Nov 16, 2022
Mainstream Country Wasn't All Bad This Year
Nov 7, 2022
New Video / Randy Houser / "Note to Self"
Apr 28, 2022
The 300 Best Country Songs: 2000-2009 (Part 1)
By Bobby Peacock
1. "Ain't Nothing 'bout You" by Brooks & Dunn (#1, 2001)
From the opening line -- "Once I thought that love was something I could never do" -- to quirkier later lyrics like "the list goes on and on and on,” this upbeat ode to that one true love is tailor-made for B&D. But they'd had such a tough time in 1999 and 2000 that they almost broke up. So what do they do? They turn everything up to 11. This one's packed with electric and steel, and one of the heaviest rhythm sections I've ever heard in a country song. Not just a great song on its own merits, it's also one that explodes from the speakers with a clear message: B&D are back, and they're bigger and better.
2. "All Comes Floodin' Down" by Brian McComas (did not chart, 2006)
This guy should have gotten more of a chance. A long-delayed debut album, a label re-structure, and a failed single left him in the indies. No doubt inspired by Hurricane Katrina, he tells of a preacher who prays for rain -- and then when the rain refuses to let up, prays for it to stop. His delivery is very warm in painting the picture of devastation and underlying efforts to curb it. (The fact that New Orleans has since witnessed Hurricane Ida as well adds another layer in hindsight.) I've never been to New Orleans, but it's a culturally unique and fascinating city whose vitality I fear for every time a major storm hits it.
3. "Almost Home" by Craig Morgan (#6, 2002-03)
While homeless people are a common trope in country songs, this one has always resonated with me by not resolving its central plot. The narrator rouses a sleeping homeless man with a selfless offer of help, only to be turned down because said homeless man was running through some fond memories. Were they daydreams of a happier time, or was he legitimately on the brink of death? Is he comfortable where he is, or is he about to be more comfortable in whatever afterlife may exist? The fact that this song can be such a fascinating character sketch, yet still leave so much room for interpretation, is ultimately is greatest asset.
4. "And the Crowd Goes Wild" by Mark Wills (#29, 2003)
I disliked "19 Somethin'" and I can't even remember "When You Think of Me.” But this was the most intriguing song Mark put out since "She's in Love.” Two amateurs -- one a race car driver, one a musician -- are both berated for their career choices and inexperience, but their hard work and dedication pay off in the end. (Is this the first country song since "Convoy" to use the word "chartreuse"?) Mark sounds like he's having a blast singing this anthem of determination, and it sounds like even his producer did -- what with the crowd noise and George Plaster's play-by-plays over the bridge.
5. "Angels in Waiting" by Tammy Cochran (#9, 2001)
One of the inevitabilities of life is the loss of a loved one. Tammy's story is even sadder, as both of her brothers died of cystic fibrosis at a fairly young age. Despite this, she sings of the good times she had playing with them, and how much she treasures their memories decades later. There is a relaxing comfort amid the bittersweet as she realizes that their death will also mean the end of their pain. This song's peak in airplay came right after 9/11, a time when many across the country were no doubt feeling the same sense of loss that she did -- and I hope at least a few were comforted by her words.
6. "Another Side of You" by Joe Nichols (#17, 2007)
The lady in this song stubs her toe and burns the coffee, then spends her day running the kids around in the minivan. All the while, the man in this song is uniformly sympathetic and supportive -- even when she's making mistakes, he admires her ability to do everything she can to keep the family functional. Obviously, not all relationships run this smoothly, but from the same genre that's given us far more goofy and condescending takes on the same material such as "Honey,” "Little Moments,” or "Mr. Mom,” it's extremely refreshing to hear someone just tell it like it is.
7. "Anything but Mine" by Kenny Chesney (#1, 2005)
The Kenny song that even non-fans seem to agree on. Summer love nostalgia is a staple of country radio, but this finds new ground by setting the story in medias res -- instead of looking back, we're in the moment. A richly-detailed moment full of local bands playing beachside concerts, boardwalk games, warm ocean winds, and great lines like "I tell her I love her and we both laugh but we know it isn't true / Oh but Mary, there's a summer drawing to an end tonight.” Chesney's performance and the production are pitch-perfect in carrying that melancholy feeling of "this is about to end, but I'm gonna enjoy it when I can.”
8. "Anything Goes" by Randy Houser (#16, 2008-09)
"Anything goes when everything's gone" is a killer hook. This guy's brokenhearted and clearly doesn't want to subject himself to a one-night stand -- but all bets are off because the woman he once loved isn't present to show any concern. Even better, we actually see at least one consequence come from this: "I'd wake her up and say goodbye, but I can't recall her name.” Houser sings the hell out of every line, filling it with the dejection and resentment called for in the lyrics. It's a shame it took him so long to return to this hardcore honky-tonk style, because he was clearly made for it.
9. "Anywhere but Here" by Brice Long (#51, 2005) or Chris Cagle (#52, 2006)
The guy in this song has gotten back on the wagon, all thanks to his broken heart -- even though he doesn't want to be drinking and pleads for his friend to tell his ex that he's literally anywhere else. It's such a credible story full of detail, down to said friend being sympathetic toward the narrator's backsliding, the woman's care for the narrator, and the narrator's attempts to try again. Amid similar piano and electric guitar-based arrangements, both vocalists turn in different yet equally compelling deliveries that convey determination through despair. This was a song that deserved to be released twice.
10. "Arlington" by Trace Adkins (#16, 2005)
It's hard for me to attach emotions to media involving soldiers; while I have respect for those who serve, I find that so often, that works focused on them fall prey to motivational clichés or worse, to aggressive jingoism. But this song gets it right. The portrayal is not only sincere and respectful to the fallen soldier, it also shows that he has respect for his fellow soldiers and his family. There's little talk of the actual battles, but that's not the song's intent. Instead, it's seen as a sort of bittersweet threshold that this dedicated man has crossed. And the tender delivery and fiddle just make it all the more emotionally resonant.
11. "Austin" by Blake Shelton (#1, 2001)
When he started out, Blake seemed like a throwback to early-90s neo-trad that had only recently left us. His first single takes the simple, commonly used concept of answering machine messages (remember those?) to convey a breakup. I love how the chorus changes each time to work with the progress of the song; I love the dual meaning of "Austin" being both a name and the setting; and I love that Blake was able to bring some grit to his voice right out of the gate. This song sounded fresh and unique then, and it still does today. If only Blake would return to songs like this instead of the bland, pandering mush he does now...
12. "Baby Girl" by Sugarland (#2, 2004-05)
Every member of Sugarland (we all know that Kristen quit after the first album) had spent much of the 90s and early noughts in Atlanta's folk circuit. So they speak from experience when they sing of struggling to make ends meet in the music scene -- begging mom for money, chasing the dream, and then finally making the big time. The fact that Sugarland's debut single actually did propel them from obscurity to fame is just another one of those little meta twists that I feel enhances an already great song. Jennifer's distinct voice and the smooth, harmony-driven production sure don't hurt, either.
13. "Back of the Bottom Drawer" by Chely Wright (#40, 2004)
Making several bad decisions that result in a good decision is such a common trope that it can sometimes be hard to find new material. And finding material is exactly how Chely puts a new spin on it: those wrong turns are immortalized in a box of random items. A hotel key, a champagne cork, Mardi Gras beads, and a poem on a napkin are among the detritus from past failures. Each one of these has its own story to tell, but they add up even more neatly into a story of someone who is clearly better off. It's an extremely original, well-written, and well-sung look at what's clearly far more than just a "box of stuff.”
