The Best Classic Old Country Songs

Crystal Gayle - Don't It Make My Brown Eyes Blue

Crystal Gayle was at the top of her game in a golden age of country in the mid-'70s. ‘Don’t It Make My Brown Eyes Blue’ became something of a theme song for Loretta Lynn's younger sister when it became her third No.1 and elevated her to household name status as Crystal Gayle became the foremother of modern day pop country.

The song was the opening track on Gayle's 1977 album We Must Believe In Magic, which went on to be the first platinum album recorded by a female artist in country music. The single itself – a jazzy, late night pop-country ballad that made full use of Gayle's extraordinary silky smooth vocals – even reached No.1 on the all-genre Billboard Hot 100 and set a template for pop country that everyone from Kacey Musgraves to Kelsea Ballerini still uses today.

The song’s writer, Richard Leigh, had been responsible for all three of Crystal Gayle's previous Top Ten hits when Gayle's producer Allen Reynolds approached him to write ‘Don’t It Make My Brown Eyes Blue’.

It was Leigh's landlady – who also happened to be ‘When I Dream’ songwriter Sandy Mason Theoret – who suggested to Reynolds that he should pop in on Leigh. It was here that Leigh sang him a song he’d written for Shirley Bassey.

“Shirley Bassey my ass”, Reynolds apparently replied when he heard it. “I want that song!”

- Jof Owen

Ray Charles - I Can't Stop Loving You

One of the countless examples of Don Gibson’s superb songcraft and impact on the history of country music. ‘I Can’t Stop Loving You’ would be recorded by over 700 artists throughout Gibson’s life, but it was Ray Charle’s cover for his groundbreaking album Modern Sounds in Country and Western Music that would finally take it to No.1.

The layered choral introduction acts as a velvet curtain that slowly opens, revealing Charles at center stage with that grab-your-chest voice. In the song, he’s broken hearted but gripping steadfastly to keep the memory of a loved one from being forgotten, making for one of country's stop-in-your-tracks moments.

‘I Can’t Stop Loving You’ remains to be one of Charles' many incomparable performances that is just as impactful today as it first was in 1962.

- Soda Canter

Jeannie C. Riley - Harper Valley P.T.A.

Written by Tom T. Hall, this track surmises everything you’ve ever wanted to say to local busybodies with an inch too much nose in other people’s business.

When a schoolgirl arrives home with a note stating that her mother’s short skirts, drinking and male fraternising are causing concern with the PTA, its subject decides to teach them a lesson. Dressed in the offending miniskirt, she delivers a searing takedown which variously sheds light on her accusers’ drinking, womanising and adultering.

The song was a No.1 hit for Riley, even inspiring a movie and TV show, and two sequel songs; an official one penned by Tom T. Hall, and Jeannie’s unofficial sequel, 'From Harper Valley to the Mountain Top,' in which she denounced the fame and fortune the song had bought her in favour of her born again Christianity.

Despite this, the song has lost none of its punch, with its plain talking jabs becoming more brutal with every verse. The decision to address the listener directly through the lyrics set against a twangy guitar that sounds like a series of winks and raised eyebrows holds our attention right until the closing notes, giving it a place in our top 50.

- Holly Smith

Buck Owens - Streets of Bakersfield

‘Streets Of Bakersfield’ is a symbol of the ‘Bakersfield sound’ sub-genre, of which Owens was a central proponent.

The song was written by Homer Joy, a frustrated artist that happened to be recording a Hank Williams-esque album in Owens’ studio at the time.

Although not garnering a great deal of traction upon it's original release in 1973, Dwight Yoakam revamped the Latin-inspired track into a duet with Owens in 1988.

This collaborative version of ‘Streets Of Bakersfield’ surged to No. 1 on Billboard’s Hot Country Singles chart, and helped to cement the song’s place in the country music canon.

- Maxim Mower

Brenda Lee - I'm Sorry

A smash hit that surged to No. 1 on the Billboard Hot 100 in July 1960, as well as being inducted into the Grammy Hall of Fame more than thirty years later in 1999, Brenda Lee's 'I'm Sorry' is a forlorn, string-backed balled that only actually totals about 95 words; yet, it's remained a standard in the country canon.

Recorded when Lee was just 15, her label home, Decca Records, originally held it from release, believing that a teenager wasn't mature enough for its weighty prose on unrequited love. As evidenced by its commercial performance, though, consumers everywhere disagreed.

Written by Dub Albritton and Ronnie Self - who also penned 'Sweet Nothin's' - 'I'm Sorry' was one of the first songs to come out of Nashville using strings, providing a rich sonic element that has bolstered its appeal far beyond the confines of the country genre.

"I never expected to have a big old record like that. I didn't really have an agenda for my talent. I just wanted to be able to sing," Lee explained. "I knew the song was great when I first heard it. We all did. We all felt there was something very, very special about the song... That song has withstood the test of time."

- Lydia Farthing

David Allan Coe - You Never Even Called Me By My Name

If you were to take the cynic’s view of country music, to have a hit single on your hands in the 70s, you needed to include five key narrative points - trucks, trains, prison, getting drunk and Momma. That was according to David Allen Coe, who took 'You Never Even Called Me By My Name' - a satirical observation of the genre - to No.8 on the Hot Country Songs Chart in 1975. You could argue it’s not changed too much since.

A parody written by Steve Goodman and John Prine in a boozy writing session in their then manager Paul Anka’s plush suite in the Waldorf Astoria hotel in New York, the song was covered by Coe for his 1975 album Once Upon A Rhyme. Over sullen acoustic blues and the tears of a chorus of choirs, Coe’s version channels the outlaws’ teeth-bared pessimism towards the country industry and community at the time.

