Favorite Hit Country Songs of the 2000s

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The end of a decade and the first big milestone of this feature. I know most people are likely excited for me to just get to the ‘90s and leave the 2000s behind, but this is the one retrospective list I’ll make for this feature that will feel special to me. I grew up with 2000s country – this is my decade. Not that it was all perfect, mind you. The genre felt mostly directionless during this decade and more transitional in setting up the next one above all else. But when it comes strictly to the music at hand, I liken it to the ‘80s – not as great or as grandiose as the decade that came before it, but underrated and better than one might remember it.

If anything, then, my goal as I compile each of my lists from this decade into one top 50 list is to convince someone out there of that. Also, don’t think that this will just be a simple list completely identical to those past lists. Thinking about what I actually wanted spotlighted in the top 50 caused me to reconsider certain placements and even some omissions in general, so there may be a few surprises. However, since this is just my list of personal favorites and personal bias is to be expected, I’ve limited slots to up to three entries per artist … which came in handy more than you might think! Also, because I’ve already written about these songs at length on a technical level, expect the conversation this time around to be focused on the bigger picture and the decade in general.


Of course, though it’s only officially a top 50 list, I had to include some honorable mentions, presented only in order of the year they peaked, starting with:

Martina McBride, “When God Fearin’ Women Get the Blues” (2001)

Blake Shelton, “Austin” (2001)

George Strait, “Run” (2001)

Patty Loveless, “The Last Thing On My Mind” (2001)

Joe Nichols, “Brokenheartsville” (2003)

Shania Twain feat. Billy Currington, “Party For Two” (2004)

George Strait, “You’ll Be There” (2005)

Montgomery Gentry, “Back When I Knew It All” (2008)

Carrie Underwood feat. Randy Travis, “I Told You So” (2009)

and finally, Zac Brown Band, “Toes” (2009)


On with the list, starting with …

No. 50 – Julie Roberts, “Break Down Here” (2004)

Against all odds, Julie Roberts made her mark – albeit a minor one – with a track about weathering a storm she’s not sure she’ll carry on through. Her tone is just weathered and ragged enough to show the toll her journey away from an ex-partner is taking on her, complete with car trouble and everything she owns stuffed in a Hefty bag, at that. But she’s going to prevail anyway, and it’s that hopeful confidence that marks why I consider this an underrated hit of the decade that should have paved the way for more. As it is, I’m still happy with what we got, and while I hope her character has enough fight to keep going, I don’t mind making a sudden stop to revisit this. 

No. 49 – Little Big Town, “Boondocks” (2006)

In some ways, while I like that Little Big Town has taken on a more mature direction over the past few years with some underrated projects, part of me still misses this band’s wilder, punchier moments. Because, while I’ve typically always loved this just for those harmonies, I’m even starting to appreciate the content and framing of it – a country pride song that eschews that theme’s usual hackneyed details in favor of something with plenty of underrated sensory details. Suddenly, this didn’t just sound good because of just its technical aspects; there’s a youthful exuberance captured here emblematic of a band just breaking through. They didn’t necessarily dominate this decade, but with that unstoppable hook and rattling rollick where I can still feel and hear what they’re singing about – even if it’s as far removed from my personal experience as a country music fan as it gets – they certainly proved why they could have.

No. 48 – George Strait, “Living For the Night” (2009)

I’m a bit surprised this ended up being the George Strait single to make my list proper. One could argue he dominated pretty much any decade in which scored hits, and I do think some of his most underrated work can be found here. And as for this … well, I get why it may not be anyone’s immediate choice for a favorite Strait single. It’s far darker and more polished than what he was typically known for in his prime, which actually comes as a surprise, given that this is one of the few hits he’s co-written.

But I don’t know, there’s something about that darker mystique and swell of strings that’s always made it sound like a long-lost gem from his Road Less Traveled album, a moodier and more contemplative effort that veered away from the norm and yet still somehow worked so well for Strait’s style. And I think it’s because of Strait himself, who’s always had a straightforward tone (pun intended?) to his delivery but is also an underrated emotive interpreter as well, especially on tracks like this. It may not go down as an especially remembered hit, but it deserves to, at least to me.

No. 47 – Kenny Chesney, “I Go Back” (2004)

In a decade where Kenny Chesney rose to prominence as a fun-loving beach bum, my favorite moments of his tended to be his more reflective sentiments; go figure. Of course, personal nostalgia has always been a favorite coping mechanism of his … and mine, hence why I’m old enough now where this track about romancing nostalgia is nostalgic in its own right. It’s his hugely anthemic ode to life and memories made, that, yes, is fairly broadly sketched until that final chorus, but is also painted with so much realism and a progression to its story regardless, especially in its note of how music can remind us of both good and bad times. More celebratory than dour, even if there’s just a slightly sad fondness for what was and what will never be again, except for in our minds. Maybe it’s why I always love and hate going back to this one.

No. 46 – Sara Evans, “A Real Fine Place to Start” (2005)

I could make the argument that Sara Evans’ best work from this decade is only rarely represented by her hit singles, and maybe someday I will. But when I see this song, I can’t help but smile. Radney Foster is oddly great at writing love songs and Evans is great at singing them. And, though she’s always been somewhat labeled as neotraditional, she’s also always had a knack for soaring pop-country. And that’s the simple nugget right there with this song – it’s a track brimming with the possibility of love and a bit of a rush in knowing there’s a potential danger in just jumping into it, but Evans is going to lean into it for a fantastic, shimmering hook, all the same. There’s one track of hers I like just a bit more from this decade, but this? This is, indeed, a real fine place to start with her music.

