100 Best Country Songs of the 2000s- Part Two (80–61)

Alright, let’s dive right back in to Part Two! You’re going to start to see songs we both have identified as worthy of a place on the list.


80. Kenny Chesney — “Don’t Blink” (2007) — Zack
Songwriters: Casey Beathard, Chris Wallin

Kenny Chesney has always been at his best when he’s reflective instead of just a beach bum. “Don’t Blink” is one of many songs of his from the 2000s that explored the concept of life itself without feeling cheesy or preachy. The scene surrounding the story of an old man recounting his life gives this a more honest perspective, and the overall message is still relevant to this day.

80. Gary Allan- “I Just Got Back From Hell” (2005) -Nathan
Songwriters: Harley Allen and Gary Allan

Standing alone, this is a hell of a painful song. When given its context, the song becomes even more powerful. Just a year earlier, Gary Allan’s wife committed suicide. What came out of the ashes of that heartbreak was one of the darkest, most agonizing albums in country music history. And “I Just Got Back From Hell” is the center-piece.

79. Brad Paisley — “Southern Comfort Zone” (2013) — Zack
Songwriters: Brad Paisley, Kelley Lovelace, Chris DuBois

Brad Paisley’s “Southern Comfort Zone” speaks from a unique perspective — the Southern man experiencing life outside the South and realizing that it’s alright to be different from everyone else. Not everyone who loves country music is driving trucks. Of course, Paisley is honest. Those experiences feel weird at first, but it’s also not long before he realizes that it’s normal for people to just be who they are instead of living up to stereotypes placed. This isn’t a knock on the South either. Paisley mentions multiple times that he misses home, and that’s true for all of us I think at times. Still, the chance to go out and experience new things ultimately helps us grow as people, and this song speaks to that sentiment.

79. Alan Jackson- “Drive (For Daddy Gene)” (2002) -Nathan
Songwriter: Alan Jackson

Songs about nostalgia can go one of two ways. Either wishful thinking for days the singer will never get back and refusing to grow up. Or two, using nostalgia to show maturation and formative experiences. “Drive” is one of the latter. Alan Jackson’s songwriting is always Haggard-esque. Working man anthems, songs of love and heartbreak. Seemingly so simple but so powerful. So many of his hits were solo writes from Jackson himself.

78. Lori McKenna — “The Bird and the Rifle” (2016) — Zack
Songwriters: Lori McKenna, Caitlyn Smith, Troy Verges

Lori McKenna’s stories are usually woven with strong details and metaphors, and this is no exception. This tale of domestic oppression is bolstered by the symbolism of a bird needing to break free and airy production that bolsters that sentiment nicely. This is one of those tracks where it’s easy to lose yourself and get swept away by its beauty.

78. Eric Church- “Where She Told Me To Go” (2009) -Nathan
Songwriters: Eric Church and Casey Beathard

Like I said earlier in the list, it’s often forgotten how well Church can write and record classically influenced country music. The production of “Where She Told Me To Go” is the best of that mid-2000s country sound- light fiddle and acoustic driven that goes electric in certain places for emphasis. And the title line is a fantastic play on words.

77. Craig Morgan — “The Ballad Of Mr. Jenkins” (2006) — Zack
Songwriters: D. Vincent Williams, Steve Mandile

If this list will prove anything by the end, it’ll be that mainstream country songs just used to better stories (or stories at all). The story of an old man who’s seen it all comes with a twist at the end that might bring a tear to your eye. This track almost serves as a nice prequel to Morgan’s hit song, “This Ain’t Nothin’ ” from 2010. This is one of those songs where words can’t capture its greatness or attention to detail.

77. Dierks Bentley- “Can’t Be Replaced” (2016) -Nathan
Songwriters: Dierks Bentley, Luke Laird, and Hillary Lindsey

Black certainly lost Dierks some fans, but I wasn’t too bothered by it. It’s not my favorite work of his, but there are some stand-out album cuts, particularly on the second half of the album. “Can’t Be Replaced” almost signals The Mountain was on its way next. Dierks is almost saying, “Yeah, I’m doing some exploring; I’m trying some new things. But I know my roots, and I know where I’ll always be.”

