Keep Your Soul Clean and Your Boots Dirty – the Best Country Songs Ever Written

Originating back in the 1920s and descending from old American folk music, the country genre is distinctly American and hugely popular across the states, as well as internationally. It has also spawned all kinds of subgenres like Bro-Country and Nashville Sound. Typically consisting of ballads and folk-style harmonies with lyrics that tell a story or delve deep into the feelings of the songwriter, country songs are typically moving, emotional, and sometimes quite jaunty too, encouraging listeners to get on their feet and hit the dance floor. Here are 50 of the finest country music songs ever written!

50. Guitar Town by Steve Earle

Released in 1986, Earle’s Guitar Town was written in the wake of a tough divorce from his third wife. He was consuming a lot of alcohol, among other substances, at the time and belts out this classic anthem with the fire and fury of a much older man.

Steve Earle performing at the Cambridge Folk Festival UK July 27, 2007

Photo by Frank Bach / Shutterstock.com

Earle was only 31 years old at the time but had already lived enough for several lifetimes. In the years following the release of Guitar Town, he released a few more great songs but slipped further into his heroin addiction too.

49. The Christian Life by The Louvin Brothers

The Christian Life was released in 1959 and stood out as one of the best tracks on The Louvin Brothers’ second gospel album, Satan Is Real. The brothers took inspiration from other sibling singers in their harmonious performance.

The Louvin Brothers

Source: Courtesy of Capital Records

A deep, resonating song fueled with all the spirit and sadness of the Depression era, this song was later covered by The Byrds for their 1968 release, Sweetheart of the Rodeo.

48. Blue Eyes Crying in the Rain by Willie Nelson

1975 classic and a staple of any good country music playlist, Blue Eyes Crying in the Rain by Willie Nelson was originally written way back in the 40s by Fred Rose.

Willie Nelson performs at LOCKN' Festival.

Photo by Sterling Munksgard / Shutterstock.com

Plenty of singers, including the great Hank Williams, tried to sing it over the years, but nobody made it their own quite like Nelson. It was his first country number one song too.

47. Ode to Billie Joe by Bobbie Gentry

Shared with the world in 1967, Ode to Billie Joe offered an interesting crossover between pop and country. The song tells the tale of the narrator and her family, all talking about the suicide of a local boy named Billie Joe McAllister.

Bobbie Gentry at the BBC, 1968

Source: udiscovermusic.com

Gentry later called the song “a study in unconscious cruelty” as it shows the way the family simply fails to acknowledge the emotional effects of suicide, preferring to gossip instead. The original song was seven minutes long and had to be edited down to be more radio-friendly.

46. Wabash Cannonball by Roy Acuff

The 1930s hit for Roy Acuff, Wabash Cannonball is a very old American folk song that talks of the beauty and charm of the Wabash Cannonball Express. This song dates back to the 19th century and has been sung by many artists over the years.

Roy Acuff

Source: GAB Archive/Redferns

Acuff’s version was particularly popular, selling over 10 million copies worldwide and becoming a major success. Acuff’s rendition really helped the country genre start to evolve too.

45. Long Black Veil by Lefty Frizzell

Long Black Veil was released in 1959. It tells the story of a man who was wrongly accused of murder and got executed. He decided not to share the truth that could have saved his life since his alibi was that he’d been sleeping with his best friend’s wife at the time.

Lefty Frizzell

Source: Bear Family Records

This indiscretion leads Frizell’s protagonist to his doom. The song is grim and melancholy, yet innately moving and has since been covered by legends like Johnny Cash and Bruce Springsteen.

44. The Grand Tour by George Jones

Originally released in May of 1974, The Grand Tour was Jones’ sixth number one hit on the Hot County Singles chart and was one of the biggest and most popular songs of the year. It’s also regarded as one of the saddest country music songs ever written.

George Jones

Source: latimes.com

Jones’ performance and gravitas help to convey the emotions of the song perfectly, as he discusses the protagonist’s lonely, loveless existence.

43. Act Naturally by Buck Owens and the Buckaroos

Originally recorded by Buck Owens and the Buckaroos and later re-recorded by Johnny Russell and Voni Morrison, Act Naturally is a chart-topping country song that has been consistently ranked as one of the genre’s best hits. Even The Beatles did a cover version.

