When she turns you down for a date to the Sawyer Brown concert
Apr 14, 2022
Mar 17, 2022
RIP Bad Guy.
Sep 30, 2021
Editor’s notes: These are Bobby’s picks - not staff selections. They are in no way predictable; you might even call them eclectic, but I like that. They are in alphabetical order, not ranked. I added a few links in the song titles, particularly a few more obscure choices, and there are a few videos scattered throughout. This is the 3rd and final edition. Here’s part 1 and here’s part 2 if you missed them. ~Trailer
By Bobby Peacock
201. "Ready to Run" by The Chicks (#2, 1999)
Speaking of songs off the Chicks' Fly album... Pennywhistles are freaking cool, and we need to use them way more often. This very heavily Celtic-tinged number captures a youthful energy. And that energy is called on to convey -- what else? -- a bride who gets cold feet and ditches her own wedding because she just wants to have some fun. Natalie imbues the song with the right amount of sass, and the melody is great, but it's really that fiddle and pennywhistle combo that burrows this so far into my brain. I guess sometimes all I'm ready to do is have some fun, too.
202. "Rebecca Lynn" by Bryan White (#1, 1995-96)
Skip Ewing knows how to be cute and charming without going over the top, and this may very well be the best example of that. The lyrics are extremely colorful and specific in their portrayal of a childhood romance blossoming into adulthood -- we get all these names and scenarios, and the utterly matter-of-fact realization that their having a child is a "common little miracle". I don't think any singer other than Bryan White at age 21 could have imbued just the right balance of youthful energy and mature thoughtfulness that hits me right in the feels when I least expect it.
203. "Remember When" by Ray Vega (#56, 1996)
Rarely has remembering a lost love been so... catchy. Big, spacey, guitar-heavy production and a soft yet impassioned vocal give an unusual sense of atmosphere and loneliness lightened by a heavy dose of "na na na"s. And the overall lyrical craft -- I remember all of these very specific things, but "all I wanna do is remember when" -- mines extremely new material out of a common hook. Almost nobody even knows about this song because the album was never released, but I hope that my inclusion of it here drives you to remember "Remember When".
After leaving the majors, the Bellamys got more experimental. This harder-than-usual number for them points out that sometimes, just about any music becomes 100 times better in the heat of a great moment. (I especially likes how it touches on winning radio prizes, something that our family did a lot.) To me, it's almost a meta-commentary on how a good enough memory can boost even a silly little earworm. You know, like how a song like this keeps popping in my head every time I research this extremely interesting duo.
205. "The River and the Highway" by Pam Tillis (#8, 1996)
Two people in an incompatible relationship are allegorically portrayed as a river and a highway; the metaphors are cleverly chosen, and the first two choruses are tailored accordingly. I also like how the line "every now and then, a bridge crosses over" actually occurs in the bridge, and especially how the third chorus is just the first two laid on top of each other. Just like album-mate "It's Lonely Out There", Tillis' vocal is more downbeat but all the more evocative alongside moody, minor-key melody and production.
206. "The Road You Leave Behind" by David Lee Murphy (#5, 1996)
It was a toss-up between this and the rightfully lauded "Dust on the Bottle", but I felt that the underdog deserved some attention. Like "Dust on the Bottle", this one has a nearly universal life lesson conveyed through gritty storytelling. I was raised by a mom who always went out of her way to help others because she felt it was the right thing to do -- just like the narrator being on both ends of some car trouble in this song. In a way, it kind of forms its own trifecta with "The Chain of Love" and "Help Somebody" to portray this extremely relevant message.
207. "Running Out of Reasons to Run" by Rick Trevino (#1, 1996-97)
One of the more joyous takes on "one true love". Although Trevino leaned closer to Nashville formulae than the aforementioned Mavericks or Emilio did, his material never lacked in passion. And this was the point where he really started to find his own style. There's a palpable sense of joy when Trevino, 25 at the time this song came out, completely shuts down the sense of wanderlust you think the first verse is going to set up. It's such a well-executed first verse twist that you're more than engaged for the rest of the song, and his youthful, energetic delivery helps sell it.
McBride & the Ride had a great sound anchored by Terry McBride's distinctively twangy voice, and their biggest chart hit (co-written and originally cut by a pre-Brooks & Dunn Kix Brooks) paints a very convincing picture. A man politely asks another not to commit adultery with his wife in a very even, measured tone. He worked hard to get the relationship going, and feels bad for letting things slip enough for her to even consider cheating. Lesser hands probably would have made this idea preachy virtue-signaling, but the lyrical and musical talents create an extremely likable end product.
209. "Sawmill Road" by Diamond Rio (#21, 1993-94)
There actually is a Sawmill Road not too far from me, and this song makes me think of it. Three friends grow up in a small town and all get caught up in the nightlife; the other two move on, but the narrator stays behind. But instead of being preachy small-town conservatism, the focus is on the passage of time, memories of the past, and concern for the well-being of others. While the band admits that they rushed this album, both this song and "In a Week or Two" showed that they could still find some treasure.
The man behind the definitive version of Richard Thompson's "Tear Stained Letter" charted for the last time with -- what else -- a Dennis Linde cut. Death of a broken heart is a common trope, but here it's adeptly built out into crime metaphors. A body outline, dusting for fingerprints, ransom, and a "blunt goodbye" all fill out the clever expansion of this image to perfection, while hinting at the darker themes that would permeate some of Linde's later writing. Sonnier, as usual, gives a spirited vocal and plenty of accordion.
211. "The Secret of Life" by Gretchen Peters (did not chart, 1997) or Faith Hill (#4, 1999)
"The secret of life is there ain't no secret / And you don't get your money back" is one of the greatest lyrics in country music. And it's at the end of this interesting tale of two men pontificating at a bar. They offer all kinds of theoretical "secrets", each of which could be convincing on their own, until reaching that amazing conclusion. Granted, lines like "One of them says, 'you know, I've been thinking ' / Other one says, 'that won't get you too far'" are just as strong. While Faith's version is a bit glossier, I think that both she and Gretchen give equally beautiful reads, so screw it, this is another double entry.
212. "Seminole Wind" by John Anderson (#2, 1992)
I'm surprised that the environmentalism of the '90s didn't seep into country more often. This one is superbly sung and arranged on all accounts, giving an almost ghostly feel at times (I keep telling you that Dorian mode is criminally underused). Its lyrics manage to touch on destruction of natural land for profit, the beauty of the Everglades, and even a mention of war chief Osceola (oh, and otters -- how many other songs mention those?) to paint a picture of a decently educated man defending a worthy cause without being preachy.
