100 Best Country Songs of the 2000s- Part Three (60–41)

These are some damn fine songs. And the selections are only getting tougher.


60. Charlie Worsham — “Mississippi In July” (2013) — Zack
Songwriters: Charlie Worsham, Ryan Tyndell, Marty Dodson

Summer love tracks are hard to make interesting these days, but Charlie Worsham delivered a winner with this track. His vivid storytelling almost makes you feel like you’re there as he finds love and subsequently gets his heart broke years later as both parties move on and form their own lives. It’s simple, but the restrained production really allows the story and emotion shine.

60. Josh Turner featuring Trisha Yearwood- “Another Try” (2008) -Nathan
Songwriters: Chris Stapleton and Jeremy Spillman

Some songs are timeless. As in it could be dropped in any era and become an instant classic. “Another Try” contains themes that are relatable in any single year. Lost love. Regret. Guilt. Everlasting topics in country music. Trisha Yearwood’s harmonies provide such a beauty to the gloomy lyrics and powerful vocal performance of Josh Turner.

59. Dixie Chicks — “Travelin’ Soldier” (2002) — Zack
Songwriter: Bruce Robison

It’s a simple, somber tale of a young romance crushed under the weight of war, but the emotion truly shines through in the story, finding both parties finding what they always wanted before having it taken away.

59. Joe Nichols- “Man with a Memory” (2002) -Nathan
Songwriters: Charlie Black and Roy Michael Bourke

Such a great story song. The title track of his fantastic 2002 album, “Man with a Memory” takes a deep look at the human condition after both a man and a woman find themselves with a broken heart. Nichols sings with a soft and touching vocal that pulls the listener in ever so closer; he’s always been best at playing the part of that wise ‘ol balladeer.

58. Alison Krauss & Union Station — “Paper Airplane” (2011) — Zack
Songwriters: Robert Lee Castleman

It’s dark, poetic and depressing. In other words, it’s Alison Krauss at her best. The melody really soars during the chorus. It’s one of the prettiest sounding ways of saying “it’s over” between two lovers I’ve ever heard.

58. Drive-By Truckers- “What It Means” (2016) -Nathan
Songwriter: Patterson Hood

Writing a protest song is incredibly easy. With so much material to work with, especially in today’s environment, any songwriter can sit down and rage against whatever he or she wants. But making a protest song stand out- that’s a whole other bag. It has to be clever but also not too obscure. It has to be biting without leaning into righteous indignation. Simply put, it should be something along the lines of “What It Means.” Several of the lines are purely phenomenal, and the production gives the lyrics the perfect sense of urgency.

57. Zac Brown Band — “Colder Weather” (2011) — Zack
Songwriters: Zac Brown, Wyatt Durrette, Levi Lowrey, Coy Bowles

To me, 2010 was the last year we saw any chart topping hits that will go on to become classics for the genre. “Colder Weather” is an example of multiple songs I’m referring to from that year. To put it simply, it’s an example of the best that modern country music has to offer. We often hear about musicians singing about life on the road, but it’s unique and heartbreaking to sometimes hear the ramifications of living that life. It’s one of the band’s best songs lyrically.

57. Turnpike Troubadours- “Diamonds & Gasoline” (2010) -Nathan
Songwriters: Evan Felker, John Fullbright, and R.C. Edwards

The roots of Turnpike Troubadours can be traced to songs like “Diamonds & Gasoline.” It’s soft and warm without being melodramatic. Felker’s songwriting was already some of the best in music on their debut album, and though the band would become a little more electric and alt-country as it released more albums, a listener can always count on a few songs on each record to sound as though they were plucked from Diamonds & Gasoline.

56. Alan Jackson — “The Older I Get” (2017) — Zack
Songwriters: Adam Wright, Hailey Whitters, Sarah Allison Turner

As much as it pains anyone to admit it, artists don’t usually start making the absolute best music of their careers the moment their radio stardom dies. Sure, you get outliers like Johnny Cash and Marty Stuart, but the norm is to usually try and do what the “cool kids” do or just record material that’s pleasant but ultimately safe and forgettable. Alan Jackson can join the former camp though, because “The Older I Get” is exactly what you expect it to be — a country song born to be a classic coming from an artist who knows how to paint a song with nuance and real weight to it. It’s also a nice, different spin on looking at what the rest of our days entail once we reach “old” age.

