Favorite Hit Country Songs of 2000

Previous: Favorite Hit Country Songs of 2001

And so, we’ve arrived at the end of our 2000s run with this series, by exploring where it all began for a decade filled with change … both of the good and bad varieties. We’ve explored both through this series, and before we take one last comprehensive look at the decade as a whole, let’s take a look at its first year …

… and wow, we’re not exactly ending with a bang here, are we? This is one of those years that had some really easy top contenders for me, but because of an excessive reliance on sleepy balladry and syrupy sentiments that characterized both the early half of this decade and the latter half of the ‘90s (meaning we’re not done wading through this. Joy), this is one of those years where I seriously struggled to fill out a top ten (the opposite problem of 2001, then).

All in all, though, I’m still happy with how it turned out, and there is some great stuff to discuss ahead. So, as always, As always, these lists are compiled according to what peaked within the top 20 during a given year on Billboard’s country charts. I invite you to share your own picks below! Let’s get started.


No. 10 – Brad Paisley, “Me Neither” (written by Brad Paisley, Chris DuBois, and Frank Rogers)

“Me Neither” was sort of perfect for this point in Brad Paisley’s career. Then, he was just was the shy, quirky newcomer who subtly imbued genuinely great humor into his material that helped him stand out. And that’s what makes “Me Neither” quiet standout in his discography among many, a twangy, shuffling tune that finds an awkwardly shy Paisley trip over himself trying to impress a woman to hilarious degrees, all of which Paisley slyly underplays. And that fake ending is just brilliant, and a fantastic instrumental showcase. It’s still not quite among my top favorites of his from this decade, but you don’t think there’s anything wrong with having him on this list one last time for the decade, do you? Yeah, me neither.

No. 9 – Chely Wright, “It Was” (written by Gary Burr and Mark Wright)

It’s a damn shame that “She Went Out For Cigarettes” can’t qualify for this list, because while most of the world remembers Chely Wright as a one-hit wonder from “Single White Female,” she was so much more than that. I guess I’ll settle for discussing her other minor hit, a simple, straightfoward song that I nevertheless find alluring. Maybe it’s because it’s wrapped in a minor melancholic tone off the underplayed mandolin and great little pedal steel licks despite sporting a happy ending, making it feel a bit more hard-fought and lived-in to get to that point of true happiness. I’m not sure, but in a year where similar lovestruck sentiments felt cloying and plastic, this just managed to capture the pure, exhaustive joy of finally finding the right one well.

No. 8 – Trisha Yearwood, “Real Live Woman” (written by Bobbie Cryner)

The common story associated with this song is that it was originally a demo tape placed in Trisha Yearwood’s mailbox by songwriter Bobbie Cryner, and I’m thankful the stars aligned on that one, because this is another hit I’m glad to have from this particular year – a picture of a real, everyday woman who’s happy with herself and doesn’t need to build a fantasy to find true happiness, even if it isn’t glamorous. And that’s a good way to describe the actual music, too, where only Yearwood could let an anthem on body positivity soar through subtlety, with little more than a quaint, soulful arrangement guiding her along the way. It’s refreshingly direct and in control of itself in a way so few songs from this year were.

No. 7 – Vince Gill, “Feels Like Love” (written by Vince Gill)

This is one of those songs that snuck up on me in preparation for this list – a relentlessly joyful ode to falling in love that Vince Gill sells with his usual exuberance and a really great instrumental flourish with that fiddle supporting the uptick in drive on the hook. In a way, it reminds me of Josh Turner’s “Would You Go With Me,” putting a modern spin on a refreshingly organic arrangement and lost in an air all its own. It’s just such a charmingly likable melody as joyful as the sentiment itself, and that’s enough to work for me.

No. 6 – Phil Vassar, “Carlene” (written by Charlie Black, Rory Bourke, and Phil Vassar)

You know, between this and “Rose Bouquet,” I’m starting to think I may have underrated Phil Vassar, because his best material showcased a strong sense of melody (especially in the piano lines) and true songwriting chops. And debut single “Carlene” really set him on the right track. The interplay of the fiddle and piano creates an undeniably jubilant mood and fun, memorable chorus, and there’s a more interesting story here than what initially meets the eye. Both characters left their town to see the world only to chase their own paths that probably disappointed their families who thought they were destined for more. It’s a lighthearted story of two wayward souls coming back together, where the characters have a surprising amount of personality and will be both alright in the end. Lookin’ good, indeed.

No. 5 – The Chicks, “Cowboy Take Me Away” (written by Marcus Hummon and Martie Maguire)

It’s the Chicks at their surprisingly most tender, and with a sweet, straightforward country bedrock and that huge hook capturing the urgency of wanting so desperately to love someone and deciding to just go ahead and take the plunge, it works just as well as their seedier, more playful material … which, trust me, is still to come. Simple yet enchanting in what it captures, it’s the surprising standout in their discography, and yet one that still sounds so good to me.