14. "The Back of Your Hand" by Dwight Yoakam (#52, 2003)
Going back to just acoustic guitar, strings, and vocal, he offers a more mellow and intimate flavor that is still as Dwight as it can get (even if he didn't write it). He offers a lot of quirky observations such as "who's the dude with the extra role,” "pick a number, one to two,” and "you take two sugars with a splash of cream" to let his lover know: it's either him or me, but if it's him, we both know each other way too well to successfully break up without a lot of emotional stress left behind. Like most of his best songs, this one excels by taking an uncommon approach to common themes.
15. "Back That Thing Up" by Justin Moore (#38, 2008)
It's easy to cringe at a line like "throw it in reverse, let Daddy load it up.” But if you stick around long enough to hear "Ain't no time to play today, no rollin' in the hay,” you'll realize why I put this song on the list. In a song laden with double entendres, this is just about the only one I've heard that blatantly sides with the non-sexual interpretation. In fact, with his high-energy, high-twang delivery, I think this guy's too eager about his job to even think about anything sexual and in fact, may not even notice any such implications. Remember how blatant "Donkey" was about all of its dumbass sex jokes? This is the total opposite, and I think it should be commended for that.
16. "Back There All the Time" by Drew Davis Band (did not chart, 2005/#58, 2008)
Who hasn't hooked back up with an old flame at a restaurant, just to sit, chat, and reminisce? Friendly, conversational lyrics, a softly grained vocal underpinned by fine harmonies, and a great banjo hook do a lot to lead into a killer hook ("And you asked me if you ever crossed my mind / Hey girl, I go back there all the time"). The picture painted here is full of detail and charm, and it's performed to perfection. I thought these guys were done when 903 Music suddenly closed, but Lofton Creek gave them a second chance. And I can see why -- this song is too utterly charming not to get at least a few more ears listening.
17. "Backseat of a Greyhound Bus" by Sara Evans (#16, 2003)
My favorite song of hers for vastly different reasons than my other favorites of hers. Our protagonist is an unwed pregnant woman who flees small-town conservatism and ends up giving birth on the titular bus. It's credible, sympathetic, detailed, and ultimately positive. Evans' voice is right on point, a respite from the then-waning trend of belting divas; the bracing production is full of mandolin, acoustic guitar, and strings, showing that it's still possible to add pop without removing country. And that's probably what pushes the song to the top for me: it's not just a great song lyrically, but also in terms of composition.
18. "Bad Things" by Jace Everett (did not chart, 2005/#49 UK, 2009)
My props to whoever chose to make this the theme of True Blood, because it's a damn fine song. A few country singers have dipped their toes into a Chris Isaak gone rockabilly sound (Eric Heatherly in particular), but Jace probably did it best. There's an unusually high level of eroticism for country radio in the lyrics. But the proceedings are entirely in good taste, never feeling gross or TMI. Thank Jace's vocal -- playful yet sensual -- and the heavy rockabilly groove built on echoing electric guitar and Hammond organ. These "bad things" sound like some really good things from this talented guy.
19. "Bama Breeze" by Jimmy Buffett (#58, 2006)
"Margaritaville" is so firmly entrenched in pop culture that it's easy to forget Buffett is capable of far more. On its own, it's a somewhat lighthearted yet sincere ode to an actual bar in Perdido Key, Florida, and no doubt to other similar coastal bars like it across the Southeast. I don't know how true any of the stories are about drunken 21st birthdays and visits from Mick Jagger, nor who the various characters within the song are, but they all feel so real and vivid. The Flora-Bama was in the midst of being rebuilt after Hurricane Katrina at the time of this song's release; even absent this knowledge, I feel this one enough not to include it.
20. "Barbed Wire and Roses" by Pinmonkey (#25, 2002)
Youthful, twangy, lyrically sharp, and unafraid to use as much Dobro as possible, this song uses sharp imagery (literally) to describe an unfaithful woman. I especially like how the line "I found rust and I found thorns" leads into the hook. Pinmonkey had an amazingly distinctive sound right out of the gate. Maybe they were a bit too twangy for the mainstream, but they still had a damn tight thing going... only for it to abruptly disappear in 2004. But what we did get was one of the best hidden treasures of the decade. My only complaint is that lead singer Michael Reynolds' name is so generic that I don't have a clue what he's up to now...
21. "Bearing Straight" by Bering Strait (did not chart, 2002)
A rare country act from Russia crams a lot into a four-minute instrumental. Electric guitar/mandolin/steel rave-up, haunting Dobro and piano, then a calming guitar/banjo/fiddle outro, and it's all amazing. Maybe it's me reading some recent life changes into the title (gotta love a pun that still stands up on its own), but I feel this one in a way I rarely feel instrumentals. By shifting between electric and acoustic, minor and major, it feels like a sonic illustration of life. Just keep "bearing straight" through all the hard times and distractions, and the result will be just like this song: unpredictable, varied, and beautiful.
22. "Beautiful Goodbye" by Jennifer Hanson (#16, 2002-03)
One of the best opening lines I've ever heard skillfully compares a fading relationship to "the most amazing sunset" and "the end of a movie that makes you cry,” two vividly unique metaphors that more than set the scene for an amicable breakup. She knows it's for the better, even if she thinks that it's "so confusing / To do the right thing and be losing.” Hanson's voice recalls a slightly mellower Rosanne Cash, and the production is full of electric guitar and Hammond organ, adding Sheryl Crow and Dwight Yoakam to the list of obvious influences here. And that's a very "beautiful" mix I can get behind.
23. "Beautiful Mess" by Diamond Rio (#1, 2002)
One of many 21st century Diamond Rio songs to experiment with their sound without abandoning the core elements. Against a strangely nuanced production -- somewhat melancholic but still energetic at the same time -- this guy makes a lot of mistakes because he's too in love to concentrate. Harmonies are at full tilt here, as are the mandolin and electric guitar. And it's a clever, amusing, tuneful, and unique look at being in love. (Who else would sing about putting salt in their coffee?) Is it your words? Is it your style? All I know is that you're driving me wild. All "beautiful,” no "mess.”
24. "Been There" by Clint Black feat. Steve Wariner (#5, 2000)
After "Like the Rain,” Clint Black's quality seemed to drop off a cliff. Maybe he ran his well dry by insisting on doing all the writing himself. So what better way to find one last great song than by adding Steve Wariner? Lyrically, it may not seem conclusive -- they've both had some bad times that they don't want to repeat -- but by framing it as a back-and-forth, it seems like two guys sharing experiences and unintentionally bonding over it. This song also maxes out the whole D'lectrified experience with a buttload of acoustic guitar and harmonica interplay that never overstays its welcome. You know, I've been there, and I wanna go back to this song again.
25. "Before I Knew Better" by Brad Martin (#15, 2002)
Many songs focus on past mistakes, particularly those done when one was younger. This guy did a lot of stupid things as a teen or young adult before he "knew better.” This leads to a twist ending: the last thing he wishes he "knew better" about was breaking up with his lover. It's that sudden shift in the lyrics that caught my attention every time. Of course, the production -- neo-traditional when it wasn't in fashion, warm yet still energetic -- and the well-executed key change don't hurt either. This guy had some good stuff, but unfortunately radio didn't "know better" and he quickly faded into obscurity before his untimely death earlier this year.
