Favorite Hit Country Songs of 1999

Previous: Favorite Hit Country Songs of the 2000s

Ah, and so it begins: the oft-beloved time period critics, fans, and historians have dubbed – quite simply – “’90s country.”

And you know, despite sounding sonically similar to the slicker early years of the decade that would succeed it, it does feel like we’re entering another time and world. Many names familiar to this decade seemed to have their last hurrah during this particular year – as if the industry decided that a turn of the millennium signaled a needed changing of the guard – and many names that would define the next decade were still in their artistic infancy period here.

I’ll admit, too, that upon an initial quick glance through this year’s hit contenders, I was pretty underwhelmed. The classics didn’t jump out at me as much as I had hoped, and certain selections here reminded me of the era’s worst tendencies: way too slick production and overly sentimental lyrical tropes aimed at Hallmark cards everywhere, not unlike 2000.

But that difference I mentioned earlier between this year and the next? It came through when I actually stopped to revisit these selections, where a lot of underrated singles came to remind me just how great they really were and how versatile they could be; I think “forgotten classics” is the theme for this year. And I’ll admit that, compared to an era we just explored that I grew up with and felt comfortable exploring, the ‘90s will carry some unexpected surprises for me I’m just hearing for the first time – including this year. I think, then, that what I’m looking forward to most with this new decade isn’t exploring the time-honored classics we all know by heart, but rather the new discoveries to be made and savored.

With that long introduction out of the way, then, if you need a refresher for this particular 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 invited you to share yours, as well. If you’re curious as to what qualifies for this list, here’s a handy guide. Also, be sure to follow along with this ’90s country-centered playlist, to be updated frequently as we explore every year! Anyway, onward!

No. 10 – Terri Clark, “Everytime I Cry” (written by Bob Regan and Karen Staley)

Man, Terri Clark just never got enough credit – especially outside of Canada. I’m almost tempted to call this a great little slow-burn, what with the burnished warmth and potency shining through in a lot of the neotraditional tones that always provided the backbone for her work. But this isn’t so much a burn as it is an explosion – maybe an implosion. Hence why I think the real star of the show is Clark herself, whose character is caught in a viscous circle of a toxic on-again, off-again relationship that’s very one-sided in terms of who’s benefiting from it … and yet, she returns time and time again, hoping for something different from someone bound to never change. With that said, I like that it ends on a self-aware, optimistic note that hints she’s finally saw her partner for who they are, hopefully breaking a familiar country song trope once and for all, if only for herself.

No. 9 – Brad Paisley, “Who Needs Pictures” (written by Brad Paisley, Chris DuBois, and Frank Rogers)

Those who grew tired of seeing Brad Paisley mostly dominate my 2000s lists can rest safe knowing this is the only time we’ll hear from him this decade. And of course he’s here again, because I think this is one of his mostly solidly underrated cuts, and one that can still fit squarely among his best. Sure, the overall references to getting film developed and other old-school camera mechanics sound somewhat strange now, but that overall sentiment of not needing a picture to capture a memory so eloquently in one’s mind? Hell, that couldn’t be more timely. And leave it to a great interpreter like Paisley to simultaneously capture the pain of knowing those snapshots capture what never will be again, and the joy of running down a bittersweet memory lane, where at least for him, those memories still mean something. It’s the hit that started it all, and I’m going to miss hearing from him for this feature.

No. 8 – Sammy Kershaw and Lorrie Morgan, “Maybe Not Tonight” (written by Keith Stegall and Dan Hill)

This is one of those new discoveries that genuinely snuck up on me in a great way, a big ol’ emotional ballad that finds Sammy Kershaw and Lorrie Morgan playing the part of a couple that’s felt the years creep up on them for far too long. And the fact that it’s a duet means that only we, the listeners, understand how desperately they want to rekindle those old flames and that the only emotion they pick up from the other side is, at best, general apathy. Genuinely heartbreaking, especially when the end is near for a relationship that’s actually nowhere near dead and gone. And while the smoother polish is a natural fit for Morgan’s work, it’s genuinely interesting to hear Kershaw slide into near-crooner territory. It wasn’t a huge hit, but I’m comfortable calling it a forgotten gem nowadays.

No. 7 – Martina McBride, “Whatever You Say” (written by Ed Hill and Tony Martin)

On the flip side to the previous entry, this is one of those songs I knew but didn’t really appreciate until I revisited it for this list. I’ve always felt Martina McBride sounds best as a performer when there’s genuine (or just any) dramatic stakes and urgency to her work, and this is handily one of my favorite examples. I could even draw further comparisons to both the previous entry and “Everytime I Cry” for what I love about it – a portrayal of another spent relationship that, much like the latter cut, is very one-sided and dismissive … until that frustration boils over and signals the long overdue turning of a page, anchored not only in some great burnished tones – especially those fiddle and mandolin flourishes after the hook – but in McBride’s powerful range. It’s just another great song I overlooked; I’m glad I rectified that.

