100 Best Country Songs of the 2000s- Part One (100–81)

I’m not doing a “Best Of 2018” this year. There’s so much out there I’ve enjoyed, and it’s been a somewhat improved year for mainstream country as well. We got outstanding albums from Dierks, Eric Church, Brothers Osborne, and LANCO. The underground and Texas Country circuit gave us new material from Whitey, Red Shahan, and Cody Jinks. Kip Moore released an acoustic EP. And Kacey Musgraves did whatever the hell she wanted, and it turned out pretty cool.

So continuing the the tradition of the “100 Best,” next up is the 100 best country songs of the 2000s. But this time we’re joined by my good friend Zack over at The Musical Divide (@themusicdivide). We certainly have different tastes and likes for our country music. And this list should really show the best of what all forms of country had to offer in the 2000s. Maybe it was never as bad as we’ve bemoaned! The ultimate goal of this is for it to be fun. And while I certainly agonized over some of the songs I left out, making this list was a good time. Enjoy!

Zack: Nathan and I have been talking about doing something like this ever since Taste of Country released their list for the top albums of the 2000s so far awhile back. Before you see my list (and his), please note that this is all in good fun. I know I’m forgetting quite a bit of great material. I don’t claim to know every song or keep track of everything. I’m still catching up with a lot of old favorites. Also, this isn’t my attempt to say what the “best” songs are. I’m just showing off a collection of my 100 favorite songs so far this century, and the order truly doesn’t matter here. Even my № 100 song would rank high on my individual year end lists. I hope to show off some great country music and hopefully remind you of some old gems, but please don’t take it that seriously. Also, I’ve excluded material from 2018 since I don’t want to spoil my year end lists (especially since I don’t have them in order quite yet).


100. Kellie Pickler — “I Wonder” (2007) -Zack

To me, this is what country music is all about. It’s a real and honest narrative stemming from Kellie Pickler’s relationship with her estranged mother. Pickler’s achingly sincere delivery coupled with the poignant lyricism and spirit of the track easily landed it a spot on my list.

100. Josh Thompson- “Comin’ Around” (2011) -Nathan
Songwriters: Josh Thompson, Rodney Clawson, Kendell Marvel

Songs like this are what the foundation of country music is built upon. Nothing groundbreaking- Just solid life lessons in a three minute song.

99. Cody Jinks — “David” (2015) -Zack

Just when you think Cody Jinks hits you with everything “David” could muster, there’s one more line waiting around the bend to punch you in the gut. The unnerving story between estranged friends ending with demise shows Jinks at the top of his game lyrically and vocally.

99. Sturgill Simpson- “Call to Arms” (2016) -Nathan
Songwriter: Sturgill Simpson

I don’t think there’s a better song that sums up the enigma that is Sturgill Simpson at this point in his career. Starts off as an alt-country rocker. Morphs into some Motown-Big Band cluster. But it works. And the songwriting is formed by his own time in the Navy.

98. George Strait — “I Saw God Today” (2008) -Zack

Faith is something that few country artists touch today without getting preachy or, on the other end, hateful. George Strait however handled this track masterfully, focusing more on the optimism we need to hold onto in frightful situations. If anything, “I Saw God Today” proved that no matter what decade you listened to Strait, he was always at the top of his game.

98. Steve Earle- “Galway Girl” (2000) -Nathan
Songwriter: Steve Earle

References to local geography, a black-haired/blue-eyed girl, and heartbreak. Just a day in the life of Steve Earle.

97. Eli Young Band — “Even If It Breaks Your Heart” (2011) -Zack

There’s very few songs this past decade that have gone №1 and deserved it. “Even If It Breaks Your Heart” is one of those rare gems we’ll remember down the road. It’s centered around music, but the message itself is universal. Despite having a softer rock sound, it’s an anthem for the country music genre.

97. Rodney Atkins- “Angel’s Hands” (2006) -Nathan
Songwriters: Rodney Atkins, Nicole Witt, and Bobby Tomberlin

A gut-wrenching song. Sometimes no matter how hard one tries, he or she simply cannot change the outcome that’s the result of someone else’s decisions.

