Untrue Facts: FGL, Faith Hill, George Strait, Marty Stuart, Kenny Chesney

 

The 300 Best Country Songs: 2000-2009 (Part 3)

By Bobby Peacock

These are in alphabetical order. Here’s part 2. Here’s part 1.

201. "One Second Chance" by Jeff Bates (#59, 2006)

Jeff Bates knows a thing or two about second chances: in 2001, he was arrested for drug possession and grand theft. It's very easy to see him as the man losing job opportunities due to his criminal record, or watching his ex leave with custody of their son while he struggles to pay alimony. Bates has a gravelly, impassioned delivery that perfectly conveys how dejected he is by his mistakes. Lines like "I was young and I was stupid, I regret it every day...I've finally got my freedom, but what good is now?" are brutally honest and heartbreakingly desperate; he didn't write it, but he sure as hell lived it.

202. "One Wing in the Fire" by Trent Tomlinson (#11, 2006-07)

My own dad was a flawed man. He showed up in church, but I don't know where his faith lied. Despite the issues that drove them to divorce, my parents still had almost no animosity toward each other. I was taught that everyone is a child of God who can be forgiven, and that "love one another" has no exception. Trent does a fantastic job highlighting details about his father's flaws, avoiding religious mawkishness for straight truth and concern. While I don't consider myself a believer, I am sure that whatever outcome exists beyond death (Dad died in 2016) was a positive one for the man in my life who was also "an angel with no halo and one wing in the fire.” 

203. Paint Me a Birmingham" by Ken Mellons (#54, 2003) or Tracy Lawrence (#4, 2003-04)

I've said it before: I'm a sucker for an original concept. This man finds a painter at the beach, painting the scenery around him, and asks him for another scene. Specifically, he asks for a picture of the house that he imagined he and his lover would have before they broke up. (I would imagine he provided the painter with a picture for accuracy's sake.) Both Ken and Tracy -- who released the song almost simultaneously -- have twangy yet grained deliveries backed by lush production, giving equally convincing yet distinct reads of this heartwarming, highly inspired material.

204. "The Pearl" by Jeremy Boz (did not chart, 2007)

Sometime in 2007, I took a road trip through Petoskey, Michigan and heard one of their DJs pit this song against Taylor Swift's "Our Song" in a listener poll. (Result: 64% voted Taylor.) This one has that Orbison-meets-Yoakam production that I love so much and a great opening line ("That full moon looks like a perfect pearl / Hangin' on a string between our worlds"). The use of the pearl as a metaphor and the underlying themes (wealth, family, good and evil) almost seem like subtle yet classy nods to the John Steinbeck novella of the same name. Why didn't this guy catch on?

205. "People Are Crazy" by Billy Currington (#1, 2009)

The only contemporary country song that my late grandma ever said she liked. We've all heard feelgood stories about the kindness of strangers, so this one doesn't seem out of reach at all. It's an old man sharing life stories with a younger man, and then leaving him a fortune as a reminder of the three certainties brought up in their conversation: "God is great, beer is good, and people are crazy.”  Currington's delivery and the production are positive and relaxing. Simple on the surface, instantly relatable, but deep in scope when you least expect it. In short, what great country should be.

206. "Pour Me" by Trick Pony (#12, 2000)

I always thought that Trick Pony sounded like a harder-edged version of Highway 101, thanks in no small part to Heidi Newfield's distinctive twang. The poor me/pour me homophone has been used before, but Trick Pony breathes new life into it. She doesn't want to party or dance; she just wants to drink her troubles away. We learn a lot about the guy through quirky lines like "I always thought he was a simple-minded Okie / Little did I know he was the king of karaoke,”  The upbeat honky-tonk delivery and vocal harmonies sounded amazingly fresh and country two decades ago, and still hold up today. And even better, they hung onto this sound for three albums.

207. "Portland, Oregon" by Loretta Lynn and Jack White (did not chart, 2004)

Lynn's quirky lyrics about feigning an affair ("well, sloe gin fizz works mighty fast / When you drink it by the pitcher and not by the glass") -- something she actually did with Cal Smith -- are already as Loretta Lynn as you can get. Then you bring in Jack White, who gives the song a nearly two-minute psychedelic guitar-and-drums intro. And then the sparks fly when a 72-year-old woman trades off with a rocker young enough to be her grandson and enough energy to spare. Sometimes the best results come from the least likely pairings, and I can hardly think of one that exceeded my expectations any more.

208. "Pray for the Fish" by Randy Travis (#48, 2003)

The repentant sinner is such a common image that I'm surprised to find a new, witty, truthful take on it. Eddie Lee Vaughn in this song is deemed to be such a sinner that some scoff at his baptism entirely; the pastor de-fuses the situation by joking that they should "pray for the fish" once all the sin washes off. This leads to thunder and lightning backing Vaughn's redemption just to drive the point home. As I've said before, I was always taught that any sinner can be forgiven. And Eddie, his pastor, and most importantly, Randy Travis -- who imbues the song with the perfect level of deadpan -- got it right.

209. "Real Bad Mood" by Marie Sisters (#46, 2002)

As I said back at "Bomshel Stomp,”  sometimes I just need a good "weird" song. This woman doesn't even want to eat or listen to music because she's too pissed off at whatever. But the quirky lyrics ("them cold store-bought tomatoes, Lord, they just make me wanna fight") are unlike anything else on radio. Their sassy back-and-forth vocals, the groovy guitar riff, the talk box, and Hammond organ set a very ear-pleasing soundscape. But then the song unravels into an off-the-cuff jokey conversation, interrupted by the producer telling them to "quit messing around.”  In a way, it seems the two are laughing away their bad mood by finding common ground.

210. "A Real Fine Place to Start" by Sara Evans (#1, 2005)

It's hard to go wrong by covering Radney Foster, one of the more thoughtful country writers of our time. She "could waste time tryin' to figure it out,”  but this budding relationship just feels too right to hold back. There's an interesting mix of tension, mystery, assurance, and Tom Petty references in the lyrics, and the guitar-focused production calls back to not only Foster & Lloyd, but also to the work of other co-writer George Ducas. And it's just got a great melody sung to twangy perfection. If I'm going to list off some of my favorite songs of Sara Evans's, then this is a real fine place to start.

211. "Real Live Woman" by Trisha Yearwood (#16, 2000)

This is a bold message even by the standards of Trisha Yearwood, no stranger to feminist themes. She may not have the best job, but she's unapologetically who she is: an everywoman with a comfortable relationship. But ultimately, this isn't just about her: it's about the man who accepts her as she is, and it's a message of positivity and confidence. Women don't need to hold themselves to unrealistic body standards (a message ahead of its time), or judge themselves by what Hollywood stars are doing (a mindset I've never understood). The best that you can be is yourself. And with her assured performance, I believe she stands by what she sings.

212. "Red Dirt Road" by Brooks & Dunn (#1, 2003)

Another late-career high for B&D. There are a lot of stories woven into these memories of an old dirt road: sneaking out to drink, getting into a relationship that doesn't work out (until it does), and learning about life in general. We all make mistakes, and not all parts of life turn out the way we wanted, but there's still happiness to be found in all of it. Unlike "Sawmill Road" and its compelling worries for others' well-being, this is a more bittersweet take that mixes the ups and downs for the ultimately uplifting message of a life well lived. And don't we all want that?

