Top 30 Greatest Country Songs of All Time | Articles on WatchMojo.com (2024)

#30: “Tennessee Whiskey” (2015)
Chris Stapleton

One of the first things that leap out at the listener from this version of “Tennessee Whiskey” from Chris Stapleton is the production. The song sounds crisply modern, yet simultaneously vintage, possessing a nice separation of instruments to go along with Stapleton’s vocals, and the production highlights his soulful, almost bluesy delivery. Chris Stapleton clearly possesses a love for this song, an appreciation that seems to date back to its famous 1981 recording from David Allan Coe [xref]. As a result, his “Tennessee Whiskey” manages to transcend generations to find a whole new audience.

Every musical genre possesses its idea of a novelty song. This takes nothing away from the quality at play, of course, with Jeannie C. Riley’s “Harper Valley PTA” existing as one of the best. Riley made history with the song’s meteoric chart success, becoming the first woman to top both the Billboard Top 100 and U.S. Hot Country Singles charts with “Harper Valley PTA.” Songwriter extraordinaire Tom T. Hall crafted an absolutely scathing critique of small-town life, while Riley lends the song her own charisma, flair and sass. This was a star-making turn for Riley, whose natural beauty imbued single, LP and compilation album artwork in record racks across the country. The song was even adapted into a 1978 movie starring Barbara Eden!

#28: “Knoxville Girl” (1956)
The Louvin Brothers

The subject matter of a murder ballad can often be, well, depressing and downright murderous. “Knoxville Girl” is one of the most grim and shocking examples of this genre, and perhaps nowhere has it been better performed than with this version by The Louvin Brothers. These siblings were masters of close harmony singing, and the effects of their combined efforts are chilling, yet also hypnotic. The Louvin Brothers had a bevy of amazing tunes to their credit, from “I Don’t Believe You’ve Met My Baby” [xref] to the infamous “Satan Is Real,” but “Knoxville Girl” serves as a great place for newcomers to discover the pair’s enviable talents.

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Robert John “Mutt” Lange is no stranger to collaborating on hit records. The now-legendary producer gained fame in the heavy metal community after working with bands like Def Leppard, and he adapted his approach for his success with former wife, Shania Twain. The results were on Twain’s “Come On Over” album, and this international smash single, “Man! I Feel Like a Woman.” The song, from top to bottom, feels unapologetically pop, and practically shimmers with studio finesse. Twain’s massive charisma and confident vocals sell the song (and accompanying video) for all its worth, retaining country twang while also boldly going for crossover chart success.

There are a number of great versions of “Sunday Mornin’ Comin’ Down” to enjoy, from Ray Stevens’ to one from the immortal Johnny Cash. However, we also gotta recommend the version that was cut by the song’s actual songwriter, Kris Kristofferson. This take from Kristofferson’s 1970 debut album is absolutely steeped in the warm, analog production style of that decade. Kristofferson’s vocals on “Sunday Mornin’ Comin’ Down” are drenched in echo and reverb, while the electric piano and drum accompaniment lend the song a folk-rock backbeat. The end results speak for themselves, really; a melancholic ode to those bittersweet mornings where capturing an optimistic mood feels like a challenge.

There are any number of songs that well-represent just how much of a legend Charley Pride is within the world of country music. “Kiss an Angel Good Mornin’' is one of those classically-composed tunes that could’ve probably been sung by any country star, but it’s Pride that makes the song truly his own, and something special. His rich and textured voice lends the otherwise straightforward material layers of realistic and depth that help it transcend its to-the-point composition. Country music hasn’t historically been a place in which African-American artists have flourished, but it’s artists like Charley Pride and songs like “Kiss An Angel Good Mornin’” that helped pave the way.

There’s absolutely no doubt that Carrie Underwood is one of the true success stories to spawn from “American Idol.” That said, her musical success wasn’t necessarily a foregone conclusion, particularly given that show’s track record. It was with “Before He Cheats” where Carrie Underwood’s stature within the world of country music became assured, because the success of this song struck like a bolt of lightning. It’s the lyrical content that hammers home Underwood’s credibility as a storyteller, bringing to life the words of songwriters Josh Kear and Chris Tompkins. “Before He Cheats” is well-produced, but not too slick, and retains enough honky-tonk soul ‘n swagger to make it a full-blown, modern country classic.