The twangier Sara gets, the more likely I am to dig her. This one feels like one of the quick, simple 1960s ditties you'd expect to get to #7 and then quickly become forgotten for decades until someone digs it back up -- and it's all the better for it. Her performance is playfully unsympathetic to a man who's left her, and has now gotten dumped by the next lady in line too. There's just so much that is said without using a lot of words (in particular, I like "Excuse me for my lack of sympathy, I don't mean to be cruel"). And it sounds extremely country, to boot.
214. "Shameless" by Garth Brooks (#1, 1991)
I like Billy Joel, but even he admits this is the better version of his own song. The shifting song structure and powerful guitars of the original prove Joel more than capable of getting his Jimi Hendrix on. No stranger to both influences present, Garth saw the underlying country lyric (it is, at its core, the common trope of "I didn't think I'd love anyone until you came along") and seamlessly added enough steel guitar and twang without removing any of the things that made the original work -- and in doing so, he proves that maybe there is some merit to this whole "arena country" thing after all.
215. "She Can't Save Him" by Lisa Brokop (#63, 1995)
Mom spent a great part of her marriage fighting my dad's alcoholism until they divorced. When this came up on my playlist, I asked her if she ever felt like the woman in this song -- clearly trying her best to keep him on the right track, no matter how far he strays from it, only to realize that the final move is his. And sure enough, she said yes; she remembers so many situations just like Lisa's character in the song (maybe not the nightmares of being pulled underwater). I would love to believe that my dad was "saved" before his death because I, too, knew there was a good person underneath it all.
One of the best Vince Gill songs not actually sung by Vince Gill. The lady in this song has been burned by love so many times that she's given up -- a mood that I, an openly aromantic person, can certainly relate to. Fairy tales are such an overused image for love that it's great to see someone deconstruct them, and Jon does this so effortlessly: a sword in the stone, knight in shining armor, etc. The production and vocal are extremely relaxing as well, and like so many other Randall cuts, it's a shame that this one didn't even get to be on an album.
217. "She's in Love" by Mark Wills (#7, 1999)
I'm not a big Mark Wills fan, but his was his best. While one might consider the "we can still be friends even though I've found someone else" premise derivative of JMM's "Friends", and the line "I just want what's best for her, so I lied" indebted to "Just to See You Smile", I feel that the result is greater than the sum of its parts. Wills' vocal is more emotive than usual, mainly due to him not relying as heavily on his head voice (and singing his own backing vocals for once), and the lush classical guitar-and-mandolin production makes for an extremely pretty listen overall.
218. "She's Sure Taking It Well" by Kevin Sharp (#3, 1997)
Kevin Sharp is an extremely likable and sympathetic artist, as he was a cancer survivor and affiliate of the Make-a-Wish Foundation. Thankfully that likability also came off on record, starting with his warm cover of the Tony Rich Project's "Nobody Knows". And that song was no fluke, as the followup is even better. These are just so many great damn lyrics all in a row: "...give each other some space, but I never dreamed it would be miles", "something isn't wrong enough", "melting like sugar in the rain..." and the melancholy production matches Sharp's borderline-tearful delivery to a tee.
219. "Ships That Don't Come In" by Joe Diffie (#5, 1992)
Joe Diffie is so associated with novelty that his skill as a balladeer often gets overlooked. The heartbroken narrator meets an even older man who imparts some wisdom on the human condition. Even people who have had negative life experiences have gotten to live life at all; there are others who are worse off, and being alive means you haven't run out of chances. Sometimes I feel like I've wasted too much of my life, but knowing how much I still have left is a ray of hope. And I think this song convinced me.
220. "Shut Up and Drive" by Chely Wright (#14, 1997)
The narrator is rambling to herself as she tries to drive away from a relationship that isn't working out. She keeps calling herself out as an an indecisive fool who ignores warning signs and lets her guard down. Every time I hit one great line in this song, an even greater one follows it. In just a few moments we go from "your heart has a way of making you stay" to "you'll only miss the man that you wanted him to be" to a blunt "get out of here". Wright's voice is right on par, packing an urgency that drives this song.
221. "Since I Don't Have You" by Ronnie Milsap (#6, 1991)
Ronnie was no stranger to revitalizing doo-wop standards, as "Lost in the Fifties Tonight" already proved. But instead of staying fully true to the doo-wop origins, he goes for a much bigger style. Full of keyboards, strings, and sax, it also boasts one of his best and rangiest vocal performances (especially near the end). While one might be tempted to dismiss such an arrangement as dated, especially in the post-class of '89 world, I find it to be a refreshing throwback to some of the more dramatic country-pop arrangements of the '70s and early '80s.
222. "Small Town Saturday Night" by Hal Ketchum (#2, 1991)
Hal Ketchum's folk-meets-rockabilly approach paints a complete picture of two small-town folks doing what small-town folks do on a Saturday night: they get drunk, raise hell, and shoot the breeze. The first two verses are already poetic in their portrayal of just that, but best of all is the third verse: "Lucy, you know the world must be flat / 'Cause when people leave town, they never come back". It's a perfectly executed, nostalgic, bittersweet character sketch that caught my ear when I was only 4, and still holds up amazingly to this day.
223. "Smoke Rings in the Dark" by Gary Allan (#12, 1999)
This was the song that first made me stand up and notice Gary. Forecasting the gloominess of Tough All Over, this one emanates bitter dejectedness from the first note. This guy has hit rock bottom and is now sitting outside, smoking and drinking and musing over his broken heart. (It even sounds like it was a mutual breakup; they both tried to fix it and failed.) It's such a moody picture, paired with a very well-executed falsetto and extremely downbeat, evocative production that leans heavily into spacious electric guitar and haunting background vocals.
224. "So Much Like My Dad" by George Strait (#3, 1992)
Being so much like one's parents can be a good or bad thing. However, it seems that the guy in this song took the phrase positively, and is now turning it on its head. He's on the verge of a breakup, and asks mom for her advice in keeping a relationship alive -- since after all, he's "so much like" the guy to whom she's still married. Sometimes it's best to ask for help from an experienced party (a theme that does seem rather underused in scenarios like this). I could almost see this being a sequel song to "The Chill of an Early Fall".
225. "Some Kind of Trouble" by Tanya Tucker (#3, 1992)
We've all got "some kind of trouble" in our lives. This lady is late on her rent, her man's cheating on her, and she's lost her job. She turns to her preacher, who points out the truth -- "All God's children got to deal with their own kind of trouble". I'd like to think that she finds her way out of all of this after everything goes wrong, but in the meantime I'm just stunned by the truthful simplicity of that last line. (Another gem from Mike Reid.) I especially like the production with those heavy backing vocals, slide guitar, and triplet tom-tom beats.