26. "Bomshel Stomp" by Bomshel (#46, 2007)
Sometimes just being balls-to-the-wall silly is a surefire way to win me over. While maybe a little late to ride the "weird" wave that Big & Rich started, this song is still uniquely compelling to me by being, well, unique. The banjo and power chords production, the weird sound effects, the heavy use of sevenths -- it's a very distinctive sonic foundation for a "this is how you do the dance in the title" song (à la "Watermelon Crawl") that was originally intended as a joke. This clearly isn't going to be everyone's cup of tea, but damn it, I just want to let my freak flag fly and romp to the "Bomshel Stomp.”
27. "Break Down Here" by Julie Roberts (#18, 2004)
It's not uncommon to just start driving away from a relationship that isn't working. Even if your phone battery is low and you're almost out of gas, afraid that you'll run out. Not just run out of gas and end up sitting on the side of the road -- you might be crying on the shoulder of the road instead. The double meaning of "break down here" is extremely clever, and the little details throughout (I like how the mile markers change at either end of the song) give a sense of urgency and progress. Roberts also has a beautifully full-bodied voice that, combined with her song choices, has me wonder how she never managed to hit top 40 ever again.
28. "Breath" by Cledus T. Judd (did not chart, 2002)
My favorite from the country parodist, and not just because the target song (Faith Hill's "Breathe") is one of my least-favorites. It's also his sharpest lyric, matching the original far closely than many of his others do in terms of meter and scansion. Best of all, as a parody should be, it's funny -- line after line about someone having bad breath, and literally all of the jokes land. (Obscure references like "halitosis" and "Binaca blast" help.) Judd is often compared to "Weird Al" Yankovic for his prolificacy as a parodist, but this is one of the few times that he matched Al's quality and wit.
29. "Breathless" by River Road (#45, 2000)
"Nickajack" wasn't a fluke. This one doesn't have as ear-catching of a title, but it makes up for it with an unending energy and a ton of harmony. Cute lyrics that compare love to a dog chasing a squirrel (and subtle key changes) do a lot to enhance this already bracing tale of that big emotion known as falling in love. I also love the nod to Buck Owens' "I've Got a Tiger by the Tail.” This is but one of many entries on this list that faded into obscurity by means of a label closure, although at least Jeffrey Steele (who wrote it) and Little Feat also got to cut it. So I guess someone other than myself heard and loved this one...
30. "Bring It On Home" by Little Big Town (#4, 2006)
Back when LBT wasn't All Karen, All the Time... "Boondocks" was a great take on the country pride anthem thanks to its extremely nuanced vocal arrangement, but this was the song that convinced me they were here to stay. Philip Sweet's lead vocal is well, sweet when conveying the common trope of offering solace to one's partner after a bad day. While straightforward on paper -- outside a couple twists like "baby, let me be your safe harbor" -- the lyrics have a warm, conversational tone to them, and it's elevated by the calm yet harmony-driven production. By merit of being their most evocative, this is my favorite Little Big Town song.
31. "Bring On the Rain" by Jo Dee Messina and Tim McGraw (#1, 2001-02)
As I said in the '90s list, I could never get into Jo Dee because her you-go-girl shtick wore thin on me fast. However, she executed it best here by going for a slower tempo and a great hook: "Tomorrow's another day, and I'm thirsty anyway / So bring on the rain.” That lyric may seem absolutely haunting in hindsight given that the song was released only one day before 9/11, but even separating it from that, there's a lot to enjoy here. Jo Dee's voice is softer and more vulnerable than usual, blending greatly with Tim's to lend a more subtly slow-burning conviction free of cliché or hyperbole.
32. "Brokenheartsville" by Joe Nichols (#1, 2002-03)
I told you that I like unique song titles. As I was one of the ten people who bought Joe's debut album in '96, I was cheering for him when he finally got a real hit. "The Impossible" was a grower, but this one hooked me immediately. The twangy production, the bitterly funny lyrics ("He wore that cowboy hat to cover up his horns" and "Here's to the past, they can kiss my glass" are forever etched in my brain), the hard-country vocals -- this one is just great in portraying a man watching his woman get away with another man. With how chill Joe usually is, it's also cool to hear him recording something with some bite to it.
33. "Brothers" by Dean Brody (#26, 2008-09)
Another sympathetic soldier song that works with a different perspective. Here, the narrator is a young man expressing the anxiety over his older brother going to war. When said brother does come back, he is wheelchair-bound and has to be pushed around by the narrator. The song succeeds by keeping the bond between the brothers real, while not sparing us on what happens to the one in combat -- nor by resorting to patriotic soundbites or forced messages of hope. That their relationship can continue despite drastic, life-changing events is heartwarming and more importantly, real in a way that most songs like this aren't.
34. "Buy Me a Rose" by Kenny Rogers, Alison Krauss, and Billy Dean (#1, 2000)
Kenny Rogers was one of the most deserving comebacks of the 2000s. I already put "The Greatest" on the '90s list, but this one deserves as much praise. The production is beautifully minimalist at a time when that wasn't the style, relying on acoustic guitar and congas (not to mention two fine vocalists on harmony duty). It's already great in portraying a man trying too hard to please his wife with material objects. But then he gets to the bridge, where he reveals that he's the man who's just seen the error of his ways and has finally chosen to correct them. And it's that twist that makes this song such an endearing character sketch.
35. "The Call" by Matt Kennon (#33, 2009-10)
A person attempting suicide and a couple seeking an abortion both have their minds changed by a phone call. The heavy subjects could easily be mishandled without a careful read, but Matt and company keep things even-handed and realistic. The man in the first verse very well could have called a prevention hotline or other form of intervention, and the couple in the second verse aren't pushed in any obvious direction favoring or opposing their decision. Completing the package is a gruff yet sincere delivery that sounds as real as the situations it's portraying. I still remain amazed that he slipped through the cracks.
36. "Can You Hear Me When I Talk to You?" by Ashley Gearing (#36, 2003)
It'd be easy to scoff at a 12-year-old girl charting, but she makes it worth your while. Her voice is strong enough for the big time, and while the production is very pop-influenced, it's not overbearing -- light drums and strings lead the way. It'd be just as easy to dismiss the lyrics as trite and vague in their expression of not getting to say good-bye to someone gone too soon. But really, who hasn't experienced that? I love how the song keeps its smooth, heartwarming pace up until the very end, when she whispers "I miss you, Daddy.” That's an emotional payoff that hits all the harder because of how able she is to keep the buildup going.
37. "Can't You Tell" by Diamond Rio (#43, 2004)
One of their most interesting songs didn't even make it onto an album. Diamond Rio's strength has always been their wide variety of influences and near-exclusive use of their own membership. This one adds on horns and percussion without removing the key ingredients of the Diamond Rio sound -- tight harmonies, twangy guitar, piano, and strong rhythms -- to show this guy's desperate attempts to advance his relationship. There's a conversational quality to the lyrics, and the melody twists and turns all over the place. This was the last great Diamond Rio song before they began wasting their immense talent on badly-written Christian songs.