213. "Red Rag Top" by Tim McGraw (#5, 2002)

Speaking of ups and downs in life, Tim McGraw took a chance with covering this Jason White cut about a relationship that didn't work out. He remembers them sneaking out in her car for a sexual encounter, which in turn leads to a child and then an abortion (something which caused some stations not to play this song). Unspecified events drive the couple away, but he still can't stop thinking about her from time to time. The picked dobro and McGraw's relaxed vocal tone combine with the detailed story to convey that wistful "one that got away" feeling in one of the most distinct ways I've ever seen this theme executed.

214. "Remember When" by Alan Jackson (#1, 2004)

Why do I usually find Alan Jackson's love songs among his best work? I don't know, but maybe it's the tenderness he brings to every one. The arc feels completely real: their first meeting, their marriage, loss of loved ones, the birth of children, increasing age, and even a nod to his highly-publicized separation from longtime wife Denise. Not a second of it is oversold or forced, and as a whole, it seems like a cousin to my personal favorite "Song for the Life.”  I also love the production's subtle use of mandolin, steel, and string sections, combined with a downward-then-upward key change. Best yet is the way the hook "remember when" becomes "we'll remember when" at the end.

215. "Riding with Private Malone" by David Ball (#2, 2001-02)

David Ball's best song is a unique spin on the patriotic imagery of the day. Here, the narrator buys a car owned by a soldier who supposedly dies in combat, leaving a letter for whoever should own the car after him. That in and of itself is touching, but it becomes even more so when the narrator swears that he can see the soldier's ghost in the car -- and especially when the car is in a wreck and it's implied that the soldier's ghost saves him. Regardless of whether or not you believe in anything supernatural, Ball's matter-of-fact storytelling makes this one engaging -- haunting, even -- from start to finish.

216. "The River" by Chely Wright (did not chart, 2005)

I grew up by a river that, every summer, was full of people fishing or canoeing. In the second grade, one of my classmates drowned in that river. So I believe every important event that happened in the river she sings about. We learn about after-party car accidents, accidental drownings, and baptisms, each vignette showing the character behind them and the impact on the narrator. The song's 6:29, but never feels like it's dragging or wasting time. Wright's always had a hard-edged emotive voice, and songs like this or "Back of the Bottom Drawer" find her matching it to impressively nuanced narratives that are both personal and cinematic.

217. "Rose Bouquet" by Phil Vassar (#16, 2001)

After two bright and bouncy everyman scenarios, Phil proves himself to be a highly effective balladeer. The lyrics seem fairly simple on the surface in their chronicles of a breakup, but repeated listens reveal surprising nuance: "Passion flows like a long white gown / But it ain't easy to keep your love alive" is a winning line, and of course we can't forget the parallel between tossing the bouquet and tossing a failed relationship away. As is expected of early Phil Vassar, the vocal is impassioned without being overbearing, and the production lush and full of piano. It's surprising he didn't really do another song like this...

218. "Run" by George Strait (#2, 2001-02)

This song has a spacious, moody sound full of synthesizers and acoustic guitar, almost seeming to be a deliberate defiance of the urgent lyrics. Run, don't walk back to me, because I miss you. It's a premise that's been done, but lyrics like "I swear, out there ain't where you oughta be" and "Leave Dallas in the dust / I need you in a rush" are slightly off-beat enough to add nuance. I also love how George goes for a bigger vocal than usual on the chorus. As much as Strait is lauded for his consistency, this decade finds several examples of him adding a few extra seasonings to the meat and potatoes.

219. "Same Ol' Song and Dance" by Leland Martin and Chalee Tennison (did not chart, 2006)

An old-school barroom shuffle with tons of steel, vocal chemistry, and wordplay, not to mention two great vocalists who sound amazing together -- it'd be almost too easy to start making comparisons to Conway and Loretta or Porter and Dolly, so I'll let the song speak for itself. They know not every relationship is the same in terms of how it starts, sustains, or ends, but they've got a good solution. If the sparks start dying, they just "put on that same ol' song and dance.”  Instead of referring to a tired old routine, it's an oldie they both love and dance just like when they first met. Sometimes a traditional approach is the best one -- both in love and music.

220. "September When It Comes" by Rosanne Cash and Johnny Cash (did not chart, 2003)

"I cannot move a mountain now; I can no longer run / I cannot be who I was then; in a way, I never was." Just hearing Johnny sing those lines to his own daughter is enough to make this song an instant winner. The strained relationship between the two is already well-known, but healing was evident as early as her cover of "Tennessee Flat Top Box.”  And when I hear Rosanne warmly sing about "September when it comes,”  it's clear to me that the two of them had not only reconciled, but had also taken comfort in his impending death. Which, hauntingly enough, came in September of that year.

221. "17" by Cross Canadian Ragweed (#57, 2002)

As Wide Open Country pointed out, this is the inverse of "My Hometown.”  This guy points out that others seemingly have nothing better to do than judge him ("You keep on runnin', boy, you'll run yourself in the ground"), that he's chickened out on a budding relationship again, and that no one will miss him when he finally chases his dreams in music. I love the hook "you're always 17 in your hometown" because I've seen far too many people unfairly judge me like that. It's got plenty of Dust Bowl grit with Cody Canada's snarky bitter tone and the ample guitars; it's also one of the most thematically relevant debut singles this side of "Baby Girl.” 

222. "She Ain't the Girl for You" by The Kinleys (#34, 2000)

The Kinleys had a rough go after their first album, and I'm at a loss as to why. Their second album was led off by an unusual perspective: a woman telling a man to dump the other woman she's with. Usually, such a song would have the man tell the woman to end her current relationship. But by switching up the sexes, we find the man to be both vulnerable and stubborn ("She makes you cry and still you stay / Why can't you just walk away?"). And the narrator is every bit as defiant, bluntly telling him out even as she's willing to help. The twin sisters' throaty harmonies are as on-point as ever, and they're helped through this moody melody with some backing vocals from Chely Wright.

223. "She Didn't Have Time" by Terri Clark (#25, 2005)

"Girls Lie Too" marked a point where Terri started to feel like she was trying too hard to be a "tough girl.”  But the real strength of a woman comes through here. Specifically, we see a recently-divorced single mother who doesn't "have time" in the standard "three scenarios" style of country music songwriting. Through all the "time" she's dedicating to motherhood and work, she does her best to get by and finally meets the one. Each scenario is completely natural and human, not to mention deserving of someone who worked hard to get where she is. I also like that Terri drops into almost talk-singing at times,

224. "She Misses Him" by Tim Rushlow (#8, 2000-01)

A few years ago, my stepdad began showing signs of dementia. As of right now he's still able-bodied enough for mom to take him to concerts, even if she has to help him get dressed. And I'll sit and listen to him ramble about his rebellious youth in Flint. But soon, he'll be like the man in this song: still alive, but clearly without a lot of time left. Soon, mom and I are going to remember the concerts and he's not even going to remember my name. But we'll still dress him, find his chair, and read to him until he's no longer with us at all. I liked this sympathetic portrayal and the former Little Texas frontman's grained voice, but the personal connection makes me enjoy this song a hundred times more.

225. "Sing Along" by Rodney Atkins (#37, 2002)

Yet another one that makes the list by pure weirdness factor alone. Lyrics like "bunnies in a bramble,”  "ain't no kangaroo lawyer but I will get you off,”  "slower than a broke-kneed turtle" are silly, charming, and slightly lewd all at once. It's one of the most offbeat falling-in-love songs to have made the charts at all during this decade, and it's emphasized by some clever production tricks (reverberating fiddle, synthesized hand-claps, backwards guitars) and a tricky chord pattern. This proto-MuzikMafia approach may not be for everyone, but if you like it, then jump on in and sing along.