#23: “Wagon Wheel” (2004)
Old Crow Medicine Show

This song certainly possesses a strange and piecemeal history. Folk-rock icon Bob Dylan actually composed the chorus way back in 1973, but the song was left unfinished until Nashville’s Old Crow Medicine Show added verses and completed the work. The final version of “Wagon Wheel” melds together bluegrass, country and folk-tinged Americana to create pure musical magic. The spirit of Dylan’s original vision can be heard within an intentionally-nasal approach to the vocals, while the internal melodies stir the show in a manner that feels wistful and nostalgic. “Wagon Wheel” would also get recorded by Darius Rucker [xref] , but it’s the Old Crow Medicine Show version that stands alone as something truly awesome.

We admit that “Courtesy of the Red, White and Blue (The Angry American)” would’ve been a more predictable choice for a Toby Keith song [xref] . However, we ultimately chose to go with this comparative upbeat and optimistic cut from the late Keith’s debut album. The production is surprisingly bright-sounding, and “Should’ve Been a Cowboy” actually wouldn’t sound out of place on a rock record, minus the country instrumentation. This is a testament to Keith’s ability to combine the old with the new, adding a fresh coat of paint to that reliable fence. The major chord phrasings and Keith’s unapologetically bold vocals make “Should’ve Been a Cowboy” sound large and in-charge, an anthemic crowd-pleaser.

The late-nineties and early millennium were halcyon periods for country music crossover success, particularly when it came to female artists. Lee Ann Womack was a wonderful singer whose career followed in the paths of artists like Faith Hill, Shania Twain and The Dixie Chicks. This wasn’t a new phenomenon, of course, and the pop instrumentation and arrangements of “I Hope You Dance” weren’t born in a vacuum. Instead, Womack’s bold career choice echoes the bravery of Dolly Parton before her, since “I Hope You Dance” never goes half-measures with the former’s voice. The song is, honestly, just beautiful; an emotional tune that balances melancholy and hope in a manner that truly deserves all of the flowers.

This one’s for the old-schoolers. Marty Robbins’ “Gunfighter Ballads and Trail Songs” LP from 1959 is a classic from the country music genre, featuring an iconic cover shot that immediately jumps out from the racks on vinyl on a shelf. The Spanish guitar instantly puts you in a time and place, an Old West cantina south of the border, where danger lurks around every corner. Bobby Sykes and Jim Glaser sing the song with amazing skill, harmonizing beautifully as they tell a tale of love, death, yearning, and loss. The protagonist’s story in “El Paso,” predictably, ends in tragedy, but let’s be honest: would we really want it any other way.

Songwriting is a key component to a great country music song, with many compositions being performed by multiple singers, sometimes charting in completely different decades. The Chicks didn’t write “Goodbye Earl,” but their version from 1999 was released a number of years after its original songwriter, Dennis Linde, had his version recorded by a different band. “Goodbye Earl” deals with the controversial subject of domestic violence, both lyrically and with its accompanying music video. Despite this, the song was a hit for The Chicks, with a lot of money and attention raised to benefit battered women’s shelters in the wake of its success.

Some songs are just born for the live arena. In this case, Conway Twitty’s “Hello Darlin’” was one of the legend’s go-to openers, a bittersweet ballad full of the sort of love and loss so often found in some of the best country songs. Twitty’s voice almost sounds at the point of breaking when he sings the line, “gotta go now,” and it’s this believability that lends “Hello Darlin’” such an emotional resonance. There’s a pathos to Twitty’s performance that lifts the song’s arrangements from good to great, all the while making “Hello Darlin’” one of country music’s most recognizable standards.

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There’s a certain wistfulness and innocence to John Denver’s smash hit, “Take Me Home, Country Roads.” The song’s melodic nature is evocative, painting a picture of long drives (or perhaps hitchhiking, 1970s style) and thoughtful contemplation. Denver’s vocals are clear as a crystal stream, untouched by grit yet possessing a likability that’s uniquely John and John’s alone. The backing vocals accompany Denver beautifully, while acoustic and steel guitar interplay make “Country Roads” a song we can spin over and over again, with no worries whatsoever.

The term “standard” comes up again and again within country music, those songs that make up The Great Book of music covered again and again by different artists. “It Wasn’t God Who Made Honky Tonk Angels” is one of those standards, a tune that lives forever, thanks to the magic present within its construction, and the performances of those who try their musical hand. Kitty Wells first made the song popular back in 1952, with words and music composed by J. D. “Jay” Miller. Wells was the first female solo artist to hit the Billboard country number one with her version, an ode to cheatin’ men and the dance hall girls who, to paraphrase Hank Williams, “live on the wild side of life.”