38. "Carlene" by Phil Vassar (#5, 1999-2000)
Although he already did the "conversation in a car" trick only a year prior as co-writer of Neal McCoy's "I Was,” Phil Vassar's first bow as a singer was far from a repeat. Here, the woman is an old classmate who's progressed from her humble beginnings, unlike the narrator; they reunite and catch up on everything they've missed. What sounds so simple when described is made excellent by way of sharp details (I especially like the "failed historian"/"valedictorian" rhyme) and a subtle nod to Vassar's own budding music career that doesn't feel forced. Add to that a chill yet still energetic vibe full of piano and personality, and it's clear why Phil had such a strong start.
39. "Carry On" by Pat Green (#35, 2001)
When I first heard this on American Country Countdown, I didn't like it. But then it grew on me. I think the more rough-and-tumble, guitar-stuffed approach to the common "let go of everything" approach was off-putting to 14-year-old me, but there's something I just kept coming back to that made me realize the unpolished truth. Sometimes all you need is friends, music, tacos, and beer to help let go of worldly stresses. In his distinctly Texas-flavored way, this song captures the feeling of "forget[ting] about [my]self for a while" that I get when I take a road trip with my mom and/or sister, or when I go to a convention with my friends,
40. "Change" by Sons of the Desert (#45, 2000)
Drew Womack's beautiful voice is as expressive as ever, and the production is every bit as crisp as their debut. The lyrics are the same kind of offbeat character sketches I've always been a sucker for -- a man hitchhiking out of Odessa, Texas and a woman impressing her man with new lingerie and a tattoo -- capped off with the perfect line "It's the human condition / A part of us wishes that life wouldn't get so tame.” Even the melody gets on the whole "change" thing by dipping into a lower key near the end. In short, it's a relatable message with a clever execution; sadly, it didn't "change" this band's fortunes.
41. "Chasin' Amy" by Brett James (#34, 2002)
The best of his inconsistent songwriting catalog is one that he actually sang. A strong down-tuned guitar riff drives this detailed story about having a fling with a pretty girl after graduation. After pizza, ball games, and late night radio, they part when summer ends and he's been pining for her since. It may not seem extraordinary when described, but I find it all the more relatable because it just sounds like something an everyday dude would go through. While his second turn as a singer didn't pan out, James would continue to write, including (spoilers) a few more entries further down this list.
42. "Cheater, Cheater" by Joey + Rory (#30, 2008-09)
I'm not sure which is the more ballsy move here: going full-tilt bluegrass (Dobro, fiddle, and all) at a time when that was very out of fashion, or working the phrase "white trash ho.” There's a sass and playfulness in which she calls out her man for being unfaithful -- a country music trope as old as the genre itself -- but it's that sense of originality that made this one pop even at the time. Rarely has an act who got their big break on a singing competition (I keep forgetting Can You Duet even existed) sounded so fresh and engaging out of the gate, and this one's aged very well to boot.
43. "Cold Day in July" by The Chicks (#10, 2000)
While the original Joy Lynn White verison is pretty in its own right, I think its the Chicks who have the definitive version here. Maybe it's the jangly electric rhythm guitar; maybe it's Natalie's voice; but there's something just a little "extra" about this rendition of this fantastic broken-heart lyric. "The moon is full, my arms are empty" is a great opening line, and the chorus paints such a perfect picture of the evocative environment. (And, being a Michigander, I've actually experienced cold days in July.) Seriously, why was this brilliant, beautiful, melancholy masterpiece left off the Essential album?
44. "The Cowboy in Me" by Tim McGraw (#1, 2001-02)
A song that didn't click with me at the time, probably because I was just too young. But now that I'm in my 30s, I can identify more fully with the self-defeating behaviors (most prominently, getting too fixated on the negatives to take stock of the positives) that Tim lists off here. And that would be good enough, but what really turbo-charges this song is the last verse (after a break from standard verse-chorus format, no less) where he reveals that he's got support in the form of a woman just as messy and imperfect as he is. At least by the terms this song uses, there is a little "cowboy in us all,” and that can make for a hell of a support system.
45. "Cry" by Faith Hill (#12, 2002)
Faith Hill's pivot to pure pop post-"Breathe" left a lot of people scratching their heads, myself included. And I was never that big a fan! But even though I despise "Breathe" and "The Way You Love Me,” this was one of the few times that Pop Faith worked for me. It's so much bigger than her usual fare and doesn't even try to sound country, but maybe that's for the better -- lines like "If I had just one moment at your expense / Maybe all of my misery would be well spent" and "I don't want pity, I just want what is mine" are incisive enough to call for a bigger delivery. And Faith delivers in a way that is "big" without blowing out my eardrums or settling for hackneyed lyrics.
46. "Dead Flowers" by Miranda Lambert (#37, 2009)
Dead Valentine's Day flowers, burnt-out Christmas lights (I wrote this in April and one of my neighbors still has those up), and worn-out car tires are interesting images for a relationship that's soured. If that sounds like a bunch of random and disconnected imagery, there is an internal logic that belongs on a game of Only Connect: she's so sick of him that she drives off in that car, leaving the lights and flowers in the yard behind her. The production leans heavily on an electric rhythm guitar that's both muted and reverberated, creating a sound as unusual as the lyrics in all the right ways. This is one of her most underrated cuts.
47. "Designated Drinker" by Alan Jackson and George Strait (#44, 2002)
It wasn't a single, but it charted so it qualifies. The hook is the level of wordplay that I've always loved in country, especially regarding the common "drowning my sorrows" trope. As is expected of Alan, the execution is mannered, traditional, and full of personality. But then King George joins in and the chemistry is instantaneous. This song sounds like two people who've become buddies after realizing that they're both drinking away their broken hearts, and as I've said many times, it's always good to know someone's got your back. Why couldn't this have been the Jackson/Strait collab that everyone remembers instead of "Murder on Music Row"?
48. "Devil and the Cross" by Halfway to Hazard (#50, 2007)
Like the parable of the Prodigal Son, the narrator wanders away from his father and gets lost in sin and extravagance. However, the father also undergoes an arc of his own, evolving from a stern fire-and-brimstone preacher (whose Bible is compared to a gun) to an utterly non-judgmental benefactor of forgiveness. Because he knows the truth: everyone is a sinner, but everyone can be forgiven, too. With how often I've seen Christian viewpoints distorted into weapons of hate, it's utterly refreshing to see a Christian viewpoint used for good. The twangy, clean, harmonious production doesn't hurt any, either.
49. "Diddley" by Elbert West (#56, 2001)
Engagingly in-your-face, this one starts off with a great line: "I wanna face my accuser / Point out the one who's comin' down on me.” And this guy has good reason to say that: he's gonna dance with that woman and take her home, no matter what anyone else says. It's simple on paper, but the lyrics are full of cute little details (not to mention a common factor on this list -- a break from verse-chorus-verse-chorus structure), and both Elbert's voice and production have the swagger to sell this utterly confident lyric. What you say don't mean diddley; this song slaps.
50. "Different Breed" by Carter's Chord (#52, 2008)
Speaking of songs that are engagingly in-your-face, this sister trio offers an interesting triplet-heavy melody and plenty of guitar, not to mention some tight harmonies, to shoot down stereotypes. Those other girls have fancy clothes and hair, even if the line "they'll do anything just to please you" indicates that all of the glitz is just for show. And they don't like how this smoking, drinking, unpredictable narrator has claimed the man in question, nor does she know why he's into her. There's a lot of internal conflict here, and it turns all three perspectives on their heads. A "different" song indeed.