226. "Small Stuff" by Alabama (#24, 1999-2000)

Alabama spent most of their twilight years embarrassing themselves with lame trend-chasing songs. But buried in all of that is their last truly great single. I get too wrapped up in whether or not I'll still have food tomorrow or whether I'll ever get my roof fixed. But I have a job, family, a cat, a guitar, and people who read my rambling reviews. Randy Owen's voice is warm and weathered when he sings about "coming of age" and driving a broken car home from work. While the production is more glossy, it still sounds like Alabama after all these years -- and there's a comfort in an iconic band just being themselves again, even if only for one song.

227. "Small Town Radio" by Todd Fritsch (did not chart, 2005)

I grew up on country radio: mostly WKJC, but I began mixing them with WATZ in 2005. And it was the latter that exposed me to this ode to those exact kind of stations. The ones that play whatever songs they want, alongside raffles, classifieds, Paul Harvey, farm reports, church services, and baseball games. It's not just a memory of what I grew up on in the same vein as "I Watched It All (On My Radio)"; it's also an ode to the treasure trove of new music WATZ exposed me to that year. Hell, Todd even wrote a new closing verse just for WATZ to play. And now you know... the rest of the story.

228. "Some People" by LeAnn Rimes (#34, 2006)

The truth is, not everyone finds the one they love. Some just don't want to (that would be me); some don't realize it; and some are only in it for the short term. She never feels like she's claiming superiority, in part because she admits her and her partner's flaws: "Look how much we've been given, baby, in spite of all of our mistakes.”  But the real reason this made the list is that vocal performance: warm, confident, and throaty, slowly building in intensity and changing phrasing on each chorus. I liked LeAnn all the way back to "Blue,”  but the sheer amount of growth she showed as an artist in just one decade is stunning.

229. "Some People Change" by Montgomery Gentry (#7, 2006)

A racist and an alcoholic both see the error of their ways, with implications that their upbringing and societal norms are to blame. There have been people in my life whose harmful actions I've dismissed, only to see them make an unexpected turnaround. Hell, I'm pretty sure I've done it at some point. And as socially charged as the world has become since this song's release (especially with issues pertaining to race), this song's message is as timely as ever. Plus, like most middle-career MG songs, it's got Eddie on the verses and Troy on the chorus for extra vocal impact (not to mention a well-placed choir). Some people really do change, and I hope this inspires more.

230. "Somethin' in the Water" by Jeffrey Steele (#33, 2001)

Five years after Boy Howdy, Jeffrey's singing voice evolved from "poor-man's Tim Rushlow" to a playful raspy shout, and it's for the better with this raucous production. Cute lines like "skinny as a toothpick turned sideways" and "she don't look like her mother, nothin' like her father" give a lot of whimsical detail to our sultry protagonist. But then, not unlike "Evangline,”  she disappears after turning the narrator on with her spicy Southern charm. It's that combination of mystique, sensuality, and grit that makes me wish Jeffrey had gotten more shots at a solo career -- not that his songwriting and production careers have been lacking, mind you.

231. "Something Like a Broken Heart" by Hanna-McEuen (#38, 2005)

Their fathers founded the Nitty Gritty Dirt Band and one of them used to tour with The Mavericks, so good music is in their DNA. Jaime Hanna's lead vocal brings the right amount of passion to this inability to describe his low mood. Images like "a lonely Friday night downtown" and driving until the radio signal fades add perfectly to the tone, as do the guitar-heavy production (both electric and steel) and perfect chorus melody. Although I hear hints of the Everly Brothers, The Mavericks, Foster & Lloyd, and Dwight Yoakam, the result is refreshingly unique. This album was a masterpiece that undeservedly got shunned by a label closure.

232. "Something to Be Proud Of" by Montgomery Gentry (#1, 2005)

Not unlike "Help Somebody" (also a Jeffrey Steele co-write), this one finds an authority figure using his life experiences to form a central thesis. The father tells stories of combat, then watches his son struggle to get by when things don't turn his way (dead-end job, new wife). But the father isn't let down by his son's failures, and dispenses this winner of a line: "And if all you ever really do is the best you can / Well, you did it, man.”  Sometimes I get too wrapped up in my own perfectionism and curse that my life hasn't turned out better. But it's turned out good, and with their country-rock chemistry, fine voices, and wise song choices, Montgomery Gentry convince me every time.

233. "Space" by Sarah Buxton (#38, 2008-09)

Sarah Buxton has one of the most distinctive voices in country music, balancing a youthful sweetness with a raspy edge, and it was best put to use here. He's afraid the relationship is moving too fast and that he wants "space,”  so she shoots back with "I'll give you space...does it make you feel free, make you feel young?" The following lines (co-written with the extremely underrated Lari White) don't hold back, either; I also like how she doesn't finish the last line. Strings-and-steel production creates the right sonic atmosphere, but it's the incisive lyrics and Buxton's delivery that really make this one great. She deserves better than singing backup for Big Loud artists.

234. "Speed" by Montgomery Gentry (#5, 2002-03)

It's ironic that a song named "Speed" would be fairly laid back, but that's the point. This guy is looking to trade in his truck for something new -- because that truck is too tied to memories of the one that got away. While there is a level of masculinity to lines like "one of them souped-up muscle cars / The kind that makes you think you're stronger than you are,”  it's tempered by how torn up he is over his relationship ending. Rare is the song that can balance brains and brawn, and it's all the more credible from an assured baritone like Eddie Montgomery. And it's leagues better than "7500 OBO.” 

235. "Startin' with Me" by Jake Owen (#6, 2006-07)

His first genuinely good song, and one of his most genuine, period. I don't kow how true any of these tales of misdeeds are -- one-night stands gone wrong, pawning heirlooms, fighting with his parents, and losing his job and his wife. But they're the kinds of things that happen every day, and the kinds of things that one can regret. This guy lays it on thick, but never to the point of a pity party; just dejected and introspective. Jake has the charismatic kind of vocal to sell this material without feeling too rough or smooth, and I wish he'd ditch Joey Moi and go back to stuff like this already.

236. "Stay with Me (Brass Bed)" by Josh Gracin (#5, 2005)

Remember that "rainy" sound I praised in Clint Black's "Like the Rain"? Here's a similar take, only in 6/8 time with a mandolin and strings instead. This song sounds like the most beautiful rainstorm that could possibly exist, and it's paired with a fantastic invitation to just stay inside the warm house and make love instead. There's so much passion and warmth in every second, combined with a unique title and melody. Even the opening line is delightfully conversational. And then add on that fantastic production, and the result is one of the best love-making songs on the country charts in the 21st century.

237. "Stealing Kisses" by Faith Hill (#36, 2006)

This tale of an unhappy housewife almost feels like an antithesis to "The Lucky One.”  The woman in this song gets caught in an underaged, beer-fueled encounter with a young man whom she later marries, ignorant of the red flags. And now she's trapped in a loveless relationship with the same man, who's now late for dinner and left her without any adults to talk to. There's a bitter dissatisfaction in the lyric "Don't you know who I am? I'm standing in your kitchen,”  and it boils over with her warning other young women not to repeat her mistakes. That is a lot  to take in, and Faith gives a beautifully dramatic read.

238. "Stronger Woman" by Jewel (#13, 2008)

I'm surprised Jewel didn't try country sooner. Maybe she got gunshy after genre-hopping with 0304? This is fronted by her distinctly soft chirpy voice, mixed with some of her best writing ("I've lived on hope just like a child / Walking that mile, faking that smile") as she finds the inner confidence to break up a relationship. It feels like a throwback to "You Were Meant for Me,”  just with more steel and banjo; at the same time, it's an extension of the more literate, soulful style that artists like Tift Merritt, Ashley Monroe, and Elizabeth Cook were honing. This really could have been the start of something big, but it's still a great song on its own.

