Favorite Hit Country Songs of 1998

Editor’s note: This will likely be our last examination for this series and my final list-driven piece of content for the year (meaning Neko Case is our final featured artist of the year for Fifteen Favorites as well). With December and year-end list-season on the (somewhat) near horizon, I’d like to distance myself from this sort of content in order to start focusing on those and revisiting favorites of the year. Our deep-dives of this nature will, of course, resume next year, but for the remainder of the year I’d like to focus more heavily on reviews and other long-form content (like the Unbroken Circle). Thank you for your understanding, and for reading! – Zack

Previous: Favorite Hit Country Songs of 1999

We’ve entered the second decade of the golden age … although I’d be remiss not to mention that we’re still caught in a very time period in country music history. At least running through this particular year, I found that sentimental, cloying ballads were the popular flavor of the day, and the everlasting divide between country and pop surely remained an interesting talking point, albeit one that can be dissected through, well, almost any year. But I think the bigger divide – which we’ve already discussed in other features of this series – is a changing of the guard in what would follow through country music’s next decade; hell, millennium. This was the year Johnny Cash won a Grammy award for Unchained, for instance, but you definitely won’t find him listed among country music’s radio hit-makers of the year.

But you know, I said it for the 1999 list and I’ll say it again – as far as the cream of the crop is concerned, this is a better time period than many may remember. And it’s also the first year where I think a lot of those instantly recognizable staples of the decade start to surface. Whether they’ve clicked with me enough to be featured here is another story altogether, so let’s dive into the time machine. As a refresher, 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 list, here’s a handy guide. Let’s get started.

No. 10 – Alan Jackson, “Between the Devil and Me” (written by Harley Allen and Carson Chamberlain)

I noted last time how “Little Man” was something of a departure for Alan Jackson lyrically, and funny enough, we’re back in similar territory with “Between the Devil and Me.” It’s built all around that huge hook with a much fuller production than what one would expect from Jackson, and indeed, though I’ve always loved him as an interpreter, it’s strange hearing a song built squarely around his range. But when the dramatic stakes of tried-and-true heartbreak still manage to shine through crystal clear, it winds up being one of his darkest-sounding moments on record, in turn supporting the delirious nature of the content itself extremely well. And whatever temptation awaits his character’s descent, he may not be able to escape, but he can surely go down swinging.

No. 9 – Wynonna, “Come Some Rainy Day” (written by Billy Kirsch and Bat McGrath)

Yes, Wynonna did have two minor comeback hits toward the end of the decade, and yes, this one in particular is a big ol’ emotional ballad that’s very indicative of the era in general. And yes, it’s meant to tug on the heartstrings, all through broadly sketched pictures of faded memories and the sentimentality attached to them … so OK, why, then, did this manage to punch me in the gut regardless? For one, I’m a sucker for songs about personal nostalgia, especially when it’s Wynonna herself doing the heavy lifting for this particular track, a song she didn’t write but sings as if she did. For as powerful of a presence as she is, though, it’s an exercise in restraint and a test of emotional interpretation she masters here, able to point to the bittersweet feeling at the core of this song – that though we can never go back to relive fond moments again, we can lock them away in our memories and unearth them when needed, rainy day or otherwise.

No. 8 – Patty Loveless, “To Have You Back Again” (written by Annie Roboff and Arnie Roman)

We’ve seen Patty Loveless’ name a time or two before through this feature, but this is the first year where we’ll really start diving into her best material more consistently (as far as just her singles are concerned, that is). But for as many great kiss-offs as she has in her discography, this song finds her on the opposite end as the one who inflicted the hurt, and she’s still a character worth rooting for regardless. Like with “Come Some Rainy Day,” it’s the artist behind the song who does the real heavy lifting here. Not only does Loveless get to wail on the chorus, but she does so with a lot of genuine urgency and regret over what she’s done, all with enough self-awareness to understand that she doesn’t deserve forgiveness. But she’s going to give it a try anyway, and at least for me, apology accepted.