96. Keith Urban — “Nobody Drinks Alone” (2004) -Zack

I originally had “But For The Grace Of God” here, but considering it’s technically from 1999, I swapped it for Keith Urban’s best album cut instead. While Urban had been known for making good, lighter pop-country, he hadn’t yet tackled something dark. “Nobody Drinks Alone” is a haunting song where the title says it all, but it gets even more intense by its end thanks to Urban’s incredible solo. It was different for Urban, but it worked damn well.

96. Brad Paisley- “You’ll Never Leave Harlan Alive” (2001) -Nathan
Songwriter: Darrell Scott

Appalachia is a mystical place. Murder, coal-mining, beautiful music. It’s the most misunderstood region in the United States. “You’ll Never Leave Harlan Alive” encapsulates all the ups and down miners have faced.

95. Gary Allan feat. Willie Nelson — “A Showman’s Life” (2003) -Zack

If drinking, cheating and heartache are the three most common tropes in country music, songs about life on the road have to be a close cousin. Of course, those worn-in perspectives usually lead to excellent results no matter times the theme is recycled. “A Showman’s Life” is one of the more masterful examples, mostly because both Gary Allan and Willie Nelson are experts at handling these wistful, melancholic tunes. It’s pure poetry by two of country music’s finest.

95. Jack Ingram- “Why I Left Atlanta” (2017) -Nathan
Songwriter: Jason Eady

Recorded for Bruce Robison’s The Next Waltz, Ingram took Jason Eady’s great original and made it even better. Melancholy soaks the listener to the core, and the groove is soft and soothing despite the rather forlorn lyrics.

94. Lee Ann Womack — “Last Call” (2008) -Zack

Even by 2008, mainstream country music was rarely this smoky and biting. This is one of many tracks that capture Lee Ann Womack at her best. The brutal, honest lyricism coupled with the moody production make this a staple for Womack’s impressive catalog as well as country music in general.

94. Taylor Swift- “Our Song” (2007) -Nathan
Songwriter: Taylor Swift

Truth be told, T-Swift could’ve easily had two or three more songs on here. But I went with “Our Song.” The fiddle drives the song spectacularly, and the lyrics are an early example of Swift’s uncanny ability to write insanely relatable songs for her fan-base.

93. Kenny Chesney feat. Grace Potter — “You and Tequila” (2011) -Zack

“You and Tequila” is one of those “good” songs on paper that truly comes alive with the chemistry between Kenny Chesney and Grace Potter. It shines more for its simplicity than any other element, and the warm, intimate mood of it all makes it easy to get lost within the track.

93. Eric Church- “Jukebox and a Bar” (2018) -Nathan
Songwriter: Eric Church

Eric Church is an artist known for pushing boundaries. But lost in all of that sometimes is Chief’s mad respect for the genre and his ability to write a straight-ahead country song. “Jukebox and a Bar” takes familiar, Haggard-esque themes and turns them into something for the 21st Century.

92. Eric Church — “Record Year” (2016) -Zack

Perhaps it’s just the music nerd in me, but I can totally get down with healing heartache through sitting at home listening to records. “Record Year” just has everything going right for it — the sincerity of Church’s perspective and respective album references, a clever hook and an uplifting mood to give some life to this ode to music.

92. George Strait- “Kicked Outta Country” (2016) -Nathan
Songwriters: Jamey Johnson and George Strait

It’s easy to write a country protest song nowadays with all the subject matter a songwriter has to work with. The tough part is getting the song to stand out. But when Jamey Johnson and George Strait are involved, the song is bound to be memorable. “Kicked Outta Country” both pays tribute to the legends who radio ignored as they grew old and bemoans the state of the entire industry. Well-deserved, biting criticism.

91. Ashley Monroe — “The Blade” (2015) -Zack

“The Blade,” along with featuring one of the best hooks in recent memory, is Ashley Monroe at her best. Her aching delivery makes the listener feel like they’re in the picture watching this relationship unfurl as she finds herself on the losing end. It’s sharply poetic and aching in the best possible way.