Dwight Yoakam; Buck Owens at a ceremony where Dwight Yoakam receives a star in Los Angeles, California

Photo by Joe Seer / Shutterstock.com

Act Naturally talks about a character who was jilted and can use those emotions to play the role of a sad and lonely individual in a movie, despite having no acting training or experience.

42. Coal Miner’s Daughter by Loretta Lynn

Released in 1970, Coal Miner’s Daughter is a bit of an autobiographical song from Loretta Lynn. This marked a turning point in her career, as it felt and sounded a lot different from work she’d previously done.

Loretta Lynn and Sissy Spacek at the 44th Annual CMA Awards, Bridgestone Arena, Nashville, TN

Photo by s_bukley / Shutterstock.com

The song was originally six minutes long and had no less than eight verses, but was severely edited down, with a lot of unnecessary details crossed out of the lyrics.

41. Pancho and Lefty by Townes Van Zandt

Arguably the best and most famous song Van Zandt ever recorded, this song has since been covered by the likes of Merle Haggard and Willy Nelson and has repeatedly been ranked by leading experts as one of the best country songs ever.

Townes Van Zandt

Source: YouTube

The song charts the adventures of a bandit named Pancho and his sidekick, Lefty. The lyrics suggest that Lefty has betrayed Pancho, leading to the latter’s death.

40. $1000 Wedding by Gram Parsons

Released in 1974, $1000 Wedding is a mysterious song with a whole myriad of interpretations. Many country music fans and aficionados have spent years trying to analyze and evaluate its true meaning.

Gram Parsons

Source: rollingstone.com

The story follows a groom at a cheap wedding where he gets jilted. We never know what exactly happened to the bride or why she didn’t show up, but the groom and his friends decide to go on a crazy drinking spree, culminating in the closing line “It’s been a bad, bad day.”

39. Follow Your Arrow by Kacey Musgraves

One of the latest and greatest additions to the country music genre, Follow Your Arrow by Kacey Musgraves, was gifted to the world in 2013 and featured on Musgraves’ album, Same Trailer Different Park.

Kacey Musgraves performs in concert on NBC's 'TODAY' show on July 19, 2019, at Rockefeller Plaza in New York City.

Photo by Debby Wong / Shutterstock.com

The song earned the award for Song of the Year at the 2014 CMA Awards, and it features inspiring lyrics, encouraging the listener to be themselves and stay true to what they believe in.

38. I Want to Be a Cowboy’s Sweetheart by Patsy Montana

An iconic Western track that was first recorded in 1935 by Patsy Montana, also known as Ruby Blevins, I Want to Be a Cowboy’s Sweetheart, was the first female-led country song to sell over a million copies in total.

Patsy Montana

Source: historyforsale.com

It was written by Montana one day when she was missing her partner and feeling blue. She was working with the Prairie Ramblers at the time, and the song’s melody is based on another old country song called Texas Plains.

37. Golden Ring by George Jones and Tammy Wynette

Originally released in 1976 as part of George Jones and Tammy Wynette’s album of the same year, Golden Ring made it to number one on the country chart and has gone on to be covered by the likes of Jason Sellers and Pam Tillis.

George Jones and Tammy Wynette

Source: classiccountrymusic.com

This unique duet tells the story of a young, loving couple from Chicago who go to buy a ring from a local pawn shop for their wedding. Sadly, the subsequent verses show how the marriage breaks down, and the ring ends up back in the pawnshop.

36. Lost Highway by Hank Williams

One of Hank Williams’ most defining and emblematic songs, Lost Highway, was actually written and recorded by Leon Payne back in 1948. Interestingly, for Payne, the song wasn’t metaphorical. He really did get lost on a highway from California to Texas.

Hank Williams

Source: Michael Ochs Archives

The very title of the song has been used for several books and even a TV series, and the song itself has been covered by everyone from Bob Dylan and Leon Russell to U2 and Coldplay.

35. Bye Bye Love by The Everly Brothers

Written by Felice and Boudleaux Bryant and recorded by The Everly Brothers in 1957, Bye Bye Love is a popular country hit that made it to number two on the Billboard pop charts and number one as a country release.

