Favorite Hit Country Songs of 2008 (Collaborative Edition)

Previous: Favorite Hit Songs of 2009

We now move on to 2008 as the next focus for this particular feature, a year that, for all intents and purposes, isn’t too far removed from the year after it, as far as the cultural conversation goes. For as much as the late 2000s tend to be viewed as a negative and/or low point of contention for the larger country music conversation, I think the following lists of hits we’re about to summit are proof that, while there was plenty of bad country music in 2008 (oh, hey there, Kid Rock and Rascal Flatts with that awful “Bob That Head” atrocity), the good stuff provided something for everyone. Still a fairly lost time period, as far as a defining sound or trend goes, but an underrated one nevertheless.

As always, we compiled our lists based off of what peaked within the top 20 in the particular year featured, organized here by Wikipedia. We invite you to share your picks for your favorite hit songs of this year below. – Zack

Anyway, onward!

No. 10 – Ashton Shepherd, “Takin’ Off This Pain” (written by Ashton Shepherd)

At a time when we were a good five years past Gretchen Wilson’s peak and the country music industry fed some asinine competition between Carrie Underwood, Miranda Lambert, and Taylor Swift as country music’s leading queen, as if there could be only one, here comes a shit-kicking modern honky tonk classic from a singer filled with so much righteous piss and vigor. Ashton Shepherd deserved so much better at country radio, but man, what a start. Seriously, the explosiveness of the presentation is what sells this, from Ashton Shepherd’s declaration that she’s going to ease her pain with a beer in one hand and her wedding band in the other while tearing into her neglectful significant other, to the ragged production that lends this song a ton of punch. A “twanger” if there ever was one. – Zack

No. 10 – George Strait, “I Saw God Today” (written by Rodney Clawson, Monty Criswell, and Wayne Kirby)

“I Saw God Today” is the type of sappy and sentimental religious song that was recorded over and over again throughout the 1990s and 2000s, usually to mediocre effect. Give it to an unseasoned young buck, and it’s an unqualified dud. But in the hands of one George Strait, it manages to be more than the sum of its parts. Way more. It has almost everything working against it, from its syrupy pop-country production to its predictable Hallmark message, but it rarely fails to move me for reasons I can’t quite articulate. – Andy

No. 9 – Montgomery Gentry, “Back When I Knew It All” (written by Gary Hannan, Phil O’ Donnell, and Trent Willmon)

I honestly thought I’d have “Roll With Me” here instead, but then I revisited this and that irresistible groove and harmonica play sucked me in for a song that has way too much fun examining its past. And really, the pure joyfulness of this song is what clinched this spot for me and convinced me that this is one of Montgomery Gentry’s most underrated singles, a song that can acknowledge that while we’d all like to change our pasts, there’s also comfort in knowing in how much we’ve grown, too – and how much we’ll keep growing, because we’ll never truly know it all anyway. The duo has a few excellent songs within this vein, but this is by far one of their most punchy and cheerful. – Zack

No. 9 – Taylor Swift, “Love Story” (written by Taylor Swift)

Taylor Swift’s preternatural songwriting ability is fully on display here. Yes, its appropriateness as a “country” single can certainly be questioned, and yes, its legion of shoehorned literary allusions understandably struck many critics as superficial … but sue me, I love this song. It’s fun, it’s whimsical, it’s original, it’s catchy, it tells a good story, it’s nostalgic, and it’s a brilliant tribute to young, optimistic love. “You were Romeo, I was a scarlet letter, and my daddy said stay away from Juliet!” Come on, you know you love it. – Andy

No. 8 – Heidi Newfield, “Johnny & June” (written by Heidi Newfield, Deanna Bryant, and Stephony Smith)

Yes, it’s a huge pop-country power ballad with some spotty production at times (the “loudness war” of the late 2000s is an interesting case study that probably needs more proper documentation), and at a time now where I can’t stand songs that base their premises off of name-dropping other country songs and/or legends, I shouldn’t like this as much as I do. It’s just that … the Johnny & June simile is actually used effectively to describe the kind of love Heidi Newfield wants to aspire to with her partner, and any references made to the titular singers are surprisingly well done and never aim to distract from the song itself. Which is to say that, it’s the pure passion by Newfield herself that’s always really worked for me and just may be the best part of it all, coupled with that huge hook. So no, with her debut single, Newfield wasn’t quite a one-trick pony after all (get it? Get it?!). – Zack

No. 8 – Ashton Shepherd, “Takin’ Off This Pain”