226. "Something in Red" by Lorrie Morgan (#14, 1992)
How often is an entire story told purely by outfits? It's an extremely original concept, and it's done to perfection here. While one might consider the massively orchestral production and almost Broadway-caliber vocal performance blatantly un-country, the underlying story of a lasting love is extremely undeniable. We learn so much about this woman just by a freaking dress: They meet, they marry, they fight, and yet they stay together -- going back to that red dress that turned his head in the first place. This isn't just a song; it's an extremely poetic and inspired character study.
227. "Somewhere in My Broken Heart" by Billy Dean (#3, 1991)
Spare acoustic guitar driven production and a great melody (major-seventh chords always work) are at the forefront of Billy Dean's take on a country-folk approach. His best moments are when he lays all of his emotions on the line -- big emotions like being so in love with someone that you know that letting go is the best choice. It may hurt, but in the end, it's the right choice to make. And he's going to keep going on, and she's going to keep going on. There's an easily discernible bittersweetness throughout that makes the minimalist approach soar.
228. "Somewhere in the Vicinity of the Heart" by Shenandoah featuring Alison Krauss (#7, 1994-95)
How much better can you get than Marty Raybon and Alison Krauss on the same song? The two people in this song have been looking forever, and are so jaded that they don't think they'll ever find the right match -- but both are equally surprised at their own immediate chemistry. Great lyrics that set the scene make the experience seem as enriching as the feelings that are portrayed (I especially like how it begins in a café -- good call from the underrated Bill LaBounty). Although slick on the surface, this one cuts extremely deep, mainly by merit of the two absolutely stunning voices behind it.
229. "Song for the Life" by Alan Jackson (#6, 1995)
This great Rodney Crowell lyric had been around the block by the time AJ got to it. And it's such a natural fit for his easygoing charm. By leaning heavily into the waltz time and piano, the sonic landscape is different than usual for him in all the right ways. Lyrically, it manages to be straightforward enough to match his artistic strengths (favorite: "And the hard times don't hurt like they used to / They pass quickly, like when I was a child"), yet slightly more poetic as well. I could easily see Alan singing this to Denise every morning and both of them still believing every note of it.
230. "The Song Remembers When" by Trisha Yearwood (#2, 1993-94)
Trisha Yearwood doing a Hugh Prestwood song is an almost ridiculously great choice. She's done so much to forget every last detail of a relationship that hasn't worked out (the line "My heart must have been broken though I can't recall just why" captures so much). But then she hears an unspecified song, and suddenly, everything comes back into view again. The power of music is a great lyrical theme, and in true Hugh Prestwood fashion, this one finds a richly detailed and original take on a common theme to absolutely stunning results.
231. "Soon" by Tanya Tucker (#2, 1993-94)
An uncommon twist on an affair. He's still in a relationship, but keeps promising that "soon" he'll be available to the other woman. She keeps holding out hope that never comes, leading her to promise that "soon" she'll give up the pursuit entirely. As Leeann Ward of Country Universe pointed out, it's rare to garner sympathy for the other woman. But the pretty melody (I hear you, ever-elusive diminished-seventh chords!) and Tucker's relaxing delivery, combined with the detail-packed lyrics, make me put this one on my favorites list as "soon" as possible.
Yeah, this being #1 on my "Top 10 Eddy Raven Songs" list was a dead giveaway that it'd make this list too. It's got an extremely catchy synth riff that sounds retro without sounding dated; a playful sense of pursuit; a great driving tempo; and of course, Raven's distinctively laid-back, charismatic, Cajun-tinged delivery. In other words, it has every ingredient not found in the Forester Sisters' original. If I want to explain to someone why Eddy is one of my favorite underrated country singers, I have a catchy, three-minute package (and another Bill LaBounty co-write) that gives just about every single reason.
This song gives us everything in its extremely long, rambling diatribe on its narrator's heartbreak: how long the problems have been going on, the narrator's belatedly-admitted denial, their "tendency to overreact", interference by a sister-in-law, and getting locked out of the house and having to call a lawyer. It's so delightfully, amusingly TMI, and expertly produced to boot -- it fades out mid-verse to imply his continued rambling, and a few mariachi horns sneak in without overstaying their welcome. Really, I could have picked any track off Gone.
Missed opportunities are an utterly relatable scenario for everyone. For those who've let their contact with friends and loved ones slip away. For those who are financially rich but have no personal gain from it. For a music writer who won big on Wheel of Fortune, but still feels he wasted most of his 20s by not being employed. Far too often I feel like I've focused too hard on what I haven't gotten out of life at the expense of what I have, and that's a nuance that I don't think I've even seen touched on outside this song.
235. "Standing on the Edge of Goodbye" by John Berry (#2, 1995)
"I can't eat and I can't sleep, sometimes I find it hard to breathe" just looks like such a cliché line on paper. But John Berry's emotive delivery of a relationship on the ropes is so utterly convincing to make this song pop out of my speakers every time I hear it (his voice, effectively a rougher-edged Gary Morris, certainly doesn't hurt). Like "Lucky Moon", the relationship is faltering; unlike that song, the man can't even seem to piece together a reconciliation. There are lots of emotions that can come from an impending breakup, but this is one of the only times I can add "panic" to the list.
236. "Still Gonna Die" by Old Dogs (did not chart, 1999)
Waylon Jennings, Bobby Bare, Jerry Reed, and Mel Tillis answered Shel Silverstein's call for a lack of songs about growing old. And I can hardly think of a better group of people to convey this song's simple, yet witty message. No matter how young or old you are, no matter how much care you take of your body, everyone dies eventually. So don't stress out too much about your age and enjoy yourself while you can. The facts that Shel died only months after this project's release, and Waylon recorded no further material before his, are somewhat bittersweet indications that they took the message to heart.
237. "Strawberry Wine" by Deana Carter (#1, 1996)
It's common to have two teen lovers meet in the summer and then part ways, but this is the one that all other songs like it are measured against. They meet; they drift apart; and she comes back to find everything drastically different. I've always felt that what made this song an enduring classic is the extreme amount of detail in the lyrics -- we learn a lot about these two, and the lyric "Is it really him or the loss of my innocence I've been missing so much?" is a great endcap. Deana's voice is perfectly wistful and bittersweet for such a lyric, too.