No. 45 – Keith Urban, “Somebody Like You” (2002)

And hey, speaking of shimmering country-pop exuberance that hits all my joy receptors on a primal level, that was Keith Urban’s exact bread and butter in the 2000s, before he got trigger-happy with the drum machines. I’m always tempted to call him a terrific one-trick pony in that regard, but there’s one other selection here we’ll get to that somewhat disproves that. Even still, on a track like this, while all of the credit (rightfully) goes to his guitar work – especially that end solo you don’t get with the radio edit – and the big focus being on melody and presentation, I’ve always appreciated his approach to writing, too. He always chooses to remain optimistic, never making his material devoid of deeper drama so much as choosing not to face it head-on in favor of looking toward tomorrow, which can add a subtle weight to any sentiment … even a simple song like this about the joys of learning how to love again.

No. 44 – Randy Houser, “Anything Goes” (2008)

It genuinely bums me out that the only times Randy Houser has delivered on all the potential his richly expressive voice will allow him, he hasn’t been rewarded for it. It’s easy to point to projects like Magnolia and They Call Me Cadillac as examples, but reach all the way back and we have this tried-and-true heartbreak song that Houser’s more mature, lived-in gravitas strengthens to become something all his own, where he’ll own most of his misery as self-made and ride it all the way to the bottom. And he’s just going to make it sound great in spite of itself, too. This has become something of a hidden gem in his discography as time has went on, but when Houser delivers, the results deserve a placement here.

No. 43 – Eric Heatherly, “Flowers on the Wall” (2000)

Depending on whether or not I actually finish this entire feature as intended, we just might see this song again someday soon. But, controversial as it might sound, I won’t enjoy the revisit quite like I did with Eric Heatherly’s weirdly off-beat cover. Granted, I mean that in a good way, as it what it loses in the terrific Statler Brother harmonies, it gains in a moody, idiosyncratic angst that’s arguably way more fitting in tone for this song anyway. A very odd choice for a debut single, and I’m honestly not too surprised this was Heatherly’s only hit. But by turning this into a dark, uncomfortable rockabilly shuffle where he plays into the ominous paranoia so damn effectively, I’d argue he left a mark anyway, at least here.

No. 42 – Sugarland, “Baby Girl” (2005)

It’s a far messier and more complicated debut than it should be in hindsight – especially when this is probably the only Sugarland song where I’d praise the harmonies. Setting that aside, though … yeah, it’s still one hell of a debut. A fitting one, too, given that it captures the wide-eyed dreamer determined to make it who’ll either remember the path that got her there if she does, or go down swinging if she doesn’t. It’s a classic tale familiar to an unforgiving city like Nashville, and while it’s not quite my favorite song by this band, it does, at least to me, belong in the upper echelon of songs that capture the ethos of this crazy industry.

No. 41 – Trace Adkins, “You’re Gonna Miss This” (2008)

Man, Trace Adkins could really be heartfelt and sincere when he chose to be, a side of him that will last far longer than the one shown on his gimmicky cuts, at least I hope. When that huge, expressive presence is used for something with so much heart and passion to it, good things naturally come from it. And this is one of my favorite examples, where that feeling of failing to enjoy moments as much as we should and wanting to recapture them years later is simple but relatable. But there’s also empathy present here by framing it mostly from the perspective of the older generation who can sympathize with the woman this song is mostly directed toward who just wants to grow up already, because they were all her once – hell, I’m old enough now to say I was that person once. And while both perspectives are valid … time only moves one way anyway, and it’s better to hold on while you can. And as if that note of somber reflection isn’t driven home by its understated production and supple mandolin work, you’ve got a great lived-in character like Adkins there to tie it all together.

No. 40 – David Ball, “Riding With Private Malone” (2001)

There’s a few one-hit wonders present here, but this may be the lone example of the often beloved comeback hit – which mostly happened for David Ball with this song because of events surrounding its release but deserved the boost nevertheless. I mean, yeah, it’s a song about a soldier whose legacy is imbued into a car left behind, and apparently he becomes a bodyguard in the afterlife … but damn it, it’s still a beautifully moving story about the late titular soldier’s memory living on through his car sold to Ball’s character. Maybe a bit oversold in concept, but when you have a reserved interpreter like him doing his best only to add solemn respect and nothing more against generally warm and rollicking country-folk-like production, along with the subtle details of the life Malone left behind and didn’t get to live for himself – plus a final verse that is genuinely moving – it feels grounded in a way that’s truly gripping all the way throughout. A fitting song for the year it was released, but one that had staying power beyond it, too.

No. 39 – Miranda Lambert, “Famous in a Small Town” (2007)

Miranda Lambert is just so good, that any of the (spoiler alert!) three tracks I have here are all pretty equally awesome. And this song just may one of her more underrated and forgotten singles, which is a shame.  I mean, thinking back to the era in which it was released, it’s just refreshing to hear a single lean into its honest portrayal of a small town with a rare sort of self-deprecating humor and a ragged arrangement of a meatier electric guitar and harmonica to bolster it; there’s no odes to the simple life here, that’s for sure. Granted, there is some sort of glorification to the entire affair, but it’s also a subtle way for Lambert to poke fun at it too. She’s got her fair share of rockers, and we’ll get to a few of them in due time. But this is just a blast of a different kind that rolls through with a wink and a smile and has every bit of fun it can with it.

No. 38 – LeAnn Rimes, “Probably Wouldn’t Be This Way” (2005)

I love that LeAnn Rimes’ brief mid-2000s comeback streak included this gem, and I’m glad that it plays around typical listener expectations, at first rolling through the motions of a typical break-up … until it’s revealed that her significant other passed away and she’s faced an uphill battle in trying to find closure. What elevates it for me further is a sense of lived-in detail, namely in how she looks to friends and family for support but doesn’t find it. It’s not really their loss like it is hers, and with the subtext suggesting that it’s possibly been years and years since the tragedy occurred, it makes a small step like going out with someone new seem so significant, even if she’s still nowhere near ready to move on. The other tragedy is that this didn’t lead to more hits from Rimes, but it only makes this one worth savoring and remembering – an absolutely devastating song.