51. "Dixie Lullaby" by Pat Green (#24, 2007)
A wonderfully unpolished tale of a wonderfully unpolished man. The narrator's father is described in loving detail throughout; even after the narrator leaves home, he still spreads his father's love on to his own kids. Even if you know the death is coming (as it often does in songs like this), Pat finds the right amount of emotional grit, to the point that he sounds on the verge of tears in the last verse. Even though my relationship with my father wasn't this consistent, I still feel that he loved me, and I have to keep the Kleenex nearby every time I hear this one.
52. "Dixie Rose Deluxe's Honky-Tonk, Feed Store, Gun Shop, Used Car, Beer, Bait, BBQ, Barber Shop, Laundromat" by Trent Willmon (#36, 2004)
I swear, the title isn't the only reason this is on here. Trent has a gritty and detailed style to set the scene ("this town ain't got a Walmart and never ever will"). I've seen so many small towns where nearly every business seems to be inside the same building. Unlike Trent, I've never seen any extremely attractive eye candy inside of such a store, but he completely sells me on this cute little story about pursuing her. (Why else would you buy 100 cans of Skoal if you don't even chew?) Just like so many other entries, this one is a sharp, witty character sketch with a winning delivery.
53. "Do We Still" by Rockie Lynne (#46, 2006)
Rockie Lynne has such a charismatic, weathered voice that sells everything he sings. However, being 42 at the time of your second single isn't usually a sign of career longevity (sadly). On the flip side, that age adds a great deal of warmth to this detailed take on a crumbling marriage. It's clearly nearing the end, as he can feel the tension without her even saying anything -- even if he admits they're "too tired to try and too scared to quit.” Between his vocal delivery and the strong slide guitar, not to mention the devastating hook "We said 'I do', but do we still?,” it's nearly impossible not to root for him.
54. "Don't!" by Shania Twain (#24, 2005)
I usually prefer Shania's up-tempos to her ballads, so it's interesting that a ballad is actually my favorite song of hers. There's an added warmth to the production (I like the contrast of the heavy bass strings and Dobro, plus the suspended chords in the backing vocals) and a huskier delivery than usual. It adds a uniquely moody atmosphere to her attempts to stop a faltering relationship. While the lyrics sound simple written out, they're delivered so convincingly that I wonder if she and "Mutt" Lange were subconsciously telegraphing their then-impending divorce. Either way, it's a different vibe that I find uniquely compelling in her discography.
55. "Don't Make Me Beg" by Steve Holy (#29, 1999-2000)
The very first cut for Steve Holy -- who I swear has more non-album singles than anyone else on the planet -- finds him nailing a countrier Chris Isaak vibe full of backing vocals, guitar, drums, and fiddle. (Wilbur C. Rimes' best production job by far.) There's a playfulness, even a subtle irony, in this man's attempts to spark a relationship. Between the ear-catching production, Holy's likable vocal, and the witty lyrics, this is a very original musical package that holds up extremely well. It's a shame that he only ever had two big hits, because if he was finding gems like this, he deserved way more.
56. "Don't Worry 'bout a Thing" by SHeDAISY (#7, 2005)
I tried not to make like, half this list consist of songs from 2005... Like most of SHeDAISY's catalog, this one excels at being an offbeat look at a common theme. Not only are the things being worried about delightfully silly ("ever found yourself in bed with Uncle Sam or Mickey Mouse?"), they're also self-deprecating ("ever found your last record in the bargain bin?") and even humbling ("remember everything will be just fine / If I laugh at yours then you'll laugh at mine"). The vocal arrangements, harmonica, guitar, and "blah blah blah"s help complete a package that's far deeper and unifying than its brightly-colored surfaces would suggest.
57. "Down the Road" by Kenny Chesney and Mac McAnally (#1, 2008)
I liked this song when Mac did it, again when Restless Heart cut it, and a third time with this version. Mac's addition makes the song seem like either two parallel stories, or a perspective shift on the same story. It's normal, healthy even, for parents to be concerned about their children's romantic interests. As is expected, Mac's lyrics are minimalist yet vivid, not to mention sympathetic (I especially like how the last line suggetss that Dad approves after all). The production is similarly understated, bringing both vocalists' strengths to the forefront and reminding me yet again of Mac's knack.
58. "Dream Big" by Ryan Shupe & the RubberBand (#27, 2005)
I usually hate songs that just list off a bunch of motivational phrases. But on the lyrical front alone, this already has the upper hand by actually having a theme, thanks in part to the repeated "when you X, Y" structure. Even better, it keeps from being too overly cheery with lines like "don't let them know that they have won.” "When you dream, dream big" is an insanely simple hook, but these guys sell it through a calming arrangement consisting entirely of acoustic instruments and fine harmony. Country music and inspirational messages have often gone hand in hand, but rarely have they been this beautifully simple.
59. "Drinkin' in My Sunday Dress" by Susan Haynes (#51, 2005)
A crisp, shuffling, twangy take on the Maria McKee song brings us through a lot of smoking and drinking and "what did I do last night?" panic. Details like cigarette ashes in coffee show just how messy the setting and the person singing it are. But best is how it ends: feeling guilty, she confesses to her preacher, who caps things off with the non-judgmental "remember who's beside you when it's no business of mine.” And that's what I think makes this song so compelling: the intentionally scattershot structure reveals the simple truth that everyone, no matter how "messy,” is a child of God.
60. "Drinkin' Me Lonely" by Chris Young (#42, 2006)
Chris Young's first single drew from the classic drinkin' and heartbreak tropes and found a good, sturdy, original hook. Details like "these tears I've been crying have left me bone-dry" keep the idea fresh, and the minimalist production leans heavily into the iv chord for some added sonic texture. And the vocal performance is top-notch, seamlessly moving from honky-tonk baritone to falsetto and back. Merle Haggard, Marty Robbins, and Mark Chesnutt are all obvious influences here, but the result is far from derivative. Unfortunately by the time we got to "Aw Naw,” this was already a distant memory of what could have been.
61. "Drive (For Daddy Gene)" by Alan Jackson (#1, 2002)
Alan's memories of a powerboat and an old truck both resonate with me; I used to go out boating with one of my mom's friends, and the road where Alan and his dad would dump trash sounds just like the dirt road behind my high school where we'd dump trash and pick berries (not at the same time). Add to that my memories of getting to use my aunt's riding mower for the first time, and... we're still not done. Because then Alan twists the premise and watches his own daughters drive a Jeep behind the house, letting himself -- and us -- know that some of the greatest memories of one's childhood can still apply to the next generation, too.
62. "Earthbound" by Rodney Crowell (#60, 2003)
My '90s list made it pretty clear that I'm a mess. When I'm feeling down, Rodney has exactly what I want. Faced with cynicism, negative outcomes, and advancing age, I can easily lose track of the good things. Sometimes all you need is a reminder -- the beauty of nature, well-placed advice, the mere fact that you're still alive, even any of the parade of famous people that "make me wanna stick around.” This song is mature and nuanced, yet accessible and relatable in delivering its message, and every time I hear it, I want to keep staying "earthbound" a while longer.
