Katie Peterson
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Last updated on July 24th, 2023 at 02:29 pm
Sometimes you’re just in the mood to remember when country music was at its very best. With simple songs that told everything from love to heartbreak and everything in between, it’s no wonder they set the stage for the country music singers of today.
From Patsy Cline to Tanya Tucker and every other old country singer we love, these are some of our favorite classic country music songs of the olden days. Be prepared before you dive in. There will be no songs released in 1980 and beyond included.
Here’s our list of the 16 best old country songs to add to your childhood playlist.
16. “Delta Dawn” – Tanya Tucker
“Delta Dawn” was a breakout single for Tanya Tucker when she released her version of the Bette Midler classic in 1972.
It immediately soared her to the top of the country charts, peaking at number six, and is still one of the most notable and famous versions of the old country song today.
15. “Man of Constant Sorrows” – The Stanley Brothers
This classic American folk song, covered by The Stanley Brothers in 1951, has stood the test of time with multiple versions complete with melodic and lyrical variations.
The Stanley Brothers recorded “Man of Constant Sorrows” after learning it from their father, Lee, who created a cappella hymn version in the Baptist tradition.
The brothers brought it to the world of bluegrass in their up-tempo arrangement and are the ones who made it the most popular version to hit radio waves.
This classic hit will always remain one of our favorites we’ve ever heard.
Related: The 50 Best Country Songs from Jimmie Rodgers to Morgan Wallen
14. “Chug-A-Lug” – Roger Miller
One of the older old country songs to make our list, “Chug-A-Lug” by Roger Miller, was a hit on both the country and pop charts upon its release in 1964.
Written by Miller, this song is a fun one about youthful encounters with homemade alcohol, as the song’s title refers to the act of quickly downing a drink.
The song became a top 10 for the King of the Road, and one of our favorites of all time from the legendary singer.
13. “Mama Tried” – Merle Haggard
When Merle Haggard released “Mama Tried” in 1968, who knew it would become the cornerstone song of his career?
As the Haggard shares with the world his experience of serving three years in San Quentin (157-1960) on a robbery conviction, and the pain he caused his mother because of it, we can’t help but applaud him for being vulnerable and sharing that story with the country music world, even if the song is more dramatic than things played out.
The Grammy world agrees as it earned him a Grammy Hall of Fame Award more than 30 years later in 1999 and a spot-on Rolling Stone’s “500 Greatest Songs of All Time” list in 2021.
Related: The 15 Best Male Country Singers of All Time: A Definitive List
12. “Mamas, Don’t Let Your Babies Grow Up to Be Cowboys” – Willie Nelson and Waylon Jennings
This classic duet released by two outright country music legends embodies the genre at its core.
When Willie Nelson and Waylon Jennings covered this Ed Bruce tune in 1978, it peaked at number one on the country music charts and even won them a Grammy Award for Best Country Performance by a Duo or Group with Vocal.
We don’t care how brutal and rootless the cowboy culture is: we’d have no problem letting our babies grow up to be cowboys if it meant having another hit song like this.
Related: Willie Nelson’s Net Worth and Other Essential Facts
11. “Hello Darlin'” – Conway Twitty
“Hello, Darlin'” is one of those old country songs that we love more than any other, as Conway Twitty perfectly expresses the feelings of running into that old flame that we still love and miss while putting on a face that tells them otherwise.
This classic 1970s hit, which peaked at number one on the charts, gives us the hope that perhaps, one day, that old flame that we lost due to our mistakes will forgive us and return one day, too.
10. “Louisiana Woman, Mississippi Man” – Conway Twitty and Loretta Lynn
If there’s anything we like better than Conway Twitty and Loretta Lynn by themselves, it’s when they come together as a team, and “Louisiana Woman, Mississippi Man” is the prime example of that.
This classic back-and-forth duet is one of the best old country songs the two ever gifted us as the duo sings about the trials of a man and woman in love who are separated geographically by the one-mile-wide Mississippi River.
This up-tempo, Cajun-sounding tune is one we’ll always find ourselves tapping our foot along to and queuing up on the karaoke system to belt out with our lover every date night.
Related: The Best 15 Female Country Singers of All Time: Who Made the List?
9. “Walkin’ After Midnight” – Patsy Cline
Patsy Cline is another artist on our list with many old country songs to choose from, but we had to go with her 1957 hit, “Walkin’ After Midnight.”
Although we know “Crazy” would have been the more obvious choice, this song because it’s the one that gave the world Patsy Cline in the first place after she performed it on an episode of Arthur Godfrey’s Talent Scouts.
We’d be crazy not to give this song credit where it’s due.
Related: Patsy Cline’s Net Worth: The Country Star’s Vast Fortune
8. “Kiss an Angel Good Mornin'” – Charley Pride
Charley Pride shares the secret to a long, happy marriage in his 1971 hit single, “Kiss an Angel Good Mornin.'”
This single Top 40 hit by Pride is his signature as the narrator tells his friends that the secret to lasting love is to “kiss an angel good mornin,'” meaning his wife, and then “love her like a devil,” meaning himself.
We sure love this song like the devil to where we want to queue up every time we get back home.
Related: The 15 Best Black Country Singers Spanning Over 100 Years
7. “Rhinestone Cowboy” – Glenn Campbell
In this Billboard number-one single, Glenn Campbell gives a sincere performance of the song, perhaps because the singer reportedly identified with the premise of survival and doing anything to make your dreams come true even when it seems as though the odds are against you.