238. "Suspicious Minds" by Dwight Yoakam (#35, 1992)
"Suspicious Minds" is already my favorite Elvis song -- I just love how well its "caught in a trap" hook lays out a relationship in limbo. But somehow, Dwight managed to make the best even better. That Pete Anderson guitar? Ever present, complete with some cosmic-sounding fills in the intro. Drums for days. Huge backing vocals. Freaking pizzicato strings. And up front, Yoakam adding his distinct delivery without removing any of the trademark Elvis swagger. It's almost as if Elvis and Dwight somehow fused Steven Universe-style into a massive musical powerhouse.
My grandmother had a "worn out wooden swing" just like the one in this song, and I think of it every time I hear this. While hers was merely an aging decoration in her yard, the one in Bonamy's catchy, clever, upbeat little ditty is the centerpiece of a boy-meets-girl tale gone right. Mom and dad met on that swing, and now the son hopes to do the same with his girl. The twangy guitar riff is extremely catchy, and the nod to "The House That Jack Built" is an unexpected but charming little shout-out. I probably don't even have to tell you that being a Robert Ellis Orrall co-write doesn't hurt it any, either.
I like wanderlust songs, okay? Especially if they take me back to the exact spot I remember hearing them: a scenic overlook off highway M-32 in Lachine, Michigan. There, you'll find a roadside park on top of a hill, looking down on the farmland and highways below. It's just one of the many scenes I could see the escaping couple in this song partaking of on their charming, meandering journey. More than anything else -- including Lari's pitch-perfect vocals -- I love how this one goes into a lower key on the chorus before going back up again.
241. "Tell Me About It" by Tanya Tucker feat. Delbert McClinton (#4, 1993)
Two people who've been burned by love find solace in each other's company. There's no indication that they're trying to match up; they just want to have a conversation about their experiences. And that alone makes it a more interesting and unconventional character sketch (I'm using that phrase an awful lot, am I not?) courtesy of frequent list entrant Bill LaBounty. And of course, giving it to not one, but two gritty singers who supercharge the song with country-rock-blues energy and passion, was clearly the right move.
242. "Tempted" by Marty Stuart (#5, 1991)
Marty Stuart brings some much-needed rockabilly flair to the proceedings. Lyrically it's a very direct look at, well, being tempted by an extremely eye-catching girl, but it succeeds by not overselling that theme. And it becomes great by the production: chugging electric guitar, jangly rhythm guitar, a gallop beat, and even a timpani (the last three clearly being Richard Bennett trademarks) just make the entire simply-presented package sound so damn cool from the first note to the last. And that's really a great descriptor of nearly all of Marty's best.
243. "Texas Tornado" by Tracy Lawrence (#1, 1995)
Bobby Braddock wrote this song about a woman who considered leaving him to become a storm chaser. Just like the title suggests, the relationship here is quite tempestuous. It's a unique look at being "blown away" by that one on-again, off-again fling that keeps playing with his emotions. Producing entirely by himself for the first time, Lawrence not only finds the right level of twang, but also an extremely warm yet "stormy" production tailor-made for the clever lyrics. "Time Marches On" may get all the accolades, but to my ears this is the better of the two Braddock cuts that Lawrence got.
Emmylou's soulful vocal, the guitar-driven production, and the ooh's and hand claps would make it a lovely entirely on its own. But there's an off-kilter charm to this redemption arc, woven into lines like "It would take a baby child to know the way I feel". Even better, said arc isn't even completed, as the last verse drops this even brighter gem: "You're a mess but you're my child". I was always taught that everyone is a child of God, and in a world where far too many hateful words are thrown around in distorted perceptions of Christianity, it's extremely refreshing to see a song get the whole thing right.
245. "That Ain't My Truck" by Rhett Akins (#3, 1995)
My mom calls this the ultimate "stalker song". She's been flip-flopping between two men, and ultimately chooses the one who's not the narrator. So he drives by just to be sure. And there's nothing he can do about it, so he's just dejected. Sure, it was similar to its contemporary "Who's That Man", but it's a different enough flavor that I find just a little bit more compelling. Maybe it's the youthfulness to his delivery that makes him seem merely anxious and curious, which is a different take than Toby's (admittedly compelling) dejectedness.
246. "That Ol' Wind" by Garth Brooks (#4, 1996)
Two lovers separated reunite at a concert, reigniting an old flame that hasn't yet burned out. It's already a sweet, detailed story-song in its own right, but the ending is really what pushes this song to greatness. Each party has a secret hidden from the other, but these extras are not important in the moment -- what is important is their reunion. By telling us so much about these two and then working up to a fully organic twist ending, Garth is able to prove that his storytelling craft had not diminished as the '90s continued.
Tom T. Hall's lyrics are fantastic storytelling as usual, showing a guy who's wandering all around trying to find his love. He's lonely, hungry, tired, and desperate to the point of asking a friend for help. Dodd's version is a bit more energetic but no less plaintive than Bobby Bare's original, and the production filters in some piano, twangy guitar, and female backing vocals. Bare's version would almost certainly go on a "best of the '70s" list if I ever made one, but Deryl should be commended for an extremely well-executed revitalization.
248. "That's Just About Right" by Blackhawk (#7, 1995)
A painter goes up to the mountains to clear his head and hone his craft, but comes back with a new understanding of the human condition and the value of individuality. Anything you might learn about yourself or others might hit you out of nowhere, so just do your thing, don't overthink, and let the world come at you. Even when you're not looking, you might find something. Just like eight-year-old me finding this song's video on CMT at my grandma's house and instantly falling in love with both it and Blackhawk as a whole.
249. "That's Why I'm Here" by Kenny Chesney (#2, 1998)
Yet another charming tale of a recovering alcoholic. While "Little Rock" had the couple torn apart, and "Flowers" had one half of the couple die, this one differs but hits just as hard by ending on a hopeful note. It turns out the woman isn't out of the picture yet, and he's going through all of these recovery efforts to keep her. (And his sincere delivery makes me really want to root for him, too.) Even though this was clearly well before Kenny found his signature style, it still shows that he was more than able to stand out by merit of great song choices.
250. "Then What?" by Clay Walker (#2, 1998)
Another more contemporary take on adultery. Here, a friend has a surprisingly nonchalant yet nuanced bit of advice: go ahead and do what you want, but consider the consequences of your actions. (This list has really put a lot of strain on the seventh commandment.) He doesn't sound at all like he's being preachy or nagging; he's just telling the guy straightforwardly to think before he acts. And all of this is matched to a ridiculously catchy steel drum-driven production (seriously, who else was even using steel drums in the '90s? Or ever?) that doesn't distract from the proceedings one iota.
