Favorite Music Guide: Top 50 Country Songs of All-Time

*Last Updated: 11/28/2022  

Songwriter coined the phrase, "Three Chords and the Truth" to summarize the best of what country music could be. Many years ago now I put out a Top 100 Songs list and while I was happy with how it generally turned out, I always felt there was more work I could do the field of music. Long story short, I thought it might be nice to take a magnifying glass to various music genres and start building new lists. The past few weeks I turned my limited time to the Country music genre and published lots of little sub-lists on my social media accounts. The fruit of that work I am sharing with you here. A few notes about my list before we get into it.

I didn't really get into "music" until my family moved from an Air Force base in Japan to the states in the early 1990's. I would say I really became a fan of country music around 1994 and it lasted until 2004 or so. I was a mostly a fan of Garth Brooks, Tim McGraw, and Kenny Chesney back then and that era of country will definitely have a large bias on this list.

*At the George Strait Country Music Festival with a friend

 However, my tastes have expanded over the last couple decades to encompass more eras and artists than what I grew up with. Still, most country purists will take issue at the lack of names like Hank Williams, Merle Haggard, Tammy Wynette, George Jones, and others of their like. To be honest, I just don't connect with that style of music, though a couple of their peers have made it on my list. My mindset in making this list was to try and be as diverse as possible - including as much of the full range of country music sound as I enjoy.

The list here will begin with songs 50-11 alphabetically ordered by artist. It will then segue into something like a top ten where I will share my individual commentary on each song. As always, this list is just my personal tastes, I'm no expert on the subject. Think of it as an invitation to enjoy the songs I have found highly impactful and enjoyable in my life. Feel free to share your thoughts.

Songs #50 to 11
(Alphabetical Order)

*No Fences (1990) by Garth Brooks

- “Song of the South” -Alabama (1989)
- “I’ll Take Today” -Gary Allan (1998)
- “Red River Valley” -Suzy Boggus (2011)
- “The Dance” -Garth Brooks (1989)
- “I’m Much Too Young (To Feel This Damn Old)” -Garth Brooks (1989)
- “Wolves” -Garth Brooks (1990)
- “She’s Not the Cheating Kind” (1994) / “That Ain’t No Way to Go” (1993) -Brooks & Dunn
- “Neon Moon” -Brooks & Dunn (1991)
- “The Stones in the Road” -Mary Chapin Carpenter (1994)
- “A Boy Named Sue” (1969) / “One Piece at a Time” (1976) -Johnny Cash
- “Crazy” -Patsy Cline (1961)
- “In Hell I’ll Be in Good Company” -The Dead South (2014)
- “Go Rest High on That Mountain” -Vince Gill (1994)
- “Remember When” -Alan Jackson (2003)
- “Grandpa (Tell Me ‘Bout the Good Old Days)” -The Judds (1985)
- “Should’ve Been a Cowboy” -Toby Keith (1993)
- “Meant to Be” -Sammy Kershaw (1996)

- “Need You Now” -Lady Antebellum (2010)

*Everywhere (1997) by Tim McGraw

- “The House that Built Me” -Miranda Lambert (2009)
- “I See it Now” -Tracy Lawrence (1994)
- “Dance the Night Away” -The Mavericks (1998)
- “Blank Sheet of Paper” -Tim McGraw (2004)
- “Where the Green Grass Grows” -Tim McGraw (1997)
- “Heads Carolina, Tails California” -Jo Dee Messina (1996)
- “The Little Girl” -John Michael Montgomery (2000)
- “You Don’t Care Enough For Me to Cry” -John Moreland (2015)
- “Fishin’ in the Dark” -Nitty Gritty Band (1987)
- “Whiskey Lullaby” -Braid Paisley featuring Alison Krauss (2003)
- “Jolene” -Dolly Parton (1974)
- “Love, Me” -Collin Raye (1991)
- “El Paso” -Marty Robbins (1959)
- “I Let Her Lie” -Daryle Singletary (1995)
- “Tennessee Whiskey” -Chris Stapleton (2015)
- “Fool Hearted Memory” -George Strait (1982)
- “Don’t Think Twice” -Billy Strings (2020)
- “I Told You So” -Randy Travis (1987)
- “Before He Cheats” -Carrie Underwood (2005)
- “The Devil Wears a Suit and Tie” -Colter Wall (2015)
- “Don’t Close Your Eyes” -Keith Whitley (1988)
- "I'll Think of a Reason Later" -Lee Ann Womack (1998)