#15: “Mammas Don't Let Your Babies Grow Up to Be Cowboys” (1978)
Waylon Jennings & Willie Nelson

“Mammas Don’t Let Your Babies Grow Up to Be Cowboys” was a mild hit for songwriter Ed Bruce when he included it on his 1976 solo album, but most country fans are probably more familiar with a more famous cover version from 1978. Waylon Jennings and Willie Nelson gave the tune an up-tempo spit shine with airtight musical backing on their studio rendition. The pair also drop plenty of their own classic charisma onto the track, giving “Mammas Don’t Let Your Babies Grow Up to Be Cowboys” a fresh lease on life for some new fans.

The world of country music, perhaps more than any other genre, delved deep into emotional catharsis and reflection after the events of September 11th, 2001. This owes largely to its uniquely American origins, as well as the patriotism that usually comes part-and-parcel with country music as a whole. Still, “Where Were You (When the World Stopped Turning)” is particularly poignant by anyone’s standard, thanks to Alan Jackson’s legitimately focused delivery. There isn’t a lot of rah-rah jingoism or revenge-speak here, but rather a moment of connection with all of those who felt something on that day. There’s a sense of shared loss and reverence for the dead, and a memory that many of us will never forget.

“The Devil Went Down to Georgia” is something of an outlier on this list, in that it absolutely ROCKS. Country music has always shined with its contemplative nature, but who said there was anything wrong with letting loose once in a while? Charlie Daniels’ musical knowledge is set on full display with “The Devil Went Down to Georgia,” taking his experience as a sideman and songwriter by utilizing both hard rock and soul to tell his tale. The fiddle battle between Old Scratch and Johnny tosses bluegrass, rock, and even some funk into the mix, with the end result being one of the most gleeful and fun country hits to ever crossover into mainstream radio.

#12: “Coal Miner’s Daughter” (1970)
Loretta Lynn

It’s difficult hedging out just one track from Loretta Lynn’s storied career in country music. “The Pill” was a controversial anthem of female empowerment, while “One’s on the Way” humorously took a mirror image look into the life of a harried mother. “Coal Miner’s Daughter” might be among the most personal and well-known songs from Lynn, and with good reason, because it’s an all-time classic. The song is an autobiographical tale of Loretta’s childhood and upbringing, and boasts amazingly rich production by the engineering legend Owen Bradley. Meanwhile, Lynn’s vocals are full of charisma and mesmerizing depth, capturing our imagination every time we hear them, right to the present day.

#11: “Friends in Low Places” (1990)
Garth Brooks

Garth Brooks is unquestionably one of the most well-known and popular names of modern-day country music, and “Friends in Low Places” is perhaps a fan favorite of his enviable musical repertoire. The song had been written and performed by a couple of other artists prior to Brooks getting his mitts on it, but his version definitely seemed to resonate with an audience ready to hear Garth deliver the goods. The man’s vocal is full of sass and attitude, while the arrangements swing low and slow like good barbeque. It’s a meat-and-potatoes tune that begs for fun (perhaps slightly inebriated) singalongs and good times.

There’s just something magical about the DNA of a truly great song, something that keeps bringing back, again and again, to singers that can work their own unique magic to the melody. Willie Nelson’s “On the Road Again” is one, while “Always on My Mind” is another, having been recorded by legends such Elvis Presley and Brenda Lee over the years. Nelson leant his own unique stamp to the song in 1982, a decade after it was originally composed by songwriters Wayne Carson, Mark James, and Johnny Christopher. Willie’s version had crossover success outside of the country music world, while retaining its soft, balladeering structure. It’s just a tender and melancholic song that tugs at the heartstrings every time.

#9: “Amarillo by Morning” (1983)
George Strait

George Strait’s version of “Amarillo by Morning” was a hit for the Texas-born singer a decade after the tune was originally co-written and recorded by Terry Stafford back in 1973. The processed eighties production style doesn’t hurt Strait’s version in the slightest, with the end results sounding somewhat similar to George’s other big hit, “All My Ex’s Live in Texas.” Here, both songs come across as smooth, but never soulless, and Strait’s soulful vocal carries both tunes to the places they need to go. “Amarillo by Morning” may be a hard-luck song about a rodeo rider, but George Strait sells it in a way that brings us nothing but joy.