239. "Stuck" by Ash Bowers (#42, 2009)

Who hasn't felt like they're "stuck" in a dead-end job in a dying town? I felt like that for a long time. This guy's had enough, so he's gonna get the hell out of it while he still can. With the infinite number of small-town odes in country, this one joins "I Hate This Town" in being one of the most inspired subversions. This song leans more into mood and action (he really does leave!) than the latter, but is every bit as engaging. Bowers' rough-edged everyman delivery and the guitar-heavy production are completely on point. While his turns as a vocalist stayed "stuck" below the top 40, it's clear he knew his way around a good song, as he's now producing for Jimmie Allen.

240. "Swingin' Door" by Joey Daniels (did not chart, 2006)

I love the metaphor of an uneven relationship being seen as a swinging door. This Brett James/Ashley Monroe co-write uses an unusual rhyme scheme and unexpected references like convenience stores and rest stops to add to its central metaphor. For the only time on the album, Joey Daniels found a twang and bite to her voice, and the production is crisp and edgy. If she had more material like this and less like "Crazier Than Usual,”  I think she might've broken out of the indies and into something big. But the fact that other artists still found this song at all is a testament to its strength.

241. "Swinging for the Fence" by Billy Dean (did not chart, 2006)

This is the most upbeat he's ever sounded. It's a cleverly-written ode to taking chances, and I like how each reference continues the story. He goes from being a little league baseball player to a teenager in love, to a minor-league player who gets his big break -- all because he's, both literally and metaphorically, "swinging for the fence.”  I love the way the slide guitar goes up and down, almost as if it's musically suggesting the big swings he's taking, and I love how he calls out ball park concessions at the end. Even from a creative standpoint he seemed to be taking bigger risks than usual; while it didn't pay off this time, it at least resulted in one of his most interesting songs.

242. "Takin' Off This Pain" by Ashton Shepherd (#20, 2007-08)

I love her bold, twangy voice and attitude; I love the hook (she's removing her wedding band; the other hand's holding a beer); and I love her unwavering confidence ("I'm the only one who can set myself free"). I also think it's cool that she wrote the song entirely by herself. As many songs as there are in country about a woman telling off a wayward man, it's always been a trope I've enjoyed when it's done right. This is neck and neck with "The One in the Middle" for being one of the best takes from that year alone; unfortunately, the only thing that didn't "take off" was Ashton's career.

243. "The Talkin' Song Repair Blues" by Alan Jackson (#18, 2005)

Even if you don't understand the musical jargon being thrown around, the point still remains: there's always that one person who claims to know what they're doing, but micromanages your stuff into oblivion in perceived attempts at improvement. Dennis Linde, a perpetually left-of-center songwriter squeezed out of relevance by the Nashville machine (something he was expressing as early as "Down in a Ditch"), was no doubt venting frustration in his distinctively off-kilter way. No stranger to deadpan meta-humor himself, Jackson was the right choice to convey this uniquely charming song.

244. "Tennessee" by Marcel (did not chart, 2003)

While the premise is one that many country songs have done -- the simple "plead for your lover to come back" -- it's absolutely crammed with details. He's headed back from California to Tennessee and leaving her behind, all while drinking Coke and eating Corn Nuts, seeing a postcard fall out of a book that she gave him on his birthday, and then coming home to take a bubble bath. Lines like "Then I think to myself, 'will I ever get a break / Or did I make a big mistake?'" add humanity, as does the contrast between the lush string-heavy production and Marcel's unpolished voice.

245. "That Train" by Doc Walker (did not chart US/#10 CAN, 2007)

Sometimes it's hard to beat old habits. These three scenarios are all hard-hitting and credible: a man waking up alone in a hotel room, a woman trapped in an abusive relationship, and a touring musician all know the harmful consequences they face, but they feel desperation. It's the shift to first person on the "touring musician" verse that really sells it; it's like this guy is saying "I know what you're going through because I've been there too" to the other two examples. The band's harmonies recall Restless Heart's layered country-pop approach, only with more guitars underneath. Considering these guys were charting in Canada since the late '90s, I'm surprised they're not bigger names even there.

246. "That Train Don't Run" by Pinmonkey (did not chart, 2006)

While Matraca Berg's original version is up to her own very high standards, there's something I find more special about Pinmonkey's. When Michael Reynolds and his tightly-harmonizing (and picking) band mates compare a long-lost love to a train whistle blowing down a defunct line (it's amazing how simple yet effective "sweet dreams, baby, wherever you are" is in this context), it encapsulates how I feel about Pinmonkey. Sometimes I swear I still hear high twangy harmony and Dobro as if this weren't the last single by a fantastic underrated band. That "train" may not run, but I still hear it often, and I remember where it took me in the first place.

247. "That's Cool" by Blue County (#24, 2004)

Being a kid and using a lawn chair as an X-wing starfighter (I was more "use Tinkertoys, dominoes, and the couch to make a bustling city street"), finally getting your first job and car, and then getting married and having kids to share those same moments with -- this is all simple, everyday stuff, but if you do it right, there is joy to be found in every second of it. Because every single one of those moments made you who you are, no matter what anyone else in the world tries to say. Between the detailed lyrics, warm vocals, and bracing production, Blue County tells it exactly like it is. They aim straight for the heart, and hit it every time. And that's cool.

248. "That's Just Jessie" by Kevin Denney (#16, 2001-02)
Memories of lost love are so common that it's pleasing to hear a fresh take. This guy is so distracted in quirky, original ways -- drawing on his notepad in a meeting, for instance -- all because he can't shake the equally vivid memory of a lost love. The images get a bit darker in the second verse (footsteps and shadows), which to me suggest Jessie may have died. Denney has a reedy voice recalling Gene Watson and Doug Stone, imbuing a sense of sad nostalgia to the lyrics that's only emphasized by the relaxing acoustic guitar. There's a reason so many people remember this song 20 years later -- just like how this guy is remembering Jessie.

249. "That's Just That" by Diamond Rio (#42, 2001)

If you thought "Unbelievable" was fast-paced, you clearly haven't heard this one. This one follows a relationship that looks like it's ended -- after all, neither of them is talking to the other, and "that's just that.”  But when they drop their egos and finally decide to work it out, what seemed unsalvageable is repaired, and once again, "that's just that.”  The super-fast delivery and picking (can't go wrong with mandolin and vocal harmony!) caught me off guard the first time; the reconciliation caught me off guard the second time. If a song surprises me twice in two-a-half minutes, I have no choice but to include it. And that's just that.

250. "That's What I Believe" by One Mile South (did not chart, 2005)

If you're looking for it on YouTube, it's titled just "I Believe" there. Will Nelson, whose voice recalls a twangier Ronnie Milsap, joins his Mississippi bandmates for a guitar-heavy plea for reconciliation. Every line is simple yet effective ("Sometimes it takes losing everything you've got / To finally realize what you really want"), the playing is finely constructed yet gritty, and the melody is highly memorable. I listened to WATZ a lot around this time, and I'm glad they leaned so heavy into indie cuts because I found some real gems. Given that I've found two covers of this song, apparently I wasn't the only one...