91. Chris Shiflett- “Room 102” (2017) -Nathan
Songwriter: Chris Shiflett

Why do artists from other genres have more respect, admiration, and understanding for country music than many of its own stars? Shiflett’s West Coast Town is 21st Century Bakersfield Country. One of the standout tracks is the Foo Fighters’ guitarist channeling The Hag with a barroom weeper

90. Carrie Underwood — “Just A Dream” (2008) -Zack

It’s that twist that really makes this song what it is. At first the somber mood seems to stem from possible butterflies and uncertainty for the road ahead, but when that chorus hits, it’s clear that this isn’t a happy occasion. Leave it to Carrie Underwood to sing the hell out of this song as always and deliver a knockout performance too. It’s a shame that this seems to be one of her more overlooked songs.

90. Justin Moore featuring Miranda Lambert- “Old Habits” (2013) -Nathan
Songwriters: Brian Maher, Josh Hoge, and Adam Hambrick

An instant classic. The lonesome piano at the beginning lets the listener know right away that it’s gonna be a sad four minute journey by song. Something that really appeals to me about songs like this is the ambiguity of why a relationship ends. It allows the listener to fill in the blanks and make it as relatable as he or she wants.

89. Taylor Swift — “White Horse” (2008) -Zack

“White Horse” isn’t one of Taylor Swift’s best known songs, but it’s quietly been one of her best. While Swift faced much unwarranted criticism for her lyricism that appealed to a younger audience, “White Horse” cleverly sees her addressing that. Relationships don’t always result in cute, happy endings, and seeing Swift come to grips with that while also sharpening her skills as a writer even further cements this as one of her finest moments.

89. Carly Pearce- “Every Little Thing” (2017) -Nathan
Songwriters: Carly Pearce, busbee, and Emily Shackelton

Super vulnerable for a debut single and one of the big successes for women in their fight for a voice on mainstream radio today. The songwriting is raw and poignant, and the production is absolutely spot-on.

88. Kip Moore — “Guitar Man” (2017) -Zack

Kip Moore is quite the presence behind the microphone, and his loud, anthemic rock moments are always welcome. “Guitar Man” however captures Moore at his finest, penning a song with imagery sound strong, it’s worthy in the same conversation as Jason Isbell, James McMurtry or Karen Jonas. It also features his witty charm in a different light. Overall, “Guitar Man” is Moore’s finest moment on record.

88. Eric Church- “Three Year Old” (2015) -Nathan
Songwriters: Eric Church, Casey Beathard, and Monty Criswell

Eric Church has an innate ability to show unbelievable maturation in his lyrics as he grows older. He’s not stuck in high school. He’s not stuck in college. He’s not stuck at the bars, playing the single man. He’s grown, and his music has taken us on a journey through his life ever since Sinners Like Me. “Three Year Old” gives us a front-row seat to where Church is in his life.

87. Alan Jackson — “Remember When” (2003) -Zack

Nobody in the country music genre does nostalgia or reflection better than Alan Jackson. Whether it’s to honor a loved one on something such as say, “Drive,” or remembering fun summer days “Chattahoochee,” Jackson has a knack for setting a scene. “Remember When” is one of those songs that doesn’t need a lot of the words to explain why it’s great. Just appreciate the simplicity of it and let Jackson set a scene once more.

87. Zac Brown Band- “Sweet Annie” (2012) -Nathan
Songwriters: Zac Brown, Wyatt Durratte, Sonia Leigh, and John Pierce

Damn, those harmonies. Magic. The subject matter is familiar to Zac Brown fans, but the band never failed to nail it back in those days. One of my favorite moments in any song, ever, comes toward the end when the song momentarily picks up speed and intensity before slowing back down again.