Top Ten Songs
(Alphabetical Order)

10. The Ultimate Fiddle Folk Song

“The Devil Went Down to Georgia” -The Charlie Daniels Band (1979) 

- Commentary: This song is now well over forty years old but continues to feel fresh. I think this is because of the primary role that the instruments take here. The fiddle gets the spotlight, but the acoustic and electric guitar backing sounds pretty great too. There have been a ton of imitators who try to capture the same magic of this song, but nothing has ever really come close since. The voice of Charlie Daniel's is perfect for the folk story, no real singing necessary here. As soon as this song begins it just kind of sucks you into its tornado of sound and story, one that surprisingly and thankfully, comes in at just three and a half minutes. It's a fun ride.

9. The Classic 90's Country Song

“Passionate Kisses” -Mary Chapin Carpenter (1993)

- Commentary: As I was putting together my list of sub-categories within the country genre, I made the realization that there was a particular style of song in the 1990's that I responded to over and over again. I don't know another name for it other than calling it "THAT 90's COUNTRY SONG". I'm not musically inclined enough to describe it as it deserves, but here are some of the hallmarks: it has a medium speed guitar strum, an easy hook, simple but driving drums, a mellow tone, and its easy to sing along with due to its easy melodies and karaoke qualities. Other songs that would qualify under this category would be ones like (in alphabetical order): “Every Once in a While” by Blackhawk, “Lost & Found” by Brooks & Dunn, “Better Man” by Clint Black, "This is Me Missing You” by James House, “Amy’s Back in Austin” by Little Texas, “I Just Wanted You to Know” by Mark Chesnutt, “That Ain’t My Truck” by Rhett Akins, “Running Out of Reasons to Run” & "Learning As You Go" by Rick Trevino, “Some Girls Do” by Sawyer Brown, and "Living in a Moment” by Ty Herndon. 

To my mind, Mary Chapin Carpenter's "Passionate Kisses" is the pinnacle of this kind of song. I love the quiet piano intro followed by the drums and then we segue into that classic sound of the driving guitar, backing drum, easy melodies, and karaoke hooks. I think it helps that the lyrics aren't just about another relationship on the rocks, but hit a nice creative note with the female character reflecting upon what is and maybe isn't appropriate to expect from a partner in a relationship. The lyrics actually qualify it for one of my favorite little sub-categories of country music that are about women gritting through life, working several jobs and trying to find love/relationship. Shoutout to Reba McEntire's "Is There Life Out There" for being a great entry into that sub-category as well. Anyways, Carpenter's voice here is commanding and enjoyable. When she laments/cries out in the third verse "It's my right! Shouldn't I have this!" she is emotive and yet still pleasing to listen to. I think it's a tough balance to pull off in such an easy listening song. This one is so easy to listen to, so easy to enjoy, and so easy to sing with. I love it.

8. The Ultimate Story-Telling Song

“Almost Home” -Craig Morgan (2002) & "She Was" -Mark Chesnutt (2002)

- Commentary: Country music incorporates diverse stories into its songs better than any other musical genre I enjoy. The stereotype is that country music stories are about three things - cheating, trucks, and dogs (okay at least two of those are the subjects of songs on this list) - but it's much broader than that. I think the two best examples of country story-telling songs are "Almost Home" by Craig Morgan and "She Was" by Mark Chesnutt. "Almost Home" is a unique story in that it's about finding a homeless man on the side of the street who looks to be upon his deathbed. When the homeless man is awakened by a troubled passer-by he describes the idyllic dream he was having. The dream was of a day in his childhood, out messing about in the woods, and making his way home. There are two keys to the impact of the song. The first one is the incredible word choice to paint the scene, it instantly transports you to a very specific moment - even if your own childhood was different. The other key to the impact, is the contrast between the man's idyllic dream and the current reality he finds himself in, near death on the side the of the road. You can find both keys present in this part of the song, "I was close enough for my own nose to smell fresh cobbler on the stove, and I saw daddy loadin' up the truck. Cane poles on the tailgate, bobbers blowin' in the wind, since July of '55, that's as close as I've been." The story, which can be dismissed as simplistic and sentimental, actually deftly handles three emotions: the glorious nature of childhood summer days, the regrets we make that lead our lives astray, and how we deal with the knowledge that we are on our deathbed. I almost never hear the song without stopping and reflecting.