No. 37 – Dierks Bentley, “What Was I Thinkin’” (2003)

On the flip side to devastating, however, we have another slam-dunk debut that still may arguably be Dierks Bentley’s best – a fast-paced story song with some hilarious twists for what was supposed to be a simple date night and a twangy accompaniment that, much to my personal delight, leans heavily on that dobro. It’s a bit of a frenzy overall, which is fitting, given that this leans headfirst into its primal instincts over anything that could be described as carefully calculated. It’s the sort of rambunctious, hangdog track that would define Bentley’s solidly underrated 2000s work, but despite the intentional messy execution, it was still a perfect storm where everything came together just right; that’s what I’m thinking.

No. 36 – Lonestar, “Walkin’ in Memphis” (2003)

This is a weird one. If you don’t remember me mentioning this once on my 2003 list, it’s because I didn’t. And it’s because I didn’t fully appreciate this one, oddly enough, until I saw Lonestar live this past summer … albeit without Richie McDonald. Even then, seeing them perform this did somewhat unlock its magic for me, a Marc Cohn cover elevated by McDonald’s usually expressive pipes but also his genuine bright-eyed wonder that does wonders for that hook. Soaring pop-country was pretty much always this band’s bread and butter, and even if they stick pretty close to the original composition, I’d argue they bring the writing to life even more than the equally solid original. All it took was a proper revisit to appreciate the sights and sounds around me to see that. It’s not their most iconic hit of this decade, but they made an excellent song their own, and that counts for something.

No. 35 – Lee Ann Womack, “I May Hate Myself in the Morning” (2005)

It feels kind of weird that to say I have three Lee Ann Womack songs here and one of them isn’t “I Hope You Dance” – and, if not for my rule, I would have had no problem counting it too, for the record. The first entry is one that snuck up on me with this feature, from the era in which Womack, ironically enough, stuck true to her promise to record the kind of country music she had always wanted to make. And the evidence here suggests her label should have relented earlier, even if, perhaps predictably so, country radio didn’t really bite. This, however, just has that classic bite in its maturity and complicated framing, especially in its way of making “sinful” indulgence in a one-night stand sound so joyously sweet and needed backed against that rich blend of strings and pedal steel (and a well-timed fiddle solo). A very subtle slow burn, and one that I somehow underrated and overlooked when discussing my own favorite Womack songs, but I’m glad I let it sank in a bit more.

No. 34 – Sara Evans, “Suds in the Bucket” (2004)

It’s the Sara Evans song most people brand as their favorite of hers from this decade – hell, one of their favorites in general from this decade – and going just off of her singles, I’d have to say it’s mine as well. And because Sara Evans is such a terrifically direct presence behind the microphone, this story about an 18-year-old woman who leaves town to elope with her boyfriend and completely rocks her small town in the aftermath of her departure is both a riot and can speak to larger issues, as well. I mean, it does make one question the kind of societal expectations in that sort of setting that could make her want to run in the first place, but it also just moves at such a breakneck speed, that it reinforces the suddenness of that hook a little too well. An escape is an escape, though, and whether that’s referring to a character’s personal catharsis from starting over or losing one’s self in the small town drama for a few minutes, it’s always a jam regardless.

No. 33 – Alan Jackson, “Drive (For Daddy Gene)” (2002)

It’s my list; of course Alan Jackson will make more than one appearance here today. And it’s his depth of human understanding and sense of profound empathy that will mark my selections from him here. He’s just one of those songwriters who understands how to sketch actual people with real lived-in stories. So, when he’s here to pull from personal experience and craft a tribute to his late father … well, of course this is an excellently moving piece. Leave it to him to deftly present a personal childhood memory of driving with so much earnest joy that it ends up feeling wonderfully relatable. And for as much as that child-like innocence shines through in this trip down memory lane, it’s equally a song about the people in Jackson’s life who helped form those memories – from the joys of what his father taught him to what he’s able to now teach his own children. Nostalgia never shined with so radiance as it did here, or with so much heart and drive to it.

No. 32 – Keith Urban, “But For the Grace of God” (2001)

Of course, my favorite element of Alan Jackson’s writing is also why this is my favorite Keith Urban single, a surprising neotraditional pivot that nevertheless feels like a good pre-cursor to his tried-and-true hook-driven pop-country, if only because this carries the same warmth and grace that would make that work so damn earnest and charming. Like most Urban singles, I never seek out the radio edit, if only because that extended pedal steel and fiddle interplay is one of my favorite moments in music from this decade. But I even love the content, a familiar message of expressing thanks for what one has that nevertheless carries a dark underbelly of unease knowing it could very well be different at any point moving forward. And by looking outward with a particularly empathetic second verse that puts things into perspective for him – not in a jovial way, but in a way that truly feels lived-in and thankful for the common, everyday things often taken for granted – he made a quiet gem here.

No. 31 – Gary Allan, “Best I Ever Had” (2005)

It almost feels weird to feature Gary Allan on a list like this, given that he’s the sort of artist who was something of an anti-hit-maker in his prime. He’d frequently release some off-beat material as singles – all for the best, really – and this is, like, the third example here of an act making a song their own. “Best I Ever Had” is a take on a Vertical Horizon song that acted as his first piece of new music following his wife’s suicide, and while the original mostly just reads as a straightforward breakup song, it’s particularly brutal piece to hear in this context. Of course, what makes this version even more brutal is the subtle line change before the last chorus to add a layer of complexity of the situation, only further amplified by the Tough All Over album itself, showing how Allan is doing his best to just … understand, and can’t seem to break that barrier no matter how hard he tries. A fitting first step to overcoming grief, though, really. It should never have had to be one of his best songs … but it is, and it still resonates today.

