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Let’s Talk About the Top Country Songs of All Time

For any diehard fan of country music, selecting the top country songs of all time is a challenge of epic proportions. The choices – going back to the Carter Family (1927) all the way through Miranda Lambert (today) -- are as diverse as the legendary performers who created them. So, if you’re up for this puzzle of opinion, pick up your guitar and, together, let’s discover the top country songs of all time.

What is the Origin of Country Music?

When discussing the origin of country music (once referred to as Country and Western) it would be impossible to omit the first family of country music, the Carter Family.

With their iconic recordings of “Wabash Cannonball,” “Wildwood Flower,” and “Keep on the Sunny Side,” the Carter Family would famously find their way from small-watt Appalachian radio all the way to the annals of genre-defining standards.

Both melodic and harmonic, the Carter Family’s easy-going twang and sweet words set the tempo for a newly discovered category embracing the best of rural rock, bluegrass, and Southern Gospel.

With the obligatory inclusion of the aforementioned “Keep on the Sunny Side” -- along with six-decades plus of guitar-picking, sad, joyous, and cheating songs – the following twelve (12) gems represent the top country songs of all time.

Agree or disagree as you see fit.

12. “You Look So Good In Love” by George Strait (1983) George Strait has long been synonymous with the apex of country music. Often thought of as one of the vital links between old country and the new traditionalist of the 80s (i.e., Randy Travis, Steve Earl, and Dwight Yoakum) Strait held his own as the godfather of the genre. In 1983, “You Look So Good In Love” was Strait’s first hit in many years. In it, he comes to grips with another man whisking away the love of his life. You look so good in Love/you want him/it’s easy to see. It’s a tale of guilt and identifiable frustration that can only come from this master of moody melodies.

11. “Mountain Music” by Alabama (1982) It’s been rumored that “Mountain Music,” one of Alabama’s biggest hits was inspired by band member Randy Owen’s youthful years on Lookout Mountain. Loving memories of his childhood -- days of swimming and frolicking kid stuff-- created a wonderful image that sparked he and the band’s musical passion.

With classics such as “Mountain Music” and “If You’re Gonna Play in Texas (You Gotta Have a Fiddle in the Band),” Alabama would define what a country and bluegrass band should sound and look like.

10. “Behind Closed Doors” by Charlie Rich (1973)

For much of his career, the Silver Fox of music was considered too far on the rock & blues side to be accepted as a country star. What he needed was a surefire smash to put his name with the elite talents of his day.

He got his wish when, one day, a writer by the name of Kevin O'Dell shared a tune with Rich that would turn a tawdry tale into a calling-card classic. It was an instant hit – so much so that Rich would go on to nab two Grammys that year along with the CMA Entertainer of the Year award. 

9. “Convoy” by C.W. McCall (1975)

There was a time in the mid 1970s when everyone with a station wagon or pick-up truck had a C.B. radio to fiddle around with. Back in the day, it was all the rage to select your own “handle” (long before Twitter) and talk to truckers and friends alike as you chewed up miles on the road.

The term “convoy” refers to the phenomenon where truckers would unite on the highway, driving in numbers as opposed to solo. Along with it, there were colorful phrases including “Can I Get a Radio Check,” “Breaker One-Nine,” and “10-4, Good Buddy,” which would find their way into the American lexicon.

There was even a movie about the craze, appropriately entitled “Convoy.” Though C.B. radios are still used by truckers today, the fad fizzled with the general public. Regardless, it was a wild ride while it lasted, and just like that, “We Gone, Bye-Bye!”

Who Were the Best Country Singers of the 80s?

Leaping from the 70s to the 80s was a defining moment in the history of country music. At the turn of the decade, a new crop of performers was ready to take the lead. Those artists, eager for the spotlight, included (the aforementioned) Randy Travis, Dwight Yoakum, Garth Brooks, Reba McEntire, Kenny Rogers, and the Judds, to name a few.

8. “She is His Only Need” by Wynona Judd (1992)

Speaking of the Judds, daughter Wynona took off on a solo career that went off with lightening. Already a household (last) name, Wynona would shake up the stage and airwaves with great songs such as “My Strongest Weakness,” “I Saw the Light,” “A Bad Goodbye” (duet with Clint Black), and, above all, “She is His Only Need.”