Ashton Shepherd announced her presence with a bang on her debut single, “Takin’ Off This Pain.” The song gets off to an explosive start as Shepherd immediately launches into that flat-out infectious, energetic chorus in which she informs her lazy and inattentive husband in no uncertain terms what the new state of play is. It’s a wildly entertaining honky-tonk scorcher and a woman’s anthem that would make Loretta Lynn proud. Ashton Shepherd was too country for country radio, but had she come along a couple of decades earlier, she could have been a star. – Andy

No. 7 – George Strait, “Troubadour” (written by Leslie Satcher and Monty Holmes)

When you’re on your third decade as an entertainer, sometimes you need to reflect and take stock of what’s been accomplished and what’s left to do, and that’s all I really need to say about George Strait’s “Troubadour.” It’s one of his finest singles of the decade next to “Run,” and though he didn’t write it – and those of you who want to drum up that argument can stick it where the sun don’t shine – he sings it like he did, adding a somber yet accepting tone to the song that’s fitting enough to be called a personal anthem anyway. – Zack

No. 7 – Alan Jackson, “Small Town Southern Man” (written by Alan Jackson)

Starting with one of his earliest songs, “Home”, Alan Jackson has repeatedly made it clear throughout his career how much he was influenced by his parents and their story. This year’s “Small Town Southern Man” is the purest tribute to his father he’s ever recorded. Stark and endearing in its simplicity, this song describes Eugene Jackson’s life from birth to death, and how the exemplary character traits he exhibited such as fidelity and devotion to family left a profound influence on the younger Jackson. “Drive” is the best-remembered of Jackson’s parental tributes, and that’s probably deservedly so, but in some ways “Small Town Southern Man” is even more powerful. I confess I don’t often think about this song when thinking of Jackson’s greatest artistic moments, but a compelling case could be made that it’s among his very best. – Andy

No. 6 – Trace Adkins, “You’re Gonna Miss This” (written by Ashley Gorley and Lee Thomas Miller)

I’m surprised this isn’t higher, because this is arguably Trace Adkins’ finest moment of his entire career and proof that he should have left the gimmicks at home more often. When that huge, expressive presence is used for something with so much heart and passion to it, good things naturally come about. That feeling of failing to enjoy moments as much as we should and wanting to recapture them years later is 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. And while both perspectives are valid … time only moves one way, and it’s better to hold on while you can. Couple that with a delicate, understated production, particularly in the supple mandolin work, and you have an example of what Adkins could muster whenever he brought his A-game. – Zack

No. 6 – Miranda Lambert, “Gunpowder and Lead” (written by Heather Little and Miranda Lambert)

You have to give Lambert credit for releasing what is pretty much a straight-up alt-country song to country radio. A highly distinctive resonator guitar riff backs Lambert playing the role of a battered woman awaiting the return of her abusive husband. It all leads to an explosive, fiery chorus in which she promises to turn the tables in a shocking way. It’s a daring song choice and one of the most unforgettable tracks of the decade. – Andy

No. 5 (both lists) – Randy Houser, “Anything Goes” (written by Brice Long and John Wiggins)

Of course, on the note of Trace Adkins … imagine that it actually is 2008 and you hear that one of the co-writers of “Honky Tonk Badonkadonk” has released his own debut single. And then imagine it being this. Don’t get me wrong, I’m glad Randy Houser bounced back with 2019’s Magnolia and am excited to see where he goes next, but this arguably still remains the crowning moment of his entire career thus far – a classic tear-in-your-beer country ballad filled with so much passionate soul courtesy of Houser’s huge and expressive range, fantastic texture in the production courtesy of the piano, organ, and pedal steel, and lyrics that smack of desperation but never ask for sympathy, either. One of his fellow co-writer for that aforementioned song would also shock listeners in due time, but this deserved just as much attention. – Zack

“Anything Goes” perfectly describes that feeling of heartbreak immediately after a breakup when you’re so overwhelmed with sadness and desperation you just don’t give a damn about anything. Randy Houser’s incredibly rangy and soulful voice is otherworldly good, and, when paired with a tasteful production that’s vibrant yet doesn’t get in the way, results in a true stunner and an underrated classic. – Andy

No. 4 – Miranda Lambert, “Gunpowder and Lead”