No. 7 – Randy Travis, “Out Of My Bones” (written by Gary Burr, Robin Lerner, and Sharon Vaughn)

Kyle is right – this is a fantastic song. And while “Out of My Bones” isn’t quite up there for me as, say, “Spirit of a Boy…” or “Three Wooden Crosses,” any artist who’s set that high of a bar deserves some leniency. And that’s kind of the hidden strength of “Out Of My Bones” anyway. It’s low-key while still carrying a lot of expressive kick in its production – particularly that fiddle lick after the hook – Travis’ character is down but far from out, and it’s paradoxically sure and unsure of itself. Basically, it’s not trying to make a grandiose statement; its only goal is to find enough strength to take things one day at a time and always keep a best foot forward, even if it’s easier said than done at this point. But you know, if anything, this is a great first step for that.

No. 6 – Jo Dee Messina, “Bye-Bye” (written by Rory Bourke and Phil Vassar)

We won’t hear from Phil Vassar himself again for this feature, but his trademark melodic chops and rapid-fire lyrical flow are all over this song. And while Jo Dee Messina’s own run was much shorter than it should have been, her star burned bright with a handful of classics still remembered today – and for good reason. It’s yet another track where the vocalist is the main reason I love this, as while Messina isn’t quite the powerhouse presence as the artists we’ve explored before, she does have the charisma needed to sell this conversational kiss-off track – especially on a song that offers little breathing room for its singer, letting those barbs fly relentlessly and without mercy. Oh, and it’s just so infectious and exuberant and carries an excellent hook, to boot. It may be called “Bye-Bye,” but I always love catching up with this one every now and again.

No. 5 – Lee Ann Womack, “A Little Past Little Rock” (written by Jess Brown, Brett Jones, and Tony Lane)

Lee Ann Womack is just so good at mining heartache, and this song is one I frequently see cited as her best. For me, it’s up there, even just off the wistful regret captured in the tempered bass, wily harmonica and strings that always reminds me of the start of a new morning and a fresh start. A fitting description for another song about trying to outrun an old flame, especially one as oddly hopeful and soothing as this, if also slightly haunting. It’s not so much escapism as it is making a clean break to find some clarity, because sometimes that’s the first step to actually finding an escape.

No. 4 – Alan Jackson, “I’ll Go On Loving You” (written by Kieran Kane)

… You know, the older I get, the more I realize that maybe it’s the unconventional Alan Jackson cuts I gravitate toward more strongly. And I get why this has always been a polarizing cut in his discography: It plays to very dark tones with the sweeping minor chords, and it’s almost too detailed of a love song in its themes of commitment after many years past, only further highlighted by the spoken-word delivery. And no, for me this isn’t quite as striking as, say, Jackson’s own “Remember When” that he penned himself, but it is the cut-throat intimacy that I find so alluring about this, where he intentionally wants listeners to hang on to every word delivered in poetic fashion. Not to mention that it sounds absolutely gorgeous throughout, especially those strings. It might not be a cut of his I revisit often, but there is something beautiful about it always worth appreciating; I’ll go on loving it.

No. 3 – Tim McGraw, “Just to See You Smile” (written by Mark Nesler and Tony Martin)

This might be my favorite Tim McGraw song in general, but for many of the same reasons as why I praised his 2000s hits equally. After all, his underlying greatest strength has always been his knack for emotional interpretation, especially on a song like this that requires a tricky balance of regret for what never will be again and what was missed and happiness for what was and what will be gained … just not for McGraw’s character. No, he plays the role of someone who has to watch a former partner move on with their life and feign happiness during an unexpected run-in with her and a new partner. It’s mature, but it’s also got enough sly amusement to denote the pain felt (“I told you I was happy for you, and given the chance I’d lie again” is one of those all-time favorite lines for me). But he loves her, so he’s going to let go if it means her finding happiness she couldn’t with him. It’s a bittersweet song, and one I think captures that feeling well in the wistful yet rollicking mandolin and fiddle interplay, able to shift at a moment’s notice and sound sweeping regardless.