251. "There Goes My Baby" by Trisha Yearwood (#2, 1998)
I swear three consecutive #2 hits from 1998 wasn't an intentional move... This is probably the best example since "A Broken Wing" of how to do belting right. Trisha is already a golden vocalist, and this lyric is a great "one that got away" emphasized by a ton of unusual chord changes (VI-ii and iv-I being two of my favorites). I love how she outright calls herself a fool; I love the line "Maybe this empty heart he left behind is all that I deserve"); and I love the warmth to the production. It's such a shame that this is the only good song on this album, though...
252. "These Arms" by Dwight Yoakam (#57, 1998)
This one is a standout by sounding like a throwback to his earlier honky-tonk days -- straightforward three-chord pattern, strong but simple heartbreak lyrics, electric guitar, and tinkling piano. But come the chorus, the song structure changes almost entirely: harder guitar, strings, and a more idiosyncratic writing style to boot: "Trying meekly to assist my struggle with the truth / Unable to resist what tears still make us view". It's the kind of out-of-nowhere style shift I would expect from almost no one else, and I don't think anyone else could even pull it off so effortlessly.
Slow and twangy production, combined with a husky warm vocal, match up perfectly to this lyric that calls out an ex who's looking for another chance. Every single lyric is a solid burn -- from "I can't believe you're calling me / Did you run out of things to do?" to "I won't be a one-night remedy / To help you live with your regret". Like so many female acts would do in this decade, she's more than standing her ground; she's actively taking control of the situation and shutting down any advances that she wants no part of.
My dad died in June 2016. Despite our on and off relationship, and his own rocky life, I still feel that I have no regrets toward him. I was there to see him through the last few years of his life and ensure his safety and comfort until the last day. And all of those emotions that I feel toward him are captured perfectly in this beautiful, minimalist ballad. Sometimes, even in the face of death for a loved one, the most comforting feeling you can have is knowing that you've made peace with someone who is now in a better place. It sounds simple, but this song is movingly poetic in conveying that.
255. "(This Ain't) No Thinkin' Thing" by Trace Adkins (#1, 1997)
Minor key is so underused, and so rarely is it upbeat. But this song always jumped out to me by being both. (Thanks again, Mark D. Sanders, for continuing to be left of center.) It's also helped by having that simple yet super-effective steel guitar riff (I especially love how near the end, all the other instruments drop out entirely to let the steel really shine). Trace was already gaining full control of his bracing baritone as he pontificated on the complexity of love and concluded that overthinking isn't the answer (boy, am I guilty of overthinking!).
I'd like to thank Country Gold with Rowdy Yates for introducing this song to me. A highly detailed narrative finds a cowboy getting mocked by a gang of bikers for his uniquely-decorated hat, until he points out the meaning of each decoration: the feather, the brim, and the hat pin all have special meaning to him. It's a wonderful little story about not being judgmental, and Chris narrates it to perfection. It helps that his has a slower tempo and more dramatic "desert sky" production, allowing a closer look at every little detail that allows this cowboy to shoot down the enemy known as prejudice.
James House should have been big: a spacious Roy Orbison-esque voice and great lyrics alone made him stand out even among the other Orbison influences already on this list. (He was ahead of his time with "Don't Quit Me Now".) Here, he goes for a convincing take on brokenheartedness. If you hear, see, and feel all of these very specific things (I especially like the reliance on storm metaphors), then those are all what it's like to have me missing you as badly as I do. His voice soars above a delightfully melancholy production, making me wonder why he gave up the major-label game only one single later.
258. "(This Thing Called) Wantin' and Havin' It All" by Sawyer Brown (#11, 1995)
Once again, Sawyer Brown twists common themes around. A dying rich man has all of the money but none of the heart; the poor man has the opposite. So the rich man, in pure selflessness and guilt, leaves everything not to his ungrateful kids, but rather to that worried poor man. Just like "Standing Knee Deep in a River", this song deftly illustrates the difference between material and emotional wealth; however, it's way more upbeat in a piano-heavy, gospel-tinged way. Hard-hitting life lessons are difficult to pull off without sounding preachy, and these guys make a hard story sound so easy.
I swear, I'm not trying to meet CanCon laws; the songs really are that good. This is a wonderfully relatable look at depression and loneliness, filtered through the view of a musician on the road. Such feelings should hit home for anyone who just wants life to be normal again after the pandemic. Pete Anderson's decision to fit the song with Byrds-esque 12-string electric fills, and Jim Cuddy's "everyman but more expressive" voice, are just the perfect sonic landscape. It feels like a missing link between '80s country-rock and '90s alt-country in all the best ways.
260. "The Tin Man" by Kenny Chesney (#70, 1994/#19, 2001)
I know he re-released it in 2001. But I actually remember it from the first go-round, and I want to make room on the 2000s list for his other great songs in that decade. As I said in the "That's Why I'm Here" blurb, Kenny had an ear for good songs long before his arena-beach-bum style came to be. And one of the first salvos was this extremely original Wizard of Oz reference. The best way to not experience heartache? Don't have a heart, just like the Tin Woodman. It's a clever and inspired image, spinning both its reference and its heartbreak themes in new directions, and Kenny gives a very convincing read.
261. "This Woman Needs" by SHeDAISY (#9, 1999-2000)
SHeDAISY caught my ear entirely by being the Bizarro World Dixie Chicks -- as harmonious and country-pop as they, but with considerably less conventional songcraft. I could easily have put "Little Good-Byes" here, but to me, their biggest test was proving that they could be serious balladeers too. Some of the lyrics are still a bit eccentric ("picks up your shirts"), but the back-and-forth yet warm harmonies, unusual chord patterns, and gentle waltz tempo? Yeah, these ladies are no joke. They can crush the hell out of a ballad, an uptempo, and everything in between. (Except "Come Home Soon".)
262. "26 Cents" by The Wilkinsons (#3, 1998)
Inflation and the obsolescence of payphones may have gotten this one's hook (not to mention the Wilkinsons' home country of Canada eliminating the penny entirely), but the emotions are still the same. Sometimes, a young adult moving away from their parents only needs a simple reminder that no matter the physical distance, the love is unchanging. Amanda has a sweet delivery that sounds perfectly tailored to young-adult story-songs like this, and she harmonizes greatly with her brother and father. I'd like to imagine that she's still holding onto that "penny for [her] thoughts" to this day.