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Some country music songs just seem destined to cross over into the cultural zeitgeist. “The Gambler” is one of those tunes, a defining song for Kenny Rogers from a career that’s spanned many different kinds of music. “The Gambler” is a little ways’ away from Rogers’ beginnings as a psychedelic rock pioneer with his old group, The First Edition, and was actually the fourth time the tune had been recorded since being written by Don Schlitz in 1976. Rogers’ version feels like pop country before pop country was a “thing,” although this doesn’t diminish the work Rogers and producer Larry Butler brought to making “The Gambler” their own. This song just seemed like it was waiting for Kenny to take hold and take control

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The world of country music has possessed so many defining and devastatingly talented female performers. Tammy Wynette, however, may be among the very best, “The First Lady of Country Music,” if you will. Her career saw plenty of hits, but there’s one song that stands above it all: the iconic “Stand by Your Man.” Wynette’s insanely powerful vocals sell this somewhat controversial song from first note to last, but particularly so during the finale, where she goes all out with her performance of its high notes. The creative relationship between Wynette and producer Billy Sherrill perhaps never saw a more bountiful harvest than the glory that was “Stand by Your Man.”

Hank Williams is often considered, and rightfully so, to be a defining personality of country music. His songs served as bedrocks for the entire genre, inspiring generations of musicians that stretch all the way to the modern day. “I’m So Lonesome I Could Cry” is just one of Williams’ classic killers, while “Your Cheatin’ Heart” may be among his best-known songs. It’s a classic tale of heartbreak, a country standard highlighted by Williams’ iconic delivery and influential songwriting skill. It’s an easy entry point for fans new to classic country music, while also one of the best examples of the genre at its most pure and undiluted.

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#5: “Jolene” (1973)
Dolly Parton

The words “legend” and “talent” get tossed around a lot, but they take on a whole new meaning when referencing the wonderful, inimitable Dolly Parton. Want proof? How about the fact that the “9 to 5” singer told “The Bobby Bones Show” in 2018 that she apparently wrote not one, but TWO of country music’s all-time classics on the same day? Yup, both “I Will Always Love You” and our next pick, “Jolene” were apparently composed by Dolly within a 24-hour period, and we’re just flabbergasted at the genius of it all. Chip Young’s hooky guitar work is the glue that holds “Jolene” together, as Dolly sings her heart out about a woman she feels has designs on her man. It’s a short and not-so-sweet slice of crossover country perfection.

The world of “outlaw country” has many classic heroes, including Waylon Jennings, David Allan Coe, and Johnny Paycheck. Merle Haggard also deserves mention in that distinguished company, thanks to his genre-defining work on songs like “Okie from Muskogee” and our next entry, “Mama Tried.” There’s a sense of futility to the song, of a life destined for danger, despite the best intentions of the narrator’s parents. The evocative beauty of “Mama Tried” and its acoustic base is undercut by the stabs of lead guitar of The Strangers’ Roy Nichols, while the ride cymbal accompaniment of drummer Eddie Burris lends the chorus of “Mama Tried” a jauntiness that makes it all the more memorable.

In the world of country music, there’s sadness, and then there’s the near-inescapable melancholy that is “Crazy” by Patsy Cline. Patsy Cline takes the Willie Nelson-penned tune and makes it irrevocably her own, and we challenge anyone to take a listen without feeling those teardrops fall. Patsy’s voice is smoky, bluesy, and mournful, backed by a choral and piano accompaniment that makes “Crazy” the kind of song that works in many different settings. It works in a dimly-lit bar, perhaps while drowning one’s sorrows or personal demons. But it also works perhaps as a coping mechanism for grief, best listened to on headphones in the dark, allowing Cline to sing us the blues in her own, inimitable fashion.

The role of producer Billy Sherrill cannot be overstated when it comes to how it helped make the careers of some incredibly talented people. George Jones was one of those people, a voice of his generation that helped lay the groundwork for all of country music, throughout his work in the fifties, sixties, and seventies. It was Sherrill, however, that convinced Jones to take on “I Stopped Loving Her Today” in 1980, just as the singer’s career was in the midst of a slump. Jones’ deadeye performance and Sherrill’s giant, cavernous production style helped the song shoot off like a rocket, becoming, in the minds of many, the best country song ever recorded.

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For many, the voice of Johnny Cash IS the voice of country music. And it’s difficult to challenge that argument. This becomes particularly true when listening to the man’s classic discography, featuring such hits as “Ring of Fire” and our number one pick, “I Walk the Line.” It took three tries for "I Walk the Line" to become Cash's first number one Billboard hit, but the end results display how much the song has entered the cultural zeitgeist when music fans tend to think of old-school country music. Maybe it’s The Man in Black’s deadpan delivery, or those iconic lyrics, but “I Walk the Line” never fails to lift our spirits every time we hear it.

What other songs could have made this list? Let us know in the comments!