The Everly Brothers

Source: YouTube

The song has proven particularly popular with members of The Beatles. George Harrison did a successful cover of Bye Bye Love for his 1974 album, Dark Horse, and Paul McCartney says it’s the first song he ever performed live.

34. Wildwood Flower by The Carter Family

A very old folk song with a history dating back to 1860, when it was first published under the name ‘I’ll Twine Mid The Ringlets’ by Joseph Philbrick Webster. Decades later, it was recorded and released by The Carter Family.

The Carter Family

Source: YouTube

The original poem lyrics were changed slightly by the group, and various versions of Wildwood Flower have existed over the years, adding new layers and meanings to a classic folk ditty.

33. A Satisfied Mind by Porter Wagoner

Porter Wagoner wrote A Satisfied Mind alongside Red Hayes. Hayes was once asked to name the “richest man in the world” by his father-in-law. He gave a few possible answers, but his father-in-law simply responded that the world’s true richest man was the one with a satisfied mind.

Porter Wagoner

Source: countrymusichalloffame.org

Thus, the name for this classic country staple was born. Recorded at a radio station in Missouri in the 50s, this song became a number one country hit for Wagoner.

32. Sitting on Top of the World by Mississippi Sheiks

A timeless classic dating all the way back to 1930, Sitting on Top of the World is more of a blues song than a traditional country number, but it does have country elements with its fiddle notes and moving lyrics.

Mississippi Sheiks

Source: last.fm

Sitting on Top of the World has been covered by countless artists over the years, including several rock groups like the Grateful Dead and Cream.

31. Your Cheatin’ Heart by Hank Williams

Another entry from Hank Williams, Your Cheatin’ Heart, was quite possibly written by Williams to get back at his first wife. At least, that’s what Williams’ second wife says, claiming that the song was intended to show off how much happier Williams was.

Hank Williams

Source: wsj.com

In truth, love was everywhere for Williams at the time. He had a pregnant girlfriend, a teenage wife, and an ex-wife with whom he had a son. Unsurprisingly, the song touches on themes of cheating and guilt.

30. Hello Walls by Faron Young

Released in 1961, Hello Walls was written by Willie Nelson. The story goes that Nelson and Lefty Frizzell teamed up for a jam, but it was only after Frizzell left the room that Nelson felt inspiration.

Faron Young

Source: countrymusichalloffame.org

He wrote his first big hit right there and then, and his friend, Faron Young, had the perfect voice to bring it to life. It went straight to number one on the country chart and did well on the pop chart too.

29. Blue Yodel No. 1 (T For Texas) by Jimmie Rodgers

This song dates all the way back to 1928, and it was a monumental moment for the history of country music. It’s fair to say that country wouldn’t be quite the same without this song, in fact.

Jimmie Rodgers

Source: YouTube

Blue Yodel No. 1 (T For Texas) created the genre’s first big star. Jimmie Rodgers’ distinctive yodel and powerful yet casual and endearing singing style gave him legions of fans and helped him earn a place among the pantheon of country legends.

28. I Saw The Light by Hank Williams

I Saw The Light was recorded in 1948 and represented an interesting shift of pace and tone for Williams. He wasn’t exactly well known for gospel-type songs about religion and salvation.

Hank Williams

Source: tennessean.com

I Saw The Light was, therefore, quite a special song for the star, but it was a very popular one too. He used to play it at the end of each show, and Hawkshaw Hawkins famously covered the song after learning that Williams had passed away.

27. Ring of Fire by Johnny Cash

Ask anyone to name a Johnny Cash song, and there’s a good chance that Ring of Fire will be one of the first tracks they mention. Released in 1963 and synonymous with Cash, this song is an undisputed classic.

Johnny Cash

Source: stripes.com

It was written by Merle Kilgore and June Carter, initially recorded under the title ‘(Love’s) Ring of Fire’ by Anita Carter but wasn’t a big hit. Cash completely transformed the song, turning it into so much more and still being covered to this day.

26. Goodbye Earl by Dixie Chicks

The Dixie Chicks gave us this country classic in 1999. The song was pretty controversial at the time of release. It touched on some deep themes, including domestic abuse and a desire for vengeance.

Country group DIXIE CHICKS at the 41st Annual Grammy Awards in Los Angeles.