Mark Chesnutt's "She Was" is a more straightforward love story that spans a couple of generations. I know, it's a sentimental weeper, but my goodness, I just love it. I'm generally a sucker for a chorus that continues the same basic lyrics but has them change meaning depending on the verses (see also: "Don't Take the Girl" by Tim McGraw). I don't think a country song does this better and more surprising than the twists and turns in the story of "She Was." Additionally, like Alan Jackson, there's a nice country baritone sound to Chesnutt's voice here as he weaves emotion into the lyrics. Two songs that tell deep and moving stories within just a few minutes of listening time. 

7. The Ultimate Break-Up Song

“You Don't Even Know Who I Am” -Patty Loveless (1995)

- Commentary: Break-up and cheating songs comprise an unusually large percentage of the genre. Often they are just the same boring song over and over, but the genre has produced some insightful ones as well. Patty Loveless' "You Don't Even know Who I Am" begins as you would expect most break-up songs to, "You don't even know who I am, You left me a long time ago, You don't even know who I am, So what do you care if I go." Patty's voice is on-point and the first verse elevate this break-up song, but at this point, it's just a high quality entry. The second verse kicks in and we get a real unexpected turn, "So he said I've been doin some thinkin, I've been thinkin that maybe you're right, I go to work every morning, And I come home to you every night," and the chorus of "and you don't even know who I am" is repeated. Most breakup songs zero in on the emotions so well - the pain and the heartbreak of a failed relationship. This one though, has an intelligence to it that provides insight and a surprise twist that sets it apart from the usual strong fare country provides. This isn't a relationship broken by cheating or where one person is a saint and the other is a scoundrel. This song dares to blame both sides for the broken relationship, both sides for not contributing to a healthy love. One could never know for sure, but my guess is that most broken relationships come closer to being a "two sides" issue than just one. This one is in a class by itself.

6. The Ultimate Cowboy/Rodeo Song

“Amarillo by Morning” - George Strait (1983)

- Commentary: The story here is simple - there's a man who loves rodeo riding so much that he's willing to give up his time, his body, and his girlfriend for it. In fact, in giving himself so much over to it, he says he is a free man. I'm not over the moon about the story here, it's more of an interesting description of a life I'll never understand than a prescription for a life we all should have. What makes this song so great is the vibe. The simple guitar strum and the instantly recognizable fiddle kicks off the song and George's simple and smooth voice mixes so perfectly with this. It's such an easy going vibe that you just want to kick back, listen, and sing-along. I'd throw Garth Brook's "I'm Just to Young (To Feel This Damn Old)" and Strait's own "Fool-Hearted Memory" as songs with a similar vibe. They are just country songs that you could play and sing over and over. Wish I could express this one better than just "it sounds so good" but hey, that's what I got!

5. The Ultimate Country Love Ditty

“Forever and Ever, Amen” (1987)  AND "Deeper Than the Holler" -Randy Travis (1988)

- Commentary: Country music has a genre I call "ditty's". I'm pretty sure no one else would admit to this category and someone more musically inclined could tell me a better way to categorize it, but a ditty to me has a particular simple beat/rhythm and is very light on accompaniment, with the vocals taking center stage. To my mind, Randy Travis put out a two of the best little love ditty's in the country genre in back to back years. These aren't great love ballads that require string orchestra's or tear inducing stories of love's greatest sacrifices, these are simple little countrified folk songs with a nice beat (how's that for a category explanation?). I love how these ode's to a committed love find their expressions in distinctly southern terms, "As long as old men sit and talk about the weather, As long as old women sit and talk about old men" and "My love is deeper than the holler, Stronger than the river, 
Higher than the pine trees growin' tall upon the hill, My love is purer than the snowflakes, That fall in late December, And honest as a Robin on a springtime window sill, And longer than the song of a whippoorwill." Randy's baritone lend a gravitas to these ditty's that might seem a little gimmicky if not for his serious take on them. Play this song on a guitar, start slapping the side of your thighs, and these two songs are ones that any two lovers would connect with.