63. "18 Video Tapes" by Jason Meadows (did not chart, 2007)
I'm a sucker for original premises. A father, knowing that he will die before his son is born, leaves advice videos for his son to watch throughout his life. (Nowadays he'd probably save them on a flash drive, but I still think that's a clever idea.) And the advice given is far from cliché -- sure, he offers tips on playing baseball and fishing, but also on driving, hygeine, sex, and family. There's a palpable bittersweetness to the entire concept that mixes with the sheer originality of the premise to really make a song that deserved a far better fate. And having Vince Gill do backing vocals is never a bad idea.
64. "800 Pound Jesus" by Sawyer Brown (#40, 2000)
Sometimes it takes the most unexpected turn of events to turn around an unfavorable situation. The man in this song attempts to hang himself, but his attempt is stopped, and his life turned around, when he lands in the arms of a giant statue of Jesus. I went back and forth on whether I should include this, because I wasn't sure how tasteful the execution was. But then I saw a YouTube comment where a person said that this song actually prevented them from committing suicide. And if your song is literally saving lives, then you have clearly handled the tough subject with tact.
65. "8th of November" by Big & Rich (#18, 2006)
This succeeds by humanizing its soldier protagonist as a sympathetic man who did "what he had to do" and, decades later, pays tribute to those who did not survive like he did. I can't even begin to comprehend the mental, physical, or emotional strains of combat, so I have respect for anyone who can fight for their country. And speaking of "country,” this one handles the patriorism deftly by neither overdoing it nor choosing sides (which is downright shocking coming from John Rich). And the melody, vocals, and production are on point, making this pack quite the emotional punch even if you don't hear Kris Kristofferson's spoken-word intro first.
66. "Every Friday Afternoon" by Craig Morgan (#25, 2003)
My parents divorced when I was 4. When I was 12, my dad moved across the state and became a truck driver, thus limiting his ability to see me. I have no doubt that he wanted to see me more than he was able, although he did move back before his death. So I relate fully to this tale of divorce only pulling parents farther apart from a child that they both clearly love. While the circumstances are slightly different here -- it's the mom who moves further away after she gets a job offer in Boston -- Craig's emotionally nuanced delivery sells this story so strongly that I'd believe every second of it even without the emotional connection.
67. "Every Other Weekend" by Reba McEntire and Kenny Chesney (#15, 2008)
My apologies to the talented Skip Ewing, but I think Kenny fit better here. Unlike the previous divorce-themed song whose title also begins with "Every,” the focus is on the divorced parents. They both run down what they're doing during their respective custodies of the kids, only to drop one important detail. Namely, that both parents still have feelings for each other, but don't want to spill the beans. It's that emotional struggle that is meant for Reba's commanding, nuanced tone to an extent that rivals other heavy hitters like "Is There Life Out There" or "For My Broken Heart,” and Kenny's more than able to keep up.
68. "Famous in a Small Town" by Miranda Lambert (#14, 2007)
It can be a good thing to be locally famous, said the guy from a small town who won on Wheel of Fortune. But it can be a positive thing, to hear about gossip and minor achievements from the people you know. (I know I've sometimes recognized the name of the guy who got the first buck of the season.) By already being somewhat famous beyond her small town, Miranda seems like she's still invested in the local scene. It's also got a jangly production style that's more rootsy than Frank Liddell's work on her later albums. Despite some of the other entries on this list, I think sometimes small town songs can be enjoyable.
69. "Feel My Way to You" by Restless Heart (#29, 2004)
I always enjoyed Restless Heart, so I was jazzed when they reunited in 2004. And they did not disappoint. By keeping the yearning open-ended in the right ways (I could easily read it as being a plea to a lover, a friend, or God), the lyric is widely relatable yet still emotionally packed. And "feel my way to you" is a great way to express that. The sound is as lush and harmonious as ever. This is but one of many great entries on this list that unfortunately got cut down by a label closure, leading me to wonder how "Miracle" or "Every Fire" had fared as singles. But we still got Restless Heart, once more with "feel"ing.
70. "A Feelin' Like That" by Gary Allan (#12, 2006-07)
Unlike this guy, I haven't "been there, done that.” I haven't even been in love. But especially coming from Gary Allan, I buy the hell out of a seasoned veteran who's gone skydiving, dived the Great Barrier Reef, and run with the bulls, but still can't find anything that compares to the love he had with the one who got away. Sharp metaphors like "I got lightning in my veins and thunder in my chest" pair with Allan's rough-edged vocal and the hard-hitting, drum-heavy production to convey the grandeur of what he's singing about. While it would be easy to read subtext of Allan's wife's suicide into this song, it still emotionally soars either way.
71. "Fightin' For" by Cross Canadian Ragweed (#39, 2005)
An awesome band name, and an awesome band. What I like about Cross Canadian Ragweed is that they keep a punk rock energy and cockiness while still staying country. This one sounds like a messy, uneven marital dispute. He's up late drinking and talking to himself; she's angry enough to throw a phone at the wall. By adding a lot of overdrive and just as much snark, the portrayal is just as "messy" as the two characters. I particularly love the hook "you don't even know what it is that you're fighting for,” which just adds that extra level of bitterness and human imperfection.
72. "Flies on the Butter (You Can't Go Home Again)" by Wynonna Judd and Naomi Judd (#33, 2004)
Childhood memories are a funny thing, aren't they? So much of what I remember from my own childhood can't be relived anymore; no matter how many times I go back to my childhood house, my pets won't come back to life and the convenience store down the street won't reopen. Even though these details aren't even close to what Wynonna is singing about here -- I didn't like watermelon, for one -- they're delivered in such a richly nostalgic, warm, inviting, yet ultimately sad tone that captures that mood perfectly. If Lari White's version were a single (her husband wrote it), then it'd be on this list too.
73. "Flowers on the Wall" by Eric Heatherly (#6, 2000)
How do you take the best Statler Brothers song -- that timeless tale of the brokenhearted, self-deprecating loser keeping himself distracted and upbeat in the most mundane of ways -- and make it even better? If you're Eric Heatherly, you bring along your guitar and a ton of drums, and build up the best Roy Orbison-meets-Dwight Yoakam groove you can make. The result? A cover song that freshens up the song while keeping its spirit fully intact. His rockabilly swagger may have been a bit left-field for 2000, and label issues screwed him over, but I'm glad that Heatherly got any chances to make things about 20% cooler.
74. "For You" by James Otto (#39, 2008)
Can someone explain to me why the utterly cool "Just Got Started Lovin' You" didn't give him any momentum? Especially with a follow-up this strong? As often as breakups are portrayed in country music, this one aces it with a totally original premise. I'll do all these other things now that you're gone -- come back, forgive, or just never see you again. But find someone else? That's just asking too much. It's a highly original premise, and James sings the hell out of it against a less-is-more production. Literally every ingredient was in place for a second hit that just never came, and I'm at a loss as to why.
75. "Forgive" by Rebecca Lynn Howard (#12, 2002)
"That's a mighty big word for such a small man.” Sick burn. This one doesn't hold back on the rest, either. She's caught him cheating and calls him out on it without mincing words one bit -- all the while, being confused about why it would even happen in the first place. Her voice is as commanding-yet-vulnerable as the lyric calls for (especially on the chorus), and other great lines like "Forgive and forget, relive and regret" fill in all the right details. I'm at a loss as to why MCA didn't promote any other singles off this album, but the one they did pick shows that Howard deserved more attention.
