The Best Hit Songs Of 1989

If I’m being honest, while this is one of my favorite features on this website, I’ve been slow at cranking out these “best hit songs” lists recently, I know. But for those who remember, this, as well as the next edition of this series when we look at 1982, are dedicated to requests from readers, with this one dedicated to ATM on Twitter.

And for those who know their country music history, 1989 was a huge year for the genre; the rise of new artists famously dubbed as “the class of ‘89” came in just as Keith Whitley tragically left us way too soon, so expect to see both him and that class represented in some fashion here. It was a transitional year for the genre that felt fitting as the turn of a new decade was upon us, but that doesn’t mean this was a weak year in the slightest. In fact, this is one of those years where I found it hard to whittle down my top ten selections (hence, too, why this list took so long to make), and, as always, a Spotify playlist of (what I consider to be) the best country music of 1989 can be found here.

As always, this feature is meant to count down the best hit songs of a particular year. This is also the only feature where Wikipedia is a handy source. Also, these are, of course, only my personal picks and preferences – I invite you to share yours down below!

On with the list, starting with a few honorable mentions, in no particular order:

  • Earl Thomas Conley – “What I’d Say” (‘80s production killed many songs this year, and that’s true of most of Earl Thomas Conley’s catalog, to be honest. This, however, was not an example of that, and it’s probably my favorite Conley song)
  • Garth Brooks – “If Tomorrow Never Comes” (In lesser hands, this could come across as campy, but chalk it up to Garth Brooks capturing a relatable sentiment with a warm charisma that makes it one of his strongest songs)
  • Randy Travis – “Deeper Than The Holler” (It’s a simple love song, but Randy Travis sells it with the kind of warm, timeless delivery that, objectively, stands as one of the best examples of what country music really is)
  • George Strait – “Baby’s Gotten Good At Goodbye” (Even one of George Strait’s lesser tunes is still an excellent listen)
  • Vern Gosdin – “I’m Still Crazy” (Vern Gosdin could make you weep like very few artists could, but this was a nice showcase of his dark side)
  • Wild Rose – “Breaking New Ground” (There’s a fiery passion to this that’s undeniably catchy and fun)

As mentioned before, further honorable mentions can be found in the Spotify playlist linked above.

No. 10 – Shenandoah, “The Church On Cumberland Road”

I originally had this as an honorable mention, but after a few more listens revisiting this, I couldn’t leave it off this list. “The Church On Cumberland Road” is undeniably overwrought in its execution, but it knows it and leans into it, and that’s part of the appeal. Whereas most songs speaking from the perspective of a musician come with a sense of yearning for home, this is just a fun song about someone trying to live that life and make it back in time for his own wedding, facing obstacles along the way that make the song all the more interestingly charming. It’s wildly creative, hence why it earns its spot here.

No. 9 – Hank Williams Jr. and Hank Williams Sr., “There’s A Tear In My Beer”

This is the kind of duet that never should have happened, yet country music is all the better because of it. Like a good chunk of Hank Williams Sr.’s catalog, there’s a jubilant melody at the forefront here with an undeniable hook, but it ultimately masks an underlying pain that shines through in both his and Hank Williams Jr.’s deliveries. Like Sr.’s best songs, this is a fundamentally simple song, enough to where it’s the common phrase people use when they describe why they don’t like those old “tear in my beer” songs, in defense of modern country music; yet all of the elements are there to make it stand up with some of his best.

No. 8 – Clint Black, “A Better Man”

And now, the first representation of the beloved “class of ‘89.” Clint Black came out swinging in 1989 in a way that even outshone his contemporary, Garth Brooks, commercially, and in a way he’d never be able to replicate. But that’s more of a testament to how strong his debut album was, spawning this song, one that tries to answer why a relationship ended and just can’t; sometimes it’s better not to focus on the wreckage or what might have been and look to the future instead, thinking about the present day, what we’ve learned from the past instead of how to fix it, and move on with the right foot forward. It’s not always an easy sentiment to swallow, but it’s a mature one that showed why Black was a compelling songwriter from the beginning.

No. 7 – The Judds, “Change Of Heart”

What I’ve noticed with the Judds as I’ve revisited them for this feature before is that they know how to craft a song. I don’t just mean the technical elements, but rather how to develop it as it goes along. “Change Of Heart” starts as a raw, intimate acoustic ballad before allowing those natural, soulful tones to crop up and compliment Wynonna Judd, with piano and pedal steel added for wonderful accent marks. Really, this song is just an exercise in showing how wonderful of a vocalist Judd is, which, to be fair, isn’t that different from other songs of theirs, but this is certainly one of the best examples of that.