263. "Unanswered Prayers" by Garth Brooks (#1, 1990-91)
This was one of the two songs that inspired my mom to divorce her dad. Even independently of that personal attachment, I think it stands out because of the unique premise: thanking God for something not happening. Sometimes, no matter how much you want something -- in this case, a partner whom you think is The One -- you don't get what you want, only to find out later on that not getting it was the right choice after all. In that sense, I find that the song is all the more commendable for averting expectations of standard Christian themes.
264. "Vidalia" by Sammy Kershaw (#10, 1996)
Yet another example of Mark D. Sanders mixing and matching to extremely memorable results. The title girl gets her unique name as a portmanteau of her parents Violet and Dale. As Vidalia is also a type of onion, this sets up one of the best puns in country music: "Sweet Vidalia, you always gotta make me cry". To carry the onion references even further, this pun setup has a lot of layers; it's like a Pearls Before Swine gag, only a million times less contrived and not ending with a threat of violence to the creator of the pun. And sung with absolute wit and charm by a guy who really knew how to pick 'em.
Dean had a debut album that displayed no shortage of talent even if it was burdened slightly by Nashville formulae. The best and least-formulaic single off said album was this honky-tonk twanger that has a few delightful twists and turns. Short verses and a long chorus; a loping rhythm; a lot of steel and piano; and a charming vocal are all present -- and oh yeah, that fantastic hook. More material like this or "Broke Down in Birmingham" could easily have made Dean an underground success, but at the very least, he proved able to separate himself stylistically from his talented father, Roger.
266. "Walk on Faith" by Mike Reid (#1, 1990-91)
Mike Reid wrote a lot of fantastic songs mainly for Ronnie Milsap in the '80s, and a few others already on this list. But it turns out he's no slouch as a singer. This one, straightforward as it is -- "walk on faith, trust in love" -- manages to be wonderfully relatable and moving, joyful even, without coming remotely close to the motivational-poster glurge it could have been. It could be the subtle turns of phrase here and there, or just the way he sings it, but this has always been a song that puts a smile on my face.
267. "Walkaway Joe" by Trisha Yearwood featuring Don Henley (#2, 1992-93)
A tale of youthful eagerness in love that goes wrong. The man this 17-year-old is pursuing ends up being a criminal and ditching her in the middle of the night. In a world where youthful eagerness in love is so often portrayed as a good thing, it's refreshing to see a moment where it doesn't. Perhaps this whole song is a cautionary tale for the young lady in the song, and I'd like to think that her next selection is more judicious. Of course, having not one, but two great voices sing this story in such a straightforward yet tuneful fashion doesn't hurt, either.
268. "Walkin', Talkin', Cryin', Barely Beatin' Broken Heart" by Highway 101 (#4, 1990)
Highway 101's last top-10 hit came in a roundabout way. Written by Roger Miller and Justin Tubb (Ernest's son) and originally cut by Johnnie Wright of "Hello Vietnam" fame, this slots seamlessly into Highway 101's high-energy country-rock sound. Paulette's unique vocal hits the right heartbreak emotions and nails the long title effortlessly; the production adds a few modern touches to the 1960s shuffle feel. These guys could rival Ricky Van Shelton in freshening up '60s deep cuts, and it's all the more impressive a show of range coming from a band that also nailed a Dire Straits cover.
Considerably more upbeat than most of his previous efforts, and at times recalling Chuck Berry's "You Never Can Tell", is this tale of a guy who's found the right woman. It's almost the opposite of "High Rollin'" in terms of using its gambling metaphors, showing a guy who hasn't even managed to break even until just now. There's just so much joy and energy in the production from the first note to the last (not the least of which comes from Parnell's guitar), and Mary Chapin Carpenter's backing vocals add a touch of class. I guess he was feeling really lucky, because the next song was practically a rewrite...
270. "We Shall Be Free" by Garth Brooks (#12, 1992)
Garth lays out all of the obstacles that keep us apart as a society: poverty, racism, homelessness, environmental awareness, freedom of religion, bigotry, and homophobia are among them. By directly targeting each issue on its own and not succumbing to vague catch-all platitudes -- and by matching them to a fantastic gospel-tinged production -- he clearly knows the impact of his words. And the fact that he supports a lot of the causes (particularly LGBT ones) of which he sings -- both then and now -- is the last extra nudge of sincerity and action to make this my favorite song of his.
His background is fascinating -- his father helped create the Discover Card, he's produced Steve Earle albums, and he's married to an English folk singer -- but the song is every bit as fascinating. He runs down a list of varied women who've done him wrong all over the country (I particularly like "tongue-tied by a teacher in Tallahassee" and "french-fried by a waitress in Idaho"). Ray has a witty honky-tonk delivery, and he made a couple lyrical changes for the better from the original late-70s version by Bobby Borchers. An underrated, funny gem from a guy who deserved more hits.
This song portrays a young woman trying to decide "yes" or "no" in a relationship. The cowbell and guitar riff alone hook you in instantly, and Mindy's voice absolutely nails everything. I especially like the spoken asides ("It figures", "I bet he does") and the giggling and wolf-whistle, all of which feel completely ad-libbed. But the best part of the song is the way she squeaks out the line "it's a test". I have never heard a vocal performance that enjoyably campy and giddy. Sometimes a unique energy is all it takes to win me over, and this one absolutely delivers.
273. "What If I Said" by Anita Cochran featuring Steve Wariner (#1, 1997-98)
Two friends are in different relationships that aren't working out. They see the dissatisfaction and offer a simple solution: each other. Rising way above the dated production of her other singles and classing up the joint with Steve Wariner, Anita finds her throaty voice extremely comfortable in this back-and-forth (I love how Steve comes in with "You tell your story, it sounds a bit like mine" in particular). It's beautiful and powerful, and the vocal chemistry is off the charts. But unfortunately, so was the greatly talented Anita after this fantastic song. Easily one of the best one-hit wonders.
I keep mentioning the Roy Orbison influence; how much more influential can you get than having him write the melody? Big guitar, breezy organ, and Rodney's vocal almost make it seem like Roy is singing these deceptively nuanced true-love lyrics from beyond the grave. "What kind of love runs through your heart with a pleasure so close to pain / What kind of love? Only this love that I have" is just a killer hook sung to perfection. The crowning lyrical achievement, however, is this brilliant chiasmus in the bridge: "This love I know is all I have / This love I have is all I know".