4. The Ultimate Country Karaoke Song

“Take Me Home Country Roads” -John Denver (1971)

- Commentary: A strange thing happened during an American football game taking place over in Munich, Germany recently, the fans in the stadium started singing, "Take Me Home Country Roads". A little less strange is that the a few years ago we had a Senior class in the high school I teach at adopt it as their kind of theme song. When we were closing out their Senior prom, what song did they want to end on? Yep, "Take Me Home Country Roads". Is it because a popular student was from West Virginia or because it was a tik tok trend? Nope, they just loved the song. More importantly, they loved singing it together. "Take Me Home Country Roads" started out a rural folk country song that was an ode to the wonder of country roads (West Virginia was really a fill-in for the songwriter who had never really been there before) in rural areas and has become an international folk song beloved by millions. The songwriters might have named West Virginia specifically, but their description of the countryside and the enchanting experience of driving rural roads is a kind of universal experience for anyone who has ventured beyond the city: "Life is old there, older than the trees, younger than the mountains, blowing like a breeze." This song has stood the test of time and ventured its way into the hearts of the world. It paints a beautiful picture, draws you into its experience, and is nearly impossible not to sing along to when a crowd is belting it out.

3. The Ultimate Country Ditty Song

“Drive (for Daddy Gene)” (2002) AND "Chasin' that Neon Rainbow" (1990) -Alan Jackson

- Commentary: I earlier described Randy Travis' two love song "ditties" earlier on this list as, "simple little countrified folk songs with a nice beat." This category recognizes Alan Jackson's knack to create perfect toe-tapping country ditties that tell heart-warming stories about family, love, and life's adventures. There's a whole well of similar songs one could draw on from Jackson's catalog here ("Livin' on Love" and "Gone Country" are fun entries), but I think "Drive (for Daddy Gene)" and "Chasin' that Neon Rainbow" are country perfection. If you forced me to choose, I'd probably pick "Drive" as the more layered song. I'll comment on "Drive" here, but nearly all the commentary applies to "Chasin' that Neon Rainbow" as well. On the surface, the song feels like a bit of a throwaway record. It's not too long, it doesn't break any new ground musically, and it the lyrics aren't typical country topics. However, if you look closer, I think it's got almost everything that makes country music great. It's a simple but catchy acoustic guitar song backed by a simple but driving drum beat and with accented by slide guitars. Jackson's easy country twanged baritone voice lends gravitas to the simple human story of parents, kids, and learning to drive. It combines three great emotions we can all relate with - the joy of driving, the joy of learning from your father, and the joy of teaching your kids. The lyrics aren't ground-breaking but they tell that story with such memorable color, "And I would turn her sharp, and I would make it whine, He'd say, You can't beat the way an old wood boat rides" that you can imagine the story in your head. By the time hits the final verse and Jackson is teaching his daughter to drive, the colorful scene setting and emotion come together perfectly, "It was just an old worn out jeep, rusty old floor boards, hot on my feet, a young girl, two hands on the wheel, I can't replace the way it, made me feel." Simple, human, catchy, a blast to sing. These two songs are country ditty perfection.