Photo by Featureflash Photo Agency / Shutterstock.com

Dennis Linde, the writer of the song, argued that it had always felt more like a “black comedy” in his mind. Either way, the song does at least have a happy ending.

25. Take This Job and Shove It by Johnny Paycheck

Released in 1977 and bearing a message that many disgruntled employees can still share to this day, Take This Job and Shove It is a classic embodiment of the frustrations of long term employment in a job that just doesn’t pay.

Johnny Paycheck

Source: YouTube

The song was written by David Allen Coe, but it just wouldn’t have been the same without Paycheck’s voice and performance style. It’s a great song to listen to after a bad day at work.

24. Mean by Taylor Swift

She might be better known for her chart-topping pop numbers nowadays, but Swift started off in country and still knows how to write a great country song. 2010’s Mean is the perfect example of her talents.

Taylor Swift performs and turns on the Christmas Lights at Westfield Shepherd's Bush, London.

Photo by Featureflash Photo Agency / Shutterstock.com

This classic Swift song made it to number two on the country charts and number 11 on the Hot 100. It’s a powerful message against the bullies, haters, and critics of the world.

23. If You’ve Got the Money, I’ve Got the Time by Lefty

Recorded in 1950 by the legendary Lefty Frizzell, this song is beautifully animated by the singer’s classic country drawl and easy-listening voice. Frizzell naturally came up with the song’s title after being invited out by a friend.

Lefty Frizzell

Source: amoeba.com

It was his first single and went on to be covered by many other country music legends like Merle Haggard and Willie Nelson. It also set the standard for how a country singer should sound.

22. Walking the Floor Over You by Ernest Tubb

Released in 1941, Walking the Floor Over You came at an interesting time for Tubb, as he lost his tonsils in 1939 and saw a sharp decline in his singing ability. Even with his voice losing its power, he bravely continued to pursue his dreams.

Ernest Tubb

Source: Wikipedia

Smartly, he started speeding up the tempo of his songs to reduce the pressure on his vocals, and this was one of the first country music songs to incorporate the electric guitar.

21. Can the Circle Be Unbroken by The Carter Family

Can the Circle Be Unbroken started off life as a hymn called ‘Will The Circle Be Unbroken?’ A.P. Carter worked his magic on the hymn, transforming it into a classic country song.

From left: Sara, Maybelle, and A.P. Carter.

From left: Sara, Maybelle, and A.P. Carter. Source: blueridgecountry.com

The song’s lyrics cover some grim topics, including deaths and funerals, but it was a big hit. It has since been covered by a huge list of singers and groups, including Moby, Johnny Cash, The Staple Singers, and Jerry Lee Lewis.

20. The Gambler by Kenny Rogers

One of the most famous country songs with a story, The Gambler, is also arguably Kenny Rogers’ greatest creation. Don Schlitz wrote a lot of it in 1976, but it was Rogers who penned the conclusive verse.

Washington, DC. The USA, 21nd March 1992 Kenny Rogers performs live during the 50th-anniversary show from the studios' of Voice of America.

Photo by Mark Reinstein / Shutterstock.com

Producer Larry Butler considered both Rogers and Johnny Cash as singers for the song, deciding that Rogers was the man to bring it to life. It went straight to number one and even led to a movie in which Rogers played the Gambler.

19. Don’t Come Home A’ Drinkin’ (With Lovin’ on Your Mind) by Loretta Lynn

Released in 1966 and still relevant and beloved to this day, Don’t Come Home A’ Drinkin’ (With Lovin’ on Your Mind) was Loretta Lynn’s first number one hit.

Loretta Lynn

Source: guideposts.org

She wrote it alongside her sister, Peggy Sue, and touched on themes of marital dissatisfaction. Jay Lee Webb recorded a response named ‘I Come Home A Drinkin’ (To a Worn-Out Wife Like You)’ one year later.

18. All My Ex’s Live in Texas by George Strait

Gifted to the world by George Strait in 1987, this song defines the star’s career and pure country roots. A handsome, home-grown Texan man who always sticks to his roots, Strait embodies the spirit of Country, and this song is one of his best.

George Strait

Source: EMG/REX/Shutterstock

It was also one of the few times where Strait dared to veer away from classic country into a more pop-based tune, and this gamble clearly paid off.