76. "4th of July" by Shooter Jennings and George Jones (#26, 2005)
Waylon and Jessi's son proved himself immediately. "4th of July" is one of those songs that just blasts out of the speakers with heavy drums and guitars. Jennings' gruff voice sets the scene of driving down the road in an RV with the one that got away and blaring some George Jones (which is humorously alluded to at the end). There's a sense of wanderlust and an unflinching energy that keeps this song firing on all cylinders even when the lyrics turn introspective ("And I'm looking for you in the silence that we share"). And it's rare that a song can pull off brains and brawn with equal measure.
77. "The Fun of Your Love" by Jennifer Day (#31, 2000)
Jennifer Day, who was 21 when she cut this, hits the right level of youthful energy without sounding bratty or strained. I like the way that the backing vocals form a call-and-response reminiscent of Ty Herndon's "It Must Be Love,” and the uncommon imagery for a love song, like "chain reaction" and "you draw the line, I'll pay the fine.” Muscle Shoals powerhouse Robert Byrne finding the right balance of country and pop in the production didn't hurt, either. Despite a strong first single and some soundtrack cuts, radio didn't bite. Which is a shame, because this was far better than most of LeAnn Rimes' output at the time...
78. "Georgia" by Carolyn Dawn Johnson (#25, 2000-01)
She thought she had it all together, but he's just been a deadbeat. Not unlike "Shut Up and Drive,” the solution is to drive away and blare the radio. Unlike in that song, the confidence is far more subdued -- she's clearly had a lot of failures here and is trying to push through them by any means possible. So she's just gonna keep driving with all of her stuff until there's no chance of ever coming back. There's an assurance in her vocals, and a lush and varied production behind her to "drive" this song along just like the theme suggests. Could this be a prequel to "Break Down Here"?
79. "Get Outta My Way" by Carolina Rain (#28, 2006)
Picking up where Pinmonkey left off in terms of harmonious twang and grit, Carolina Rain unfortunately got ensnared in single delays and label closures. Thankfully, their lone album was worth the wait. I love how conversational the verses are in terms of trying to catch the eye of an attractive woman ("Before she runs like a fast little filly / She's a five-alarm fire, a hot bowl of chili"), with every single second sounding charming and witty, not creepy. Rhean Boyer's lead vocal matches that tone perfectly, and the harmonies and banjo are country to the core. These guys deserved better.
80. "Get Over Yourself" by SHeDAISY (#27, 2002)
SHeDAISY deserved a better fate, especially within the context of their sophomore slump Knock on the Sky. Maybe it was the weird drum machine/power chord/fiddle intro; maybe it was the quirky lyrics being turned up to 11 ("Such a busy little drone that your heart beats in monotones"); whatever it was, this was an extremely aggressive, unique song (even, and especially, by SHeDAISY's already oddball standards) that fully dresses down a spineless, dramatic man. The back-and-forth vocal arrangements are just an extra little touch to fully make this one the bizarro-world "Forgive.”
81. "Getaway Car" by 4 Runner (did not chart, 2003) or The Jenkins (#38, 2004)
Another song that a ton of artists have gotten to, ranging from Susan Ashton to Hall & Oates. These two lovers got away, but now they've got a chance to get back together, leading to a twist on the term "getaway car": said car is one they'll be driving in together to capture that sense of wanderlust that I, the listener, love so much. It's such a fresh, relaxing take on a common theme, and once again we find two different versions that work equally well. 4 Runner's is a bit more peppy and harmonious, but the relaxing vibes of The Jenkins' version are equally compelling, so I'm declaring this one a dual entry.
82. "Gettin' Back to You" by Daisy Dern (#43, 2001)
Unlike "Georgia,” this song's narrator is headed back to the love she left behind. We don't know what drove them apart, but that just makes the song all the more mystifying in the right ways. Whatever it is, she can't shake it, and she's driven -- literally -- to get back to the one that she loves. Even if it means a snowy mountain pass in Colorado or the expanses of North Carolina, she'll admit her wrongs. The production is interestingly sparse and relies on uncommon chord patterns, along with Dern's warmly nuanced vocals, for one of many gems on this list that somehow never made it onto an album.
83. "Go Back" by Chalee Tennison (#36, 2001)
Two standards in one: the truck-driving song and the "use the chorus three times in different scenarios" song. Here, the trucker falls in love with a truck stop waitress, and after they marry, he nearly loses his life in an accident. Note that I said "nearly" -- this song subverts the common expectations in a manner not unlike Alabama's "Roll On (Eighteen Wheeler)" in that the trucker actually survives (even if he does get injured enough to "slip into the light"). All three uses of the phrase "go back" have a completely natural flow, aided greatly by Tennison's tender read and the beautifully spare production.
84. "Go Home" by Steve Holy (#49, 2005)
Another fantastic take on relationship advice. Here, the son finds his father in a bar and asks for help, which comes in the brilliant phrase "Leaving don't get you nowhere; you're just gone.” How does the father know? Because he's doing just that, hiding in the bar instead of facing his problems. Cue the revelation that maybe they've both got some issues they need to fix. And it's this unique sense of bonding -- not to mention the unspoken implication that they do both leave to patch things up -- that adds an extra human element. Why did Steve Holy have so many great singles that didn't even make it onto an album?!
85. "Gone Either Way" by Ray Scott (#53, 2006)
"My Kind of Music" turned a few heads, but this proved Ray Scott was no fluke. On top of a highly infectious guitar riff, this guy frankly lays out the situation. This relationship is so blatantly over that nothing can save it -- even if her friends will talk about it later on -- so he just tells her to get on with it. By having a matter-of-fact swaggering baritone and a sharp lyrical sense ("Baby, you could leave or you could stay / You're gone either way"), Ray knows what he's talking about. While the majors didn't know what to do with him, he's at least maintained a steady indie following, and I think it's songs like this that gave him staying power.
86. "A Good Day to Run" by Darryl Worley (#12, 2000-01)
My mom did 5K runs when this song was out, so this was her theme song. And for me, the eternal sucker for wanderlust songs, that also meant going all over the state to cheer her on. So we both got something different but unifying out of this. The production is evocative and spacious, just like the wide open spaces this guy and his lover are finding "down a two-lane highway.” Worley had a knack for charismatic and interesting character sketches before he dove headfirst into politics, and this was the best off his first album. Every time I hear this one, I feel like my worrying days are done.
87. "Good Hearted Man" by Tift Merritt (#60, 2004)
The horns, backing vocals, and Wurlitzer sound like Sturgill Simpson's "All Around You" traveled back in time by way of New Orleans, and the throaty assured vocals bring to mind K. T. Oslin by way of Jewel. As often as the "I thought I was a free spirit until I found the right one" card is played in country, this is the first time I can recall seeing it from a female perspective. I love the line "Hey, sweet woman, you know you're not a child,” presented as a wake-up call to a former rebel who's found Mr. Right ("So trading in that hard-headed kid for a woman I can give to him" is a close second). There are a lot of different ingredients, but the resulting stew is good and hearty.