Today, you can’t imagine another mainstream country artist breaking the fourth wall and outwardly naming a contemporary in the charts through song while mocking the genre, which is arguably a telling indictment of the state of the mainstream today.

- Ross Jones

Ernest Tubb - Waltz Across Texas

“When we dance together, my world's in disguise / It's a fairyland tale that's come true / And when you look at me with those stars in your eyes / I could waltz across Texas with you...”

Willie Nelson, Waylon Jennings, Leon Russell, Bobbie Nelson and Amanda Shires – they’ve all taken a swing at the classic country song, ‘Waltz Across Texas’, over the years, but none have done it quite like Ernest Tubb.

Written by his nephew Quanah Talmadge Tubb, who was known professionally as Billy Talmadge, Tubb, with His Texas Troubadours, was the first to record and release the moony ballad in 1965. While the tune has lived many lives since, it is his version that is widely recognized as the standard.

The sweeping waltz, with its gentle arrangement and dreamy lyrics, is one of those classic songs that has grown into an extension of country music, forever inseparable from the genre.

- Alli Patton

Dolly Parton, Linda Ronstadt and Emmylou Harris - Wildflowers

Seemingly blown straight in by the breeze that dressed the Appalachian hillsides of Dolly Parton’s childhood, this delicately jaunty acoustic number was the prime vehicle for the effortlessly sharp harmonies of the self-anointed Trio; Dolly, Emmylou Harris and Linda Ronstadt.

An inspiring story of staying true to one’s self, blooming in the most unlikely of places and staying wild, it’s Dolly-core at its finest. The fourth single from the trio’s self-titled 1987 album, the song remains elegantly beautiful as a lesson in coming-of-age, placing it firmly in the top 50 of our classic country songs.

- Holly Smith

Sammi Smith - Help Me Make It Through the Night

Written by Kris Kristofferson and originally released on his 1970 album, Kristofferson, it was Sammi Smith's version that became the definitive version when it was released a few months later in November of that year.

Smith's smooth, smoky delivery injects the song with just the perfect amount of sadness and intrigue, conjuring images of star-crossed lovers and clandestine meetings in dimly lit motel rooms.

It was no surprise when Sammi Smith's version won the Grammy Award for Best Female Country Vocal Performance, reaching No. 1 on the country singles chart as well as crossing over to become a pop hit.

Kristofferson wrote the song during the early days of becoming a songwriter while he was staying with Dottie West. The narrative was inspired by an old Esquire Magazine interview with Frank Sinatra; when asked what he believed in, Old Blue Eyes replied, "Booze, broads, or a bible...whatever helps me make it through the night.."

Kristofferson originally offered Dottie West the song, but she turned it down because she thought it was "too suggestive" for her, although she too would record it after Sammi Smith. Later in life, Dottie West said that not recording 'Help Me Make It Through The Night' when Kristofferson first offered it to her was one of the greatest regrets of her career.

- Jof Owen

Charlie Rich - The Most Beautiful Girl

A timeless heartbreak anthem, Charlie Rich’s ‘The Most Beautiful Girl’ was the centrepiece of the countrypolitan hitmaker’s 1973 album, Behind Closed Doors.

Penned by Billy Sherrill, Norro Wilson and Rory Bourke, ‘The Most Beautiful Girl’ pivots around a simple, infectious melody, with Rich longing to take back his harsh words and fall back into the arms of his love.

Like many of the songs on this list, ‘The Most Beautiful Girl’ has become so popular that it’s been covered by a host of big-name acts, including Rita Coolidge and Engelbert Humperdinck. Interestingly, ‘The Most Beautiful Girl’ is actually an amalgamation of two other tracks crafted by Norro Wilson - ‘Hey Mister’ and ‘Mama McCluskie’.

- Maxim Mower

Eddy Arnold - Cowpoke

While Colter Wall may have revived this 1951 Stan Jones-written gem for the YouTube generation, Eddy Arnold captured the quintessential version for his seminal album Cattle Call in 1963.

While it doesn’t harbour the dark shadows that pervade Wall’s reimagining, and certainly  doesn’t paint with the Cloud Nine-Era George Harrison-esque brush that Glen Campbell tarred it with, Arnold embraces the simplicity of the production, embodying the survival-by-all-costs nature of the outlaw narrative.

Arnold’s take elicits the haunting atmosphere of a weary traveller traversing the desert in a Spaghetti Western classic, his irreplaceable yodel and pining croon tailor made for the stripped back acoustic picking and horse-clopping percussion. It’s simple beauty lies in the hands of the performer.

- Ross Jones

Conway Twitty - Hello Darlin'

Though rarely acknowledged, 'Hello Darlin'' was not just recorded but also written by Conway Twitty himself.

Spending four weeks atop the Billboard Hot Country Singles chart in 1970 it was also named the No. 1 song of the year by the platform.

This should come as no surprise given the first 23 seconds of the spoken- word opening. It’s Twitty simply using that undeniable come-hither voice to gain maximum attention.

With effortless sex appeal, undeniable sensuality and the swagger of countless heroes of times gone by, ‘Hello Darlin’ demonstrates the magnitude of an era of male country stars that simply doesn’t exist anymore.

A song that was his standard became one of our collective country classics. Yes, it’s that damn good. Hello Darlin,’ indeed.