56. Randy Travis- “Three Wooden Crosses” (2002) -Nathan
Songwriters: Kim Williams and Doug Johnson

I’ve loved country music my whole life; there’s never been a point in my 24 years in which I wasn’t deeply moved by the songs. “Three Wooden Crosses” was one of the first I remember *really* sticking with me. And it holds a special place in my heart thanks to my memories of listening to it over and over with my grandparents.

55. George Strait — “You’ll Be There” (2005) — Zack
Songwriter: Cory Mayo

“You’ll Be There” might be one of George Strait’s lesser known hits, but that doesn’t make it any less great than his classics. This optimistic sendoff to an old friend with hopes he’ll see them again remains one of Strait’s most moving songs lyrically.

55. Alan Jackson- “Remember When” (2003) -Nathan
Songwriter: Alan Jackson

There’s so much praise I can give this song. But I’ll try to keep it brief. First of all, again, another Alan Jackson solo write. I’d say in country music history only Alan, Hank Sr., and The Hag were so good at consistently taking so many of their own songs to the top of the charts. It’s one of those rare *perfect* songs. The mandolin intro immediately sets such a sentimental and loving tone. The steel guitar solo is simply one of the best recorded pieces of the instrument in the genre’s history. Alan’s lyrics recall his own life and never fail to leave the listener with chills. Brilliant.

54. Don Williams — “I’ll Be Here In The Morning” (2014) — Zack
Songwriter: Townes Van Zandt

Between 2012’s And So It Goes and 2014’s Reflections, Don Williams was arguably still at the top of his game in his final years. His take on this classic Townes Van Zandt tune remains a poignant statement, and who better than to tackle a song like this than the Gentle Giant? He sounded as great as ever here too.

54. Gary Allan- “Ring” (2005) -Nathan
Songwriter: Kostas

Such a clever song. A little along the lines of Willie Nelson’s “Hello Walls” that Faron Young made a hit out of. Gary Allan is one of the best modern artists at taking songs and interpreting them in such a magnificent, chilling way. Even when the production of a Gary Allan song is upbeat and a little faster, he can still manage to really drag the feeling out.

53. Sugarland — “Stay” (2008) — Zack
Songwriter: Jennifer Nettles

The turning of the tables that occurs toward the end of this song has always been a highlight, with Nettles’ fragile, broken delivery suddenly morphing into a confident, biting one. It helps too that Nettles can sing the hell out of anything and sing it well.

53. Whiskey Myers- “Trailer We Call Home” (2016) -Nathan
Songwriters: Whiskey Myers

Seeing this song performed live takes it to a whole other level. But the recorded version will also do quite nicely. Cody Cannon is just singing about what so many people in this country go through on a weekly basis. “I got dreams what can I say?/Sometimes life gets in the way. Getting by and wanting more/Baby, there ain’t no shame in being poor…

52. Brad Paisley — “Welcome To The Future” (2009) — Zack
Songwriters: Chris DuBois, Brad Paisley

Brad Paisley has, for better or worse, always been one of country music’s more daring and interesting acts. Despite being known for his humor, Paisley has also addressed more serious topics in his singles, with “Whiskey Lullaby” being the most shining example. On “Welcome To The Future,” Paisley defies country music stereotypes while resonating with the same authenticity of the best country music has to offer. It’s not preachy, but instead offers a message of hope.

52. Dixie Chicks- “Goodbye Earl” (2000) -Nathan
Songwriters: Blake Chancey and Paul Worley

I mean, what other artist could record and release this song to mainstream radio? Country music misses these women.

51. Eric Church — “These Boots” (2006) — Zack
Songwriters: Eric Church, Michael P. Heeney

Only Eric Church could make a nostalgia song revolving around his boots not sound corny. Church, as always, is able to bring in his real life perspective to add a sense of realness to the story here. Like any good country song too, the ultimate lesson usually revolves around love lost and how, even at his toughest, Church’s recklessness wasn’t always for the best. It’s one of his most straightforward country tunes. It’s also one of his best.