86. American Aquarium — “Losing Side Of Twenty-Five” (2015) -Zack

What makes “Losing Side Of Twenty-Five” all the more depressing of a listen is the fact that everyone can relate to it at one point or another. We don’t end up where we thought we’d be at a certain age, and unfortunately we can’t map out the road ahead. BJ Barham’s upfront and honest delivery though at least gives a sense of hope by its final verse, reminding us that we don’t need the entire world as long as we have a piece to call our own.

86. Paul Cauthen- “Everybody Walkin’ This Land” (2018) -Nathan
Songwriters: Paul Cauthen and Beau Bedford

Look, this shamelessly borrows from Johnny Cash. But who cares? Cauthen’s personality and attitude make it work with a timeless message that’s certainly poignant and relevant for 2018. Special mention for the dark and foreboding production.

85. Sara Evans — “Suds In The Bucket” (2004) -Zack

“Suds In The Bucket” comes from a better time in country music when the stories would develop after each verse to tell a complete story. Granted, “Suds In The Bucket” is a tale of earned freedom to forge a new path, so Evans’ carefree, fun delivery makes this story track all the more appealing.

85. Dierks Bentley featuring Brandi Carlile- “Travelin’ Light” (2018) -Nathan
Songwriters: Dierks Bentley, Ashley Gorley, and Ross Copperman

Carefree and happy, “Travelin’ Light” finds the narrator throwing caution to the wind and taking off with nothing but the essentials. Brandi Carlile’s angelic voice really adds an extra something special to the song.

84. Rosanne Cash feat. Johnny Cash — “September When It Comes” (2003) 
-Zack

This rare gem explores the complex father-daughter relationship between Rosanne and Johnny Cash. It’s even more eerie that it was released in 2003, as Johnny sings about his regret in ways that are heartbreaking to hear.

84. LANCO- “Greatest Love Story” (2017) -Nathan
Songwriter: Brandon Lancaster

Story songs are timeless in country music. 1952, 1975, 1998, 2018. Love never goes out of style either. And a well-done country story song about love often proves to be an instance smash. The production is nostalgic without feeling cheesy, and Lancaster’s vocals are warm and friendly.

83. Sunny Sweeney — “From A Table Away” (2010) -Zack

This complex tale of an unfaithful man caught in a web of lies was an excellent breakout hit for Sunny Sweeney. Her no-frills, biting delivery gave us a peek into her personality, and it’s filled with clever twists to make this heartache track all the more poignant.

83. Marty Stuart & His Fabulous Superlatives- “Way Out West” (2017) -Nathan
Songwriter: Marty Stuart

A wild trip across the country to the mythical Southwest. References to aliens, pills, Native American chiefs, and Johnny Cash. Music that makes the listener feel like he or she has been driving across the desert for days. Truly a masterpiece.

82. Mark Chesnutt — “So You Can’t Hurt Me Anymore” (2016) -Zack

This song alone proved that Mark Chesnutt was back and better than ever when it debuted in 2016. The twist that it’s the alcohol haunting him instead of a past lover makes the song all the more chilling, and the moodier production really helped to give this song the bite it deserved.

82. Alan Jackson- “Where Were You (When The World Stopped Turning)” (2001) -Nathan
Songwriter: Alan Jackson

I can’t think of any words to do justice for what this song meant in 2001…and still means today.

81. Maddie and Tae — “After The Storm Blows Through” (2015) -Zack

Maddie and Tae are probably one of the few country acts right now addressing the concept of friendship, and on “After The Storm Blows Through” they delivered the album highlight. It features the kind of message we all wish to hear from at least one person in our lives, and considering these two aren’t afraid to stand up for what’s right, it’d be pretty damn good to have them by your side when worst comes to worst.

81. Jamey Johnson- “Angel” (2008) -Nathan
Songwriters: Jamey Johnson and Jeff Bates

Not many things go together better than Jamey Johnson and a steel guitar intro. The subject matter is incredibly dark, and the turn-of-words in the chorus is so smart. This is one of those songs you can imagine George Jones singing. Which is as big of compliment as I can give.

That’s all for Part One! See you next time.

(Courtesy of “The Boot”)