88. "The Good Stuff" by Kenny Chesney (#1, 2002)
As much of a staple as the "conversation with a bartender" is in country (see "When the Bartender Cries" on the '90s list), this one just feels natural and down-to-earth (a bit of a shocker from Craig Wiseman, who tends to overshoot this kind of song). The dual purpose of the phrase "good stuff" is perfectly executed wordplay, and it only gets better from that. We learn so much about the bartender's life and what drives him to dish out the (very solid) advice to a brokenhearted man in need. This song shows just how thoughtful Kenny is at his best, and it's deservedly one of his cornerstone songs.
89. "Good to Go" by John Corbett (#43, 2006)
I don't know much about John Corbett's acting career, other than some vague memories of watching Northern Exposure as a kid. What I do know is that he's a convincing country singer. Sure, everyone's done those songs where someone takes stock of their life and realizes that they don't have it all that bad. But this one has an extra degree of humility ("the generous and mostly undeserved blessings that I've had"), and even some narrative continuity to make it not just seem like a list of platitudes. Of course, Corbett's laid back yet gritty everyman delivery sells the message, and a well-placed harmony vocal from Sarah Buxton doesn't hurt, either.
90. "Goodbye Earl" by The Chicks (#13, 2000)
Yeah yeah, another chance for me to gush about a Dennis Linde song. But under the black comedy of Earl's abusive asshole ways and the Chicks' bracing, self-aware performance is an uplifting message. Not everyone has a helping hand to get out of an abusive relationship the way Mary Ann helped Wanda, and while the Chicks (and presumably most fans) clearly do not support murder, I think most of us can support using the power of friendship to get out of a bad situation. I've read social media comments from people who said this song helped them find the strength to escape abusers. And just like "800 Pound Jesus,” I think that's a sign the message came through loud and clear.
91. "Goodbye on a Bad Day" by Shannon Lawson (#28, 2002)
The setup is a simple breakup, but the execution is impressive. Details like "I've seen that look, I can always tell / It means 'stay away from me and go straight to Hell'" add nuance, especially in how Lawson sings the hell out of every note. And the production is probably the best part. Power chords and string sections, along with some fluttering synths, are sure to set off "not country" alarms. But I think they do a fantastic job at keeping the sound powerful and dramatic without being over-the-top -- especially when the song just explodes with emotion at the end. This song sounds like a guy who's "whole world's gone wrong,” and is all the stronger for it.
92. "Happy Endings" by Lee Brice (#32, 2007)
This song came out at the same time as Jack Ingram's "Maybe She'll Get Lonely,” another song about hoping that a broken-up lover will have a change of heart. Unlike Ingram's utterly forgettable cliché-fest, this one is surprisingly packed with detail. We know why she left and who she left with, and there's realization that his expectations are unrealistic ("I ain't setting myself up for a fall"). But even taking away the comparison, this is an extremely well-structured song on its own merits. Just like "Goodbye on a Bad Day,” the string-heavy production and dramatic yet gritty vocals elevate it to greatness.
93. "A Hard Secret to Keep" by Mark Chesnutt (#59, 2005)
As described by the second verse, this is "cheater's paranoia" at its finest. Little details are the focus here. His attempts to curb a slip of the tongue or cover up a small makeup stain on his shirt, and even how he stays up late to read just so he won't talk in his sleep, are all interesting and personality-driven touches to the commonplace theme. Even the minor-key melody, minimalistic production, and the way he sings the line "how much longer can I live this double life I lead?" suggest how terrified this man is about accidentally blowing his cover. It's hard to root for the cheater, but this song makes me want to.
94. "The Hard Way" by Pam Tillis (did not chart, 2007)
"Why you gotta learn the hard way?" Pam Tillis is asked several times in her life -- every single time, from falling out of trees to getting in a car accident (that really did happen) to the ins and outs of relationships. And every single time, she admits that she's the one who got herself into all of these unfavorable situations. With all of these bumps and scratches, she's even relucant to believe that a new love is the one; after all, she's been wrong before. This is the first single she co-wrote since "It's Lonely Out There,” and while every bit as vulnerable and personal, "The Hard Way" is considerably more optimistic at the end.
95. "Harder Cards" by Kenny Rogers (#47, 2002)
Speaking of rooting for people who make questionable decisions, how about a song about a crooked cop? He is about to arrest a woman who shot her husband to death, but upon realizing the circumstances of the situation -- the husband was abusive to her and their child, and an alcoholic and drug addict to boot -- the cop instead frames the scenario to make it appear as if the husband had committed suicide instead. Rogers' gruff delivery is as nuanced as this song's storyline, perfectly illustrating that not everything can (or should) be morally black-and-white.
96. "He Oughta Know That by Now" by Lee Ann Womack (#22, 2005)
"I May Hate Myself in the Morning" was a welcome return to neo-traditional form, but the follow-up proved not to be a fluke. There's a tension in every line about a flagging relationship, from "I don't need to wonder where he is, but I do" and "couldn't be much worse if I were gone, and in a way, I am.” .. only for said tension to resolve in the last verse when she finally dumps him. Womack's voice hits on some Dolly Parton-tier shadings, and the crisp production is full of acoustic guitar and mandolin. It's a throwback in a lot of ways, but modernized and nuanced in just as many. It's one of her best, and you oughta know that by now.
97. "Heather's Wall" by Ty Herndon (#37, 2001-02)
Another crime drama; unlike "Harder Cards,” this is about an innocent bystander caught in the crossfire during a bank robbery. The last verse makes it clear that he's about to slip into the light; there's no hope of recovery, just the comfort in knowing that his "love will last forever" over his dying visions of his wife. Ty is as impassioned as ever, and the production mixes a heartbeat-like electronic drum, soaring guitar, and big backing vocals to heighten the drama without ever feeling over the top. This is the kind of tense, sad song that I just love, and it's unfortunate that bad timing made it slip through the cracks.
98. "Heaven" by Los Lonely Boys (#46, 2004)
A combo platter of genres: Latin, country, rock, pop, and some of the best sound design I've ever heard. The guitar, drums, bass, and organ are all crystal-clear yet still full of life, and the Garza brothers' harmony is tight and soulful. There's a yearning to the hook "how far is Heaven?" as he pleads for more time to right his wayward life. The constant Christian imagery never feels forced or overdone. (Redemption arcs are great, but like Emmylou Harris' "Thanks to You,” it's great to see the moment before.) I could list fifty more reasons why this is one of the greatest songs of the 21st century in any genre. Why did these guys not catch on?
99. "Help Somebody" by Van Zant (#8, 2005)
Advice songs are a dime a zillion, but this one already sets its sights higher by characterizing the people dishing out the advice. One of my favorite character archetypes, no less: the feisty elderly person (in this case, the narrator's grandparents). And the advice they give out is solid stuff, too: don't drink too much, be nice to people, and be yourself -- "It's better to be hated for who you are than be loved for who you're not" is truly one of the best and most relatable lyrics I've ever heard in a song. The Van Zant brothers give a playful, gritty delivery worthy of both Southern rock and country.
100. "High Cost of Living" by Jamey Johnson (#34, 2009)
This man sounds like a total screw-up who threw away a relationship, a job, and a home in favor of drugs, alcohol, and prostitutes. Every line is absolutely golden (I especially like "This prison is much colder than that one that I was locked up in yesterday"), but kept from becoming too bitter or bleak by an undercurrent of remorse. It's clear, not just through the lyrics, but also through the rough-and-tumble vocals and production, that he's starting to see the error of his ways. And that's ultimately this song's greatest asset: perfectly encapsulating that first step in a major moral turnaround.