76. Montgomery Gentry — “Clouds” (2006) — Zack
Songwriters: Jeffrey Steele, Eddie Montgomery, Tony Mullins

This song gained a whole new level of depth when Troy Gentry passed away in 2017. Sung only by Eddie Montgomery, this heartbreaking track can’t help but read as a goodbye to his friend today. It’s the best vocal performance Montgomery has ever given, and in terms of pure, raw emotion, this is country music in a nutshell.

76. Florida Georgia Line- “Dirt” (2014) -Nathan
Songwriters: Chris Tompkins and Rodney Clawson

Woah, FGL making an appearance? I always use “Dirt” as an example to how a mainstream country song *can* still be substantial and successful if the artist wants it to be. “Dirt” is simply a great song. Familiar themes, but again, this is the meat and potatoes type of material that forms the foundation of the genre.

75. Emily West (feat. Keith Urban) — “Blue Sky” (2010) — Zack
Songwriters: Emily West, Gary Burr

This underrated gem from 2010 is bolstered mainly by Emily West’s stunning voice. Her ability and prowess allows this track to soar to its highest levels, and the imagery used is quite strong as well. Biting, poignant, powerful … just a few ways of many I would describe this.

75. Gary Allan- “It Ain’t the Whiskey” (2013) -Nathan
Songwriters: Greg Barnhill, Jim Daddario, and Cole Deggs

Gary Allan, for over a decade, was the king of country heartbreak in mainstream country. He seemingly had the freedom to record and release whatever type of material he wanted, even if it wasn’t guaranteed to be a smash. “It Ain’t The Whiskey” looks to have been the last of that run. But if it was the end of his mainstream career, what a way to go out. Painful, drenched in sorrow…it’s the definition of a Gary Allan song.

74. Reba McEntire — “Just Like Them Horses” (2015) — Zack
Songwriters: Tommy Lee James, Liz Hengber

The song works as a tribute to her father, Clark McEntire, but it’s the metaphors and poetic lyrics that make its message universal. Loss in country music is a pretty well-covered topic, but showing the perspective from the parent talking to the child they’ll leave behind was a heartbreaking, bold move. The message is ultimately inspiring rather than somber though, asking us to carry on the best of the people who made us instead of giving in and letting darkness take over. It’s a gut-punch of a track.

74. Red Shahan- “Memphis” (2018) -Nathan
Songwriter: Red Shahan

A great story song looking at the damage left in the wake of the narrator’s father leaving home and heading to Memphis. Later in the song, both the narrator and his mother get their own chance of revenge by, respectively, not sugar coating the truth about Grandad to his son and speaking directly to the man who left his family behind.

73. Carrie Underwood — “Blown Away” (2012) — Zack
Songwriters: Chris Tompkins, Josh Kear

The Blown Away album era was Carrie Underwood at her best. “Blown Away” (the song) is still in a league of its own — a murder ballad and revenge fable that shows mother nature stepping in to seal this man’s doom. The instrumental mix is aggressive, perfectly complimenting the song’s darker mood. The chorus literally obliterates everything in its path, and Underwood’s anguished yet triumphant delivery of the hook is one of her best moments, vocally.

73. Thomas Rhett- “Marry Me” (2017) -Nathan
Songwriters: Thomas Rhett, Shane McAnally, Ashley Gorley, and Jesse Frasure

Thomas Rhett may never fully embrace sounds other than pop-country at best. But you know what? If he continues to show maturation with his songs, he won’t be the worst thing on the radio. “Marry Me” is an excellent song, in every sense of the word. It’s melancholy without being melodramatic. It’s mysterious without revealing the entire past of the characters to the listener. And yet there’s enough detail for the listener to feel sympathetic to the narrator. The narrator isn’t trying to break the couple up or crash a wedding. He’s simply sitting back and dealing with his own pain and supposed regret.