17. New San Antonio Rose by Bob Wills & His Texas Playboys

Recorded in 1940, New San Antonio Rose would become the signature song of Bob Wills & His Texas Playboys. This song was made even more successful by Bing Crosby, earning him a gold disc.

Bob Wills & His Texas Playboys

Source: bear-family.com

A purely instrumental number to begin with and simply known as ‘San Antonio Rose,’ the ‘New’ version of the track added vocals that talk about the titular ‘Rose’ being the narrator’s lost, love.

16. Wichita Lineman by Glen Campbell

Wichita Lineman was written by Jimmy Webb in 1968 and recorded by Glen Campbell, with backing from various members of The Wrecking Crew. The song has since been covered by a host of other leading artists.

Glen Campbell

Photo by Owen Sweeney/Rex/Shutterstock

Classed by some as the best country song ever made and one of the deepest songs in terms of its lyrics and melody, Wichita Lineman made it to number three on the pop chart and got to number one on both the country chart and the adult contemporary chart.

15. It Wasn’t God Who Made Honky Tonk Angels by Kitty Wells

It Wasn’t God Who Made Honky Tonk Angels was written in response to Hank Thompson’s 1952 song, ‘The Wild Side of Life.’ That song was critical of the singer’s former fiancée.

Kitty Wells

photo by c/o Grand Ole Opry

In response Wells, launched this powerful track, chastising unfaithful men who judge women despite their own unjust actions and fail to take responsibility when they’re left all alone. It was the first number one hit for a female solo country singer and inspired by many other female artists too.

14. Settin’ the Woods on Fire by Hank Williams

Released in 1952, Settin’ the Woods on Fire was one of Williams’ more upbeat and bouncy numbers. It also contains some rather silly lyrics but is fun to listen to and endlessly repeatable.

Hank Williams

Photo by Underwood Archives/REX/Shutterst

Some say this song helped inspire the modern subgenre of Bro-Country, which tends to focus on songs talking about the simple pleasures of life like parties and good friends. The likes of Florida Georgia Line owe a lot to Hank Williams.

13. Blue Moon of Kentucky by Bill Monroe and The Blue Grass Boys

Produced in 1947, Blue Moon of Kentucky was a unique blend of blues, gospel, and swing, all coming together to form a delightful country classic, which features everything from bagpipes to Methodist choirs.

Bill Monroe and The Blue Grass Boys

Source: YouTube

A signature track for Bill Monroe, Blue Moon of Kentucky, was, in the singer’s view, a song that “touches your heart.” He called it “good, clean music,” too, but Elvis Presley’s cover a few years later helped kickstart the rock and roll craze.

12. I’ve Got a Tiger By the Tail by Buck Owens and the Buckaroos

An amusing tune, I’ve Got a Tiger By the Tail, was released in 1964. The title of this track came when Owens and Harlan Howard were driving around and saw an Esso gas station, with the slogan “Put A Tiger In Your Tank.”

Buck Owens

Source: elrancho–1.blogspot.com

Owens decided to switch the words around a little, and the pair started noting some lyrics down, later coming up with the melody on their drive home. It went straight to number one and endures as a prime example of the Bakersfield sound.

11. Man of Constant Sorrow by The Stanley Brothers

A traditional folk tune that was first published by a blind fiddler in 1913, Man of Constant Sorrow, was brought to life in a big way by The Stanley Brothers.

The Stanley Brothers

Source: classiccountrymusic.com

Bob Dylan also recorded a great version of this song, and it came back into the spotlight at the turn of the millennium after playing a key role in the story of the Coen Brothers’ movie, O Brother, Where Art Thou?

10. Mammas, Don’t Let Your Babies Grow Up to Be Cowboys by Waylon Jennings and Willie Nelson

Released in 1978, Mammas, Don’t Let Your Babies Grow Up to Be Cowboys saw Willie Nelson and Waylon Jennings, two legends in their own right, team up together.

Waylon Jennings and Willie Nelson

Source: YouTube

The dream duo came up with a stellar version of Ed Bruce’s original song, taking all the way to the top of the charts. The song, as its title implies, encourages mothers to keep their children safe from cowboy culture and lifestyles.

9. Jolene by Dolly Parton

Perhaps Parton’s most famous track, Jolene, was released in 1973. She wrote it after seeing her husband flirting with a bank teller, and it went on to become one of the most powerful and emotional cheating songs in the country songbook.