It says something when I’d categorize “Gunpower and Lead” as mid-tier on Crazy Ex-Girlfriend and it’s still one of the best hit songs of 2008. It’s the song that defined (and, unfortunately, typecasted) a new star even more than “Kerosene” did a year earlier, somehow by sounding even more righteously pissed and filled with even more fire and brimstone, though this time for an abusive partner rather than a cheater. And yeah, like with “Goodbye Earl,” there’s an argument to be made for why we maybe shouldn’t root for this leading character, but you can’t deny that the other side didn’t have it coming or that it isn’t in many ways justified. And beyond that, it’s just a modern classic that still burns with so much rage and fist-pumping energy, even to this day. – Zack

No. 4 – Brad Paisley, “Letter to Me” (written by Brad Paisley)

I was completely indifferent to this song for the longest time and regarded it as immensely overrated, but it’s one I’ve come to appreciate greatly with time. Ironically, I was seventeen when this song came out, the same age Paisley imagines sending his past self a letter, and am roughly the age now when he recorded this (although still younger by several years, mind you).

One of the things life teaches you is that you don’t know what you don’t know, and often just when we think we everything figured out, life throws us a curveball, upending everything we thought we knew. Who wouldn’t want to be able to communicate with their past selves, imparting knowledge we had to learn the hard way? This is a very original and daring song, and credit Paisley for releasing it as a single, and at the height of his mainstream success when he had a lot to lose. There’s some things I don’t like about this song – I’m not wild about the falsetto thing he does in the chorus – but overall, it’s something I admire greatly. The “P.S. Go hug Aunt Rita every chance you can” line is hands down my favorite lyric in any of these songs. – Andy

No. 3 – Josh Turner feat. Trisha Yearwood, “Another Try” (written by Chris Stapleton and Jeremy Spillman)

OK, look, you had me at “Josh Turner featuring Trisha Yearwood.” That it just so happens to be an impeccable slow burn of a country song is just an added bonus. Indeed, I’ve always loved how this song is 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). 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. But it’s easy to tell that the mistakes Turner’s character made are ones he deeply regrets, and I like that having Yearwood on backing vocals adds the subtle implication that she could play the other partner who’s equally sad it didn’t work out, either. Plus, when you can tell that his second chance likely won’t come back around, it fills the song with a deeply rich emotional resonance that proves why Turner should have come around 10 years earlier than he did. – Zack

No. 3 – Trace Adkins, “You’re Gonna Miss This”

One of the most curious aspects of the human condition is how our lives don’t seem to change from day-to-day, but look up after five or ten years, and we’re in awe over how different everything is. Most of us look back fondly on the past eras of our lives and, recognizing that they were unique times to which we can never return, might even feel nostalgic for the aspects we didn’t like at the time. I’ve never heard a song that captures this phenomenon more beautifully than “You’re Gonna Miss This.” Lyrically, the song describes a woman at three stages of her young life that she can’t wait to move on from, and how an older, wiser character reminds her to stop and appreciate the moment because it’s not going to last forever. Yeah, it’s both a “Where’ve You Been” and “Chiseled in Stone” song, but somehow manages to avoid scanning as even slightly stale. It’s another piece of evidence that Trace Adkins can be a great country artist when he wants to be. – Andy

Josh turner
Josh Turner and Trisha Yearwood’s stirring “Another Try” duet ranked very highly on our respective lists, but not quite as highly as our shared No. 1 song selection.

No. 2 – Alan Jackson, “Small Town Southern Man”

And from one modern neotraditional classic to another, we have one of my personal favorite Alan Jackson songs, and yet another reason why he’s always gone underrated as a writer and storyteller. No, I can’t say this tribute to his father is quite as immediate as “Drive” before it; this is more of a slow burn that takes its time detailing the man’s life. But 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. And Jackson has always been so adept at humanizing his characters, that this is just another classic in a career full of them. – Zack

No. 2 – Josh Turner feat. Trisha Yearwood, “Another Try”

Some beautiful and striking dobro and strings characterize this song and deftly support Turner’s impassioned vocal of a heartbroken man who had true love in his grasp and let it slip away. All he’s left with is the hope that someday, somehow maybe he’ll get another chance. Trisha Yearwood’s harmony vocal elevates this song to the stratosphere, proving that little things mean a lot. There’s not a lot to say about this song other than it is extremely well-written, performed by two stellar vocalists, produced impeccably and is one of the finest mainstream country songs of the decade. And hey, look, a Chris Stapleton co-write, years before most people were familiar with his name! – Andy

Before we get to our No. 1 picks, here are a few honorable mentions from the both of us:

Jason Aldean, “Laughed Until We Cried” (written by Ashley Gorley and Kelley Lovelace)