- Soda Canter

Johnny Paycheck - Take This Job and Shove It

Country music is riddled with workin’ songs, tunes about hard labor and the business of getting your hands dirty. However, when Johnny Paycheck released ‘Take This Job and Shove It’, he turned the workin’ song on its head.

The 1977 anthem, penned by the great David Allan Coe and the title track to Paycheck's album from the same year, would become Johnny's bread and butter, earning the rough-around-the-edges artist his only No. 1 hit and forever cementing his name in the annals of country music.

While ‘Take This Job and Shove It’ would later be recorded and released by its original songwriter, in the end, it didn’t matter who delivered the rowdy opus. The song would become a classic on sentiment alone, the brazen tune a middle finger to dead-end work and an anthem to fed-up laborers everywhere.

- Alli Patton

Bobbie Gentry - Ode to Billie Joe

Amidst all of the theories and quandaries about the legend of Bobbie Gentry, everything begins with this haunting southern gothic.

Noted as one of the first female artists in America to compose and produce her own material, Gentry released 'Ode To Billie Joe' in 1967 to almost immediate acclaim. Spending four weeks at No.1 on the Billboard Hot 100 Chart and peaking at No. 3 on the year-end chart in 1967, it also earned the Grammy Award for Best Female Pop Vocal Performance the following year.

Taking the form of a first-person narrative, 'Ode To Billie Joe' shows a Mississippi family's nonchalant reaction to the news of a local boy's suicide. Interspersed with fragments of usual dinnertime conversation, the song's last verse shows the passage of events over the following year.

While the song has since taken on the form of a puzzle for listeners to solve, including parsing out what the narrator and Billie Joe McAllister threw over the same bridge he committed suicide on, Gentry explained that most listeners had missed the point.

Regardless, the sparse acoustic guitar accompaniment backed by a collection of eerie strings has become a standard in the American country songbook and the mysteries will likely remain for decades to come.

- Lydia Farthing

Charlie Daniels Band - The Devil Went Down to Georgia

Taken from The Charlie Daniel's Band's 1979 album Million Mile Reflections, ‘The Devil Went Down To Georgia’ would quickly cement itself not only as a live-wire country classic but also as a folk-rock jig and a rockabilly opus, all in equal measure.

The production of 'The Devil Went Down To Georgia' was truly ahead of its time. It was spacious, monolithic, and sonically rich, standing out in an era when rock music was known for its stadium-sized album productions and country was still exploring the boundaries of three chords and the truth. This innovative approach to production set the song apart and continues to intrigue listeners to this day.

'The Devil Went Down To Georgia' left it's mark, peaking at No.1 on the Billboard US Hot Country Songs in 1979. It Held this position for a week before spending a total of 14 weeks on the chart, becoming a go-to for any band with a fiddle this side of Alabama. Its chart-topping success is a testament to its enduring popularity and influence.

- Ross Jones

Jim Reeves - He'll Have to Go

Gentleman Jim Reeves indulges in some quite ungentlemanly behaviour on 'He'll Have To Go', as he makes a late-night booty call from a bar to a woman, knowing full well she is with another man on the other end of the line.

"Put your sweet lips a little closer to the phone / Let's pretend that we're together all alone," he croons softly as he offers her an ultimatum. "Should I hang up or will you tell him, he'll have to go?"

The song was written by the husband-and-wife team of Joe and Audrey Allison and was inspired by a phone conversation between the two of them in which they had trouble hearing each other because of background noise and Audrey Allison's naturally soft voice.

Originally released as the B-side to 'In a Mansion Stands My Love', the song became a hit when radio stations started playing the flip side instead, taking it all the way to No.2 on the Billboard Hot 100 in early 1960 and No. 1 on the Hot Country singles chart, where it remained for 14 consecutive weeks. It also reached number 13 on the R&B Singles chart.

- Jof Owen

Kitty Wells - It Wasn't God Who Made Honky Tonk Angels

Response and takedown songs aren’t the preserve of modern day internet spats. Kitty Wells did it back in the 50s, with her controversial riposte to Hank Thompson’s 'The Wild Side of Life', which mused “I didn’t know God made honky tonk angels”.

Written by Jay Miller, 'It Wasn’t God Who Made Honky Tonk Angels' challenges the idea that women are the primary shatterers of hearts, spitting lines such as “from the start every heart that’s ever broken was because there always was a man to blame’.

The song shook conservative commentators, unused to such belligerence from a woman a decade shy of the social and cultural revolution of the 1960s. It was banned by multiple radio stations, as well as the Grand Ole Opry, but defied the odds to become the first female solo song to go to No.1 on the Billboard Hot Country chart in 1952, even breaking into the Top 40 of the Billboard Hot 100.

Wells’ distinctive nasally trill against old time honky tonk melancholy is so casually direct, you can almost see her rolling her eyes as she delivers it to a room of outraged men and quietly fist pumping women. On gumption alone, it deservedly makes our top 50.

- Holly Smith

Linda Martell - Color Him Father

First recorded by rhythm and blues group The Winstons and covered by many to this day, 'Color Him Father' was introduced to Linda Martell by her Record Label Manager Shelby Singleton, for inclusion on her 1970 debut album, Color Me Country.

Straying from the lighthearted Motown production of the original, Martell’s interpretation is traditional country to its core, giving the tender-hearted set of lyrics more nuanced meaning.

A seminal storyteller, Martell is both jubilant at the demonstration of love from this man, but adds an air of mournful regret. It demonstrates the often double-edged journey of finding that long awaited love and support.