No. 30 – The Wreckers, “Leave the Pieces” (2006)

Even despite being more than what they appear, some one-hit wonders may remain well-known for a goofy, gimmicky cut that’s very of its era; others may be remembered for one terrific moment in the spotlight and for what could and should have been. And with the Wreckers … well, if you know, you know. Not a lot of complex reasoning needed to discuss this one, either – it’s just a kickass kiss-off track built upon a foundation of burn out, tired frustration, and a quiet sigh of relief when those oddly cathartic “yeahs” kick in toward the end. And it’s all bolstered by Michelle Branch’s blunt presentation in the not-so-quiet acknowledgment that the damage was done a long time ago and that her insignificant other’s indecisiveness couldn’t possibly surprise her any more. It’s definitely worth picking up past pieces and putting them back together to relive this. “Yeah, yeah,” indeed.

No. 29 – Miranda Lambert, “Gunpowder & Lead” (2008)

I think the only bad thing about this song is that it typecast Miranda Lambert into a certain mold that fans and critics expected her to build upon with every subsequent release. And she’s awesome at that, don’t get me wrong – this isn’t even my favorite moment of hers in which people end up dead – but I think equally solid singles from this decade like “Famous in a Small Town” and “More Like Her” proved her talent as a writer and performer were pretty far-reaching. But come on, it’s “Gunpowder & Lead,” it’s explosive, it’s nasty, and it’s awesome, somehow by sounding even more righteously pissed and filled with even more fire and brimstone than Lambert’s previous material. And even when the end result is murder, it’s hard to deny the dude didn’t have it coming.

No. 28 – Alan Jackson, “Remember When” (2004)

Even coming off of monster hits like “Where Were You (When the World Stopped Turning)” and “It’s Five O’ Clock Somewhere,” this just shouldn’t have been a hit; we certainly don’t get deeply personal slow burns like this topping the charts anymore, after all. And it was a second single from a greatest hits compilation, of all things! But I’m so, so glad it extended greatness anyway, because it’s still one of my all-time Alan Jackson favorites, telling the story of his relationship to wife Denise from beginning to end in flashback montage and refusing to pull punches with every place they’ve been on that journey. And yet, it’s that sense of lived-in detail that really makes it feel like a love story that’s earned its stripes and has really stood the test of time, especially against the supple blend of strings and pedal steel to give it all a sweet yet weathered touch.

No. 27 – Josh Turner feat. Trisha Yearwood, “Another Try” (2008)

I’ve talked about it before, and you still have me at “Josh Turner featuring Trisha Yearwood.”  And really, given their general styles, it should come as no surprise that this is just an impeccable slow burn of a country song, filled with terrific and understated production in the minor swell building mainly off the burnished textures in the piano and fiddle and dobro interplay (and later, those strings), all just as an added bonus. But I’ll be honest and say that without Turner here to guide this with somber conviction, this song asking us to sympathize with a character who failed at love the first time around might not have become the underrated classic it is today. And by having Yearwood on backing vocals, it adds a nice, subtle implication that she could play the other partner who’s sad it didn’t work out, either. Turner’s 2000s run is him in his prime, but it’s a song like this alongside a veteran in her own right that reminds me why Turner should have come around much sooner than he did.

No. 26 – Trisha Yearwood, “Georgia Rain” (2005)

And hey, speaking of Trisha Yearwood, she happened to have a great comeback of her own in the mid-2000s, commercially and especially critically. And while “Georgia Rain” is pretty typical of what you’d expect from Yearwood – a huge emotional ballad that’s basically like the 2000s version of “Strawberry Wine” – sometimes playing exactly to fan expectations is a good thing; a great thing, in her case. This is a regretful yet sensual slow burn where the imagery is vivid enough on its own but made whole by its mature perspective looking at it all in hindsight. Again, it’s a familiar tale of faded summer romance to revisit, but when said revisit includes magic like this, it’s always worth one more dance in the rain.

No. 25 – Josh Turner, “Would You Go With Me” (2006)

It’s just the ultimate nostalgia song for me, and to this day, there’s just something wholly unique about its arrangement – a mix of country and bluegrass with a lot of sprawling, liquid texture to bridge an odd gap between the traditional and contemporary, sporting a surprisingly dark mystique off the pluckier, minor, liquid interplay of dobro, bass, banjo and mandolin. And for a love song, no less! But there’s a bigger focus on sketching out the idea of that journey, where the question of commitment is approached with a bit of unease in the danger that could lurk ahead, making it feel more like a sweeping journey or a dream, and one worth having, at that. It’s not the only song like that on this list, but it’s the only one that sounds this gorgeous; it’s still just strikingly unique for its era.

No. 24 – Tim McGraw, “My Old Friend” (2006)

It’s a credit to Tim McGraw skill’s as an interpreter that he can turn a tribute to a nameless person like this into something that feels so crushing and personal. The cynical part of me even wants to say it’s built entirely through clichés and wouldn’t work with a lesser performer … yet that’s the point in framing its painful relatability of how we all likely know that one person – or several – we lost touch with over the years and don’t know how to reconnect with, if we even can. Sometimes offering a few simple verses is truly the least that you can do, but at least it’s something to re-spark that connection … or squelch the pain of time lost. And by grounding in that heaviness in the minor keys, the shuffling percussion to echo how time marches on in spite of pain or joy, and scattered cries of fiddle and dobro, it never outright references death as the primary cause for what caused this particular relationship to crumble, but it certainly alludes to it. McGraw’s genuinely regretful performance kind of speaks for a lot of us, in that regard.