No. 4 – Lee Ann Womack, “I Hope You Dance” (feat. Sons of the Desert) (written by Mark D. Sanders and Tia Sillers)

Out of all the schmaltzy inspirational ballads that invaded country radio around this time period, this is the one I unabashedly love. Maybe it’s because it doesn’t feel like a cheesy, platitude-filled ballad. Tone has always mattered to me, and between the swell of darker strings and Womack’s serious delivery that works for a mother hopeful yet scared for her child’s path on the journey of life, it’s a song that can acknowledge and work with deeper stakes. It’s “I Hope You Dance,” not “You Will Definitely Dance,” after all. It’s a song that remembers to emphasize humility and empathy and encourages the confidence needed to chase after a dream, and it’s that one sticks with me even today.

No. 3 – Eric Heatherly, “Flowers on the Wall” (written by Lew DeWitt)

OK, I’ll admit it: I prefer this to the original. What it loses in not having the Statler Brothers’ terrific harmonies, it gains by capturing the moody, idiosyncratic angst that’s arguably way more fitting in tone for this song anyway. Granted, it’s a bit odd that this was Eric Heatherly’s debut single and only hit, as while we didn’t really get to know him as an artist, by turning this into a dark, uncomfortable rockabilly shuffle, I’d argue he left his mark anyway. Indeed, with that lingering drum beat and moodier bassline giving the song a much more ominous, meatier presence, it plays to the pure paranoia of the content so well, and Heatherly leans into the role effectively. Again, odd … but that’s all part of the appeal.

No. 2 – The Chicks, “Goodbye Earl” (written by Dennis Linde)

I’ve never really known what to make of this song. It’s a murder ballad, but it’s not aiming for the same raw, visceral undertones of country music’s most notable examples. And I don’t really want to call it a lighthearted tale of dark humor when domestic abuse is nothing to laugh at … but I don’t know, between Dennis Linde finally killing off his infamous “Earl” character and the Chicks having their mischievous fun raising hell for someone who definitely deserves it, I’m going to have to call it a riot. And considering there’s that line about the titular character violating his restraining order and putting his ex-wife in the hospital – forcing two women to take action to make up for a failed system – I’d say it’s just really the perfect storm of sorts. Man, Earl did have to die.


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:

Terri Clark, “A Little Gasoline” (written by Dean Miller and Tammy Rogers)

Ah, the perfect remedy to this year – a strikingly road-weary song about … well, hitting the road and finding a temporary escape from a bad breakup, bolstered by a solid neotraditional flair and Terri Clark’s more direct tone.

John Michael Montgomery, “The Little Girl” (feat. Alison Krauss and Dan Tyminski) (written by Harley Allen)

I’ve seen a surprising amount of hate for this one over the years, and while I can agree it’s hamfisted at points and probably goes overboard in its attempt as a tearjerker … I don’t know, maybe it’s because John Michael Montgomery has always been an underrated emotional interpreter, but I still respect it.

Travis Tritt, “Best of Intentions” (written by Travis Tritt)

It’s Travis Tritt in emotionally stirring ballad mode. That’s rarely not a winner.


And now, my No. 1 pick:

No. 1 – Gary Allan, “Smoke Rings in the Dark” (written by Rivers Rutherford and Houston Robert)

Man, just … that tone. Country music changed in 2000 and so did Gary Allan, albeit in much different respects. His late ‘90s material was always enjoyable, and I think hit singles like “Her Man” and “It Would Be You” capture his ethos more than they’re given credit for in hindsight. But he could never rise above being another indistinguishable hat act during this time period, until “Smoke Rings In The Dark” came along. There isn’t much I don’t love about this song: the sweeping, dreary atmosphere; the liquid strums of guitar and lingering pedal steel lingering faintly to great degree; or Allan’s tired resignation that things are over between him and his significant other, with the relationship simply running its natural course but leaving that sinking feeling that the scars run much deeper. It’s a dark wonder of a track, and one where Allan unearthed his potential to craft songs painting him as the wandering loner – not an aimless drifter, but rather someone who needs to follow his own path. And considering this was just the first song among many to showcase him doing just that … well, it may not be the most important country song from a general standpoint from this year, but it was an important next step for Allan – and it’s easily my favorite one of his because of that.


Next: Favorite Hit Country Songs of the 2000s

4 thoughts on “Favorite Hit Country Songs of 2000

  1. As one of Faith Hill’s remaining stans, I’d have to at least include one of her singles from this year – if not on the list then as an honorable mention. Breathe was the #1 BB Hot 100 song for the whole year, though was released as a single in 1999. If My Heart Had Wings is one of her all time best, but wasn’t sent to radio until January 2001. Maybe they don’t meet the criteria – ha! She definitely dominated this year though.

    Liked by 1 person

    1. I’m just pulling from what peaked within the top 20 for any given specific year and getting my information from Wikipedia, so it seems that “Breathe” will be eligible for 1999’s list when I get to that! And not to worry, I quite like that one, so I think it’ll make my top 10. ☺

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  2. I like a lot of these songs but I just wanted to comment to thank you for introducing me to the Eric Heatherly version of “Flowers On The Wall” – I love the original and this is a more creepy (in the good sense) version in so many ways, it’s wonderful and I added it to my Youtube playlist. Even if in both versions I keep mishearing “playing Solitaire ’til dawn” as “playing Solitaire alone” (my defence is it would make sense within the song context). I also love “Goodbye Earl”, “I Hope You Dance” and “Me Neither” but I knew them before the articl.

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