AllMusic’s Stephen Thomas Erlewine describes the song as “about a veteran artist who’s aware that he’s more than paid his dues during his career … but is still surviving, and someday, he’ll shine just like a rhinestone cowboy.”
All we can say is Campbell did shine like a “Rhinestone Cowboy” with this one.
6. “I’m So Lonesome I Could Cry” – Hank Williams
It’s the oldest of the best old country songs to don our list, but we couldn’t make such a list without it.
“I’m So Lonesome I Could Cry” was the signature hit of Hank Williams’ short but well-lived career as he sings of his intense, personal emotions surrounding country music’s “traditional, plainspoken directness” that has defined the genre ever since, although it was a revolutionary approach in the young singer’s day.
Even singer k.d. lang, in the 2003 documentary The Road to Nashville, that the song “is one of the most classic American songs ever written, truly. Beautiful song.”
The legendary Bob Dylan has noted the influence of Williams and the song on him in his autobiography, in which he says: “Even at a young age, I identified with him. I didn’t have to experience anything that Hank did to know what he was singing about. I’d never heard a robin weep but could imagine it, and it made me sad.”
Related: How did Hank Williams Die? A Not-So-Happy New Year
5. “The Gambler” – Kenny Rogers
“The Gambler,” written by Don Schlitz, tells the story of a man who meets a gambler on a train, upon which the gambler notices the narrator’s glum circumstances and, in exchange for a swig of whiskey, offers him some advice.
As the narrator obliges, the gambler provides some sage advice in the cleverly written chorus that uses poker metaphors to explain his outlook on life.
When the gambler ends up passing away, and the narrator is left to ponder the wise advice from this chance encounter, we can’t help but think about it right along with him long after the song comes to an end. And that’s why it’s one of those old country songs that sticks with us even to this day.
4. “I Will Always Love You” – Dolly Parton
Dolly Parton is the blonde bombshell we already loved, thanks to her bubbly personality and sweet, iconic voice. Then, she gave us this 1974 hit single, “I Will Always Love You,” and forever solidified a place in our hearts.
Written for her friend and business partner Porter Wagoner as a last farewell before ending their professional partnership, “I Will Always Love You” is the epitome of what a country love song is, and it has continued to stand the test of time.
Of all the best old country songs on our list, this one has to be one of the tops, not just because of its beginnings but because of the new life, it has continued to receive, with the likes of Whitney Houston and Kristin Chenoweth covering it.
If that weren’t enough, it became the co-theme song, along with John Denver’s “Take Me Home, Country Roads” and Willie Nelson’s “On the Road Again,” for the 50th anniversary of the Country Music Association (CMA) Awards in 2016, entitled “Forever Country.”
This classic medley featured all our favorite country artists, from Tim McGraw to Little Big Town, Brad Paisley to Jason Aldean, Reba to Alan Jackson, and everyone in between, before Carrie Underwood comes in on that iconic line.
We will always love this song, and we tip our hats off to Dolly Parton, not just for singing it but for being the sole songwriter of this timeless song that we’ll never forget.
Related: Dolly Parton Net Worth, Height, Career, and More
3. “Take Me Home, Country Roads” – John Denver
Like so many old country songs that have made our list, “Take Me Home, Country Roads” by John Denver has become such a timeless song that it’s still played on mainstream radio and covered by some of the most prominent artists of the day.
Perhaps nowhere has it been more iconic than in West Virginia, where the narrator proudly proclaims is where those country roads take him home to.
In 2017, the West Virginia Tourism Office even obtained the rights to use it in marketing campaigns, with the song’s opening words, “Almost Heaven,” serving as the slogan.
Chelsea Ruby, West Virginia Tourism commissioner, said, “‘Country Roads’ has become synonymous with West Virginia all over the world. It highlights everything we love about our state: scenic beauty, majestic mountains, a timeless way of life, and most of all, the warmth of a place that feels like home whether you’ve lived here forever or are just coming to visit.”
Although the song had to settle for peaking at the number two spot on the Billboard Hot 100 chart, it’s number one in the hearts of so many, and we can’t blame them one little bit.
Related: How Did John Denver Die: Freak Accident or Suicide?
2. “Coal Miner’s Daughter” – Loretta Lynn
Our favorite “Blue Kentucky Girl” gave us the most beautiful biographic song we’ve ever had the pleasure to hear when she released “Coal Miner’s Daughter” in 1970.
Originally intended to have a bluegrass melody to match how she was raised in singing, Loretta Lynn recounts her day-to-day life growing up in Butcher Hollow, Kentucky, as the daughter of a coalminer and her homemaker mother.
She describes how, even though she was raised in poverty, her parents were hardworking people that always managed to provide.
1. “I Walk the Line” – Johnny Cash
Johnny Cash was the king of country music in the olden days, giving us some of the best old country songs that we’ll always find ourselves wanting to listen to.
Therefore, it wasn’t easy picking one to represent the iconic “Man in Black,” but “I Walk the Line,” released in 1956, had to be the one we chose.
This classic hit song, written not long after he married his first wife, was Cash’s way of “laying out my pledge of devotion,” the singer said in a telephone interview. We’ll pretend he was talking about June Carter Cash with that statement, but we digress.
Initially meant to be a slow ballad, we can’t imagine the song without its catchy, fast arrangement, and obviously, the rest of the world couldn’t either.
The song was met with major success and has been included in a permanent exhibit at the Rock and Roll Hall of Fame as one of the “500 Songs That Shaped Rock and Roll.”
It’s no wonder this was the song chosen to be the title of the Academy-Award-winning Walk the Line biographic film of the singer, starring Joaquin Phoenix and Reese Witherspoon.
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