No. 6 – Faith Hill, “Breathe” (written by Stephanie Bentley and Holly Lamar)

Here’s the one undeniable classic here I can’t say is overlooked or underrated, and is only vilified depending on how far your definition of country or even pop-country of the era stretches. Not for me, though – this is one of the first songs I remember hearing in general, and I always remember being transfixed by the huge emotional stakes of it all. After all, it’s a sensual-as-hell love song (that I honestly find more raw and emotional than any of her actual duets with husband Tim McGraw), straightforward in the actual text of finding the true joys of love itself, but so much more in Hill’s actual performance; charisma can be the key (and often overlooked) ingredient in magic like this. Let’s be honest – this joined a growing rank of big pop-country ballads of the time that were crossover-ready, and I’d go to bat for, like, 90% of them (sorry Lonestar, “Amazed” doesn’t do much for me). But in avoiding any schmaltz and actually embedding a lot of underrated warmth in the production – particularly in the organ and acoustics – this became a classic all its own, and for good reason.

No. 5 – Joe Diffie, “A Night to Remember” (written by Max T. Barnes and T.W. Hale)

… I’m running out of new things to say about big emotional ballads. And some folks may be surprised to see Joe Diffie’s name attached to one, given the general direction of his other big, amped-up hit singles (that we’ll inevitably get to in other years, I’m sure). No one should be – after all, he could knock these types of songs out of the park just as well as, if not better than, anyone. And this is just so note-perfect in every regard, from production with a surprising amount of direct punch to it as Diffie feels the flood of emotions from an old flame conquer him, to writing that centers that night to remember as just … a personal endeavor to heal, no matter how foolish it may seem to anyone else. I go back and forth between this and “Home” as my favorite of his, but either way, it’s worth remembering – and savoring.

No. 4 – Shania Twain, “That Don’t Impress Me Much” (written by Shania Twain and Robert John “Mutt” Lange)

Look, with her it almost always boils down to a fantastic melodic hook and groove, and … yeah, enough said here, really. But as we’ll inevitably see in other entries for other lists during this decade, Twain is always in full control of her characters and more than happy to play coy with everyone else, including an arrogant jerk here who thinks he deserves the world. And while Twain herself has her share of tracks asserting her own dominance, there’s a fine line between confident and delusional, and she has no problem properly defining that line, even if it means throwing a shot toward Brad Pitt. Oh well; I’m impressed, at least.

No. 3 – Randy Travis, “Spirit of a Boy, Wisdom of a Man” (written by Trey Bruce and Glen Burtnik)

Man, I’m so looking forward to spotlighting Randy Travis’ excellent and underrated ‘90s run. And I think friend and colleague Kevin Coyne said it best in his review of this song, when he noted how not only does the latter half of this decade tend to be forgotten in the larger conversation these days, but that an artist could still release a morally ambiguous tale like this and find success with it. This is a Mark Collie cover, and whereas he sounds more suited to play the role of the boy here (not a diss – just a different perspective that this song values, mind you), Travis’ more mature delivery lends itself better to the harder choices that need to be made here. And that weight is anchored not just in the production that rightfully emphasizes a warm restraint and minor swell in the tempered acoustics and piano work, but also in the situation present – the choice for a boy to either provide for a newfound family, or run away from it all. And while it’s implied he makes the right decision and stands by his pregnant partner’s side, it is ambiguous to let the weight of that decision linger. A powerful song that would pave the way for similarly complex material like “Three Wooden Crosses,” and if that doesn’t say it all, I don’t know what does.

No. 2 – Faith Hill, “The Secret of Life” (written by Gretchen Peters)

“Breathe” was damn near inescapable when it was released (in a good way), but this quaint, coffeehouse-ready track is my favorite Faith Hill song from this year. And I don’t use those descriptors as pejoratives, either – the fact that it plays out like a natural conversation amongst friends in a natural, everyday setting and carries so much natural warmth in its tones is exactly emblematic of what I love about it. And if you know me, you’ll also see that having Gretchen Peters’ observational, introspective writing is a major advantage in its favor, keeping the questions asked about the titular topic at hand feel grounded as a natural conversation. And it’s one where the end conclusion is how the secret of life is shaped by everyone’s different perspectives of the little things that keep them going everyday – many of which we share and have in common, and some of which are more personal to us in providing inspiration. It’s also another example of me appreciating a song even more through this feature, in this case the actual hit version, if only because Hill’s natural charisma as a performer also does the underrated heavy lifting for adding so much grace to this.

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:

Lee Ann Womack, “I’ll Think of a Reason Later” (written by Tony Martin and Tim Nichols)

I can’t think of a good blurb for this humorous little cut; maybe I’ll think of one later.

Alan Jackson, “Gone Crazy” (written by Alan Jackson)

It’s classic heartbreak territory for him, which is always a good place to be … for us, at least.

Reba McEntire, “One Honest Heart” (written by David Malloy, Gary Baker, and Frank J. Myers)

Looking for love in all the wrong places, just done by Reba, which is a plus. Also, I can’t unhear how similar the opening to this sounds like Brothers Osborne’s “Stay a Little Longer.”