Dolly Parton performs in Pittsburgh Tuesday, June 28, at Consol Energy Center. Parton is currently on her first major U.S. and Canadian tour in 25 years.

Photo By Jack Fordyce / Shutterstock.com

A simple song in many ways with a pure and unfiltered message, Jolene puts Parton in a vulnerable role, with the power of her incredible voice seeing the story through to its end.

8. Mama Tried by Merle Haggard

Released in 1968, Mama Tried has gone down in history as one of the best ever prison-related country songs. Haggard himself spent time behind bars, and he understood exactly what it was like to be a prisoner.

Merle Haggard

Source: rollingstone.com

The song was originally a simple commission for a B-movie, but it ended up being one of Haggard’s most enduring and popular creations, a frank and sincere apology wrapped up in layers of stubbornness.

7. You Don’t Know Me by Ray Charles

You Don’t Know Me was written by Cindy Walker, based on a story by Eddy Arnold. It was first released by Arnold in 1956, but Ray Charles’ version in 1962 was extra special.

Ray Charles

Source: ebony.com

The song made it to number two on the Hot 100 and number one in the adult contemporary charts. Charles brings a deeper level of regret and emotion to the words, tugging the heartstrings of legions of listeners.

6. Stand By Your Man by Tammy Wynette

Shared with the world in 1968, Tammy Wynette hardly seemed like the perfect fit for the title of this song. She’d gotten divorced four times, but her vocals and performance really bring Stand By Your Man to life.

Tammy Wynette

Source: tammywynette.com

It went on to become Wynette’s signature song but wasn’t without controversy as some saw it as an anti-feminist song, leading Wynette to say she had to spend 20 years defending it after just 20 minutes writing it.

5. Standing on the Corner (Blue Yodel #9) by Jimmie Rodgers

Produced in 1930, Standing on the Corner (Blue Yodel #9) was instrumental in helping the early formations of the country genre begin to take shape and once again showed how Jimmie Rodgers played such a big part in the way the genre was created.

Jimmie Rodgers

Source: YouTube

A former railroad worker, Rodgers was a star by the time this track was created and decided to team up with jazz man Louis Armstrong for Standing on the Corner (Blue Yodel #9).

4. He Stopped Loving Her Today by George Jones

George Jones had little faith in He Stopped Loving Her Today. In fact, after recording the song, he was said to proclaim that nobody would buy it, calling it too morbid for audiences. Well, he was terribly wrong.

George Jones

Source: billboard.com

It was his first number one hit for years, but it didn’t come without a price. He spent 18 months working on the track, and he never really liked it, but audiences did.

3. I’m So Lonesome I Could Cry by Hank Williams

There are several versions of I’m So Lonesome I Could Cry out there. The likes of Bob Dylan, Johnny Cash, and Sandra Bernhard have all performed it admirably over the years.

Statue of Hank Williams, the famous country singer, in its new location on Commerce Street.

Montgomery, Alabama, USA. Statue of Hank Williams on Commerce Street. Photo by JNix / Shutterstock.com

However, even with all those great covers, the original by Hank Williams is still arguably the best of all. Crossing over the boundary between country and pop, this emotional, moving song charts Williams failing marriage and was recorded less than four years before he was found dead.

2. Crazy by Patsy Cline

An essential piece of country music in every possible way, Crazy was originally written for Billy Walker but found its way to Patsy Kline instead via her husband, Charlie Dick. Dick was working with Willie Nelson and knew the song was just right for his wife.

Patsy Cline

Source: sundaypost.com

She didn’t like it all that much at first but delivered a heart-stopping, jaw-dropping vocal performance. It went on to be used as Ross Perot’s presidential campaign anthem in 1992.

1. I Walk the Line by Johnny Cash

Without a doubt, one of the greatest country music songs of all time and perhaps the most iconic track the genre has ever provided, I Walk the Line is pure, unfiltered Johnny Cash at his very best.

Johnny Cash

Photo By Thomas Busler/The Commercial Appeal

A transcendent number with romantic lyrics, I Walk the Line was effectively a love letter to Cash’s first wife, and the singer later called it his “first gospel hit,” saying that he felt like he was singing it to the heavens.