275. "What'll You Do About Me" by Doug Supernaw (#16, 1995)
There are many versions of this song, but I find Supernaw's version to be the best. It's another stalker song, sure, but the tone reads as playful and lighthearted, not creepy (okay, maybe I can see how the "on the porch with a two-by-two" line might rub some people the wrong way). This guy's just a well-intentioned goofball with an unconventional approach to how madly in love he is (can you tell Dennis Linde wrote this?) that it's hard not to like him. And by giving a more energetic read than Randy Travis, the Forester Sisters, or even Steve Earle, I think Supernaw conveys that role the best.
276. "When It Comes to You" by John Anderson (#3, 1992)
Mark Knopfler fits so seamlessly into country music that it's almost ridiculous. With the hauntingly nuanced production style that Anderson perfected in the '90s (see also "Bend It Until It Breaks" and "Seminole Wind") and Mark's lead guitar, John gives an utterly no-nonsense read of these lyrics. He's taking a stand because he knows the relationship is over, and it comes to us in hard-hitting lyrics like "villain of the peace" and "I'm wondering where'd you get that cold cold heart". That's a hell of a burn right there.
277. "When She Cries" by Restless Heart (#9, 1992)
We've already proven that Larry Stewart was capable of greatness independently of his band, and this song proves that the reverse is also true. Drummer John Dittrich at the forefront, rivaling Don Henley in terms of "drummers who are also good singers". It sounds like this guy is beating himself up over constantly coming short of his woman's expectations, but not for lack of effort. He wants it to work out, and hates that it isn't. Although poppier than their usual fare, it's such a smooth, interestingly-written pop song that deserved to cross over as successfully as it did. Even if they were one member short.
It's common to take your broken heart to a bar. It's common to get back to drinking when you swore you wouldn't. It's... not common to use the word "domino" in a country song. Michael Peterson was one of the last "hat acts", and his debut album was full of understated charm. Here, a man's so brokenhearted that he's drawing emotions out of a bartender who's clearly been in his shoes before, down to the "trying repeatedly not to drink anymore" part. That's hardcore country, and Michael's emotive read makes the music reviewer cry, too.
279. "When the Thought of You Catches Up with Me" by David Ball (#7, 1994)
I had to have David Ball on here. Sure, "Thinkin' Problem" has a hell of an intro, but it's a bit gimmicky. The real test of Ball as an artist was the ballad, and he delivered in spades. With just vocal, fiddle, and guitar, he points out that it's easy for one's memory to show up anywhere, anytime. His twangy voice could have fit into nearly any generation of country, and the minimalist production and straightforward lyrics even more so. In short, another song that crushes it with a less-is-more approach.
Gretchen Peters can write some damn fine songs, and she's great at singing them, too. Her voice is sweet and surprisingly powerful (check out how she sings "I will be old too"), and perfectly suited to the warm production around her. Age happens to all of us, and sadly, too few of the older people I know still have anyone to comfort them. Whether it be a spouse (the presumed narrator of this song) or anyone else, there are few things more reassuring than a helping hand. And in her extremely pretty, emotion-packed way, Peters lays out the truth.
281. "When You Leave That Way You Can Never Go Back" by Confederate Railroad (#14, 1993)
A life full of mistakes becomes too much. There is no happy ending for this guy -- he's ditched his parents, a fiancee, and a son, and he's wanted for murder to boot. There's so much grit and sadness, and none of it is alleviated with even the slightest hint of redemption. By intentionally avoiding any sense of closure, the results aren't just sad -- they are absolutely devastating. You know it's way too late for this guy to turn things around, and by the time he gets to "all through eternity you'll roam alone", even a glass eye would struggle not to shed a tear.
282. "When You Say Nothing at All" by Alison Krauss & Union Station (#3, 1995)
It's easy to verbally express an emotion, but actions speak louder than words. By stating that directly -- without any hyperbole, sanctimoniousness, or overly cutesy turns of phrase, and with an inspired name-drop of Noah Webster -- the song is country greatness in any form. It was matched perfectly to Keith Whitley's hardcore honky-tonk twang, and every bit as much to Alison Krauss' ethereal beauty. (Ever heard the version that splices them together? That works too!) If both versions were released in the '90s, then I would have listed them both.
283. "Where Do I Fit in the Picture" by Clay Walker (#11, 1994)
A haunting, self-penned ode to a woman who's gotten married to someone else. This guy's surprised to find this out, yet questions whether she even remembers him at all -- and ultimately, his tone (and admission that he's apparently either holed up in a hotel or possibly imprisoned) toes the line of devastation. After a pair of solid but clearly radio-baiting singles, he took a chance with a left-of-center ballad; while it wasn't one of his biggest chart hits in the long run, it was certainly one of his more memorable, dramatic, and fascinating songs.
284. "Where've You Been" by Kathy Mattea (#10, 1990)
The "three verses re-contextualize the chorus" formula has been done so often that it's hard to forget how fresh it once was. Mattea's husband, Jon Vezner, was inspired by an encounter between his own grandparents, and that's what makes this so believable. The progression from "where have you been all my life" to "where have you been, I was worried" to the decaying mental faculties that sadly come with old age is natural, not whimsical (unlike "Forever and Ever, Amen" treating cancer and dementia as a punchline); it feels sadly real, and Mattea's spare read of it allows those emotions to shine through.
285. "Who Needs Pictures" by Brad Paisley (#12, 1999)
Hey, remember film pictures? Brad Paisley does. Or more accurately, he remembers finding the roll of film, but choosing not to develop it because the memories are better. Right out of the gate, Brad proved capable of balancing wit, emotion, and completely unique song premises to extremely affecting results. His voice was richer and twangier back then, giving him more interpretive room. Most of his career highlights come from taking an everyday idea in the most inspired direction he can think of, and this is definitely a huge success in that regard.
286. "Why Didn't I Think of That" by Doug Stone (#1, 1993)
For all of his balladry, Stone was no slouch at using his emotive, reedy voice for more upbeat material as well. One of his best in that regard is this poor guy who's realized far too late what he should have done to keep his relationship intact -- all by watching what the man she's with now is doing. Thematically it's every bit in his wheelhouse as ever, but the livelier arrangement makes him feel energized in placing all of his interpretive strengths. Turns out that all you need to make a great breakup song is a good, solid premise sung perfectly. Why didn't I think of that?
T. Graham Brown has a grainy, impassioned voice that I've loved from the first time I ever heard him. His lyrical skills are certainly far from lacking, and possibly his best is this tale of an alcoholic doing his best to kick the habit. This guy's hit rock bottom in his battle against the bottle, so he turns to the Lord for some help. With all of the recovering-alcoholic stories on this list, this is probably the most desperate, and the reference to Jesus' first recorded miracle is turned on its head without feeling like flippant wordplay.