251. "That's Why I Hate Pontiacs" by Rebecca Lynn Howard (#60, 2005)

This one maxes out the details right away: wisteria vines, watercolor sunsets, and a Trans Am. Everything looks picture perfect all until he says goodbye. Now, she can't see a Pontiac, a Cracker Jack ring, Tupelo (where he was headed after he said goodbye), or the song playing when he said goodbye (I guess the song really does remember when). And really, "we were maniacs, so wild and free / 'Til he took it back that he loved me / And he drove off like the wind" is a brilliant twist to the last chorus. Howard's voice is as assured as it was on "Forgive,”  but with a softer more wistful edge that matches the piano-and-fiddle backdrop.

252. "There Is No Arizona" by Jamie O'Neal (#1, 2000-01)

One of the most original premises I've ever heard in a song. The man is promising a "new life" in Arizona for his woman, but just uses it as an excuse to ghost her. It's a clever premise with a great chorus, and the verses fill in every detail. The production is ear-catching too, mixing drum loops with spacious guitar, mandolin, and harmonica in what feels like a more modern spin on that "desert sky" style I liked so much in the '90s. In an era where it felt like every new female act was big-voiced pop, Jamie tweaked that image with highly memorable songwriting and production that remembers the "country" side of country pop.

253. "There's No Limit" by Deana Carter (#14, 2002-03)

I seriously thought Deana Carter disappeared after Did I Shave My Legs for This? because I have no memory of any of her later singles. And I would think I would remember a song with a freaking harpsichord in it. But that highly unusual instrument choice is far from the only memorable thing here. Second in line is the "if it's X, I'll Y it" lyrical structure for what she plans to do with her lover, every single instance of which builds off the hook "There's nothing I would not do; for you, there's no limit.”  I also like that the bridge is sung on both sides of the harpsichord solo, and that Deana gets to cut a bit looser vocally.

254. "Things a Mama Don't Know" by Mica Roberts and Toby Keith (#55, 2008)

I had never heard this until it played in the grocery store the week before I wrote this entry. What I like the most is that it subverts the "chase your dreams in the big city" trend by showing that things really aren't that great; she's just too full of pride to reveal she got stranded in Vegas with a dead-end waitress job and an abusive boyfriend. One could argue Toby Keith's presence on the second verse disrupts the lyrical flow, but if that is a distraction at all, I find Mica's soulful, nuanced vocals and the detailed lyrics more than make up for it. It's a sad truth that abuse victims have tried to hide it, and my read of the last verse is that she does at least do something about that at the end.

255. "This Is Me You're Talking To" by Trisha Yearwood (#25, 2008)

She just wants to have a mature conversation with an ex during a chance encounter; after all, "You don't have to tell me that you really love me / After all we have been through / 'Cause this is me you're talking to.”  Just like "The Back of Your Hand,”  they both know each other too well to let go entirely. Even better, this song proves one thing that I wish more female singers at the time knew: it's possible to pack a vocal full of drama and nuance without belting into the stratosphere. The production follows suit, adding string and piano but never blasting -- just letting all the emotions soar and then cool down at the end.

256. "This Is Us" by Mark Knopfler and Emmylou Harris (did not chart, 2006)

Mark Knopfler and Emmylou Harris? It's less odd than Jack White and Loretta Lynn, as Mark's dipped his toes in country before, but the results are still above expectations. Both talents are on full force here: Knopfler brings his distinctive six-string tones and an unpolished, almost Dylan-esque delivery that complements her wide-ranging country-folk approach. I love how every single detail adds slowly to a story about a true love: from Mardi Gras to a barbecue to a honeymoon, all of those little memories are there. It's ultimately the unrelenting groove and the surprisingly potent vocal chemistry that make this one rank so high.

257. "This Town Needs a Bar" by Jeremy McComb (did not chart, 2008)

How does a former manager for Larry the Cable Guy end up being a good singer? Some towns are so small that they don't even have a bar (a few are within an hour of me), which has me wondering where exactly one goes to drown one's sorrows in such circumstances. The town has other places -- a bank, a church, and the house where they were going to settle down until she left. McComb sounds like a dejected small-town everyman who's probably going through this exact situation right now across the county. And less-is-more honky-tonk guitar-and-fiddle production doesn't usually go for a key change, but hell, he nails that too.

258. "Three Mississippi" by Terri Clark (#30, 2003)

Terri Clark's assertiveness got much more compelling around this time. Here, she's seen attempts to rebuild a relationship fail again and again, so she's declaring this one the final try. The "one Mississippi" hook is cute and memorable as it counts down each failed attempt, and it's balanced by harder-hitting lyrics like "My bones are achin' from the weight I'm holding now.”  The production is surprisingly nuanced, with banjo, mandolin, and guitar hitting on a tone that almost sounds like a pennywhistle at times. I love it when a song is bright and catchy on the surface, yet reveals deeper emotion on repeated listens.

259. "Tim McGraw" by Taylor Swift (#6, 2006-07)

This is no mere name-drop; it's about lost love, with a song being the specific catalyst for those memories. Still a teenager at the time, she was closer to the memories of ended summertime loves than most other writers tend to be; I particularly love the opening line "He said the way my blue eyes shined / Put those Georgia stars to shame that night / I said, 'that's a lie'." The relationship is over, but she hopes the memories remain. Both then and now, Taylor impressed me with how confident her vocals and lyrics were right out of the gate. If you wonder why Taylor Swift still has a career in 2022, I hope you think "Tim McGraw.” 

260. "Tonight I Wanna Cry" by Keith Urban (#2, 2005-06)

One of the best lyrics on this list: "I'm just drunk enough to let go of the pain.”  (Second best: "I thought that bein' strong meant never losing your self-control.” ) Even if you don't know that this came out only months before Keith re-entered rehab, there's a pain and dejectedness to the way he sings that "drunk enough" line that makes you feel what he was feeling. This is truly a stark portrait of a guy who's hit rock bottom -- so brokenhearted over what could have been that he's sitting by himself in a dark room, drinking and going through love letters. It's even stark in its arrangement, focused on just piano and strings.

261. "Tonight's Not the Night (For Goodbye)" by Randy Rogers Band (#43, 2005)

This was a boom era for Texas country, wasn't it? A rough-edged everyman has given his woman fair warning: it's too late to back out, we're falling in love. It's confident from the first line ("This is your love song, baby / This is the part where I must confess / You're looking good in that pretty dress"). He never feels cocky or manipulative, just cool and confident. Like most of the other Texas-flavored entrants on this list, it's also got a gruff but friendly lead vocal, and a ton of twangy guitar on top. Oh, and Radney Foster wrote it so you know it's good.

262. "Too Lazy to Work, Too Nervous to Steal" by BR549 (did not chart, 2001)

This is a wonderfully tongue-in-cheek look at a guy who seems at first just to be a deadbeat getting dressed down by a woman ("Why don't you find yourself a life that's real?") But in reality, it's because he's a musician, which as people who aren't musicians know, isn't "real work.”  It seems he takes her advice, as the final verse finds him leaving on a bus. Chuck Mead's vocal is tongue-in-cheek all the way through, and his bandmates seem to have ditched the cartoony faux-retro shtick of "Cherokee Boogie" in favor of some twangy and catchy guitar riffs.

263. "Top of the World" by The Chicks (did not chart, 2003)

As much as I write about forgiveness, here's someone who didn't get theirs. Specifically, a man who doesn't seem to have treated others -- especially not his wife -- with any degree of respect. This realization is made too late, as the second verse makes it clear that this man is no longer among the living. As sassy as Natalie Maines can be, she's also surprisingly vulnerable and remorseful when the song calls for it. The harmonies and string-heavy arrangement are downright haunting. The song just explodes into emotion at the end as they sing "top of the world" over and over. But that's not the only song off Home that destroys me every time I listen to it...