No. 23 – Craig Morgan, “Almost Home” (2003)

This isn’t the type of material Craig Morgan was mostly known for, and it’s a shame that the genre in general moved closer and closer away from this sort of unique, emotive storytelling this decade. And I’m referring to stories with layers of complexity to them, be they in their subtle implications or possibly even in the straightforward text. “Almost Home” is more of a case of the latter – a song that pulls from the dreamlike sequencing of, say, “Green, Green Grass of Home” to pull away from a darker reality into past times of ease and comfort. And as Craig Morgan’s character tries to do the right thing by comforting a sleeping homeless man freezing to death, he inadvertently rips away that last good memory likely keeping this person fighting. We never find out how he went from a happy childhood to where he’s at now – which mirrors reality in how we never truly know a person’s story or what has shaped it – but there’s something so potently sad knowing that all that’s left is what was left behind; perhaps even relatable, specific circumstances aside. It’s just such a deeply empathetic story told through such a unique lens, and it’s worth mentioning, again, that I miss hearing this kind of song on the radio.

No. 22 – Kenny Chesney, “Anything But Mine” (2005)

I’m not sure how well this is remembered within the context of Kenny Chesney’s discography. I mean, it’s a nostalgic summer song that fits well within his wheelhouse, but there’s something different about it – transcendental, even. And it feels like it clicks right from the shimmering high of that introduction. But it’s also a summer romance song where the characters aren’t caught off-guard by their time running out; hell, one of my favorite details is the self-awareness, especially in a line like “I tell her I love her, and we both laugh, because we know isn’t true.” They aren’t even necessarily the archetypal high-school couple. This feels older and more mature and confident and sure of itself, especially when it’s detail-rich in the way that comes when you get solo writes like these. I think what I love most, though, is how playful it all feels. Our characters are going to revel in the moment for as long as they can and part on good terms, simple as that. It’s a lightning-in-a-bottle kind of song that might just rank as my favorite song of his in general. But hey, like with the song itself, you may never be able to go back, but you can always relive that magic in some form when you please, and that’s just enough. 

No. 21 – Lee Ann Womack, “Last Call” (2009)

Oh, the irony behind Lee Ann Womack’s final big hit being called “Last Call,” especially when this is anything but a final bow – it’s just an extension of the greatness that is her discography in general, to me. Even then, this is one of those songs that’s very simple to describe and unpack: Erin Enderlin’s co-writing credit is always going to imbue a song with the necessary bite and cleverness to sell it effectively, all the more evidenced by Womack’s intolerance for her flighty, alcoholic soon-to-be ex-lover, even though there’s a lot of hurt present in her delivery to signify that it’s not an easy goodbye. And there’s a beautifully lush yet minor swell to the whole endeavor that lets this sting linger. I would have loved to hear more, but as a last call for hit songs goes, this is a surefire high note.

No. 20 – Josh Turner, “Long Black Train” (2004)

Yep, one more Josh Turner song, and those familiar with this blog had to know this was coming. I can’t deny the personal attachment I have to this through my grandparents doesn’t add the most weight in my love for it. But there’s a lot to love about the song regardless, which adopts the usual praise-and-worship presentation style for this type of rousing gospel number but feels more grounded in realism. That is, the strength has always been in its inspiring energy and accessibility in framing it around something as common as the temptations of sin, which even Turner admits is alluring at times. This has just always a gentle easiness akin to a Don Williams song for me, yet also a paradoxical unease in its lyrical framing that’s presented with sincerity over unsettling preachiness.

No. 19 – John Michael Montgomery, “Letters From Home” (2004)

It’s hard to know how to categorize the 2000s. ‘90s country, bro-country, Urban Cowboy … this decade has never really had a term to call its own, even if most would likely say the flood of patriotic songs we got in the early half of the decade is the closest we’ll get to finding one. My favorite ones of that variety tended to dial things back to focus on simple humanity, like “Where Were You (When the World Stopped Turning,”  “Riding With Private Malone,” and this song. It was John Michael Montgomery’s last big song to hit the charts, a wartime-themed song that feels more universal rather than tied to the events of its time, and in a way that doesn’t feel pandering in capturing the family relationship across the world. And really, it’s always been what isn’t said here that really grips me here, especially when there’s obvious tension between a son who chose to enlist and an estranged father trying to come to terms with it.

The song never explicitly outlines what causes that tension, whether it be that the father also enlisted at one point and doesn’t want his son to witness the horrors he did, or whether the timeliness of the song’s release was supposed to say all that needed to be said, or whether it was something else entirely. Either way, that final verse is a real gut-punch, and when you have a great performer like Montgomery against generally warm tones in the dobro and harmonica and excellent acoustics, it’s a great send-off to a stacked career, and a pretty damn underrated one, too.

No. 18 – Lee Ann Womack, “Ashes By Now” (2001)

I can’t call it the definitive version of this Rodney Crowell-penned song, especially when his version includes another verse cut here. But damn it, every time I revisit this that sharp instrumental hook lodges itself into my brain for days, and I feel more content with the choice of it as my favorite version. Lee Ann Womack’s bitterness tends to frame itself much more seriously, but I’ve always loved her performance here painted with a dramatic flair that’s just more urgent than anything else in her discography – a firestorm all the way down that smolders like none other. Couple that with a strong groove (and those bongos!) and an equally strong finish from the backing vocalists that adds potency and fire to that hook, it’s actually nearly my favorite Womack song in general, only bested by an album cut gem called “I Think I Know.” But as far as just the hits go, this one will burn for me eternally.