2. The Ultimate Country Love Ballad

“When You Say Nothing at All” -Alison Krauss (1995)

- Commentary: Keith Whitley's version in the late 1980's was really good. Alison Krauss's version is an absolute stunner. It may not be surprising that the same writer (Paul Overstreet) was behind both this song and the Randy Travis love ditty "Deeper than the Holler." Each are simple guitar songs with folksy but instantly memorable lyrics. Comparing this song to a popular one missing from my list might help you understand why I think this one is so good. Willie Nelson wrote and sang the bittersweet love song "Always On My Mind" (and it was covered by many artists with great success as well). In that song, the lover recounts the many ways he lacked action in his love (I wasn't around, didn't speak loving words, etc) but he hopes it's some consolation that his beloved was always on his mind. Eh, that doesn't do much for me. You see, being "on my mind" is the cheapest and easiest form of love. I get the mood of the song, but it has always rung hollow to me. It's like what the biblical author James writes about a life of faith, "What good is it, my brothers and sisters, if someone claims to have faith but has no needs?" (James 2:14). The point here being that it's all well and good to "say" something, but your deeds are the true fruit of that faith. This is why I love "When You Say Nothing At All" - it's like James' argument come to life. In this case, the song talks about how the lover's actions toward the beloved speak even when he remains silent - "The smile on your face...the truth in your eyes...the touch of your hands..." Wrap this beautiful sentiment in Allison Krauss' angelic voice without any unneeded angst, cheese, or  gimmicks and you have what I think is the best country ballad of all-time.

1. The Ultimate Country Song

“Hurt” -Johnny Cash (2002)

- Commentary: I think this is one of the greatest songs and music videos of all time. I will spare you the background on the song's origin and how Cash came to cover it, I feel it has been told a million times by now. If you are unfamiliar then give the song's Wikipedia entry a quick read over. The rest of this commentary will assume you are familiar with the song, it's story, and seen the music video. 

Ever since I was a young boy I have been drawn to cynical views of life. When people would toss out simple proverbs like, "The early bird gets the worm!" all I could ever think about were the counter examples of those who showed up early and never got an advantage. It's only later in life that I realized the Scriptures understood the tension in their wisdom literature as well. The entire book of Proverbs is stacked with basic "rule of thumb" proverbs that are often true about life, but are also not true. The book of Ecclesiastes is like a counter-punch to anyone who puts their entire trust into simple A+B+C proverbs. It comforted me to read that God was acknowledging, through the writer of Ecclesiastes, some of my most cynical thoughts about life: we are all going to let each other down, life's pleasures are often very unfulfilling, storing up treasure on earth is worthless, and we are all going to die. These are powerful and sobering truths about our broken hearts in a broken world.

In "Hurt" the "three chords and the truth" aspect of country music moves from individual moments of life (falling in love, teaching your daughter to drive, driving country roads) to regretful reflection on a life full of brokenness. Every insight I found powerful in the book of Ecclesiastes is represented here filtered form the pen of Trent Reznor and through the haunting and vulnerable vocals of Johnny Cash. 

- "What have I become?"
- "Everyone I know goes away in the end"
- "My empire of dirt"
- "I will let you down, I will make you hurt"
- "Upon my liar's chair"
- "Full of broken thoughts, I cannot repair"
- "Beneath the stains of time, the feelings disappear"
- "You are someone else, I am still right here"

It's heart-breaking stuff. It's wisdom coming to us from a life lived. Guys, all of the stuff country music most often is about - gaining love, losing love, working hard, having fun, family, pickup trucks, dogs, beer, etc - mean nothing in the end unless we keep who we were made to be. The final line of the song hopefully talks about redemption, "If I could start again, a million miles away, I would keep myself, I would find a way." In other words, all of those things in life are not the reason for living - they are an empire of dirt. If he could do it all over, he'd find a way to keep himself. One cannot help but here the phrase from Christ echoing here, "What profit a man if he gain the world and lose his soul?" This is why I think this is the ultimate country song - the ultimate "three chords and the truth" - because it is ultimately a gospel song about our brokenness and our need for redemption. I think that's why so many find such power in the song as well.

What is the final word from Ecclesiastes then? In light of our brokenness and our inability to control our lives, we must humble ourselves, fear and love the Lord, obey his commands, and enjoy the life we have. The only way to do this, as the New Testament reveals and proclaims, is through Jesus Christ our Lord and Savior. If that's something you'd like to know more about, then email me at kyleleaman@gmail.com and we'll chat together about it. 

Thanks for reading, hopefully I've shared something helpful here. Let me know your thoughts.