264. "Travelin' Soldier" by The Chicks (#57, 2002/#1, 2002-03)

...This is the other. The girl in this song falls in love with a soldier during the Vietnam War. He goes off to service and they communicate by mail for a while. Just like "If I Don't Make It Back,”  its skip ahead to the soldier dying is sudden and hard-hitting. Just moments before these two had found a cure for loneliness, it's ripped away from both of them. There's an acoustic spareness to the production that underscores the Chicks' harmonies at their peak, and that fiddle-and-drum outro only makes it stronger. This song's themes resonated during another time of war -- even if the mood of that same war would drive radio against this band only days after this powerful song hit #1.

265. "Trip Around the Sun" by Jimmy Buffett and Martina McBride (#20, 2004)

As I said back at the "Bama Breeze" entry, it's so easy to forget just how much of a range Jimmy Buffett actually has. My favorite single of his is further proof of this. Songs about growing old are commonplace in the myriad of emotions they bring. The guy in this song has not had the best of lives, but through age he has learned one thing: we all grow older and there's nothing we can do about it except try to enjoy the ride. Buffett has the right weathered-yet-calm sound, and Martina keeps the song anthemic without overpowering. (Fun fact: I wrote this entry on my 35th birthday.)

266. "Two Pink Lines" by Eric Church (#19, 2006)

The two unwed teenage lovers are anxious about the results of a pregnancy test; lines like "That second hand just keeps slowing down / I swear it stopped twice the last time around" add both comedy and tension. But just when you think it's going to be a surprise baby, the test comes out negative and she leaves. And it doesn't feel like an anti-climax; it feels like something that would actually happen, and it takes the pressure off both the man and the woman. Jay Joyce adds a groovy drum line and harmonica underneath Church's no-nonsense delivery. And to think a song this inspired was only his second single...

267. "Unbroken Ground" by Gary Nichols (#39, 2006)

Here's a guy who's willing to try something new: falling in love. He's kept himself too closely guarded, but somehow, she found a way in. The crop metaphors are clever, and they hold up on scrutiny: "this field ain't never been plowed,”  "it's gonna be a hard row but it'll be worth it,”  "I'm the one that built this fence" all make sense within the narrative. Nichols has a raspy but charismatic voice that recalls Chris Stapleton (whom he would later replace in The SteelDrivers), and the acoustic guitar hook is very hard to resist. Unfortunately, radio didn't bite and his album died on the vine. (See what I did there?)

268. "Unusually Unusual" by Lonestar (#12, 2002)

That title could describe my best-of lists (and the person writing them), couldn't it? Mark McGuinn hit on a great lyric about a lady with an off-kilter view of life that is clearly not on the same wavelength as everyone else ("She had a tattoo above her ankle of a trident submarine / She said it symbolizes awesome powers hidden deep within our dreams") portrays her eccentricity so positively that I really want to meet her. In fact, I think she's appeared in at least one story that I've written. The bright drum loop and fiddle production -- another show of McGuinn's influence -- is a different cup of tea that just does it for me.

269. "Up North (Down South, Back East, Out West)" by Wade Hayes (#48, 2000)

Wade Hayes is extremely underrated. His next-to-last charted single is a wonderful lost-love ode well suited to his deep yet quavering voice. "In spite of the name, Independence, Kansas didn't grow many wild roses" is just a great opening line to set the stage for this lost love who couldn't be tied down. She wanted to be free, so he let her, and now he's regretting it. As often as the premise is done, I like the urgency behind it all, especially with the hook. But most of all, I just really, really like Wade Hayes' voice -- which almost singlehandedly makes great a song that seems so simple when written out.

270. "Walking in Memphis" by Lonestar (#8, 2003)

Lonestar had already gone full sippy cup of milk by this point, so a cover song was a hard enough pivot on its own. But this one is the grittiest they've sounded since "No News,”  and in doing so, they outshine Marc Cohn's fine origina. Memphis idolized for its place in music history -- from blues to Elvis -- and the lyrics hit on all the right notes. It's not just name-drops; it's a story about walking through town and feeling the spirits of those past musicians, and having a spiritual awakening. Even if this weren't so radically different from Lonestar's syrupy standard output at the time, it's still a damn fine cover that keeps the spirit of the original (literally).

271. "Waitin' on Joe" by Steve Azar (#28, 2002)

The best song from an extremely underrated talent. The song starts lightheartedly enough with playful references to his coworker/brother, seemingly always late for his job; lines about river boats help color the song with Azar's Mississippi influence. Something starts to sound wrong when he sings "man, if I could be more like that, I'd get on with my life.”  Why? It turns out that Joe is late because he died in a collision with a train. Thanks to the lush yet twangy production and Azar's grained voice, the reveal of this twist ending is downright devastating -- and all the better for it.

272. "Waitin' on Sundown" by Andy Griggs (#50, 2000)

Andy Griggs' best single was also his lowest peaking under RCA. Shame, because this is a story that needed to be heard. In this song, the male narrator is making plans to help a woman escape an abusive relationship. The man's actions don't feel like condescension or virtue signaling; he actually sacrifices a job to get both of them out of town. It's almost like an antithesis to "Goodbye Earl" in that, instead of getting its necessary message across with dark humor, it goes for a very realistic, sympathetic portrayal. Plus, it's got a great guitar hook and it's yet another reminder of Griggs' rugged baritone.

273. "Walk a Little Straighter" by Billy Currington (#8, 2003)

I never witnessed my dad's alcoholism personally, but it's still not something I would wish to pass on if I were to have children of my own. Currington wrote some of the lyrics (about his own father) at age 12, lending a sense of wisdom beyond one's years: "Walk a little straighter, Daddy; you're leading me" still hits as hard when a mature adult sings it, because he's lived it. And you can tell he means it when he expresses his wish not to be a bad example. For all the great songs he's had as an artist, this was such an impressive first bow that I'm surprised he matched it at all.

274. "Wal-Mart Flowers" by Stephen Cochran (did not chart, 2009)

Sometimes smaller gestures can say "I love you" a hell of a lot better than luxuries can. This guy knows that he can give his woman a candy bar and a Diet Coke, and she'll appreciate the sincerity of the gesture far more. I had a former coworker who'd buy me random crap like that all the time; while there was no romance between us, it was just fun and encouraging to see what was waiting for me in the breakroom. There's a great deal of charm to this idea, and Cochran turns in a winning guy-next-door performance that enhances the mood.

275. "Wal-Mart Parking Lot" by Chris Cagle (#42, 2006)

Huh, two songs in a row with Walmart in the title... Every town has the one hangout where everyone goes on a Friday night. The hangers-out are detailed here ("freaks,”  people hiding beer from the police, kids experiencing their first love... or heartbreak), each one a character sketch in its own right. I've seen all those small towns in the South where Walmart is just about the only thing in town at all (not so much a thing where I'm from), and just like those smaller Walmarts that don't have a grocery department, it's a rapidly fading yet charming image I still see in my head every time I hear this song.

276. "Want To" by Sugarland (#1, 2006)

And the award for "hardest song title to Google" goes to... Sugarland's first song without Kristen Hall is a beautiful yearning-for-love song with a laid-back acoustic arrangement. Jennifer Nettles' voice calmly goes through the details of a budding relationship before jumping right into the chorus just as is suggested. It's like a more lighthearted "Tonight's Not the Night.”  Every detail is vivid and fun ("you got my heart and your daddy's boat / We got all night to make it float"), making perfect lead-ins to the "I don't want to if you don't want to" hook. Kristian more than pulls his weight too, providing a lot of harmony and mandolin. Plus, it was just cool to see Sugarland thrive after a membership change.