In which Aldean dropped the whole stoic thing he’s always got going on and revealed himself to be human on one of his finest songs. What happened to this side of you, man? – Zack

One of Aldean’s best songs by far. – Andy

Dierks Bentley, “Trying To Stop Your Leaving” (written by Brett Beavers, Dierks Bentley, and Jim Beavers)

It was tough leaving this one off; Dierks Bentley’s songs always tend to get buried in these features, and this is definitely one of his most underrated singles. – Zack

George Strait, “Troubadour”

Strait’s tender and sincere rumination on aging is yet another career highlight. It would make my top 10 if he had written it (just kidding, Zack). – Andy

Brad Paisley, “Letter to Me”

It says something about how wildly these lists vary when Brad Paisley would (and has) easily top(ped) my personal lists on at least three separate occasions in the 2000s, and I can’t even fit another one of his best into the top ten. – Zack

Brooks & Dunn, “God Must Be Busy” (written by Clint Daniels and Michael P. Heeney)

“Believe” received all of the accolades, but I can’t be the only one who regards this as the superior song of the two, can I? This song is admittedly theologically questionable and lyrically clunky at points, but I find its overall message that we all too often fail to think about those less fortunate than us to be extremely powerful. – Andy

Carrie Underwood, “Just a Dream” (written by Gordie Sampson, Hillary Lindsey, and Steve McEwan)

The last cut I made for this list, and arguably one of her strongest singles ever. – Zack

Montgomery Gentry, “Roll With Me” (written by Clint Daniels and Tommy Karlas)

I admit this is a song with a meaning I really need to heed more often. That second verse hits even harder in the wake of Troy Gentry’s untimely death. – Andy

Ditto what Andy said. – Zack

Kenny Chesney, “Better As A Memory” (written by Scooter Carusoe and Lady Goodman)

He’s always had an underrated strength for ballads, and this is another cut I wanted so badly to include within the top ten. – Zack

Phil Vassar, “Love is a Beautiful Thing” (written by Jeffrey Steele and Craig Wiseman)

I’ve always had a predilection for “location sketches”, for want of a better term, and by that I mean songs that describe a specific time and place and all of the people and events therein. This scene of a wedding and all of the various characters in attendance makes for a compelling sonic movie and a genial tribute to the power of love. – Andy

Heidi Newfield, “Johnny and June”

It didn’t quite make my top 10, but I completely agree with everything Zack said. A terrific love song and a rare example of name-dropping done right. Only some poor production choices hold it back. – Andy

And now, our No. 1 selections:

No. 1 (both lists) – Sugarland, “Stay” (written by Jennifer Nettles)

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 Jennifer Nettles at the front of the mix. But it was, and it became one of the duo’s biggest hit singles and undoubtedly their best. The power comes through in the 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, even to this day – 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, but for a moment in time, she dropped her guard and delivered her most emotionally packed performance to date, and easily my favorite hit song of this particular year. – Zack

Jennifer Nettles’ emotionally raw performance on this song is one for the ages. Noted for being a perfect companion piece to Reba McEntire’s “Whoever’s in New England”, “Stay” takes the bold and unusual step of giving voice and humanizing “the other woman” in what is presumably an extramarital affair. Nettles strikes every right note as the paramour who gradually comes to the devastating realization that yes, he’s stringing you along and no, he’s never going to leave her, resulting in a classic twist in the final chorus. “Stay” is minimally produced, firmly adult in its themes, and requires the listener to pay attention and think – qualities that have become increasingly scarce in hit country songs over the years. It’s the best single of the year. – Andy

Next: Favorite Hit Songs of 2007

One thought on “Favorite Hit Country Songs of 2008 (Collaborative Edition)

  1. I wasn’t paying much attention to mainstream country music in 2008, so I’m not familiar with some of these songs at all. I’ve never been a Sugarland fan, so I’ve don’t generally listen to their music on purpose, but I gave this one a try and it’s pretty good.

    Here’s my top 5:

    5. Shiftwork
    4. Love Story
    3. Gunpowder and Lead – the “Crazy Ex-Girlfriend” album is where I first discovered Miranda Lambert, so I listened to that album a lot. While this song is only my 6th or 7th favourite song on the album, it is one of my favourite hits of the year (based on the Wikipedia list).
    2. Another Try – great song and Josh Turner and Trisha Yearwood work so well together
    1. Small Town Southern Man – one of my favourite Alan Jackson songs!


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