Shania Twain, “Man! I Feel Like a Woman” (written by Shania Twain and Robert John “Mutt” Lange)

Again, fantastic melodic hook and groove. She perfected this formula so well in her prime.

Tim McGraw, “Something Like That” (written by Rick Ferrell and Keith Follesé)

Another ‘90s classic that I like, just not enough for the top 10. Sorry?

Jo Dee Messina, “Lesson in Leavin’” (written by Randy Goodrum and Brent Maher)

Lesson learned.

George Strait, “Meanwhile” (written by Wayland Holyfield and J. Fred Knobloch)

Capturing the great, lost art of the key change.

And lastly, a category of songs I love for how infectious and catchy they are, all made by bands, weirdly enough: “Unbelievable” by Diamond Rio (Al Anderson, Jeffrey Steele) / “Hillbilly Shoes” by Montgomery Gentry (Bobby Taylor, Mike Geiger, Woody Mullis) / and “All Things Considered” by Yankee Grey (Tim Hunt)

And now, my No. 1 pick:

No. 1 – Alan Jackson, “Little Man” (written by Alan Jackson)

It feels right finally having an Alan Jackson top one of these lists – spoiler alert: Judging by the other years from this decade, it likely won’t be the only time – but it feels weird to have this song be the first one, if only for how complex and twofold its meaning can be beyond the text itself. After all, this is Jackson in rare form – angry form. Angry not only at how gentrification swept away a sense of identity and community from all across America, but also how it’s a system that, ultimately, provides an easier travel and monetary accessibility to, well, everyone.

So it’s not so much a critique as it is a lament for what was sacrificed to get there, including the hard work and dreams of people from all walks of life. It’s the sort of song one could deem as uncomfortable, where even though it’s celebratory of small town personality, still holds a more complex meaning in a genre that has a strange love affair with its Walmart parking lots. And if I wanted to read way too deep into this song, I could also point to this being the year where Jackson famously honored George Jones by breaking into “Choices” during the CMA Awards, sticking up for “little men” like him with a Merle Haggard-esque social critique that showed how much the genre didn’t care about the legends by this point in time. A bit of a stretch to me, but I can see and respect it. At any rate, as always, Jackson, being the descriptive writer he is, makes a case through this sad song, and it’s one of my favorites of his.

Next: Favorite Hit Country Songs of 1998

3 thoughts on “Favorite Hit Country Songs of 1999

  1. That’s when country discovered MTV videos and learned to make everything pretty and slick. Now they’re trying to make red dirt covered pickups and six packs of beer pretty and slick.


  2. Excited to get to the 90s for this feature! Like you, I didn’t think that 1999 was as good as it was at first glance, but there are some great songs here. I’ve included some Canadian artists here since I was still actively listening to country radio at the time and I fondly remember some of these songs. Similar to the US hits, the Canadian hits get better as we move backwards through the 90s and I’m looking forward to highlighting more of these songs/artists as this feature continues.

    I couldn’t narrow it down to a Top 10, so here is my Top 15:

    15. Single White Female – Chely Wright
    14. Better Off Broken – Lisa Brokop – one of my favourite Canadian country artists who didn’t get much exposure in the US
    13. Powerful Thing – Trisha Yearwood
    12. Bit By Bit – John Landry
    11. Pop A Top – Alan Jackson – I love this covers album!
    10. Whatever You Say – Martina McBride – I agree that this is one of her better “powerhouse” songs
    9. Write This Down – George Strait
    8. Everytime I Cry – Terri Clark – I think we’ll see a lot of Terri Clark on my 90s lists – her singles were great and her albums were really solid as a whole
    7. How Forever Feels – Kenny Chesney – I’m not a big Kenny Chesney fan, but this has always been one of my favourite songs of his – I love the fiddle in this one
    6. Tonight The Heartache’s On Me – The Chicks – I recently obtained a copy of this CD and we listened to it many times this summer on vacation. I’ve always loved this song and it was great to listen to the album again
    5. No Place That Far – Sara Evans – this album was my first introduction to Sara Evans and it’s still my favourite of hers – great song and great album
    4. Crazy Little Thing Called Love – Dwight Yoakam – I’ve always appreciated Dwight Yoakam’s ability to make cover songs his own and this one is no exception
    3. Wrong Night – Reba McEntire – this is a little bit of a different style for Reba, especially during this era, but I love it!
    2. Little Man – Alan Jackson – I can’t add much to your great write-up for this song – one of his best!
    1. I’ll Think of a Reason Later – Lee Ann Womack – again, this is one of my favourite songs of hers. She has a great discography, but her first two albums are her best, in my opinion

    Liked by 1 person

    1. Me too! This will probably be my favorite decade we explore, although the ’80s and ’70s will certainly be excellent, too. Love all of your picks as well! I think the cool thing about this particular year is that there’s a lot of variety in terms of sound and style without it feeling too “out there” for certain acts in question (your Reba pick is a great example). You can definitely tell things were uncertain heading into the next millennium as far as what the next dominant “sound” in country music would be, but at least here it’s mostly a good thing!


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