72. Trace Adkins — “You’re Gonna Miss This” (2008) — Zack
Songwriters: Ashley Gorley, Lee Thomas Miller

Trace Adkins’ last huge hit was also one of his very best. What makes it so work is showing the common message of wishing we were older through three different perspectives. The characters are all different age ranges wanting different things without realizing what they have. It’s a message we all could afford to hear from time to time, and considering Adkins delivers the song with one of his most sincere vocal performances, this is country music done right.

72. Margo Price- “Hurtin’ on the Bottle” (2016) -Nathan
Songwriters: Margo Price, Mark Fredson, Jeremy Ivey, and Caitlin Rose

Directly influenced by Loretta Lynn, “Hurtin’ on the Bottle” is a prime example of how artists can record traditional country music while still moving the genre forward. The songwriting is clever and smart, and the instrumentation is like an old friend greeting you after a long time away.

71. Matt Woods — “Deadman’s Blues” (2013) — Zack
Songwriter: Matt Woods

I can usually forgive a rougher sounding voice if the passion is there, and with “Deadman’s Blues,” Matt Woods showed off his passion in spades. The loneliness takes center stage, with the raw self-flagellation bolstering a knockout performance and easily Woods’ best song to date.

71. Whiskey Myers- “Ballad of a Southern Man” (2011) -Nathan
Songwriters: Cody Cannon, Leroy Powell, Gary Brown, John Jeffers, and Cody Tate

On its surface, “Ballad of a Southern Man” seems like another Hank Jr inspired country rock tale. And while certainly not the most poignant and and detailed of Cody Cannon’s songwriting, the song nonetheless speaks to so many in America who have their way of life and are judged time and time again. I certainly don’t agree with (or relate) to everything contained in the song. But Cannon’s vocal delivery is so strong and when he sings “I guess that’s something you don’t understand,” the listener can’t help but hear the resignation in his voice. He’s not changing for you.

70. Kenny Chesney — “Better As A Memory” (2008) — Zack
Songwriters: Scooter Carusoe, Lady Goodman

To echo what I said before, Kenny Chesney is at his best when he’s reflective, and “Better As A Memory” is one of the best performances of his career. It captures his lone wolf spirit well while also being mature enough to acknowledge the relationship in question wouldn’t work out anyway. Vocally, Chesney is also spot on.

70. Colter Wall- “Thirteen Silver Dollars” (2017) -Nathan
Songwriter: Colter Wall

Colter Wall possesses one of the best and most distinctive voices in all of music. It’s a voice perfectly suited for the autobiographical folk tunes he’s singing. “Thirteen Silver Dollars” just has so many brilliant lines in it. For example, “Found myself asleep in the snow/for one or two odd reasons I ain’t too proud to repeat/for now we’ll say I had no place to go.” So much to unpack. That’s where Colter Wall’s greatness really shines through.

69. Blackberry Smoke — “One Horse Town” (2012) — Zack
Songwriters: Travis Meadows, Jeremy Spillman, Charlie Starr

If Al Bundy had written a song, it probably would have sounded something like this. Charlie Starr pours every bit of himself into this heartbreaking track about dreams never chased and opportunities left to crumble.

69. Trace Adkins- “Arlington” (2005) -Nathan
Songwriters: Jeremy Spillman and Dave Turnbull

No song can ever fully do justice to those who served. But “Arlington” is about as close as a song can get. Adkins delivers a haunting and understated vocal, and the production is beautiful and somber.

68. Taylor Swift — “Back To December” (2010) — Zack
Songwriter: Taylor Swift

For as much as Taylor Swift has been criticized for laying blame to her exes in every song of hers, it’s another thing for her to take the blame herself this time around. It’s full of one-liners that are among her best (the “roses” line is a particular favorite of mine), and the overall tone of the melody fits the song quite well.