Completely shifting gears with the same artist, we go to one of the bounciest true-love promises. The chimes and horns sound positively ebullient, and Brown's gritty voice blends right into the energetic, upbeat surroundings. It's so simple on paper, but that chorus is very happy. And that sax solo -- one of the last in country after so many abounded in the 80s -- jazzes things up in all the right ways. (Favorite lyric: "I never thought so much love / Could fit inside a little band of gold"). Sometimes all you need in life, and love, is a pure dose of joy, and this one always gives me exactly that.
289. "A Woman's Touch" by Toby Keith (#6, 1996)
One of the few times that Harold Shedd's production worked with a song instead of against it. There's a distinct melancholy to the reverberating electric piano and splash cymbals, combining with the minor-key melody. This guy is so heartbroken that he even says outright that he's "forgotten how to love", and he is desperately seeking the right woman to set things right. Early-period Toby Keith was dominated by some really standout ballads unlike anything he's cut since. And out of all of them, this one that manages not to waste a second of a 5:36 play length has always been my favorite.
290. "Words by Heart" by Billy Ray Cyrus (#12, 1994)
He finds a breakup note in his Letterman's jacket, and without even reading it, knows every single emotion tied to that letter. (This is probably the only song outside "Weird Al" Yankovic's "Word Crimes" to use the word "comma".) Best line: "I don't remember a thing from my classes, but I can quote you every line." It's easy to make fun of Billy Ray's pseudo-Springsteen growl, but I've always found it unique in country and well-suited for big emotions. Like, say, that one old flame that should have died out but hasn't. Seriously, there was so much more to this guy than "Achy Breaky Heart" let on.
Even discounting the constant Monday morning airplay of this song on local stations, I've just always found it an incredibly likable working man's anthem. Its synthesized brass, quasi-reggae guitar riffs, and lines like "sweating like a pig" may be cheesy to some, but I've always found those add to this song's charming, relatable style. "Workin' Man Blues" captures that grit and determination of the blue-collar spirit, but "Work Song" is the buddy who buys your first round because he can tell you've had a rough day.
292. "Yard Sale" by Sammy Kershaw (#17, 1992)
A breakup can be told in many ways, but this is so far the only time I've seen a yard sale as the framework. The two are selling off their possessions, and with them go the memories of the love they used to have. I actually remember hearing this song at a yard sale not long after it came out, and even at a young age, I got the theme right away. Sammy's mournful vocal nears George Jones levels, and the crying steel of John Hughey underneath him only adds even more sadness and heartbreak to the surroundings.
293. "You and Forever and Me" by Little Texas (#5, 1992)
I think it's just the melancholy yet gritty surroundings, but I just feel that this one -- in modern parlance -- "hits different" than most love ballads of the time. I love how the lyric "Almost to my hometown, it's just another mile" sets the mood, and makes you think that he's just driving around and reminiscing. But it's not until the end that we find that he's actually out looking for her. Yet more of that "desert sky" production style is present, matching perfectly to the line "there's a cool wind on the desert tonight". This just edges out "What Might Have Been" as their best '90s ballad.
An underrated and slightly off-center singer-songwriter with a voice not unlike a huskier Kathy Mattea gives us this extremely melodic, image-heavy look at a woman dissatisfied with her relationship. It seems that this man is over-protective of her, but another party has entered the picture and shown interest in getting her out of the chains that are binding her. Great lines like "a diamond is no good to anyone when it's under lock and key" combine with unusual chord patterns for a highly memorable scenario. I hope she gets "stolen" like she wants to be.
295. "You Don't Seem to Miss Me" by Patty Loveless feat. George Jones (#14, 1997)
This could have been Patty and George humming the Jeopardy! think music and it would still have been pretty damn good. But thankfully they both aimed much higher and hit their mark. It's a tale of a woman who loves, but feel that the love isn't being returned. In true Jim Lauderdale fashion, few words are used to tell a complete story; I particularly like the simplicity of the chorus ("I just can't wait to see your face / But you don't seem to miss me"). By adding both the Possum and a bunch of fiddle and steel, the result is about as hardcore country as you could possibly get in 1997.
You get a lot of good and a lot of bad, but you just get one true love. With two quick verses, that's all this song has to say -- but that's all it needs to say. As a rare outside co-writer's credit for Vince Gill, it manages to convey his mastery of the understated without feeling slight or sappy. I also think that the double-tracked guitar/mandolin solo (both of which are played by Gill himself) adds a nice sonic variety to Wood's warm vocal. Seriously, do you know how hard you have to work to outdo Ty Herndon's version of a song?
297. "You Were Mine" by The Chicks (#1, 1998-99)
The Chicks' music, for the most part, has aged extremely well by merit of their strong country-pop song craft. The lyrics mourning a divorce add a contemporary flair (clearly autobiographical in nature -- Emily and Martie wrote it about their parents), and Natalie sings the hell out of it. But the best line of the song by far (which says a lot -- "Sometimes I wake up crying at night, and sometimes I scream out your name" is a close second) is when the narrator questions how her young kids are going to fit into the picture. I was four when my parents divorced, and my mom was always frank about it.
298. "You Won't Ever Be Lonely" by Andy Griggs (#2, 1998-99)
Andy Griggs should have been big. The warm, passionate vocals and spacious production of his debut single alone are all the proof you need. Lyrically, it's very relaxing and conversational in its take on the common declarations of love and protection. Sometimes all it takes to make a song great is to take an everyday message and deliver it in a fairly conventional package (outside a couple departures from verse-chorus structure). I especially like how he goes out of his way that he'll be there in the good and bad times alike for that extra touch of emotional depth.
This one starts out entirely with spare piano-and-vocal production that underscores one of the best opening lines ever: "I said, 'Hello, I think I'm broken' / And though I was only joking / It took me by surprise when you agreed". All of the other ingredients integral to the Diamond Rio sound are subtly added one-by-one throughout this tale of a loved one's sudden departure, building to one last delivery of the simple yet devastating hook. I especially like how even the instrumental coda seems to keep the starkness going after the lyrics end.
300. "You've Got to Stand for Something" by Aaron Tippin (#6, 1990-91)
The other of the two songs that inspired my mom to divorce my dad. But even outside that personal connection, it's message transcends sociopolitical boundaries. No matter what side you're on, be yourself; it may not be the most popular or short-term profitable choice, but being yourself will pay off in the end. Aaron sings the hell out of this message that resonated to soldiers returning from the Gulf War, and it holds just as true today. And it also makes a fitting conclusion to this list, which I hope has shown me "standing" for a huge list of songs that mean something to me.