A singular cut from a groundbreaking country artist, it’s Martell at her absolute best.

- Soda Canter

Don Williams - Tulsa Time

Let’s be honest. There ain’t no song quite like a Don Williams song.

‘Tulsa Time’, especially, is among the greats, the country-funk classic a must-have on any playlist. When it was released in 1978, 'Tulsa Time' secured an eighth Billboard Hot Country No. 1 for Williams and soon garnered the attention of guitar legend Eric Clapton, who would release a rendition later the same year.

Clapton’s version of the song may have become a crossover success, staking a spot on the Billboard Hot 100, but it is Williams’ ‘Tulsa Time’ that has withstood the tests of time and gone down as a certified country classic.

- Alli Patton

Porter Wagoner - Green Green Grass of Home

What’s more country than singing wistfully about the rural idyll you grew up in, with your childhood sweetheart and loving parents running across the lawn to see you, before you awake to find out you’re not only in prison, but you're about to be executed.

Porter Wagoner’s 1965 classic, which was written by Curly Putman, captures the poetic yet tragic darkness that drives some of the best country songs, with a healthy dose of nostalgia and pastoral imagery thrown in for good measure.

While Wagoner reached No.4 on the Billboard Hot Country Chart with the soon to be classic, it was UK Crooner Tom Jones who covered it just a year after Wagoner’s version arrived, leading to it exploding into a global chart-topper.

- Maxim Mower

Emmylou Harris - Boulder to Birmingham

Across her career, Emmylou Harris has gifted the world with a sprawling collection of beloved tunes, yet none so much as 'Boulder to Birmingham.'

Included on Harris' 1975 record, Pieces of the Sky, the song pays homage to country-rock icon and her own mentor, Gram Parsons.

Harris, who wrote 'Boulder to Birmingham' alongside Bill Danoff, used the song to recount her grief following Parsons' death in 1973, at the age of 26.

Having toured and performed with the soloist, who was also a member of the Byrds and the Flying Burrito Brothers, Harris long felt a deep connection to the late singer, later explaining that 'Boulder to Birmingham' was therapeutic for her in the years following his passing.

“That song was very important,” she told The Guardian in 2018. “Words can be so powerful to help you express something you otherwise can’t. And everyone has experienced loss, so even though the song is deeply personal, I can understand how people can relate to it, having lost someone who is very close to them.”

- Lydia Farthing

Lee Greenwood - God Bless the U.S.A.

Ever since its release as part of Lee Greenwood’s third studio album, You’ve Got a Good Love Comin’ in 1984, ‘God Bless the USA’ has - perhaps unsurprisingly, given its title - become an unofficial second national anthem.

Greenwood has performed his patriotic ballad at a number of inaugurations, most recently at Donald Trump’s ceremony in 2025, while the stirring offering was also used throughout election campaigns for Ronald Reagan and George H.W. Bush.

‘God Bless the USA’ has been re-released on various occasions throughout the singer’s career, with the American battle-cry - which was penned about the Soviet shooting down of Korean Air Lines Flight 007 in 1983 - remaining Greenwood’s biggest hit.

- Maxim Mower

The Highwaymen - Highwayman

If you can believe it, the forming of The Highwaymen was deemed an opportunity for four of the biggest names in country music to cement their legendary status as they rode off into the sunset from the contemporary country landscape. The title track of their debut album did more than that.

Written and first released by Jimmy Webb in 1977, Willie Nelson, Johnny Cash, Waylon Jennings and Kris Kristofferson would release their version in 1985 after Cash was introduced to the song by Glen Campbell. Their version would peak at No.1 on the Billboard US Hot Country Songs, and would earn Webb a Grammy Nomination for Best Country Song. The quartet would eventually become known by the titular phrase, as they left a lasting legacy to be proud of.

The track, album and group would all be written into country music folklore, influencing Brandi Carlile, Maren Morris, Natalie Hemby and Amanda Shires to form their own iteration and tribute to the group, adapting Webb’s lyrics (with his guidance) to release their own version of the lauded song.

- Ross Jones

Dolly Parton and Kenny Rogers - Islands in the Stream

Well, well, well. If it isn't everyone's go-to karaoke song and one of the most iconic duets in music history.

This one really don't feel like it needs any introduction or explanation, but nevertheless, 'Islands in the Steam' was released in 1983 by the country power couple (at least when it came to duets) of Kenny Rogers and Dolly Parton.

Written by the Bee Gees and allegedly intended for Diana Ross, the country music gods gifted the world with this infectious version that went on to top the Billboard Hot 100, be certified 3x Platinum by the RIAA and be stuck in our subconscious for time immemorial.

- Lydia Farthing

Waylon Jennings - I'm a Ramblin' Man

‘I’m a Ramblin' Man’ is quintessential Waylon Jennings and undoubtedly a crucial addition to this list.

The rollicking 1974 opus, originally penned and recorded by singer-songwriter Ray Pennington, not only marked a country No. 1 for Jennings, the song would become a kind of early anthem of the outlaw country movement the legend helped spearhead just years later.

All grit and gusto, Jennings’ ‘I’m a Ramblin' Man’ is a cautionary tale of sorts, the spirited track warning listeners from giving their heart to the rough-and-rowdy titular character. With a song that good, though, we'd give it up freely.

The tune has gone on to be covered by several other self-proclaimed country outliers, like Eric Church, Randy Houser, as well as Whey Jennings, kin to the man himself.