68. Eric Church- “Dark Side” (2014) -Nathan
Songwriters: Eric Church, Travis Meadows, and Jeremy Spillman

One of the biggest problems with most mainstream country artists today is their inability to look inward or, even more-so, fail to acknowledge their own flaws. Eric Church has never had that problem. “Dark Side” finds Church owning up to his own rowdy past and hoping his wife and kids never learn about the things he did. Then, in a brilliant ending to the song, Church makes sure it’s known that his dark side will once again find the light of day if anyone messes with his family.

67. Josh Turner (feat. Trisha Yearwood) — “Another Try” (2008) — Zack
Songwriters: Chris Stapleton, Jeremy Spillman

It’s a fairly simple song on paper, but when you combine two of country music’s best vocalists, the results are astounding. Turner’s songs have always featured very warm, restrained production, allowing the song to breathe and for these two to shine. A good song on paper turns into an excellent one due the other stellar elements doing the heavy lifting.

67. Steve Earle- “The Girl On the Mountain” (2017) -Nathan
Songwriter: Steve Earle

One of the most haunting songs on the list. Earle’s vocal is quiet, reserved, and drenched in heartache. It’s a very Townes-esque performance, both production-wise and lyrically.

66. Sturgill Simpson — “You Can Have The Crown” (2013) — Zack
Songwriter: Sturgill Simpson

High Top Mountain was Sturgill Simpson’s best album not for being his most straightforward country project, but for housing some of his sharpest writing still to this day. Simpson’s smart-ass delivery is always welcome, especially when listening to this in hindsight. Overall though, Simpson was able to turn a very struggle into something lighter for a few minutes, and we all enjoyed a good laugh.

I wonder if he ever found anything that rhymes with Bronco?

66. Sam Outlaw- “Tenderheart” (2017) -Nathan
Songwriter: Sam Outlaw

Sam Outlaw is an enigma. I can’t really tell if his whole heart is into making music or not; but when I hear him talking about it, or when I hear his music, I can’t help but be engulfed in how talented an artist he is. “Tenderheart,” the title track of his sophomore album, is the best of what Sam Outlaw can offer. The intersection of the sounds of the Eagles and Keith Whitley. Warm and gentle production with breezy, Southern California production.

65. Josh Turner feat. Iris DeMent and Marty Stuart — “Pallbearer” (2012) — Zack
Songwriter: Josh Turner

As I said before, Turner will usually sing the heck out of anything presented his way, and “Pallbearer” is one of his finest moments on record. Turner is able to keep the symbolism of love actually dying poignant instead of overblown. It also proves that while Turner’s lighter songs are always welcome, it’s songs like “Pallbearer” that show him at his full potential.

65. Aaron Watson- “Barbed Wire Halo” (2007) -Nathan
Songwriters: Aaron Watson and Neal Lowry

Aaron Watson comes from the George Strait school of Texas Country. It’s mainstream-ready while still being traditional as heck. “Barbed Wire Halo” is fiddle driven country music with a great story.

64. Trace Adkins — “I Can’t Outrun You” (2008) — Zack
Songwriters: Ben Glover, Kyle Jacobs, Joe Leathers

If Trace Adkins had been more consistent with his single choices (or consistent at all), we’d regard him as one of country music’s best vocalists and artists. “I Can’t Outrun You” is proof of this, turning a short, simple song into a powerhouse of an emotional tune. Backed by little more than piano and violin, this captures Adkins at his best.

64. Miranda Lambert- “Love Letters” (2007) -Nathan
Songwriter: Miranda Lambert

I’ve always felt conflicted about Miranda Lambert’s career. I’m someone who prefers her older material. She’s evolved as an artist while still maintaining her sound and becoming more critically acclaimed. But to me, she really succeeded with songs like “Love Letters.” Simple, straight-forward material. “Love Letters” is so poignant and vivid with detail. The production is sparse with enough room to let Miranda’s vocals really shine through.