51. Joe Nichols- “Brokenheartsville” (2002) -Nathan
Songwriters: Donny Kees, Blake Mevis, Randy Boudreaux, and Clint Daniels

Like I said in an earlier piece, one of the best tests for determining if a song is a true honky-tonker is imagining George Jones singing it. “Brokenheartsville” passes the test with flying colors. Nichols’ vocal is deep and meaningful as always. A true barroom weeper.

50. Holly Williams — “Railroads” (2013) — Zack
Songwriter: Holly Williams

Listening back through “Railroads” reminded me how much we need a new Holly Williams album. The story pulls from rural Americana to create something lonely, dark, and yet hopeful. It uses old fashioned language at times, but the story of escaping to find a better life is still one that resonates today.

50. Ryan Bingham- “Dylan’s Hard Rain” (2009) -Nathan
Songwriter: Ryan Bingham

The jangly guitar is so Byrds-esque, and Bingham excels here at taking inspiration from a classic Bob Dylan song and giving it a modern-day spin. It also begins a great trilogy of classics on Bingham’s Roadhouse Sun, leading into “Tell My Mother I Miss Her So” and then “Country Roads.”

49. Jason Aldean — “The Truth” (2009) — Zack
Songwriters: Brett James, Ashley Monroe

Jason Aldean’s rougher, serious delivery has led to some misfires, but he used it his advantage on what might be his best song to date. “The Truth” just feels like a country music classic, with the steel guitar adding to the loneliness the male protagonist feels as he loses his mind to depression. Aldean pours so much of himself into this song.

49. Darryl Worley- “Shiloh” (2003) -Nathan
Songwriters: Darryl Worley, Don Poythress, and Wynn Varble

Absolutely chilling. The production lends beauty and sorrow to the excellent narrative of the Battle of Shiloh during the Civil War. Worley mixes his own personal experience of visiting the battlefield with a recap of each day’s fight. The strings in particular give the subject matter a serious sense of urgency as the song reaches its conclusion.

48. George Strait — “Living For The Night” (2009) — Zack
Songwriters: Tony Brown, George Strait

George Strait certainly has a catalog of goofier songs, and we all love him for it. But Strait has also shown his knack for pulling off more serious songs, and “Living For The Night” just may be his darkest song yet. It’s a fantastic song as is, but the lush instrumental mix of classic guitar, strings and pedal steel really give this a lost feeling (in a good way).

48. Cody Jinks- “David” (2015) -Nathan
Songwriter: Cody Jinks

A song that will absolutely rip the listener apart. If Cody Jinks had come into the country music scene in any other era apart from today, he’d be a superstar. With serious songs like “David,” “Cast No Stones,” and “I’m Not The Devil” and rollicking outlaw anthems like “No Guarantees” and “Hippies & Cowboys,” Jinks has cultivated a serious, legendary discography. “David” is one of his best. The narrative is heartbreaking, and even with the listener having a feeling of what’s going to happen toward the end, Jinks’ vocal and conclusion to the song never fail to hit like a ton of bricks.

47. Kelsey Waldon — “High In Heels” (2014) — Zack
Songwriter: Kelsey Waldon

On her debut album, The Goldmine, “High In Heels” acts as a departure from the other excellent material she houses. It’s a fierce track that owes just as much to Americana and rock as it does to country, and it’s that combination of influences that really adds to the darkness of this track. It just gets more and more intense with every verse.

47. Jeff Bridges- “Fallin’ & Flyin’” (2010) -Nathan
Songwriters: Stephen Bruton and Gary Nicholson

Ah, another case of someone outside the genre understanding better than most mainstream artists the essence of country music. The carefree lyrics clearly take inspiration from someone like a Townes van Zandt, and the chorus is so simple yet so catchy and memorable.

46. Billy Currington — “People Are Crazy” (2008) — Zack
Songwriters: Bobby Braddock, Troy Jones

Billy Currington has always been one of the most charismatic performers in the modern country music scene, and this song serves as a reason why. It’s a completely crazy story that likely wouldn’t play out in real life (unless you were really lucky), but it just adds to the fun and good-natured humor behind it.