No. 17 – Shania Twain, “I’m Gonna Getcha Good” (2002)

I always find it oddly fascinating just how bright Shania Twain’s star burned in such a short time. I feel like we didn’t get to hear her as much this decade as we should have, and even her ‘90s run is shorter than some may think. But man, what a run. I’m not sure if this is my favorite song of hers simply from being her catchiest and most infectious or if it’s something else entirely; her discography has a pretty consistent, uniform quality to it that’s also remarkably solid. I prefer the “red” version of this song to the “green” country one, though both are pretty fantastic – and in terms of the latter, I will say the spikes of fiddle and pedal steel ensure that none of that melody ever gets lost; just enhanced.

Oh, and along with being, Twain’s most hook-driven track ever, it’s also her most urgent. It’s a quest for love and a search for someone she may or may not have already met, but is determined to find no matter the cost because … you can only sit atop your mountain for so long before loneliness takes over. Yes, it’s fragrantly bubbly in a way that even some of her campier numbers manage to avoid, seeing as how love can be both fun and utter hell depending on the situation. But it’s Twain’s journey, and she’s so hell-bent and effervescent in her determination that you hope she does find it.

No. 16 – Alan Jackson, “Small Town Southern Man” (2008)

I think this song may have actually grown on me further because this series. Father-themed songs don’t tend to do much for me, but Alan Jackson is just so excellent as a storyteller and interpreter, that he can invite fans into his world and either make them relate to his own experiences, or just make them appreciative of his attention to detail. I guess for me it’s the latter, as while I can’t say this tribute to his father is quite as immediate as “Drive” before it, it is a more reflective slow burn that takes its time detailing the man’s life. And the warmth and understated presentation is part of the point and appeal – a tribute to a simple man who did the best he could and was resilient in his goal to simply provide for his family. Jackson has always been so adept at humanizing his characters, that this is just another classic in a career full of them.

No. 15 – Rachel Proctor, “Me and Emily” (2004)

That I have this song this high makes me all the sadder that we didn’t get to hear more from Rachel Proctor, because while this stretches the definition of a “hit,” it left a mark in some form, at least. On the surface, this is one song (among many here) with dark undertones to frame itself as celebratory – in this case, the story of a mother who escapes an abusive partner with her daughter – but to me it’s also another song here where the gut-punch comes only in what’s implied. They escaped and started over, for sure, but there’s still that general unease of what to do next and how the lyrics are quick to point out that they left without taking much, all while it goes without saying that they’re not quite safe yet. Yet it’s that motherly bond portrayed here that gives the song its inspiring confidence, especially when the protagonist realizes it’s because of her daughter that she found the strength to finally leave at all. Not an easy song to revisit, but absolutely underrated, and one that deserved so much more.

No. 14 – Tim McGraw, “Last Dollar (Fly Away)” (2007)

I didn’t redo my lists for 2007 or 2006 for this feature, so they probably look really out of the ordinary compared to the others here. In other words, I should have had the guts to call this my favorite hit song of 2007, and I’m making up for that now. It’s arguably McGraw’s weirdest moment on record – a track so relentlessly upbeat even in spite of having every odd against it, that it’s almost overbearingly corny; for as much as I like McGraw, he’s no Roger Miller. And I’m not sure what the hell is going on with his voice on the bridge.

But he leans into it all with a wink and a smile, enough to make it genuinely charming, maybe even humorous. Truth be told, though, I’m not sure I’d view it as fondly without my grandfather playing it endlessly at home or in the car when I was a kid; it’s got a rare spirit that’s almost childlike and perfect to hear for people who are kids at heart, even if I could do without that kids choir at the end. It found me at the right point in time. But then I reel back around to that huge hook and feel like it’d connect regardless. What can I say, I’m so glad it’s here today.

No. 13 – Miranda Lambert, “Kerosene” (2006)

I could argue Miranda Lambert didn’t really become “Miranda Lambert” until this release, and though “Gunpowder & Lead” is the more referenced ass-kicker in her discography and likely the more important song given its focus on domestic abuse, I still can’t help but love this just a little more. She busted through the doors with a uniquely raw energy. And I say that as a huge Steve Earle fan who thinks any controversy of her borrowing from his own “Feel Alright” is reaching, at best. And even then, I don’t care anyway – it transcended it off the even grizzlier, thumping drums and the intensity of its progression built off lyrical rage that goes beyond a familiar melody. I could describe quite a few songs here as incendiary in their tone or content, but this may just be the one where I could mean it literally.

No. 12 – Brad Paisley feat. Dolly Parton, “When I Get Where I’m Going” (2006)

Yep, this is the start of the Brad Paisley entries – and surprisingly enough, he’s not even the artist with the most entries in my top 10! And you don’t know how it badly it stings to leave his Dolly Parton duet just outside of it, as while Paisley is generally known for his goofy, corny material that’s far more divisive than it should be, it’s telling how adept he is at being serious and pulling off earnest emotion excellently – those are the entries that resonated most with me, so I don’t think it’s ironic at all.

Granted, this pulls from the same playful, younger, innocent perspective that’s marked his best moments on both side of that divide without being outright immature, a meditation on the peace that may come in death without getting overtly religious or preachy. Indeed, its strength lies in its humanity and hope that we’d all like to, at least, believe could exist, regardless of what we actually believe in. Simply beautiful, really, and Parton’s angelic harmony vocal is really what sets this over the edge, a gorgeous counterbalance to Paisley’s plaintive, bright-eyed wonder of that great beyond. I know he didn’t write it, but he approaches it like he did, and that requires a special strength, too.

No. 11 – Lady A, “Need You Now” (2009)

I’ve talked about this song through other features before, and while I don’t want to talk positively about Lady A these days any more than I have to, I’ll acknowledge that this is the best thing they’ve ever done and that they’ve never topped it since and never will again. The interplay between Hillary Scott and Charles Kelley is phenomenal, ironically enough coming together to capture an emptiness that resonates off of the fantastic atmospheric country-pop crossover-ready textures in capturing heartache, regret, and desperation, all in one. And yet it’s that bridge, where the entire point is just to find some sort of sweeping connection between two lonely people with an implied history between each other, even if it’s the one that hurts the most.