- Alli Patton

Faron Young - Hello Walls

Written by then struggling singer-songwriter Willie Nelson, ‘Hello Walls’ not only gave Faron Young a No.1 record for nine weeks in 1961, but gave Nelson the attention he so rightly deserved.

Legend has it that Nelson offered it to Young for a mere $500, but Young refused to purchase it to honor Nelson’s budding songwriting career. After the song became a hit, Young said that when Nelson got his first royalty check for over $20,000 he became so overjoyed, he kissed him right on the mouth.

‘Hello Walls’ remains one of Young’s finest vocal performances to date. The distant background vocals mixed with his expert croon propel with longing and heartache.

- Soda Canter

Gene Autry - Back in the Saddle Again

The signature song of the Singing Cowboy Gene Autry, 'Back in the Saddle Again' rode along with the singer and actor and his horse Champion throughout his career.

Along with Jimmie Rodgers, Autry was one of country music's early pioneers in the 1930s and '40s. The song - first featured in 1939 in the movie Rovin Tumbleweeds - was used as the theme for his radio show Gene Autry's Melody Ranch, The Gene Autry Show on TV and as the title of his autobiography in 1976, as well as opening the film of the same name.

Originally written by Ray Whitley, another country singer and actor, for his own 1938 movie Border G-Man, the song was reworked by Gene Autry with Whitley a year later.

With its sprightly fiddle and Autry's velvety croon, the tale of a life on the range told succinctly in just over two and a half minutes had the ability to transport viewers and listeners from all over the world back to a reimagined golden age of the America West and the values of the simple cowboy way of life.

- Jof Owen

Kenny Rogers - The Gambler

'The Gambler' writer Don Schlitz, responsible for other mega-hits such as 'When You Say Nothing At All' and 'Forever and Ever, Amen', initially had trouble finding the right artist for his ‘college of life’ song.

After efforts by Bobby Bare, Johnny Cash and Schlitz himself failed to make an impact, King Kenny released the song as the title track of his 1978 album. It was fourth time's the charm - the recording achieved crossover success, a Grammy, and even a franchise of films starring Rogers himself.

The song’s timeless wisdom about knowing when to hold and when to fold, its singalong chorus and pop leaning production set against Rogers’ throaty rasp has kept on winning over new fans decades later.

- Holly Smith

Lynn Anderson - Rose Garden

'Rose Garden' is a country classic that technically wasn't even country to begin with.

Originally recorded in 1967 by Billy Joe Royal and written by singer-songwriter Joe South that same year, the tune experienced a few lives before it became the Lynn Anderson standard that we know and love today.

From Royal, the song went to blues artist Dobie Gray, who like his predecessor, had little success with the song. By 1970, though, Anderson, who had grown quite the following thanks to her time on the Lawrence Welk Show. She had moved to Nashville and was in search of country-pop offerings, eventually finding South's song.

Though originally receiving pushback because it was deemed a "man's song," Anderson's rendition quickly became a crossover hit, reaching No. 1 on the Billboard Hot Country Singles for five weeks and peaking at No. 3 on the Hot 100.

Certified Gold by the RIAA and winning the 1971 Grammy Awards for Best Country Vocal Performance by a Female, 'Rose Garden' has been covered by a plethora of artists from across genres in the years since.

- Lydia Farthing

Johnny Cash and June Carter - Jackson

Despite being recorded by such venerable acts as Flatt and Scruggs, 'Jackson' had been kicking around for four years with limited impact before it landed in the mouths of country music sweethearts Johnny Cash and June Carter for their Carryin' On With... duets album in 1967.

Hitting No.2 on the Billboard Hot Country Chart that same year, 'Jackson' is a a tale of a fiery relationship that soon burns itself into sniping resentment. Johnny Cash’s vocal is reliably bleak but it’s Carter, who can inject poison into a single syllable, that truly captures the bitterness. “Ha!” she exclaims to Cash’s delusions of grandeur, as he imagines people stooping and bowing at his arrival into the titular city.

German-American actress Gaby Rodgers is often incorrectly cited as the co-writer of the song, as her then-husband Jerry Lieber, who co-wrote 'Hound Dog,' 'Stand By Me' and 'Jailhouse Rock,' used her name as the pseudonym. It’s not the only contentious part of the song’s origin, with many disagreeing on whether the Jackson in question is that found in Mississippi or Tennessee.

Listeners don’t seem to care, with the passionate chemistry and conversational cruelty of its two leads set against a frenzied guitar backdrop marking it as an enduring American standard that lands just shy of our top 20.

- Holly Smith

Roger Miller - King of the Road

If a measure of a country song's success is how far it travelled outside of the genre, then Roger Miller's self-penned 1965 crossover smash hit 'King of the Road' is an out-of-the-park home run. As well as reaching No. 1 on the US Country Chart, the song also reached No. 4 on the Billboard Hot 100 and even took the top spot in the UK.

It went on to earn Roger Miller five Grammy Awards at the 1966 8th Annual Grammy Awards Ceremony, while also picking up the award for Best Country & Western Album for his album The Return of Roger Miller.

The inspiration for the song came from Miller seeing a sign on the side of a barn that read, "Trailers for sale or rent" while he was driving past one day. It became the opening line of the song, further embellished to depict a travelling "man of means by no means" who, despite his rootless, nomadic lifestyle, still considers himself to be the "King of the Road."

- Jof Owen

Loretta Lynn - Coal Miner's Daughter

In an era when women were expected to be seen and not heard, Lynn single-handedly repositioned female artists in the country genre by choosing to tell her story from an unfiltered point of view.

