiero, and Jan Buckingham)

Goofy and corny, but in a good ol’ ‘90s country way.

Alan Jackson, “Chattahoochee” (written by Alan Jackson and Jim McBride)

See above.

Robert Ellis Orrall, “Boom! It Was Over” (written by Robert Ellis Orrall and Bill Lloyd)

Uh … see above again.

Joe Diffie, “Prop Me Up Beside the Jukebox (If I Die)” (written by Howard Perdew, Rick Blaylock, and Kerry Kurt Phillips)

I’d say “see above” again, but revisiting this now feels a bit eerie – but I’ll gladly play a Diffie song anywhere, anytime.

---

And now, my No. 1 pick:

No. 1 – Trisha Yearwood, “The Song Remembers When” (written by Hugh Prestwood)

A song about a song, and aside from an album cut of hers – “Dreaming Fields” – it’s my favorite Trisha Yearwood song. It seems odd to revisit it now, given that its theme has made recent comebacks over the years to … well, mostly middling degrees. So, in revisiting a song that shows how it’s done properly, we have something that uses memories in a painful way to revisit a past relationship. But it also indulges the memory, because sometimes remembering the good parts helps it rise to a bittersweet reflection that offers some degree of comfort from time to time.

And as a testament to her interpretation, Yearwood keeps it all remarkably balanced, as she moves from the pure shock of how many memories this one song she’d forgotten conjures to letting said memories absolutely crush her. It’s dangerous to assume a song is relatable for everyone, but considering the two subjects in question here are painful memories and a connection to a certain song, it’s safe to say every music fan understands this song’s sentiment – certainly the realistic stopping power a song can carry in various ways, at least. It’s a sparse piano ballad accented only by hints of acoustics, reverb, strings and pedal steel, and yet for as much room as Yearwood has to exercise her voice, she effectively tests her emotive range more than her pure power. How fitting that even this song can have the same type of power it describes and captures – an easy candidate for my favorite single of this year.

---

Next: Favorite Hit Country Songs of 1992