63. Jake Owen — “What We Ain’t Got” (2014) — Zack
Songwriters: Travis Meadows, Travis Jerome Goff

I’ve found Jake Owen’s material to be sub-par ever since this single under-performed (at least for his standards at the time), but I’m still happy it was released all the same. Released during the onslaught of the bro-country movement, this song was a breath of fresh air in every department. It also showed that while Owen was one of the few making carefree party music the right way, he could also dig down deep for something spectacular.

63. Justin Moore- “If Heaven Wasn’t So Far Away” (2011) -Nathan
Songwriters: Dallas Davidson, Rob Hatch, and Brett Jones

I cried the first time I heard this song. It’s a special song, and when Justin nails a vocal on a song, he *really, really* nails it. The detail here is extraordinary, particularly how there’s things specific to the narrator but also names and events that any listener could relate to. And I’ll always be a fan of most of the production on Justin’s albums.

62. Jason Isbell & The 400 Unit — “If We Were Vampires” (2017) — Zack
Songwriter: Jason Isbell

What’s there to say about this song that hasn’t already been said? Sure, it essentially rips off the concept of Twilight, but there’s more to it than that. It’s not about them actually turning into vampires, it’s about the morbid fantasy of wondering what will happen “one day.” This beautifully dark, haunting song tackles “love” in quite possibly the best way here. It’s almost as if it starts out as a joke before you get the sense they actually are thinking about the inevitable and what they can do to make the most out of it now. There’s even a disconnected acoustic solo to reflect on the heavy message. It’s a lot to take in.

62. Midland- “Drinkin’ Problem” (2017) -Nathan
Songwriters: Mark Wystrach, Cameron Duddy, Jess Carson, Shane McAnally, and Josh Osborne

It’s a great song. But, honestly, Midland have better songs. The reason I have it here (and why it’s so high on the list) is because of its impact. “Drinkin’ Problem” proved an artist didn’t have to whine and bitch about their music not being fully accepted by country radio. Is country radio a problem? Yes. Should it be easier for traditional leaning artists to fight for their place in the mainstream? Yes. Will there ever again be a fair shake given to both traditional artists and pop-leaning artists? No. But I’m a firm believer that *most* mainstream acts who lean traditional or follow their hearts can succeed if they stick to their guns. I’m not saying it’s easy. But I am saying that talent can always force its way in. Eric Church, Miranda Lambert, Dierks Bentley…hell, now Luke Combs, Jon Pardi, Kacey Musgraves, and Midland. Maybe they won’t rack up as many number ones. But they’ll be remembered. They can be damn sure of that.

61. Kacey Musgraves — “Merry Go Round” (2013) — Zack
Songwriters: Kacey Musgraves, Shane McAnally, Josh Osborne

Simply put, “Merry Go Round” is an enriching, absorbing slice of country music storytelling, flavored with everyday realism. It’s not afraid to take the myth of the American Dream and gut it. It avoids being preachy due to her impeccable and vibrantly detailed songwriting. It’s also coupled by a strong sense of self-awareness, as she knows she’s in the same boat as everyone else in this town. It’s a song of relentless despair that resonated powerfully, especially for a debut single.

61. Loretta Lynn featuring Jack White- “Portland, Oregon” (2004) -Nathan
Songwriter: Loretta Lynn

I mentioned it in my best country albums of the 2000s countdown, but Van Lear Rose really set the standard for influencing modern, traditional country artists in the ways to move the genre forward while still maintaining a grasp on the past of the genre. I would argue that Margo Price was directly influenced by the album while someone like Cody Jinks was indirectly influenced. “Portland, Oregon” is a ton of fun and the pièce de résistance of the album. And another fitting song to add to the Loretta Lynn collection.

Thanks to “Taste of Country”