‘Coal Miner’s Daughter’ was a game changer of a musical moment. First released as a single in 1970 and then as the title track on an album of the same name, both offerings became undeniable hits from an artist that refused to ever compromise across her trailblazing career.

It would be foolish to simply state that Lynn inspired only legions of female country artists after her. No, Lynn inspired everyone, regardless of their gender to proudly tell their truth at all costs.

Don’t believe me? Put ‘Coal Miner’s Daughter’ on the jukebox at any establishment then sit back and watch. There won’t be an unmoved mouth by the time the chorus hits. 55 years after its debut. Now that’s icon status.

- Soda Canter

Charley Pride - Kiss an Angel Good Mornin'

Written by Ben Peters and recorded and released in 1971 by Charley Pride from his 'Charley Pride Sings Heart Songs' Album, 'Kiss An Angel Good Mornin" holds dear and true for all love songs.

Peters wrote many songs for Pride during his career, with this particular number more centred around parental love than romantic. Peters had just had a baby daughter with his wife Jackie, thus speaking to the love he holds for his family. For Pride, he sings of the reason behind how his love for his partner has lasted, making him as happy as can be for as long as he has been. It's a beautifully simple secret to love and remains as affable as it did upon release over 50 years ago.

Peaking at No.1 on the Billboard US Hot Country Songs (Pride's 8th), it peaked at No.21 on the Hot 100, Pride's only appearance in the top 40 of the chart.

- Ross Jones

Tom T. Hall - That's How I Got To Memphis

“My first line is always something I know to be completely true”, Tom T. Hall once said of his songwriting. “And it is supposed to let the listener in on something”.

Originally released on Tom T. Hall’s Ballad of Forty Dollars album in 1978, this sweetly sad road song has been covered by Bobby Bare, Roseanne Cash, The Avett Brothers, Karl Blau, Charley Crockett and countless others over the years.

Sung from the perspective of someone who travels to Memphis on the off chance that his lover has gone back there after they have a falling out, 'That's How I Got To Memphis' has all of Hall’s trademark straightforwardness, letting the listener imagine a whole storyline with one simple line, “If you love somebody enough you'll follow wherever they go / That’s how I got to Memphis”.

The rest is left for the listener to fill in as they wish. For Hall, out of all the songs of his that were ever sung by someone else, it was Buddy Miller’s version of ‘That’s How I Got To Memphis' that he loved the most; “I’m terribly fond of that and I hate to pick out favourites, but that’s it”.

- Jof Owen

Loretta Lynn and Conway Twitty - Louisiana Woman, Mississippi Man

Conway Twitty and Loretta Lynn. We urge you to try and name a more dynamic duo.

Once upon a time, the pair were the country power couple, having blended their unique vocal gifts and musical know-how to craft some of the genre’s most enduring duets, one of them being ‘Louisiana Woman, Mississippi Man’. The 1973 classic marked their third No. 1 hit together on the country charts and further solidified their appeal as a duo.

The plucky anthem married the best of the two artists’ talents, beautifully showcasing Twitty’s dazzling charm and Lynn’s musical magnetism, as they pledged their unending devotion to one another in song.

Twitty and Lynn would have an undeniable connection during their time together as duet partners; and while they were merely great friends, their work on ‘Louisiana Woman, Mississippi Man’ still makes listeners believe they could have been so much more.

- Alli Patton

Willie Nelson - Blue Eyes Crying in the Rain

It feels strange now to think of a time when Willie Nelson was considered a ‘break-out artist’, but thanks to ‘Blue Eyes Crying in the Rain’, this was the status Nelson achieved when he released the remorseful ballad as part of his now-iconic Red Headed Stranger album in 1975.

While the song has been covered and recorded by a dizzying array of artists, ranging from Hank Williams, Sr. and Charley Pride, to Elvis Presley and Roy Acuff, one name will forever be tied ‘Blue Eyes Crying in the Rain’, and that’s undoubtedly Willie Nelson.

Nelson’s signature weathered vocals bring the weary, despondent lyrics to life, with ’Blue Eyes Crying in the Rain’ earning the Texan his first Grammy for Best Male Country Vocal Performance, and acting as the springboard for a genre-defining career.

- Maxim Mower

Tanya Tucker - Delta Dawn

'Delta Dawn' has been an iconic song for decades now.

Even if it's most recent moment in the limelight occurred thanks to Luke Combs passionately belting along to it in the crowd during the 2023 CMA Awards and providing ample memes, it's been a go to since Tanya Tucker released her rendition in 1972.

Written by Larry Collins and Alex Harvey, the first notable version of the tune was recorded by Bette Midler in 1971 as part of her debut record, The Divine Miss M. Just a year later, though, Tucker would take 'Delta Dawn' into the Top 10 on the country charts.

Almost identical in melody to 'Amazing Grace,' 'Delta Dawn' has been covered by a swath of artists over the last 50 years, including Waylon Jennings, Loretta Lynn, Kitty Wells, Dottie West and many more.

- LF

Townes Van Zandt - Pancho and Lefty

There are few classic country songs as iconic as Townes Van Zandt’s ‘Pancho and Lefty’. The ballad, a medley of muffled rhythms trotting along to gentle strings, unfurls an epic tale of desperados and Federales, friendship and betrayal.

While Van Zandt’s 1972 ballad flew relatively under the radar for much of its early existence, the song was met with great acclaim when it was retooled and re-released by Willie Nelson and Merle Haggard in 1983. Their version would go on to top the Billboard country charts and make ‘Pancho and Lefty’ household names in the genre.