No. 10 – The Chicks, “Travelin’ Soldier” (2003)

Annnnnd, this is the start of the Chicks entries – ironic, given that I got into country too late to say they impacted my childhood; they’re just that damn great to me. And while I do love this song on its own merits – the tale of a young couple torn apart by the crushing reality of war, with the emphasis rightfully placed on an intimate production and their story that began but was never rightfully finished and is just more innately familiar to the genre – I love it more because of what it spoke for beyond its content. It was their last big country hit, and it wasn’t cut from the same mischievous cloth they perfected years prior. But if you know your country music history, you might find the respectfully somber restraint as fitting as I do – if only because this was the final No. 1 hit for a group whose story was also finished long before it should have. I mean, this a beautiful song regardless, but if that doesn’t speak to the larger irony of everything surrounding this song’s descent in the wake of the incident, I don’t know what does.

No. 9 – Tim McGraw, “Red Ragtop” (2002)

You know, Tim McGraw may not be much of a writer, but he knows when to pick great songs and how to make uncomfortable messages accessible to all – all willing to listen, at least. “Red Ragtop” is a song that could either be about the freedom of choice or the consequences of being forced to make a difficult decision at such a young age, depending on your perspective. Sad that it seems like an evenly more timely track for now than it did upon its release 20 years ago, but that’s the beauty of “Red Ragtop.” It showcases a young couple clearly not ready to be parents, where even though they were probably too young to know what love actually was, who could really say? At any rate, it’s an example of the strains and pressures unexpected pregnancy can place on any couple, and how either moving forward together or separately with or without that added unit can leave scars too hard to qualify or repair. It’s not the soaring high of “Live Like You Were Dying” by any means, but it is a restrained, bitter pill to swallow that quietly ranks as an underrated gem of his today.  

No. 8 – Jamey Johnson, “In Color” (2009)

Assessing Jamey Johnson’s brief mainstream run is always an oddly fascinating exercise for me. To many, he was a country music savior who brought something heartfelt and rugged back to the forefront of the fold; to others, he wasn’t that special – it’s simply the classic (and frustrating) “real country” debate coming back around again. Of course, I find the truth to be somewhere in the middle, in that what Johnson brought back wasn’t a necessarily hard country sound, but the deep, emotive storytelling that could speak to even the most hardened of souls.

I called this country music for grownups in my original post, but that doesn’t seem right now. If anything, I remember loving this for introducing me to what country music could bring out of you at its best. Not just in the frankly stark presentation of the burnished acoustics playing off the muted keys, touches of faint pedal steel on the chorus, and the addition of the electric guitar play weaved in later on that adds a surprising amount of potency to its finish, but also for the simple truth that this wasn’t a narration of rosy nostalgia. These are hardbitten photographs of the Great Depression and war, where the reward of love in the third verse is only found after sorting through trials that had to be experienced, rather than heard about, all told from the world-weary perspective of someone who sounds like he’s lived it himself. It was unlike anything else from its era, but I suppose the “why” behind it really depends on one’s own perspective.

No. 7 – The Chicks, “Goodbye Earl” (2000)

Even despite a mere top 20 peak, this may be the song folks remember most from the Chicks today … for better or worse! Even I’ve never really known what to make of this song despite loving it. 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. Earl deserved it.

No. 6 – Randy Travis, “Three Wooden Crosses” (2003)

It’s natural to expect an air of finality to lists like these. Some names we see here will names we won’t see in the eventual 2010s list, just as that eventual ‘90s list will look alien compared to this one. It’s the sad, viscous cycle of relevancy that’s hard to stomach. It’s why I love a good comeback story, if only because it proves artists often still have a lot to say to an audience willing to listen. And this is one of my favorite examples – a redemption story in more ways than one. Though it’s unclear where exactly we’re headed with that opening line: “A farmer and a teacher, a hooker and a preacher, ridin’ on a midnight bus bound for Mexico.”

But we quickly learn that only one of those passengers will survive an accident on the way to their destination, and will be the key in spreading the message of the fallen – that who we continue to impact after we’re gone is perhaps the greatest thing we can hope of for our legacies. Granted, it’s easy to witness the mark left behind by a farmer and a teacher, but this isn’t the story of how the oft-villified-by-society hooker turns toward the straight and narrow by divine revelation. No, if anything, the song humanizes every character present not by their labels or professions, but simply by the people who they are and were while here. Everyone took the trip in search of something – be it higher education or to find themselves in a confusing world. And the aftermath of that tragedy still somehow leads to a story with … maybe not so much a happy ending as a heartwarming one. Like I said with “Almost Home” before, I miss hearing this kind of song in the genre.

No. 5 – Sugarland, “Stay” (2008)

It actually took Jennifer Nettles’ solo career for me to come around on Sugarland as a whole, if only because it highlighted what a phenomenal vocalist she is and erased my childhood memories of having to hear “All I want to do-ooh-ooh-ooh-ooh” seemingly all the time. And this is one of those singles I’m surprised was even released as a single to late 2000s country radio, a sparse ballad carried mostly by minimal acoustic strumming and organ in the low-end along with Nettles squarely at the front of the mix.

But it was, and it became one of the duo’s biggest hit singles and undoubtedly my favorite of theirs, even without the benefit of hindsight. And really, the power comes through in that rawness and vulnerability on display, a song told from the other woman’s perspective caught in a love triangle where she knows she’s the loose end and begs for her lover to at least acknowledge their hookups are about more than just that. But secretly she knows her pleading is for naught, and the switch of the hook for that final chorus is still just amazingly powerful, where she finally finds her pride and refuses to be subjected to that role any longer. Nettles always had a wry charisma that greatly benefited the group’s more uplifting tracks – although that’s a statement I am making with the benefit of hindsight – but for a moment in time, she dropped her guard and delivered her most emotionally packed performance to date.