This crossover ballad is considered by many to be one of the greatest love songs; let alone one of the top country songs of all time. It’s the tale of Billy, “a small-town loner who never did dream of leaving southern Arizona.” Billy loves and adores one thing and one thing only: Miss Bonnie. The song is homage to every man who dedicates his heart to the legacy of love for his wife.

7. “Guitars, Cadillacs” by Dwight Yoakam (1986)

Yoakam, also on our best of the 80s list, took his hillbilly/rockabilly act from a modest neighborhood in Columbus, Ohio, all the way to the prime stages of Los Angeles. Long before his musical success -- with his trademark, hat-over-the-eyes thing -- Yoakum would be in and out of local bands such as the Blasters and Lone Justice.

The biggest influence on Yoakum was his guitar hero, Buck Owens, whose light shined much brighter than just a jokester on “Hee Haw.” Owens’ inspiration help grow "Guitars, Cadillacs" into a hit. Yeah my guitars, Cadillacs, hillbilly music/Is the only thing that keeps me hanging on. Yoakum returned the favor when he penned “Streets of Bakersfield,” the accordion-inclusive California ode which became Owen’s first hit in two decades.

6. “Friends in Low Places” by Garth Brooks (1990)

There was a time in the late 80s and early 90s where it was impossible to not hear a Garth Brooks track on the radio or turn on an awards show without Brooks being nominated. With universally recognizable hits such as “The Thunder Rolls,” “The Dance,” and “That Summer,” (literally to name a few), Brooks became ubiquitous with the genre.

But even with all that wonderful material, the promo buzz had to start somewhere. Many believe the rubber hit the road in the early 90s when he performed “Friends in Low Places” on the Grammys. The stage set up was a classy party which soon morphed into a seedy saloon. Blame it all on your roots/I showed up in boots/And ruined your black-tie affair.

For Brooks, not a moment too soon.

With the above handful of acts, the question of who were the best country singers of the 80s? has a host of acceptable answers. You could make a case for any of the above with, of course, George Strait (more on him in a moment) leading the pack.

However, as cool and iconic as the 80s was for country music, let’s turn back the clock (way back) and check out a few classics firmly added to our list of top country songs of all time.

5. “D-I-V-O-R-C-E” by Tammy Wynette (1968)

The female perspective on country music was becoming all the rage. This tragic song, produced by Billy Sherrill, would create a whirlwind of energy for women everywhere going through the “Big D.” It would also become Wynette’s third #1 song -- in addition to the title track of her first gold record.

The song --- still popular today -- continues to be an anthem for love gone wrong. In many ways, this and our next song could qualify for our earlier question of: what is the origin of country music?

4. “I Fall to Pieces” by Patsy Cline (1961)

The track was originally intended for the Patsy Cline Showcase in 1961. With it, Cline would become one of the first female singers to grace the airwaves of crossover country and pop radio.

There’s a story that when Cline first recorded the track, it brought tears to every man in the room. It’s not surprising as you listen to the heart-wrenching lyrics. I fall to pieces/Each time I see you again/I fall to pieces/How can I be just your friend? The theme is as timely today as it was when those sensitive boys wept in the studio.

3. “Folsom Prison Blues” by Johnny Cash, (1955)

Johnny Cash couldn’t bear to idly sit back and let his fellow man rot in a jail cell without some kind of artistic support. This would become the story behind a man locked up in the sad hell that is “Folsom Prison Blues.”

The heartbreak of the song is a man knowing a free man is on that train “… drinking coffee and smoking big cigars.” It’s a haunting image. But in the end, the punishment fits the crime. The lyrics say it all: I shot a man in Reno/Just to watch him die. From there, life will turn from tough on the street to unbearable behind bars. Cash captures it all perfectly.

Who Has the Most #1 Country Music Singles?

There are dozens of probable answers: Maybe it’s George Jones or Dolly Parton. Perhaps its Loretta Lynn or Kenny Rogers. Each and every one mentioned is a superstar in their own right. But there can only be one “greatest ever.”