The original has since gone down in history as one of the greatest country tunes of all time, the song now inseparable from its creator.

- Alli Patton

Kris Kristofferson - Sunday Mornin' Comin' Down

Although ‘Sunday Mornin’ Comin’ Down’ was a No. 1 smash for Johnny Cash, Kris Kristofferson’s rugged, pared-down rendition remains the most revered version of the introspective ode.

Released in 1970 as part of his debut album Kristofferson, 'Sunday Morning Coming Down' is driven by Kristofferson’s trademark low-key, understated delivery, which accentuates the raw feel of the track.

The song has also been cut by country staples such as Waytlon Jennings, Gretchen Wilson, Ray Stevens and numerous others, with this forlorn musing blossoming into the paradigm for Kristofferson’s drawn-in, reflective songwriting style.

When considering its legacy, it feels somewhat apt to know that, in Kristofferson’s words, this was “the song that allowed me to quit working for a living”.

- Maxim Mower

Johnny Cash - I Walk the Line

We're going to find it hard to get more classic than this. Written and recorded by The Man In Black for Sun Records in 1956, the record was famously produced by label head and Elvis Presley’s producer, Sam Phillips.

Peaking at No.1 on the Billboard US Hot Country Songs for six weeks, it would become Cash’s first top hit, eventually also reaching No.17 on the Billboard Hot 100.

Written about Cash’ first wife Vivan Liberto, it details how Cash wanted to be faithful and resist temptation. Cash would eventually divorce Liberto and marry June Carter. The song possesses all that scratchy simplicity of the era, all single-note bass bobbing and wash-board percussion, with Cash’s deep hum echoing through your eardrums well after the song's end.

It’s no surprise that the song’s name would become the title for the 2005 biopic on Cash’ life, starring Joaquin Phoenix and Reece Witherspoon as Cash and his beloved June.

The Carter Family - Can the Circle Be Unbroken

Alvin Pleasant “A.P.” Carter, founding member of the Carter Family, reimagined Ada R. Harbershon and Charles H. Gabriel’s hymn ‘Will the Circle be Unbroken?’ to produce one of the most enduring country classics of all time.

Released as a single in 1935, the song languishes in the universal concerns of the finality of life, all while mourning the death of the narrator’s mother. Rich with crisp, mountain-gospel harmonies, it’s an immediate invitation to not just reflect on our own mortality but to join in and sing along in unity. This is the magic of the Carter Family; their ability to combine as one to share their art ensured it was never exclusionary.

Inducted into the Grammy Hall of Fame in 1998, it is unfathomable to assess the extensive impact the Carter Family and 'Will the Circle Be Unbroken' have had on the evolution of country music.

- Soda Canter

Waylon Jennings & Willie Nelson - Mammas Don't Let Your Babies Grow Up To Be Cowboys

After collaborating on the million selling-compilation Wanted! The Outlaws in 1976 and winning a Country Music Association Award for Duo of the Year, it was perhaps inevitable that Willie Nelson and Waylon Jennings would record a full duets album.

Released in 1978, the resulting album, Waylon & Willie, opened with the Ed Bruce-penned 'Mammas Don't Let Your Babies Grow Up to Be Cowboys.'

A warning to mothers about the dangers of letting their children adopt a cowboy lifestyle, it was originally written by Bruce for his then-wife Patsy, while Chris Ledoux had already recorded the song for his Songbook of the American West album in 1976. At the same time, Waylon cut a version on his own but felt it was lacking something, so had yet to release it.

Wil§ie Nelson's vocal turned out to be the missing magical ingredient and the pair took it to No. 1 in March 1978, spending four weeks on top of the Billboard Hot Country Songs charts and winning the 1979 Grammy Award for Best Country Performance by a Duo of Group with Vocal.

- Alli Patton

Dolly Parton - Jolene

Not only one of the greatest songs of all time, 'Jolene' may also hold the distinction of being the only song to have received Grammy nods in four different years. 

The tune’s anxiety inducing-narration of a woman desperate not to lose her man to a red-headed beauty was inspired by a real situation when a bank worker flirted with Parton’s husband.

The brazen act became a song that was nominated at the Grammys in 1975 and 1976 for its studio and live versions respectively, and finally achieved success in 2017 when Pentatonix and Dolly’s joint rendition of the song won Best Country Duo/Group Performance.

With Beyoncé reimagining the song for her Grammy-nominated album Cowboy Carter, the tendrils of awards success continue to keep it in their grip 52 years later. It’s even inspired response songs, with ripostes from the likes of Chapel Hart, Cam, Jennifer Nettles and Kirsty MacColl.

Featured on Dolly’s powerhouse album of the same name, which also contained classics like 'I Will Always Love You' (which she may have written on the exact same day!), the song’s ominously dusky, desert-tinged rolling guitar and racing heartbeat imitating backbeat gave Parton her second No.1 and a track that deservedly ranks in the top ten of our list.

- Holly Smith

John Denver - Take Me Home, Country Roads

It’s hard now to separate Denver from his synonymous tune, but ‘Take Me Home, Country Roads’ was first intended to be sold to Johnny Cash.

This was until Denver discovered it at an impromptu jam session in late 1970 with writers Bill Danoff and Taffy Divert. His begging and support in writing the bridge persuaded the writers to alter their intended course. The rest is music history.

The tender ballad was a major hit and sold millions of copies due to the visceral imagery brought to life by Denver’s emotional vocal performance. While a deep ode to the glory of West Virginia, the song became an anthem for all who simply long for home, no matter where that might be.