277. "Wasted" by Carrie Underwood (#1, 2007)

I swear this one got like, no airplay in my market. When I sampled Carrie Underwood's debut, this was one of the only songs that got a reaction out of me at all. It shows two people overcoming addiction -- possibly parallel cases, as one fights a toxic relationship and the other alcoholism -- before each concludes their only ways out are to break free from what's left their lives "wasted.”  This is one of the times I'll allow a powerhouse delivery, and Carrie delivers without over-selling the moment. I also like the production, which finds a few convenient places to put some timbales. You can have your "Jesus, Take the Wheel"; this was the Carrie Underwood anthem I wanted to hear.

278. "Way Too Deep" by Sixwire (#55, 2002)

Sixwire seemed to be following the leads of early Rascal Flatts or Emerson Drive in offering high-gloss, catchy country-pop. Lead singer Andy Childs has a slightly edgier vocal reminiscent of Blackhawk's Henry Paul, and his band-mates offer harmony for days. (Seriously, this song has more call-and-response than Ty Herndon's "It Must Be Love.” ) There's a big clean guitar hook weaving its way throughout, and the melody is absurdly catchy. Clever lines ("Don't even bother throwin' me a line") add to the "too deep in love" premise. Just like South 65's "Baby's Got My Number,”  this one makes the list by being very high-quality ear candy.

279. "We Shook Hands (Man to Man)" by Tebey (#47, 2003)

Another song of fatherly forgiveness from both sides. The father informs his son of an impending divorce; the son realizes he needs to leave now that he's grown; and then the father is on his deathbed. Even if the arc is easy to see, the details about both figures are sharp. The father's unafraid to cry; the son is rebellious in his young-adult years; and even though they don't see eye to eye, they're not blinded by pride or machismo. They make peace at the end, not unlike "Things I Wish I'd Said.”  Tebey has an unpolished voice that makes the story arc seem real while nicely complementing the lush production. Why did it take this guy eight years to release another single?

280. "Welcome to the Future" by Brad Paisley (#2, 2009)

Brad channeled a lot of early Obama-era positivity into this song, pointing out the positive growth he's seen on technological, societal, and racial fronts. At the time, I thought we were truly turning a corner as a nation. Sadly, the next administration saw a lot of that positivity come undone in brutal ways I feel will take decades to restore. But a lot of the positives are still there; chatting with businesspeople from Tokyo would have seemed impossible right after WWII. More importantly, he nailed the hope that things will continue to get better in a way that doesn't preach or cling to stereotypes. And I love the production: Heartland rock strumming, 8-bit synths, "whoa oh"s, and one of his best vocals. My only question: can we find this level of positivity again?

281. "What Hurts the Most" by Rascal Flatts (#1, 2006)

I waffled for years on whether or not I actually liked this. But what made me give it the thumbs-up is realizing the emotion crammed into the lyrics. He can take all these other things you'd think would bother him about his failed relationship. But realizing he just let her walk away in what he thought was an act of love? That's the deal-breaker for him. I think the "bigger" production style put me off at first, but (especially compared to their later work with Dann Huff) this is a meatier mix of strings, synths, and banjo that never goes over the top or forces Gary LeVox out of his range. And the melody's great, too.

282. "What I Really Meant to Say" by Cyndi Thomson (#1, 2001)

Cyndi Thomson has a uniquely breathy vocal style that doesn't hold back emotionally. The production is an interesting mix, combining organ, mandolin, and penny whistle to push this further into sounding like nothing else I've heard. Lyrically, it's about hiding emotions from an ex whom she still loves -- "What I really meant to say is I'm dying here inside.”  The narrative continues throughout, with her admitting that her lies about being fine "cut so deep it hurt.”  I also love how the chorus changes the last time, offering "I'm really not that strong.”  It's a surprisingly nuanced lyric with an even more nuanced production.

283. "What Was I Thinkin'" by Dierks Bentley (#1, 2003)

2003 was a good year for strong debut singles. This one caught my ear right away with its heavy Dobro runs and gritty vocals. And it's a very detailed detail of a rough-and-tumble relationship. He's "dating what Daddy hates" (as TV Tropes puts it) and runs off with her even after dad shoots up his car and the police chase after him. And why is the narrator doing all this? Because he's too sexually attracted to her. It helps so much that this song is as fast-paced and rowdy as the lyrics call for, with a vocal delivery and tone that leans into self-deprecation at times. I had no expectations of this ever hitting #1, but I'm glad it did.

284. "What'll I Do" by The Bellamy Brothers (did not chart, 2001)

I like the Bellamy Brothers more than I'd care to admit. Long past their last chart hits, they seemed to use their independent releases as a means of experimentation. One such experiment is of the most downbeat songs they've ever cut. While the lyrics of lost love ("Come to my rescue / Heavens above, what'll I do?") seem simple on paper, they soar thanks to sweet Everly Brothers-flavored harmonies and a lush production. We've got a lonesome minor-key guitar hook that wouldn't be out of place in the 60s and some well-placed pizzicato strings for a truly lonesome, melancholic sound. I've never heard another country song sound like this, and sometimes that's all I need.

285. "When God-Fearin' Women Get the Blues" by Martina McBride (#8, 2001)

This is my favorite song of hers. It's got a hell of a sing-along chorus, and an infectious country energy that I don't think she's had since "Safe in the Arms of Love.”  This woman's "got the blues,”  so you've gotta hide all the whiskey and close the Neiman Marcus. It's a silly premise on paper, but it's one crammed full of quirky line ("I've stirred my last batch of gravy") after quirky line ("Call all the Pentecostals, and bring that anointing oil, too") in her warnings. It's also one of Martina's edgier vocals, and there's almost no way to go wrong when a song has this much Dobro. Martina should have spent more of the noughts cutting loose like this.

286. "When Somebody Knows You That Well" by Blake Shelton (#37, 2004)

I think this song has a bit of mystique because I didn't know it existed until over a year after its release. Still, it's a great take on the "use the chorus in three different situations" lyrical trick leading up to a common thesis. There is no point in hiding certain emotions from loved ones. The second verse about crying over the death of a father has hit harder ever since my own died, and even though I don't consider myself a believer, I won't deny when a religious-themed song moves me. If there is a God, then He knows everything we're doing. Blake at his most moving somehow resulted in a lead single that flopped, and I'm at a loss as to why.

287. "When You Come Around" by Deric Ruttan (#46, 2003)

He may be from Ontario, but he's got a great handle on a Texas country/Red Dirt vibe. His voice even sounds a bit like a young Jack Ingram. There's as much electric guitar as there is fiddle, and it's got a great Dorian mode melody. Much like "Happy Endings,”  it's a plea for a woman who's split to come to her senses and return. More poetic than story-telling, it still paints a complete picture with lines like "The trance you were in made me crawl in my skin" and "The moon can't see out from behind the winter clouds.”  Whatever drove her away, this guy's determined to see her come back... and with how skillfully he recounts the scene, I'm hoping she does come around.

288. "Whiskey Lullaby" by Brad Paisley and Alison Krauss (#3, 2004)

One that everyone can agree on. Even my friend who listens to almost nothing but metal says that this is his favorite country song. And for damn good reason, too. It's as sad and human as you can possibly get: depression and guilt drive both halves of a broken relationship to drink themselves to death. Lyrics like "He put that bottle to his head and pulled the trigger" lend an evocative mood that's only enhanced by the Dobro-heavy production -- not to mention Brad's best vocal and the downright haunting duet vocals from Alison Krauss.  Everything adds up to the perfect country tear-jerker, and my favorite of the decade.