46. Turnpike Troubadours- “Every Girl” (2010) -Nathan
Songwriter: Evan Felker

A great example of Turnpike at their very best. Felker is, in my opinion, one of the two best songwriters of this generation with Ryan Bingham. Felker can write Southern story songs, love songs, love-gone-bad songs…you name it, he can write about it. “Every Girl” is one of the band’s signature songs, with the first line just begging to be screamed at the top of your lungs.

45. David Nail — “The Sound Of A Million Dreams” (2011) — Zack
Songwriters: Scooter Carusoe, Phil Vassar

It’s a well-written song as is, and songs about the love of making music are always welcome. But it’s David Nail’s powerful performance accompanied by sparse piano that really gives this track the elegance it deserves.

45. Eric Church- “These Boots” (2006) -Nathan
Songwriters: Eric Church and Michael P. Heeney

Those who know me are well aware of the connection I feel to Eric Church’s music and why and how I’ve been a fan from the beginning. “These Boots” is the song that started it all. It’s the essential live track from Chief’s discography and an album cut that defines the early Church sound. Seeing Chief perform the song live is a spiritual event.

44. Gary Allan — “I Just Got Back From Hell” (2005) — Zack
Songwriters: Harley Allen, Gary Allan

This is a rare instance where it feels wrong to point out what the song did “right” to end up on this list. It serves as a crucial moment on Allan’s masterpiece album, Tough All Over where Allan is brutally honest and justifiably angry. It’s one thing to sing a song and act the part, but it’s another to have actually lived it and literally pour every bit of yourself into the song.

44. Steve Earle- “Lonelier Than This” (2000) -Nathan
Songwriter: Steve Earle

One of the best songs for a broken heart in country music history. It’s dark. It’s deep. It’s poetic. It’s Steve Earle at his best.

43. BJ Barham — “Unfortunate Kind” (2016) — Zack
Songwriter: BJ Barham

The beauty of this song is the juxtaposition between the aching sadness behind the ending of the story and the optimism it carries. Despite what ultimately happened with these two lovers and the hell they went through, the fact they were together at all was a blessing. BJ Barham has a ton of depressing songs in his catalog as well as American Aquarium’s, but this is his finest moment on record.

43. Jamey Johnson- “In Color” (2008) -Nathan
Songwriters: Jamey Johnson, James Otto, and Lee Thomas Miller

From the first couple guitar strums, country radio listeners knew they were in for something different. Without a song like “In Color,” I honestly doubt we get Stapleton. It was an incredibly influential song that laid the groundwork for a traditionalist revival that would not be fully realized until almost a decade later. It spent almost a year on the charts and has sold over a million copies. The writing is fantastic with the narrative so poignant and touching. And the production is as close to perfect as a song can get.

42. Aaron Watson — “Bluebonnets (Julia’s Song)” (2015) — Zack
Songwriter: Aaron Watson

Dedicated to the late Julia Grace Watson, “Bluebonnets” is simply a beautiful song. To echo what I said about “I Just Got Back From Hell” earlier, this is an instance where Watson is truly living the part rather than simply acting it.

42. Josh Turner- “Long Black Train” (2003) -Nathan
Songwriter: Josh Turner

“Long Black Train” is, quite simply, one of the finest pieces of country music the genre has ever seen. The songwriting is Cash-esque, and Turner’s vocal is unbelievable. The train analogy is so relatable to all of us who struggle with sin every single day. “That train is a beauty making everybody stare/but its only destination is the middle of nowhere…”

41. Sunny Sweeney — “Bottle By My Bed” (2017) — Zack
Songwriters: Sunny Sweeney, Lori McKenna

It’s a good thing relatability doesn’t automatically dictate what we love, because obviously I’ll never relate to the pain Sunny Sweeney is showing on this song. It’s a cutting song that shows her yearning for the ability to have a child and how it haunts her that she doesn’t. The title really throws you off, but Sweeney opts more for elegant production to help deliver the message. It’s a hard song to listen to, but when artists bear their heart and soul out like this, the least you can do is listen.

41. Johnny Cash- “God’s Gonna Cut You Down” (2006) -Nathan
Songwriters: Traditional Folk Song

Many things amaze me about The Man in Black’s career. But one of the most impressive is Cash’s ability to make any traditional folk song sound like he wrote it. He was, and will always remain, an unstoppable force.

Part Four coming soon!

Courtesy “The Chicago Tribune”