Its eventual selection in 2023 for addition to the Library of Congress for preservation in the National Recording Registry in the United States is a beyond fitting celebration of such a revered piece of treasure.

- Soda Canter

Merle Haggard - Mama Tried

Did Merle Haggard really turn 21 in prison, doing life without parole, as he proclaims in this 1968 classic?

Sort of.

He did turn 21 in prison, whilst serving a much shorter sentence for burglary, but, in demonstrable defence of the power of artistic licence, he once told a journalist, “I couldn’t get that to rhyme”.

The track, which featured on the soundtrack of the western classic Three Killers, was inspired by Haggard’s increasingly troubled childhood and adolescence, after his mother struggled to keep him on the straight and narrow following his father’s premature death.

The song spent four weeks at No.1 and, in its commercial success, turned a sad but familiar tale into a country music origin story.

Its mournful dobro steel and pacy fingerpicked guitar are the perfect scene setters for the lonesome whistles and freight trains it describes, with Haggard’s vocal mysteriously straddling the line between regret and boasting, while resigned in its acknowledgements of his mother’s best but ultimately failed efforts.

Its role in launching Haggard’s career combined with its cultural impact, cemented by its place in both the Grammy Hall of Fame and the National Recording Registry, lands it at number six in our ranking.

- Holly Smith

Hank Williams - Hey Good Lookin'

Written and recorded by Hank Williams and produced by Fred Rose, ‘Hey Good Lookin’’ would not only become a singular emblem of Hank Williams’ influence and legacy in country music, but a notable reference of the genre on the whole.

Peaking at No.1 on the Billboard Hot Country Songs Chart in 1951, Williams famously wrote the song in 20 minutes, initially for Jimmie Dickens. This was all before recording it himself, telling Dickens it was too good a song for him.

Jo Stafford & Frankie Laine, The Mavericks and the late Jimmy Buffet would all go on to cover the song with chart success, but none could match the note-for-note joy of the original.

- Ross Jones

Tammy Wynette - Stand By Your Man

Released in September 1968 at the height of the women's liberation movement, 'Stand By Your Man' might have sat uncomfortably alongside the politics of the time with its reactionary and politically conservative tone, but Tammy's towering, lip quivering vocal has always held enough pathos and contradiction within it to complicate what on paper might be a submissive call to side with the patriarchy.

Written in just 15 minutes, Wynette always insisted she was just trying to write a “pretty love song,” and wasn't conscious of its political weight. Nevertheless, she became a unwitting spokeswoman for white working-class housewives experiencing marital disappointments and changing gender roles in the late 1960s.

The Chicks recorded a version of 'Stand By Your Man' and include it as the B-side to 'Goodbye Earl' when it was released as a single in 2000, which maybe speaks more to the multitudes of readings contained within the song.

- Jof Owen

Glen Campbell - Wichita Lineman

Penned by prolific songsmith Jimmy Webb, ‘Wichita Lineman’ not only consolidated Glen Campbell’s status as one of the great country crossover stars in the genre's history, but also helped pave the way for the subsequent wave of songs romanticising blue collar vocations.

The undulating, meandering instrumental combines with Campbell's mournful vocals to accentuate the jaded spirit of the narrator, with the orchestral backing giving ‘Wichita Lineman’ a truly cinematic feel. As he demonstrates so unforgettably on ‘Rhinestone Cowboy’, one of Glen Campbell's greatest qualities was his ability to bring a fictional character to life through his enchanting delivery and the sincerity of his storytelling.

Upon its arrival in 1968, ‘Wichita Lineman’ spent two weeks at No.1 on the Billboard Hot Country Songs chart, as well as securing a six week stint at the peak of the Adult Contemporary ranking.

George Strait’s ‘I Can Still Make Cheyenne’ and countless others have drawn from the spirit that drives ‘Wichita Lineman’, with Bob Dylan famously donning it “the greatest song ever written”.

- Maxim Mower

Patsy Cline - Crazy

Nearly 65 years since its release, 'Crazy' is still one of the most iconic country classics in the world, and frankly, what's not to love about it?

Written by Willie Nelson– who in one week wrote 'Crazy,' 'Night Life' and 'Funny How Time Slips Away' – the song was originally titled 'Stupid,' and try as Nelson might, no one in Nashville or elsewhere would record the song due to its use of so many chords.

'Crazy' may not have been "three chords and the truth," but once Cline took the chance on it, it became her signature hit, reaching No. 2 on the Billboard Hot Country Singles chart and becoming a Top 10 single on the Hot 100.

While Nelson eventually recorded his own version of 'Crazy,' which has its own distinctive charms, it will always be Cline's that reigns supreme, becoming one of the most played songs in jukeboxes across the US and being inducted into the Grammy Hall of Fame in 1992.

- Lydia Farthing

George Jones - He Stopped Loving Her Today

“He said, ‘I’ll love you till I die’ / She told him, ‘You'll forget in time’...”

George Jones’ ‘He Stopped Loving Her Today’ is undoubtedly one of the greatest country songs ever, full stop.

The 1980 ballad, written by Bobby Braddock and Curly Putman and released on Jones' I Am What I Am album, is everything a country song should be. The deeply emotive, slice-of-life song has always had a finger on the pulse of what it means to be human, to hurt and to love unconditionally in spite of the pain, all made classic by Jones’ sturdy artistry.

‘He Stopped Loving Her Today’ has been covered time and again, but no version has come close to touching the original.

- Alli Patton