289. "Why" by Rascal Flatts (#18, 2009)

As a song questioning why a loved one committed suicide, it treats its subject with a mix of straightforward sincerity ("Who told you life wasn't worth the fight? They were wrong") and surprisingly poetic imagery (.” ..why you'd leave the stage in the middle of a song"). It never feels overdone or manipulative, and it's matched to a beautifully soft piano-focused delivery (no screaming guitars or "ooh ooh yeah"s here). I get this may not be the kind of heavy subject matter is not usually made for radio success ("Whiskey Lullaby" being an outlier), but they should be commended for taking a chance with a well-executed, necessary message.

290. "Why Ain't I Running" by Garth Brooks (#24, 2003)

As much as I love wanderlust songs, there has to come a time when the wanderer settles down, and it sounds like this guy's found it. Every single line is a winner, but I especially have to single out "Once happiness was only whenever I was on my own / So now why do I feel lonely anytime that I'm alone?" Garth hasn't sounded this assured since The Chase, and there's a bit more grain in his voice than usual. Even his backing band sounds more spirited than usual (especially Milton Sledge's usually too-light drums). If Garth had found more songs like this instead of bizarre alter egos, re-re-re-re-releases, and boring soundtrack cuts, then I think he might have had a more dignified start to the 2000s.

291. "Why Me" by The Lost Trailers (#45, 2006)

The Lost Trailers were a lot different on this album, what with the grittier vocals, heavier guitar, and interesting lyrics. This guy starts off with tales of struggling musicians and crooked politicians (hitting its mark without over emphasizing a side), which are relatable on their own. But the song takes an interesting turn with the Book of Matthew's account of Jesus in the Garden of Gethsemane ("My Father, if it is possible, may this cup be taken from me"). And it's this realization that even the Son of God had human struggles that drives this ramshackle guitar slinger to "rock on.”  I didn't see that twist coming, and regardless of my own beliefs, it still hits me every time.

292. "Wild at Heart" by Gloriana (#15, 2009)

This song is so full of youthful energy and charm, not to mention harmonies for days. And the production is top-tier, mixing in synthesized bass, Dobro, mandolin, hand clapping, fuzzy synth bass, and even beating on road cases for an extremely bright and bracing sound design unlike anything else I heard on radio at the time. There's a unique charm and energy to its falling-in-love lyrics, what with winning lines such as "I've got forever on the tip of my tongue" and "light me up like a bottle rocket.”  This song is like a Jawbreaker: colorful and sweet, but surprisingly layered.

293. "Wild West Show" by Big & Rich (#21, 2004)

"Save a Horse (Ride a Cowboy)" deservedly turned a lot of heads, but I remember how blown away I was when I first heard the single before it.With massive drums, double-tracked acoustic guitar, and high-low harmony backing (not to mention a wood flute and even a peanut can), this oddball spaghetti Western theme is done to perfection. Comparing a faltering relationship to an Old West shootout is an inspired image, and they don't hold back: Tonto, riding into the sunset, buffalo, it's all there. This is the kind of gonzo creativity Nashville needed at the time and still needs now. It's a shame that they lost that spark so quickly, but it was too good while it lasted for me not to pay attention.

294. "Would You Go with Me" by Josh Turner (#1, 2006)

This is a fantastic vocal, stretching all the way from basso profondo to falsetto and back again along a beautifully-rising melody. And then it's dressed with plenty of mandolin and Dobro. This beautiful soundscape is matched to a completely charming falling-in-love lyric. I like how nearly every line is a question, and each individual image ("streets of fire,”  "fields of clover,”  "accompany me to the edge of the sea / Help me tie up the ends of a dream,”  "rode the clouds together") is whimsical without being saccharine. "Long Black Train" was his grittiest, but this was his prettiest.

295. "Wreck This Heart" by Bob Seger (did not chart, 2006)

As a Michigander, I can't turn down a song that mentions "another early winter Michigan storm.”  Most of this song builds on the troubles of life, such as feelings of rejection and separation. There's even a nod to "Stopping by Woods on a Snowy Evening.”  My impression of the last verse is that he wants a one-night stand to ease his mind, which puts this alongside "Turn the Page" in terms of un-glamorous portrayals of rockstar life. His delivery is deeper but no less energetic than in his prime, and there's plenty of cowbell and electric guitar. One could argue why it was sent to country, but this is one of many songs that proves Heartland rock and country aren't so different.

296. "You Can Let Go" by Crystal Shawanda (#21, 2008)

The "three scenarios, same chorus" makes one of its latest appearances. The father "lets go" of a bicycle when teaching her how to ride; of her hands when giving her away; and of her hand again when on his deathbed. If it's easy to see the third verse, that's more than balanced out by the focus on details that seem natural and real -- from "It still feels a little bit scary" to "It was killin' me to see the strongest man I ever knew / Wastin' away to nothin' in that hospital room.”  Best of all, Shawanda has a very distinctive husky voice that cracks and whispers at various points, showing that a vocal delivery can be dramatic and emotive without blowing out the speakers.

297. "You'll Be There" by George Strait (#4, 2005)

My favorite George Strait song, and possibly his most ambitious. The opening metaphors paint a wonderful image about the journey of life, and said imagery (ships, waves, anchor, etc.) carries throughout the entire song. This guy has lost a loved one, and hopes to reunite with them in Heaven in spite of his own backsliding and misguidedness. The picture, though grand, still manages to be completely human (again, "all have sinned") -- what better match could there be for Strait's everyman charm and and the surging production behind him? I hope this guy makes it to his destination, luggage rack or no.

298. "You'll Think of Me" by Keith Urban (#1, 2004)

I do love a breakup song. And what I love about this one is how chill of a take it is. Even though he's waking up early and driving around to clear his head, he ultimately seems to be at peace with what's going on. After all, there's nothing left to say, so he's just telling her calmly that she can take her cat and her record albums. Like most great songs of this sort, there's no animosity toward the ex, just admissions that it'll be for the better ("It seems the only blessing I have left to my name is not knowing what we could've been"). The production is gently minimalist, focused mostly on acoustic guitar and brushed snares to push Urban's impassioned vocal to the forefront.

299. "Young Man's Town" by Vince Gill (#44, 2003)

Vince Gill had a very fruitful '90s, but at age 46 in 2003, he was no doubt starting to feel left behind by the changing music scene. He's saddened by the changing times for sure, but as would be expected from Vince, there isn't a hint of bitterness. Vince knows that no one can stay on top forever, and that it's better to accept and encourage newcomers who just want to follow their dreams. Also as is expected, the delivery is smooth and relaxing, with just gentle percussion and guitar. As often as Vince is portrayed as one of the nicest men in Nashville, it's songs like this that prove it. Now if only more of Music Row could follow his lead...

300. "You're the Ticket" by Billy Hoffman (#75, 2000)

On the surface, this might not seem like much. It's a cover of a John Michael Montgomery album cut, and a cute little song full of falling-in-love metaphors. But they're vivid and cute; I particularly like "steal a kiss when we stop at the top of a great big Ferris wheel.”  And there's a fascinating man behind it all. Born 97% deaf (you honestly can't tell from his laid-back voice), he learned guitar to compensate for underdeveloped hand muscles. This man's story is an entire album in its own right. While that story isn't in any of his songs, I find his music so charming and inspiring no matter what he's singing.