No. 2 – The Chicks, “Wide Open Spaces” (written by Susan Gibson)

Ah, that opening acoustic rollick that characterizes the start of quite a few great country songs and tales to tell, where one can tell we’re in for something comfortable, but also something adventurous as we actually charge ahead. And yeah, that’s exactly what “Wide Open Spaces” is all about, a song about striking out on one’s own carried by a huge, almost cathartic hook that was larger than life enough to become this group’s signature song, and a late-decade gem.

But it’s also the framing that matters here, a song built specifically for all young women looking to grow up and conquer their own frontiers – perhaps too fast, but this song’s optimistic focus keeps the dream what’s to come alive and well at the forefront. And what a fitting breakthrough for this particular group, right? We know what eventually happened, but as we’ve already explored through this feature, this group blazed their own trail and conquered just about every space there was to take – spaces that were theirs anyway. It’s the last time we’ll hear from them for this feature, and I can’t think of a better way to go out.

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:

Martina McBride, “A Broken Wing” (written by Phil Barnhart, Sam Hogin, and James House)

A broken wing, but she soars anyway.

Jo Dee Messina, “I’m Alright” (written by Phil Vassar)

The other Phil Vassar-penned hit of hers delivered with rapid-fire that’s also excellent.

Toby Keith, “Dream Walkin’” (written by Toby Keith and Chuck Cannon)

Ah, ‘90s Toby Keith really is great. And if this is all just a dream, at least it’s a sweet one.

Gary Allan, “It Would Be You” (written by Dana Hunt Black and Kent Robbins)

Straightforward bitterness – it’s an early prototype of Gary Allan’s established style he’d master in the 2000s, but this is still an underrated gem worth recognizing.

Brooks & Dunn, “How Long Gone” (written by Shawn Camp and John Scott Sherrill)

Catchy ear-candy that you typically expect from this duo, and I’m not complaining about that.

The Chicks, “I Can Love You Better” (written by Pamela Brown Hayes and Kostas)

I don’t normally like these types of songs, but the Chicks are just so playful here that I can go along with it anyway.

Kenny Chesney, “That’s Why I’m Here” (written by Mark Alan Springer and Shaye Smith)

It’s not the type of song one would normally associate with Kenny Chesney, but this reflection of alcoholism and treatment for it is just really delivered with grace – and in a genre that could use some more sobering truths like this.

And more honorable mentions, featured through our ongoing ‘90s country playlist!

And now, my No. 1 pick:

No. 1 – Mindy McCready, “You’ll Never Know” (written by Kim Richey and Angelo Petraglia)

I … did not expect to love this as much as I did. I mean, I was familiar with songwriter Kim Richey’s version off of her debut album (which, for the record, is a hidden gem of a project you should all seek out immediately). But prior to hearing Mindy McCready’s own version that was actually her last hit in general, albeit a minor one, I thought for sure it’d be a close race between “Just to See You Smile” and “Wide Open Spaces.”

But in what has become a theme for this year, it’s McCready herself who really pushed this over the edge for me, a post-breakup track where she has to put on a brave face and pretend to be the life of the party, even if it’s the furthest thing from what she’s actually feeling. And she delivers the complicated, messy feelings so, so excellently, spitting some not-so-subtle venom toward a former partner through gritted teeth, all because of her frustrations of what could have been that will never be realized. And you get the feeling that by the end of this encounter she may not be able to hold it all together, but damn if she isn’t going to try regardless, through a huge pop-country hook and all. It’s something of a hidden gem from an artist who really did deserve better, but as far as swan songs go, I can’t think of many better.