The answer for the performer holding the most number ones is none other than George Strait. He owns the mark, hands down, with 44 songs (and counting) that managed to reach the top of the Billboard Hot Country Songs chart. Here are a few of his best-known:

  • “Fool Hearted Memory”
  • “A Fire I Can’t Put Out”
  • “I Hate Everything”
  • “Right or Wrong”
  • “Let’s Fall to Pieces Together”
  • “The Chair”
  • “Ocean Front Property”
  • “All My Ex’s Live in Texas”
  • “Am I Blue”
  • “Famous Last Words of a Fool”

2. “Run” by George Strait (2001)

And for good measure, add this other one. It seems “Run” just came out – but it’s actually been over two decades since landing on the charts. Once again, Strait paints the image of desperation – a man so hungry for the affection of his lover, he wishes her the speediest route to get to him.

Baby, Run, cut a path across the blue skies/Straight in a straight line/You can't get here fast enough

The song has a soft, easy-going melody and flowery, instrumental background, but it’s the lyrics, full of “want” and “need” that pulls the audience into an emotional state of curiosity. For anyone who ever yearned for romance, “Run” easily makes our list of the top country songs of all time.

What Was Hank Williams Best Song?

The O.G. bad boy of country music had a major effect on the drinkin’ and carousin’ side of the industry. Williams had 11 number one hits over the length of his career. Selecting the best of that near-dozen isn’t easy, but if there’s one Hank Williams song you absolutely have to bring on a deserted island, it would be "Your Cheatin' Heart.” It’s his most memorable and accessible song, always a go-to on the best “cheating” songs ever.

Here are some other rough and rugged options to answer the question; what was Hank Williams best song?

  • "Lovesick Blues"
  • "Long Gone Lonesome Blues"
  • "Why Don't You Love Me"
  • "Moanin' the Blues"
  • “Cold, Cold Heart"
  • "Hey, Good Lookin'"
  • "Jambalaya (On the Bayou)"
  • "I'll Never Get Out of This World Alive"
  • "Kaw-Liga"

What is the Most Dramatic Country Song?

Drama is all over country music, whether it’s a love song, a cheating song, or the world’s most devastating break up. No one can put tragedy to a tune like a country musician. Consider some of the following, as we ask, what is the most dramatic country song?

You could say “A Boy Named Sue” by Johnny Cash where a man must go through life with a sissy girl name so he can defend himself after his father deserts him. Or – you can go with Carrie Underwood’s “Before He Cheats,” which urges men to think long and hard before “running out” on their woman. What “Fatal Attraction” did for film, this song does (even better) for music.

Here are some other drama-filled songs for the ages:

  • “The Highwaymen” by the Highwaymen
  • “Papa Loved Mama” by Garth Brooks
  • “Highway 20 Ride” by Zac Brown
  • “The Bridge” by Dolly Parton
  • “Don't Take the Girl” by Tim McGraw
  • “He Stopped Loving Her Today” by George Jones
  • “The Chicago Story” by Bobby Bare

… And one more.

1. “Where Were You (When the World Stopped Turning)” by Alan Jackson (2002)

The world was in shock and disarray the days following the terrorist attacks on America. Leave it to the generational talent of Alan Jackson to put it in perspective; an essay to bring us – if only for a moment – to reflect, not on what’s missing in our lives, but what we have.

Jackson scored big on such hits as “Remember When,” “The Older I Get,” and “Little Bitty” – but it was the gut-wrenching words of the healing “Where Were You (When the World Stopped Turning)” that blew us away the most.

Did you rejoice for the people who walked from the rubble
And sob for the ones left below?
Did you burst out with pride for the red, white, and blue
And the heroes who died just doin' what they do?
Did you look up to heaven for some kind of answer
And look at yourself and what really matters?
I'm just a singer of simple songs
I'm not a real political man
I watch CNN, but I'm not sure I can tell you
The diff'rence in Iraq and Iran
But I know Jesus and I talk to God
And I remember this from when I was young
Faith, hope, and love are some good things He gave us
And the greatest is love

Summary

There is a treasure trove of possibilities for the top country songs of all time. That’s the beauty of debate; more than one offering can be correct, especially when you’re dealing with the subjectiveness of music.

Looking at the list above, the number one song could have gone a thousand different ways. Our best of the best, given its timing and importance, fills a void in our society for peace and compassion. Alan Jackson eloquently gifts us with what the world needs most, And the greatest is love.