No. 4 – Brad Paisley, “Welcome to the Future” (2009)

I think what I’ve always appreciated about Brad Paisley is his approach to songwriting and delivery. There’s always a likable sincerity present – even on his goofier cuts – carried by a ton of earnest charisma and affable charm. It’s why I love this just on the basics alone: it’s huge, it’s sweeping, and it’s carried by a relentlessly upbeat hook. And, more specifically now, it’s celebratory of the progress we’ve made as a society made thus far without skirting over the darker details. Indeed, it’s that third verse that really hammers in and elevates what could have just, admittedly, been a silly little ditty instead about Pac-Man at the arcade, likable as it still would have been.

And what I love more is that Paisley never frames anything here as the end journey, but rather gives us a good reminder of the world we could and still can create for the better in so many more ways than one. It’s bold yet lighthearted enough to know that hope comes in all forms, and that even though he’s welcoming us to the future here, it’s more of a declaration that it’s constantly being shaped and reformed every moment – especially 13 years after its release. And while I can see detractors disregarding Paisley’s execution as hackneyed – especially when compared to a certain future song of his that kinda-sorta went for this same theme and failed miserably – this is emblematic of everything I’ve always loved about him as a performer. And it’s still somehow not my absolute favorite moment of his!

No. 3 – Gary Allan, “Smoke Rings in the Dark” (2000)

It’s always so hard for me to see this as a 2000s song. I’ve always viewed it as a late ‘90s gem that simply mapped the framework for Gary Allan’s artistic evolution in the 2000s. In a way, then, I’m still glad to have it featured here. Allan’s 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 – we’ll likely see them as we revisit the ‘90s. 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. 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, which he did this d 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 decade, but it was an important next step for Allan – and it’s easily my favorite one of his because of that.

No. 2 – The Chicks, “Long Time Gone” (2002)

I don’t use the term pop-country as a pejorative, so it feels strange to have this specific song this high up on this list, especially when it really does live and die by that incendiary final verse – a sly takedown of modern country music that, while certainly not revolutionary for this particular genre’s yin-and-yang relationship with trends, did become a surprise hit anyway. It’s as if country radio was so fed up with the message that they just said, “Fine, here!” Or, you know, they couldn’t deny the Chicks’ star power and influence at this point. Hell, neither could pop radio.

I just can’t see it under the “us versus them” narrative, though. Maybe it started out as the everlasting “traditional versus contemporary” debate in the hands of writer Darrell Scott (and maybe it didn’t), but with the Chicks, I think it took on new meaning. After all, they certainly had their fair share of pop-country numbers that wouldn’t exactly fit in well with those Johnny Cash and Merle Haggard records. But to be featured on an album that was revolutionary by, ironically enough, downplaying the scales and showing how fresh pure, unfiltered country music could still sound in the modern era, I think it digs at the deeper heart of the matter – a lack of soul and ambition to rise above corporate expectations and satiate the artistic hunger from within. For as much as I think every year from this decade has something great to offer – I’ll say it, the songs that truly cut to the heart and had that strong emotive core became harder and harder to come by.

And that’s why I lied – this song is much more than that final verse. It’s unbridled, swinging bluegrass-folk with nary a drum but loads of harmonies to be found around every corner, featuring a simple core story of dried-up dreams along the way. It’s the tried-and-true country music argument updated for the new century, and a sign of leadership that hasn’t been matched quite yet … and may never again. It’s the complete opposite of “Welcome to the Future,” but both perspectives can be valid, can’t they?

No. 1 – Brad Paisley feat. Alison Krauss, “Whiskey Lullaby” (2004)

If I gave one iota of a damn about cultural significance or importance – a metric that critics can’t possibly measure, no matter how much they think they can – I’d pick a different song for this position. Even now, I can’t really name what it does “better” than what’s before it. I can’t even point to what it does differently from other Paisley songs. After all, I’ve already noted that he was just as adept at penning and recording deeply serious material as he was comedic one-offs – and my favorite material of his tended to meet somewhere in the middle anyway.

But I wouldn’t expect something this dark from any artist – not even from Alison Krauss, and she’s got the haunting quality in her voice to bring beauty out of pure misery. I guess I’m shocked to be discussing it at all for this feature, then – a song about a double suicide caused by whiskey that almost seems to go too far even for country music, even given its fondness for its alcohol-fueled binges. And then, to recruit Krauss to deliver one of her most haunting verses and vocals in general, and have Dan Tyminski add an additional background vocal? It’s a perfect, unexpected setup, where even though both Paisley and Krauss act as observers and storytellers here, there’s so much added weight in having each of them contribute a verse to the larger story – as if they’re friends with the characters they honor and understand what it’s like to lose someone so close to you.

Which is to say that the song is, of course, exceptionally written, sketching the breaking point for each partner in the relationship and how their own unfortunate actions caused a domino effect that eventually led them back to each other … hopefully to find a peace they couldn’t find on Earth, too. And with a sparse production carried only faint touches of bass and dobro to highlight that stark and lonely contrast, in a really strange way it also does provide that needed sense of closure and peace by its end while also sounding utterly bleak and melancholic in the beginning. Honestly, it’s so depressing and frank in what it’s going for, that I’m actually thankful the “la’s” can provide some semblance of peace and levity to this lullaby. For me, it was never a question. “Whiskey Lullaby” is my favorite hit country song of the 2000s, and while I hate to end on this solemn note, I will say there are many more decades to look forward to exploring, so I’ll see you next time.

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