No. 6 – Dwight Yoakam, “I Sang Dixie”

“I Sang Dixie” is a song that could derail its momentum if it wasn’t so properly crafted. Here, a southern man tries his luck in Los Angeles, for reasons unknown, and ends up homeless and dying in the arms of someone who understands him while others look on. It’s a song that could very well try to set up a city versus country debate, yet skirts around that by going down a route akin to, say, Porter Wagoner’s “Green, Green Grass of Home,” where this vagrant likely left home for promises of a better life out west and finds that’s not the case. The song never really dives into as many of its grittier details as it could, admittedly, but leave it to Dwight Yoakam to still flesh out the song with nuance and poise anyway.

No. 5 – Randy Travis, “Promises”

Perhaps it’s just because I easily grow tired of campy ‘80s production, but there’s always been something so refreshing about “Promises,” even when matched against Randy Travis’s own catalog. “Promises” is raw, and not even in the sort of way that develops much further as it moves along; it starts and ends as a lone acoustic ballad with only some synthetic-sounding backing vocals entering the mix later on, letting Travis’s voice sit upfront in the mix and letting the lyrics really take hold of the listener. The twist of the hook coming is fairly obvious given the tone of the song, with the narrator making promises to change for his lover, yet knows it’s all for naught as she moves on when he can’t keep those promises. It’s a song that’s never meant to cast Travis in any positive light, and his downbeat performance symbolizes that, yet it’s a crushing blow to both parties that stands as one of his finest moments on record.

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No. 4 – Garth Brooks, “Much Too Young, (To Feel This Damn Old)”

Even as someone who often defends Garth Brooks’s place in country music history, I can admit “Much Too Young” stands in stark contrast to the remainder of his discography; trading in Brooks’s usual, jubilant charisma for a song that finds him beaten and battered. It’s an odd choice for a debut single, yet it’s sold with all the conviction needed to capture a relatable sentiment for anyone at that time in their life that feels like they’re doing all they can, yet doesn’t know if it’s enough. For anyone who often finds themselves on the perpetual edge of exhaustion, this rings as a low-key anthem. Oh, and it gave a boost to Chris LeDoux’s own career, so what bad thing can one really say about this song?

No. 3 – Suzy Bogguss, “Cross My Broken Heart”

Suzy Bogguss isn’t really considered to be part of the “class of ‘89,” but “Cross My Broken Heart” was her breakthrough “hit,” with that word only in quotations because, really, this deserved so much better than a mere top 20 placement. From that opening brush of light acoustic guitar with the well-woven Spanish textures, Bogguss demonstrated her power as a vocalist, both in technical terms and her ability as an emotive interpreter. Whereas the narrator here should move on from a lost love, there’s too many painful reminders in her everyday life to keep her from taking that next step, and damn, is Bogguss ever convincing of that. Yet despite all of that, Bogguss admits she doesn’t want to move on, if only because she’ll always love her past significant other, and if nothing else, the pain is worth it if it means getting to still hold on to the good memories. There’s a sad tinge of optimism to this track, even if it sounds crushingly defeating.

No. 2 – Clint Black, “Killin’ Time”

“Killin’ Time” shouldn’t work as well as it does, and by that, I mean a song this downtrodden shouldn’t be as sharp and infectious as it is. But beyond that stellar hook, “Killin’ Time” is simply a classic country “drinking to forget” song that comes with a healthy dose of attitude; the narrator can admit that he shouldn’t engage in his soon-to-be reckless behavior, but he’s going to have one night anyway to forget his troubles, so don’t get in his way. Again, very few artists can boast a stronger run of debut singles that resonated as much as Black’s did, artistically or commercially.

No. 1 – Keith Whitley, “I’m No Stranger To The Rain”

It’d be easy to name this as the best hit song of 1989 based off of pure sympathy, but “I’m No Stranger To The Rain” cuts much, much deeper than that. It’s ironic that I had the chance to discuss Hank Williams Sr. earlier on this list, as Whitley, too, would end up releasing a final song in his lifetime that would ring as dark foreshadowing, in retrospect. Unlike Williams’s plea that he’ll “never get out of this world alive,” though, “I’m No Stranger To The Rain” is filled with perseverance and optimism, an ode to Whitley’s spirit, even if his demons won out. But even speaking to its power as a song, “I’m No Stranger To The Rain” evades any distinctive ‘80s tones for something that feels timeless; a light brush of warm, rollicking acoustic guitar leads into some piano and pedal steel to keep things sunny and optimistic, and the poetic undertone of the lyrical sentiment helps to really stamp this song’s place in country music history. Not a lot of country singers are strangers to the rain, nor would they willingly engage with their demons any more than once, but Whitley assures the listener he won’t let that get to him, a chilling sentiment in the years to come, but one that rang with potency, and showed why we lost a legend way too soon.