Next: Favorite Hit Country Songs of 1997

7 thoughts on “Favorite Hit Country Songs of 1998

  1. Wow i’m surprised that Mindy was #1 but I love it. Random story. Sometimes I like to take a deep dive on artists I’m not familiar with and listen to all their albums and randomly fell on Mindy McCready. I thought her debut album was her best but really fought with the hits from her debut album and “You’ll Never Know” as her best song. I was familiar with “You’ll Never Know” due to songwriter’s version but Mindy’s recording and especially her Music video always captivated me. If you haven’t taken the time listen to last album “I’m Still Here” for the song “Wrong Again”. Tragic end to star that should’ve burned a little brighter. But man 98 was a great year looking at this list. I used to dismiss the lates 90’s country, but these songs are all great tunes.

    Liked by 1 person

    1. I do that too sometimes! It’s such a great feeling, and obsessing over a new favorite for days, weeks, or months on end really can’t be beat – heck, it’s why we love music in the first place I think! I have to admit I’m only familiar with her big hits, so I’ll be sure to check out her albums, especially the song you mentioned!

      I agree, too. I wasn’t sure how these first few years would shake out, but they’ve been solid. A quick glance of 1997’s list looks pretty solid too, so I guess we’ll see. Thanks for sharing your thoughts!


    2. I do that too! I was a big fan of Mindy McCready’s first two albums – they were really solid through and through and this song is a great example (even though it didn’t make my personal Top 10 of 1998 – see below).

      Liked by 1 person

  2. This is an interesting year in that I don’t think the biggest hits are on par with the biggest hits from 1999, but there is great depth here.

    I think you and I have similar tastes in 90s music, in general, so I was surprised to see very little overlap in our Top 10s, which also speaks to the depth of quality in this year (although, if I were to extend this to a Top 20, there would be more overlap).

    A couple of notes on some of the songs you’ve included that aren’t on my Top 10 (or honourable mention list).
    – “Just to See You Smile” is one of my favourite Tim McGraw songs (as is “Where the Green Grass Grows,” also from 1998). I do like a fair amount of his earlier music, but this era was probably his best.
    – I’m not a big Kenny Chesney fan, but “That’s Why I’m Here” is easily one of his best songs and one of my favourites of his.
    – I was surprised with your #1, but, as noted above, I was a Mindy McCready fan back in the day and this is a great song (and I suspect she’ll be making my list in some of the future versions of this feature).

    Here’s my list. First, honourable mentions:
    – “Out of My Bones” – Randy Travis
    – “Things Change” – Dwight Yoakam
    – “Diamond” – Julian Austin
    – “Dream Walkin'” – Toby Keith – yes, 90s Toby Keith was great
    – “High on Love” – Patty Loveless

    Top 10:
    10. “How Long Gone” – Brooks & Dunn – although they were past their peak by this point, this album was really good. I knew all of their previous hits, but this was the first B&D album I actually owned.
    9. “I Wanna Fall in Love” – Lila McCann – she is close to my younger brother’s age, so he bought her album when it came out and we listened to it a lot. This is a great pop-country song.
    8. “It Would Be You” – Gary Allan
    7. “Movin’ On” – The Rankins – check this out if you’re unfamiliar – great East Coast Canadian music!
    6. “Nothin’ New Under the Moon” – LeAnn Rimes – super catchy and this album is underrated.
    5. “Nothin’ But the Taillights” – Clint Black
    4. ” The Day That She Left Tulsa (In A Chevy)” – Wade Hayes – he had some really good songs, but this one might be my favourite.
    3. “A Little Past Little Rock” – Lee Ann Womack
    2. “Stepping Stone” – Lari White – I don’t know what it is about this song, but I’ve always loved it.
    1. “A Man Holdin’ On (To A Woman Letting Go”) – Ty Hearndon – I never got into much of his music, but I’ve always thought that this was a great song and a great performance.

    Liked by 1 person

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